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EUGENOL
CASRN: 97-53-0
For other data, click on the Table of Contents
Human Health Effects:
Evidence for Carcinogenicity:
Classification of carcinogenicity: 1) evidence in humans: No adequate data. 2) evidence
in animals: Limited evidence. Overall summary evaluation of carcinogenic risk to
humans is Group 3: The agent is not classifiable as to its carcinogenicity to humans.
/From table/
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. S7 63 (1987)]**PEER REVIEWED**
Human Toxicity Excerpts:
NOT CORROSIVE LIKE PHENOL BUT INGESTION RESULTS IN
GASTROENTERITIS. SYSTEMIC TOXICITY IS SIMILAR TO BUT LESS THAN
THAT OF PHENOL PERHAPS BECAUSE OF ITS INSOLUBILITY IN WATER.
AQUEOUS EMULSIONS BY MOUTH INDUCE VOMITING IN MAN ...
PROMOTE/S/ GASTRIC SECRETION OF MUCIN.
[Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products.
5th ed. Baltimore: Williams and Wilkins, 1984.,p. II-257]**PEER REVIEWED**
EUGENOL SHOWED WEAK CYTOTOXIC ACTIVITY AGAINST HELA CELLS.
[Opdyke, D.L.J. (ed.). Monographs on Fragrance Raw Materials. New York: Pergamon
Press, 1979. 377]**PEER REVIEWED**
Smoking of clove cigarettes /SRP: 60-65% tobacco, 30-35% clove buds/ has recently
been associated with high altitude pulmonary edema.
[Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of
Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988.
920]**PEER REVIEWED**
Patch tests for eugenol in patients suffering from 'cosmetic dermatitis' were positive in
2.6% (4/155) of cases.
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 87 (1985)]**PEER REVIEWED**
The cytotoxicity of eugenol to replicating cells, as mediated by the intracellular level of
glutathione and by metabolic activation, was evaluated with the neutral red assay. The
cytotoxicity of eugenol to human HFF fibroblasts and human HepG2 hepatoma cells was
increased somewhat in the presence of a hepatic S9 microsoma fraction from Aroclor
induced rats or hamsters. Exposure of human HepG2 hepatoma cells to eugenol depleted
the level of intracellular glutathione. Cells treated with 1-chloro-2,4-dinitrobenzene or
buthionine sulphoximine, agents that deplete intracellular glutathione, were
hypersensitive to eugenol. A 1 hr pretreatment with 1- chloro-2,4-dinitrobenzene
enhanced the cytotoxicity of eugenol, as did a 24 hr pretreatment with buthionine
sulphoximine. Intracellular glutathione levels were, apparently significant in mediating
the toxicity of eugenol.
[Babich H et al; Toxicol In Vitro 7 (2): 105-9 (1993)]**PEER REVIEWED**
84 patients with contact dermatitis (38 dentists, 18 dental nurses and 28 dental
technicians) were studied. All were patch tested with standard patch test series of the
Council for Mutual Economic Assistance countries and with some professional allergens.
31 (36.9%) of them had allergic occupational contact dermatitis and 39 (46.2%) had
irritant contact dermatitis. The highest prevalence of irritant contact dermatitis was found
among dental surgeons. The percentage of atopics in the group of patients with irritant
contact dermatitis was twice greater compared to that in the group of patients with
allergic contact dermatitis. The contact allergens most frequently encountered were
acrylic compounds, disinfectants (eugenol, thymol, trioxymethylene) mercury compunds
and anesthetics.
[Berova N et al; Dermatol Monatsschr 176 (1): 15-8 (1990)]**PEER REVIEWED**
Probable Routes of Human Exposure:
... LIKELY TO OCCUR BY DIRECT CONTACT OF SKIN & EYES WITH OIL OR
SOLUTIONS OF OIL. EXCESSIVE EXPOSURE TO VAPORS DOES NOT SEEM
LIKELY IN VIEW OF LOW VOLATILITY & PUNGENT ODOR ... IN HIGH
CONCN.
[Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New
York: Interscience Publishers, 1963. 1691]**PEER REVIEWED**
Emergency Medical Treatment:
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The following Overview, *** EUGENOL ***, is relevant for this HSDB record
chemical.
Life Support:
o This overview assumes that basic life support measures
have been instituted.
Clinical Effects:
0.2.1 SUMMARY OF EXPOSURE
A) WITH THERAPEUTIC USE
1) Contact dermatitis, direct tissue damage, and allergic
reactions have occurred following therapeutic use of
dental products containing eugenol.
B) WITH POISONING/EXPOSURE
1) Vomiting, metabolic acidosis, CNS depression, seizures,
hepatotoxicity, hypoglycemia, and disseminated
intravascular coagulation have been reported in
children following clove oil ingestions . Dermal
exposure to eugenol-containing products may result in
irritation and inflammation.
2) Clove cigarette smoking may cause nausea, vomiting,
angina, increased incidence of respiratory tract
infection, exacerbation of chronic bronchitis,
increased incidence and severity of asthma attacks,
dyspnea, chronic cough, epistaxis, hemorrhagic
pulmonary edema, bronchospasm, pneumonia, bronchitis,
and hemoptysis.
0.2.4 HEENT
A) Mucous membrane burns may occur. Permanent right
infraorbital anesthesia and anhydrosis have been
reported following the spillage of clove oil into the
eye.
B) 0.2 mL instilled in rabbit eyes was moderately
irritating in 30 minutes and severely irritating in 8
hours.
0.2.6 RESPIRATORY
A) WITH POISONING/EXPOSURE
1) Hemoptysis, sore throat, epistaxis, bronchospasm,
pneumonia, bronchitis, and pulmonary edema have been
reported in humans.
2) Pulmonary edema has occurred in dogs following high
dose injection and in rats after IP eugenol. Acute
emphysema and pulmonary edema resulted from
intratracheal administration in animals.
0.2.7 NEUROLOGIC
A) WITH POISONING/EXPOSURE
1) Local analgesia may occur. Coma and seizures have
developed after large doses. Permanent local anesthesia
has been reported after dermal application. Ataxia has
occurred in dogs given 5 grams of eugenol.
0.2.8 GASTROINTESTINAL
A) Gastroenteritis and anorexia may occur, as has been
reported in experimental animals.
0.2.9 HEPATIC
A) WITH POISONING/EXPOSURE
1) Liver dysfunction may occur.
0.2.10 GENITOURINARY
A) WITH POISONING/EXPOSURE
1) Proteinuria was reported in a 7-month-old child.
0.2.11 ACID-BASE
A) WITH POISONING/EXPOSURE
1) Metabolic acidosis was reported in two children
following clove oil ingestions.
0.2.13 HEMATOLOGIC
A) WITH POISONING/EXPOSURE
1) Disseminated intravascular coagulopathy has been
reported.
0.2.14 DERMATOLOGIC
A) WITH THERAPEUTIC USE
1) Transient, mild inflammation and erythema have been
reported after topical application. A chemical burn due
to eugenol has been reported. Contact dermatitis and
allergic reactions can occur.
B) WITH POISONING/EXPOSURE
1) Anhidrosis has been reported after dermal exposure.
0.2.17 METABOLISM
A) WITH POISONING/EXPOSURE
1) Severe hypoglycemia has occurred in a child following
clove oil ingestion.
0.2.19 IMMUNOLOGIC
A) WITH THERAPEUTIC USE
1) Anaphylaxis has been reported in sensitive patients.
0.2.20 REPRODUCTIVE
A) At the time of this review, no data were available to
assess the potential effects of exposure to this agent
during pregnancy or lactation.
0.2.21 CARCINOGENICITY
A) Limited evidence, from animal models, suggests that
eugenol may possess carcinogenic potential.
0.2.22 OTHER
A) WITH POISONING/EXPOSURE
1) CLOVE CIGARETTES contain 60 to 65% tobacco and 30 to
35% ground clove buds. Respiratory irritation, nausea
and headache have been described as well as more
serious illness, including pulmonary edema,
bronchospasm, and hemoptysis.
Treatment Overview:
0.4.2 ORAL/PARENTERAL EXPOSURE
A) Following ingestion and/or prior to gastric evacuation,
immediately dilute with water or milk.
B) Emesis is NOT advised with ingestions of concentrated
eugenol due to potential for caustic effects. Endoscopy
may be performed within 12 to 24 hours post-ingestion to
assess severity.
C) ACTIVATED CHARCOAL: Administer charcoal as a slurry (240
mL water/30 g charcoal). Usual dose: 25 to 100 g in
adults/adolescents, 25 to 50 g in children (1 to 12
years), and 1 g/kg in infants less than 1 year old.
0.4.4 EYE EXPOSURE
A) DECONTAMINATION: Irrigate exposed eyes with copious
amounts of room temperature water for at least 15
minutes. If irritation, pain, swelling, lacrimation, or
photophobia persist, the patient should be seen in a
health care facility.
0.4.5 DERMAL EXPOSURE
A) OVERVIEW
1) DECONTAMINATION: Remove contaminated clothing and wash
exposed area thoroughly with soap and water. A
physician may need to examine the area if irritation or
pain persists.
Range of Toxicity:
A) No toxic dose has been established, but established
acceptable daily maximum intake is 5 mg/kg. Animal
studies indicate the lethal dose to be near 2 to 3 g/kg.
UENE
[Rumack BH POISINDEX(R) Information System Micromedex, Inc., Englewood, CO,
2004; CCIS Volume 122, edition expires Nov, 2004. Hall AH & Rumack BH (Eds):
TOMES(R) Information System Micromedex, Inc., Englewood, CO, 2004; CCIS Volume
122, edition expires Nov, 2004.]**PEER REVIEWED**
Animal Toxicity Studies:
Evidence for Carcinogenicity:
Classification of carcinogenicity: 1) evidence in humans: No adequate data. 2) evidence
in animals: Limited evidence. Overall summary evaluation of carcinogenic risk to
humans is Group 3: The agent is not classifiable as to its carcinogenicity to humans.
/From table/
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. S7 63 (1987)]**PEER REVIEWED**
Non-Human Toxicity Excerpts:
POISONED RATS EXHIBITED PARESIS OF HIND LEGS AND JAW WITH ...
PROSTRATION & COMA. DEATH BELIEVED TO BE DUE TO PERIPHERAL
VASCULAR COLLAPSE.
[Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products.
5th ed. Baltimore: Williams and Wilkins, 1984.,p. II-257]**PEER REVIEWED**
... ANIMALS THAT SURVIVED ACUTE EFFECTS REMAINED LETHARGIC,
SHOWED KIDNEY INJURY AS MANIFESTED BY URINARY INCONTINENCE &
SOMETIMES HEMATURIA & EXHIBITED MALFUNCTION OF HIND LEGS FOR
SEVERAL DAYS.
[Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New
York: Interscience Publishers, 1963. 1692]**PEER REVIEWED**
... DOGS EXHIBITED VOMITING AFTER SINGLE DOSES OF 250 OR 500 MG/KG.
DEATH OCCURRED AT HIGH LEVEL. PULMONARY EDEMA...NOTED IN SOME
DOGS EXPOSED IV ... IV INJECTION ... DILUTED TO 1:20 TRANSIENTLY DECR
SYSTEMIC ARTERIAL BLOOD PRESSURE & MYOCARDIAL CONTRACTILE
FORCE, IMPAIRED MOTOR ACTIVITY, & INCR SALIVARY FLOW.
[Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology:
Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982.
2534]**PEER REVIEWED**
AQUEOUS EMULSIONS BY MOUTH INDUCE VOMITING IN ... DOGS &
PROMOTE GASTRIC SECRETION OF MUCIN.
[Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of
Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976.,p. II-168]**PEER
REVIEWED**
THE STOMACHS OF RATS & GUINEA PIGS GIVEN ORAL DOSES ... SHOWED
DESQUAMATION OF THE EPITHELIUM, WITH PUNCTATE HEMORRHAGES IN
PYLORIC & GLANDULAR REGIONS OF THE STOMACH. ADDITIONAL
EVALUATIONS TO MUCOUS MEMBRANES SHOWED THAT APPLICATION ...
TO VENTRAL SURFACE OF THE TONGUE OF DOGS CAUSED ERYTHEMA &
OCCASIONALLY ULCERS.
[Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology:
Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982.
2534]**PEER REVIEWED**
... 20 MALE RATS GIVEN INITIAL ORAL DOSE OF 1.4 G ... /KG, WHICH WAS
GRADUALLY INCR TO 4.0 G/KG ... 15 ... LIVED LONG ENOUGH TO RECEIVE
MAX DOSE. ... ENLARGEMENT OF LIVER & ADRENAL GLANDS ... OBSERVED
& HISTOLOGICAL EXAM OF FORESTOMACH ... REVEALED ... HYPERPLASIA
& HYPERKERATOSIS ... FOCAL ULCERATION. SMALL DEGREE OF
OSTEOPOROSIS ... SEEN.
[Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology:
Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982.
2534]**PEER REVIEWED**
RATS GIVEN 4 DAILY DOSES OF APPROX 900 MG/KG SHOWED MINOR LIVER
DAMAGE. NO LIVER DAMAGE ... IN RATS FED ... AT 1% IN DIET FOR ABOUT
4 MO. FEEDING OF ... 0.1 OR 1% IN DIET ... /TO/ RATS FOR 19 WK EXHIBITED
NO EFFECT ON GROWTH, HEMATOLOGY, OR ORGAN WEIGHS &
HISTOLOGY. NO ADVERSE EFFECT ... IN ... RATS FED ... 79.3 MG/KG ... /DAY
FOR 12 WK.
[Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology:
Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982.
2534]**PEER REVIEWED**
RESPIRATORY INHIBITION OF ISOLATED RAT LIVER MITOCHONDRIA BY
EUGENOL WAS DOSE RELATED & UNCOUPLED OXIDATIVE
PHOSPHORYLATION FROM ELECTRON TRANSFER.
[COTMORE JM ET AL; ARCH ORAL BIOL 24 (8): 565 (1979)]**PEER
REVIEWED**
COMPARISON OF INFLAMMATORY RESPONSES PRODUCED BY
COMMERCIAL EUGENOL & PURIFIED EUGENOL. EACH MATERIAL WAS
INJECTED SC BENEATH ABDOMINAL SKIN OF 40 WALTER REED RATS.
STUDY SUGGEST THAT IMPURITIES IN COMMERCIAL EUGENOL DO CAUSE
INCR IN INFLAMMATORY RESPONSE.
[WEBB JG ET AL; J DENT RES 60 (9): 1724 (1981)]**PEER REVIEWED**
In rats, the intratracheal administration of eugenol produces interstitial hemorrhage and
acute pulmonary edema.
[Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of
Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988.
920]**PEER REVIEWED**
Dogs given oral doses of 0.25 g/kg of eugenol demonstrated vomiting, weakness,
lethargy, and ataxia. At 0.5 g/kg eugenol is capable of causing coma and death within 24
hr. The LD50 in eugenol in rats has been dtermined to be 1.8 ml/kg (1.93 g), with
postmortem findings consistent with sudden cardiovascular collapse.
[Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed.
Philadelphia, PA: W.B. Saunders Co., 1990. 1471]**PEER REVIEWED**
Iv administration of varying doses (0.05-0.15 ml of a 1:20 or 1:60 dilution) in dogs led to
a transient fall in blood pressure and a reduction of myocardial contractile force. After
single oral doses of 500 mg/kg body wt eugenol, 2/4 dogs with predominant symptoms
of vomiting died; all animals receiving doses of 250 mg/kg body wt survived. Single and
repeated oral administration of a 5% aqueous eugenol emulsion to dogs caused
degeneration of the gastric mucosal cells.
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 85 (1985)]**PEER REVIEWED**
Groups of 50 male and 50 female B6C3F1 mice, 6-7 wk old, were fed diets containing
USP extra grade eugenol (purity >99%, with up to 4 trace impurities) at levels of 0, 3000,
or 6000 mg/kg of diet for 103 wk. Survival at 106 wk was 41/50, 35/50, and 35/50 among
control, low dose, and high dose males, respectively; survival in females varied between
80-90%. ... The total numbers of male mice with hepatocellular tumors were 14/50 in
control, 28/50 in low dose, and 18/49 in high dose animals; and those of females: 2/50 in
control, 7/49 in low dose, and 9/49 in high dose animals. For hepatocellular tumors in
female mice a trend test was significant (p= 0.02), as was a pair wise comparison test
between the high dose and control groups (p= 0.02). For male mice, the trend test was not
significant, but the pair wise comparison test between the low dose group and the control
group was significant (p= 0.004).
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 83 (1985)]**PEER REVIEWED**
Eugenol was not mutagenic to Escherichia coli WP2 uvrA when tested in the presence
and absence of S9 derived from the livers of Aroclor induced rats.
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 86 (1985)]**PEER REVIEWED**
Eugenol induced chromosomal aberrations in Chinese hamster ovary cells in the absence
of an exogenous metabolic system. In a second study, chromosomal aberrations were
induced by eugenol in Chinese hamster ovary cells only in the presence of S9 from
Aroclor induced rats; a small increase in the incidence of sister chromatid exchange was
also observed in the presence or absence of S9.
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 87 (1985)]**PEER REVIEWED**
THE HYDROXYLATION OF DIMETHYLAMIDOPYRINE & HEXOBARBITONE
BY MOUSE LIVER MICROSOMES WAS WEAKLY INHIBITED BY EUGENOL IN
VIVO. HEXOBARBITONE /CNS DEPRESSION/ & ZOXAZOLAMINE PARALYSIS
WERE SLIGHTLY PROLONGED IN MICE TREATED WITH EUGENOL.
[Opdyke, D.L.J. (ed.). Monographs on Fragrance Raw Materials. New York: Pergamon
Press, 1979. 377]**PEER REVIEWED**
Bioassay directed fractionation of clove terpenes from the plant Eugenia caryophyllata
has led to the isolation of the following five active known compounds: betacaryophyllene, beta-caryophyllene oxide, alpha-humulene, alpha-humulene epoxide I,
and eugenol. Their structures were determined on the basis of spectral analysis. These
compounds showed significant activity as inducers of the detoxifying enzyme glutathione
S-transferase in the mouse liver and small intestine. The ability of natural anticarcinogens
to induce detoxifying enzymes has been found to correlate with their activity in the
inhibition of chemical carcinogenesis. Thus, these sesquiterpenes show promise as
potential anticarcinogenic agents.
[Zheng GQ et al; J Nat Prod 55 (7): 999-1003 (1992)]**PEER REVIEWED**
The effect of betel leaf extract and some of its constituents, eugenol, hydroxychavicol,
beta-carotene and alpha-tocopherol, on benzo(a)pyrene induced forestomach neoplasia in
male Swiss mice was examined. Betel leaf and its constituents decreased the number of
papillomas per animal with the maximum protection, considering molar dosage, exhibited
by beta-carotene and alpha-tocopherol. Except for beta-carotene, eugenol,
hydroxychavicol and alpha-tocopherol increased the levels of reduced glutathione in the
liver while glutathione S-transferase activity was enhanced by all except eugenol.
[Bhide SV et al; J Ethnopharmacol 34 (2-3): 207-13 (1991)]**PEER REVIEWED**
Regulatory guidelines suggest testing chemicals up to cytotoxic doses in chromosomal
aberration assays. To investigate the utility and limitations of various cytotoxicity
indicators Chinese hamster ovary cells were used to test 8 chemicals with differing ratios
of cytotoxicity to clastogenicity. Immediate or delayed cell killing and growth inhibition
(adenosine triphosphate levels, cell counts, colony-forming efficiency) and cell-cycle
perturbations (mitotic index; average generation time) were measured. Aberrations were
scored 10 and 24 hr from the beginning of the 3 hr treatment. All 8 compounds induced
aberrations at concentrations that reduced cell growth at 24 hr by 50% or less.
Concentrations of each chemical which induced at least 15% cells with aberrations, gave
little loss of colony-forming efficiency (0-20%) for mitomycin C, adriamycin, cadmium
sulfate and 2,6-diaminotoluene in contrast to the marked loss of colony-forming
efficiency (70-80%) for eugenol, 2-aminobiphenyl and 8-hydroxyquinoline. 2,4Diaminotoluene was intermediate. Higher aberration yields were found at 24 hr than at 10
hr, even when minimal cell cycle delay was detected by average generation time
estimates from BrdUrd labeled cells. Cells with multiple aberrations were seen at 24 but
not at 10 hr, and often confirmed clastogenicity when there was only a weak increase in
the percentage of cells with aberrations. Total adenosine triphosphate per culture did not
always correlate with cell number, especially at later times after treatment. This is likely
due to metabolic perturbations or altered cell biomass that are known to affect cell
adenosine triphosphate content. Mitotic index suppression often did not correlate with
average generation time, eg, only small increases in average generation time were seen
for 8- hydroxyquinoline, 2,4-diaminotoluene and eugenol despite severe mitotic
suppression at 10 hr. By 24 hr the mitotic index for all chemicals had recovered,
sometimes exceeding control levels. Marked mitotic accumulation was seen at 10 hr for
2,4-diaminotoluene, indicating cell synchrony. Thus, the mitotic index has limited value
for dose selection. In conclusion, even weakly active chemicals were detected at a single
time without exceeding a 50% growth reduction at 24 hr.
[Armstrong MJ et al; Mutat Res 265 (1): 45-60 (1992)]**PEER REVIEWED**
Choice of harvest time is one of the most important variables in the assessment of
whether a compound is clastogenic and in establishing a dose relation. The effects of
sampling time on aberration yield was examined for 7 diverse chemicals in Chinese
hamster ovary cells by harvesting at intervals from 9 to 30 hr after treatment for 3 hr with
or without S9 metabolic activation. Both the percentage of aberrant cells and the total
number of aberrations were observed. Data suggest that for most compounds a single
harvest time approximately 17-21 hr after the beginning of a 3 hr treatment is optimal for
aberration detection in Chinese hamster ovary cells. Maximal aberration yields were
observed for eugenol from 15 to 21 hr. The use of 3 or more closely spaced
concentrations, carefully selected to yield up to 50% toxicity, allowed detection of a
positive response at a single harvest time for all 7 chemicals.
[Bean CL et al; Mutat Res 265 (1): 31-44 (1992)]**PEER REVIEWED**
The effects of phenolic dental medicaments on lipoxygenase activities of rat dental pulp
and human platelets were studied. The major product derived from (14)C arachidonic
acid by the homogenate of rat dental pulp was 12-hydroxyeicosatetraenoic acid (15hydroxyeicosatetraenoic acid). Eugenol and p-chlorophenol dose dependently inhibited
hydroxyeicosatetraenoic acids formation. The IC50 values of eugenol and pchlorophenol were 0.62 and 0.34 mM respectively. The concentrations of these
compounds that inhibit lipoxygenase were similar to those required to inhibit
cyclooxygenase. These compounds also inhibited 12-lipoxygenase of human platelets
with a similar range of concentrations. The results show that phenolic dental
medicaments inhibit pulpal and platelet lipoxygenase. Thus, inhibition of arachidonic
acid metabolism by phenolic dental medicaments via the lipoxygenase pathway may be
involved in the analgesic and anti-inflammatory effects of the medicaments in endodontic
therapy.
[Dohi T et al; Dent Jpn (Tokyo) 27 (1): 45-9 (1990)]**PEER REVIEWED**
Eugenol is widely used as a food flavoring agent and a dental analgesic. Mice treated
with eugenol (400-600 mg/kg, orally) in combination with an inhibitor of glutathione
synthesis, buthionine sulfoximine (1 hr before eugenol, 4 mmol/kg, ip) developed
hepatotoxicity characterized by increases in relative liver weight and serum glutamicpyruvic transaminase, hepatic congestion, and centrilobular necrosis of hepatocytes.
Eugenol (up to 600 mg/kg) alone produced no hepatotoxicity. Drug metabolism
inhibitors such as carbon disulfide, methoxsalen, and piperonyl butoxide prevented or
significantly reduced the hepatotoxic effect of eugenol given in combination with
buthionine sulfoximine. On the other hand, pretreatment with phenobarbital increased the
hepatotoxicity. These results suggest that eugenol is activated by a cytochrome p450
dependent metabolic reaction and that the liver injury is caused by inadequate rates of
detoxification of the resulting metabolite in mice depleted of hepatic glutathione by
buthionine sulfoximine treatment.
[Mizutani T et al; Res Commun Chem Pathol Pharmacol 71 (2): 219-30 (1991)]**PEER
REVIEWED**
The local lymph node assay is a novel predictive test for the identification of contact
allergens. The collaborative study reported here was performed to evaluate the reliability
of the method when performed in independent laboratories. Eight chemicals were
examined in each of 4 participating laboratories and results compared with predictions of
skin sensitizing activity made from concurrent Magnusson and Kligman guinea pig
maximization tests performed in a single laboratory. The local lymph node assay has as
its theoretical basis the fact that contact allergens induce T-lymphocyte proliferative
responses. In practice, predictions of contact sensitizing potential are made following
measurement of proliferation in lymph nodes draining the site of exposure to chemical,
and derivation of a stimulation index using control values as the comparator. Although in
the present study there was some variation between laboratories with respect to the
absolute stimulation indices recorded, it was found that with all chemicals each
laboratory made the same predictions of sensitizing activity. Six chemicals (2,4dinitrochlorobenzene, formalin, eugenol, isoeugenol, p-phenylenediamine and potassium
dichromate) yielded positive responses, and two (methyl salicylate and benzocaine) were
negative, in each laboratory. Furthermore, with 7 of the 8 chemicals tested there was no
significant difference between laboratories in terms of the characteristics of the doseresponse relationships recorded. With the exception of one chemical (benzocaine),
predictions made with the local lymph node assay were in accord with those derived from
guinea pig maximization tests. These inter-laboratory comparisons demonstrate that the
local lymph node assay is a robust and reliable method for the identification of at least
moderate and strong contact allergens.
[Kimber I et al; Toxicol Lett 55 (2): 203-13 (1991)]**PEER REVIEWED**
The naturally occurring alkenylbenzene, eugenol, was examined for its ability to form
DNA adducts in the livers of mice that had been treated with up to 10 mg of the
compound. No adducts were detected by (32)P postlabelling with a limit of detection of 1
adduct in 1X10+9 nucleotides. Under these conditions adducts were readily detected in
liver DNA from the structurally related hepatocarcinogen safrole.
[Phillips DH; Mutat Res 245 (1): 23-6 (1990)]**PEER REVIEWED**
Eugenol, previously found to behave as a genotoxin in in vitro systems and as a
noncarcinogen in rodents, was evaluated for its ability to induce genotoxic effects in
vivo. Rats were given by gavage a single or two successive doses equal to one-half the
corresponding LD50, killed at different times after treatment, and examined for the
following end points: the frequency of both micronucleated polychromatic erythrocytes
in the bone marrow and micronucleated hepatocytes (after partial hepatectomy), the in
vivo-in vitro induction of DNA fragmentation, as measured by the alkaline elution
technique, and of unscheduled DNA synthesis, as measured by autoradiography, in
hepatocyte primary cultures. The two latter end points were also evaluated after in vitro
exposure of hepatocytes to log-spaced subtoxic concentrations. Eugenol never produced
effects indicative of genotoxic activity.
[Allavena A et al; Teratog Carcinog Mutagen 12 (1): 31-41 (1992)]**PEER
REVIEWED**
Eugenol produces hepatic injury in mice depleted of glutathione by pretreatment with
buthionine sulfoximine. Several eugenol analogs were examined for their ability to cause
hepatic injury after administration to mice in combination with buthionine sulfoximine.
Hepatotoxicity was assessed by measuring relative liver weight, liver blood volume, and
serum glutamic-pyruvic transaminase activity in mice. Comparison of the treated
compounds showed that the structural requirements for toxic potency was a phenolic ring
having an allyl substituent at the 4-position. These structural requirements can be
explained by assuming that a vinylogous quinone methide formed by metabolic oxidation
of eugenol plays a role in inducing hepatotoxicity in glutathione depleted mice.
[Mizutani T et al; Res Commun Chem Pathol Pharmacol 73 (1): 87-96 (1991)]**PEER
REVIEWED**
Eugenol, an extract of cloves, has been associated with pulmonary edema when inhaled
from commercially available clove cigarettes. The hypothesis that eugenol directly
causes lung edema through oxidant mediated mechanisms was tested by infusing eugenol
(0.1 and 1.0 mM) into isolated rabbit lungs perfused with a cell free albumin and
physiologic salt solution. Lung edema (1.0 mM) was observed as demonstrated by
increased lung weight gain and wet to dry lung weight ratios without alterations in mean
pulmonary artery pressure. The oxygen metabolite scavengers catalase (1,000 unit/ml)
and dimethylthiourea (30 mM) attenuated lung edema. Instillation of dimethylurea,
superoxide dismutase, or heat-inactivated catalase did not prevent lung edema formation.
It was concluded that eugenol causes lung edema in isolated lungs through oxidant
mediated mechanisms in the absence of circulating formed blood elements.
[McDonald JW, Heffner JE; Am Rev Respir Dis 143 (4 part 1): 806-9 (1991)]**PEER
REVIEWED**
The effects of treatment with naturally occurring antioxidants, selenium, beta-carotene,
ferulic acid, esculin and eugenol during the promotional phase of tumor development
were investigated in male F344 rats pretreated with 1,2-dimethylhydrazine and 1-methyl1-nitrosourea. Animals were given 3 sc injections of 1,2- dimethylhydrazine at a dose of
40 mg/kg body weight within 1 wk and then were injected with 1-methyl-1-nitrosourea ip
at a dose of 20 mg/kg body weight 2 times per wk for 2 wk. Thereafter, the were
maintained on a diet containing either 0.2% beta-carotene, 2 ppm selenium, 1% ferulic
acid, 1% esculin or 0.8% eugenol. At week 52 surviving rats were killed and complete
histological examinations were performed. Administration of eugenol enhanced the
development of both hyperplasia and papillomas in the forestomach. Eugenol decreased
the incidence of kidney nephroblastomas. The results thus showed that eugenol exerts
promoting activity for forestomach carcinogenesis while the other antioxidants might
have weak organ specific inhibitory effects under these experimental conditions.
[Imaida K et al; Cancer Lett 55 (1): 53-60 (1990)]**PEER REVIEWED**
A number of alkenylbenzenes related to safrole and estragole are known to be
hepatocarcinogenic in rats and/or mice, apparently by a genotoxic mechanism. However,
they are not bacterial mutagens in the Ames test. The ability of a series of carcinogenic
and non-carcinogenic congeners to induce unscheduled DNA synthesis was studied in
freshly isolated rat hepatocytes in primary culture. The cytotoxicity of these compounds
was assessed by lactate dehydrogenase leakage. Eugenol, for which evidence of
carcinogenicity is equivocal or negative, did not induce unscheduled DNA synthesis. All
compounds were markedly cytotoxic at concentrations between 1X10-3 and 1X10-2 M,
irrespective of their structural features.
[Howes AJ et al; Food Chem Toxicol 28 (8): 537-42 (1990)]**PEER REVIEWED**
A study was conducted in male Fischer rats to assess the effect of dietary administration
of eugenol on the activities of liver detoxifying enzymes, specifically, uridine
diphosphate glucuronyltransferase, uridine diphosphate glucose dehydrogenase, and
glutathione-S-transferase. Groups of rats were given diets containing 0, 1, 3, or 5% by
weight eugenol for 22 days; in long term experiments lasting 23 wk, one group of rats
received control diet and another group was alternatively fed the above named
concentrations of eugenol. The activities of uridine diphosphate glucuronyltransferase in
liver microsomes were tested of 1-naphthol, 4-nitrophenol, 4-hydroxybiphenyl, 4methylumbelliferone, and bilirubin as substrates. The activities of uridine diphosphate
glucose dehydrogenase and glutathione-S-transferase were tested using liver cytosol. The
activities of liver microsomal uridine diphosphate glucuronyltransferase toward 1naphthol, 4- nitrophenol, 4-hydroxybiphenyl, and 4-methylumbelliferone were enhanced
by dietary administration of eugenol; activity on bilirubin was almost unchanged. Similar
results for uridine diphosphate glucose dehydrogenase and glutathione-S-transferase
activities in liver cytosol were obtained by dietary administration of eugenol.
Glutathione-S-transferase activities toward 1-chloro-2,4-dinitrobenzene and 1,2-dichloro4-nitrobenzene were increased markedly by dietary administration of eugenol. All
enhancements of enzyme activities were related to the dietary level of eugenol. The
content of cytochrome p450 in liver microsomes was not increased during the 13 wk
period. No significant change in gamma-glutamyl transpeptidase, a marker for chemical
carcinogenesis, was noted. It was concluded that eugenol may be a safe and nontoxic
inhibitor of carcinogenesis.
[Yokota H et al; Biochemical Pharmacology 37 (5): 799-802 (1988)]**PEER
REVIEWED**
... Under these experimental conditions, there was no evidence of carcinogenicity
observed for male or female rats. For mice there was equivocal evidence of
carcinogenicity since eugenol caused incr incidences of both carcinomas and adenomas
of the liver in male mice at the 3,000 ppm dietary level and because eugenol was
associated with an increase in the combined incidences of hepatocellular carcinomas or
adenomas in female mice. Levels of Evidence of Carcinogenicity: Male Rats: Negative;
Female Rats: Negative; Male Mice: Equivocal; Female Mice: Equivocal.
[Carcinogenesis Bioassay of Eugenol in F344/N Rats and B6C3F1 Mice (Feed Studies)
Technical Report Series No. 223 (1983) NIH Publication No. 84-1779 U.S. Department
of Health and Human Services, National Toxicology Program, National Institute of
Environmental Health Sciences, Research Triangle Park, NC 27709]**QC
REVIEWED**
National Toxicology Program Studies:
Carcinogenesis studies of eugenol (>99% pure), ... were conducted by feeding diets
containing 6,000 or 12,500 ppm of eugenol to groups of 50 female F344/N rats and by
feeding diets containing 3,000 or 6,000 ppm to groups of 50 male F344/N rats and
B6C3Fl mice of each sex for 103 weeks. Groups of 40 rats and 50 mice of each sex
served as controls. ... Eugenol was given in the diets of female F344/N rats (0, 0.6, or
1.25%) and of male F344/N rats and male and female B6C3F1 mice (0, 0.3, or 0.6%) for
103 weeks. Under these experimental conditions, there was no evidence of
carcinogenicity observed for male or female rats. For mice there was equivocal evidence
of carcinogenicity since eugenol caused incr incidences of both carcinomas and
adenomas of the liver in male mice at the 3,000 ppm dietary level and because eugenol
was associated with an increase in the combined incidences of hepatocellular carcinomas
or adenomas in female mice. Levels of Evidence of Carcinogenicity: Male Rats:
Negative; Female Rats: Negative; Male Mice: Equivocal; Female Mice: Equivocal.
[Carcinogenesis Bioassay of Eugenol in F344/N Rats and B6C3F1 Mice (Feed Studies)
Technical Report Series No. 223 (1983) NIH Publication No. 84-1779 U.S. Department
of Health and Human Services, National Toxicology Program, National Institute of
Environmental Health Sciences, Research Triangle Park, NC 27709]**QC
REVIEWED**
Non-Human Toxicity Values:
LD50 Rat oral 1930 mg/kg
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 85 (1985)]**PEER REVIEWED**
LD50 Mouse oral 3000 mg/kg
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 85 (1985)]**PEER REVIEWED**
LD50 Guinea pig oral 2130 mg/kg
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 85 (1985)]**PEER REVIEWED**
Metabolism/Pharmacokinetics:
Metabolism/Metabolites:
FOLLOWING IP INJECTION OF (14)C EUGENOL INTO RATS, RADIOACTIVITY
WAS DISTRIBUTED IN VARIOUS ORGANS & PRESENCE OF (14)CO2 IN
EXPIRED AIR INDICATED THE DEMETHYLATION OF EUGENOL.
[Opdyke, D.L.J. (ed.). Monographs on Fragrance Raw Materials. New York: Pergamon
Press, 1979. 376]**PEER REVIEWED**
Two metabolites of eugenol, 3-piperidyl-1-(3'-methoxy-4'-hydroxyphenyl)-1-propanone
and 3-pyrrolidinyl-1-(3'-methoxy-4'-hydroxyphenyl)-1-propanone, have been isolated
from rat urine.
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 86 (1985)]**PEER REVIEWED**
The metabolism and toxic effects of eugenol were studied in isolated rat hepatocytes.
Incubation of hepatocytes with eugenol resulted in the formation of conjugates with
sulfate, glucuronic acid and glutathione. The major metabolite formed was the glucuronic
acid conjugate. Covalent binding to cellular protein was observed using (3)H eugenol.
Loss of intracellular glutathione and cell death were also observed in these incubations.
Concentrations of 1 mM eugenol caused a loss of over 90% of intracellular glutathione
and resulted in approximately 85% cell death over a 5 hr incubation period. The loss of
the majority of glutathione occurred prior to the onset of cell death (2 hr). The effects of
eugenol were concentration dependent. The addition of 1 mM N-acetylcysteine to
incubations containing 1 mM eugenol was able to completely prevent glutathione loss
and cell death as well as inhibit the covalent binding of eugenol metabolites to protein.
Conversely, pretreatment of hepatocytes with diethylmaleate to deplete intracellular
glutathione increased the cytotoxic effects of eugenol. These results demonstrate that
eugenol is actively metabolized in hepatocytes and suggest that the cytotoxic effects of
eugenol are due to the formation of a reactiv intermediate, possibly a quinone methide.
[Thompson DC et al; Chem Biol Interact 77 (2): 137-47 (1991)]**PEER REVIEWED**
Absorption, Distribution & Excretion:
NO ABSORPTION OF EUGENOL OCCURRED WITHIN 2 HR OF APPLICATION
TO INTACT SHAVED SKIN OF MICE. ... OVER 70% OF AN ORAL DOSE OF
EUGENOL WAS EXCRETED IN URINE OF RABBITS.
[Opdyke, D.L.J. (ed.). Monographs on Fragrance Raw Materials. New York: Pergamon
Press, 1979. 376]**PEER REVIEWED**
Mechanism of Action:
THE INHIBITION BY EUGENOL OF GLUCURONIC ACID CONJUGATION IN
STOMACH OF RATS & GUINEA PIGS & OF DOGS MAY HAVE SOME BEARING
ON THE REPORTED MUCINOGENIC ACTIVITY OF EUGENOL & ITS
BENEFICIAL EFFECT ON GASTRIC ULCER FORMATION.
[Opdyke, D.L.J. (ed.). Monographs on Fragrance Raw Materials. New York: Pergamon
Press, 1979. 377]**PEER REVIEWED**
Interactions:
VAN DUUREN BL, GOLDSCHMIDT BM; J NATL CANCER INST 5 (6): 1237
(1976). EUGENOL PARTIALLY INHIBITED BENZO[A]PYRENE
CARCINOGENICITY. COMPD APPLIED TO MOUSE SKIN.
**PEER REVIEWED**
EUGENOL SHOWED WEAK TUMOR-PROMOTING ACTIVITY FOLLOWING ITS
APPLICATION TO MOUSE SKIN SUBJECTED TO INITIATING TREATMENT
WITH 7,12-DIMETHYLBENZ(A)ANTHRACENE. EUGENOL FAILED TO
POTENTIATE GASTRIC TUMOR PRODUCTION BY 20METHYLCHOLANTHRENE IN MICE.
[Opdyke, D.L.J. (ed.). Monographs on Fragrance Raw Materials. New York: Pergamon
Press, 1979. 377]**PEER REVIEWED**
MUTAGENICITY OF EUGENOL IN AMES SALMONELLA TYPHIMURIUM
ASSAY WAS INCREASED BY ADDITION OF 3'-PHOSPHOADENOSINE-5'PHOSPHOSULFATE TO MICROSOMAL ASSAY.
[TO LP ET ALL; BULL ENVIRON CONTAM TOXICOL 28 (6): 647 (1982)]**PEER
REVIEWED**
Effects of topically applied betel leaf extract and its constituents, beta-carotene, alphatocopherol, eugenol and hydroxychavicol on 7,12-dimethylbenz(a)anthracene induced
skin tumors were evaluated in two strains of mice. Eugenol showed minimal protection
in both strains of mice. The mean latency period and survivors in betel leaf extract, betacarotene, alpha-tocopherol and hydroxychavicol treated groups were remarkably high as
compared to 7,12- dimethylbenz(a)anthracene alone treated group. Ip injection of betal
leaf constituents showed a significant effect on both glutathione and glutathione Stransferase levels in the Swiss mouse skin.
[Azuine MA et al; Indian J Exp Biol 29 (4): 346-51 (1991)]**PEER REVIEWED**
Pharmacology:
Therapeutic Uses:
... HAS BEEN USED AS AN ANTIPYRETIC BUT IT IS RELATIVELY
INEFFECTIVE. ... IT HAS... BEEN USED IN MEDICINE FOR THE STUDY OF
MUCOUS SECRETION & GASTRIC CYTOLOGY, WITHOUT GASTRIC
RESECTION OR GASTROENTEROSTOMY. IT HAS BEEN SHOWN TO HAVE
ANTHELMINTIC PROPERTIES.
[Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New
York: Interscience Publishers, 1963. 1691]**PEER REVIEWED**
Nonprescription medicines for toothache commonly contain eugenol, and some products
for canker-sore may do so also.
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 78 (1985)]**QC REVIEWED**
Eugenol ... has been used as a topical dental anesthetic for many years.
[Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of
Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988.
920]**PEER REVIEWED**
Eugenol is used as a component of several dental materials (e.g., dental cements,
impression pastes and surgical pastes). Such products are principally combinations of
zinc oxide and eugenol in varying ratios. They are reported to be widely used in dentistry
as temporary filing materials, cavity liners for pulp protection, capping materials,
temporary cementation of fixed protheses, impression materials and major ingredients of
endodontic sealers. In addition, eugenol has been used in dentistry for disinfecting root
canals.
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 77 (1985)]**PEER REVIEWED**
Analgesic (dental)
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 613]**PEER REVIEWED**
Interactions:
VAN DUUREN BL, GOLDSCHMIDT BM; J NATL CANCER INST 5 (6): 1237
(1976). EUGENOL PARTIALLY INHIBITED BENZO[A]PYRENE
CARCINOGENICITY. COMPD APPLIED TO MOUSE SKIN.
**PEER REVIEWED**
EUGENOL SHOWED WEAK TUMOR-PROMOTING ACTIVITY FOLLOWING ITS
APPLICATION TO MOUSE SKIN SUBJECTED TO INITIATING TREATMENT
WITH 7,12-DIMETHYLBENZ(A)ANTHRACENE. EUGENOL FAILED TO
POTENTIATE GASTRIC TUMOR PRODUCTION BY 20METHYLCHOLANTHRENE IN MICE.
[Opdyke, D.L.J. (ed.). Monographs on Fragrance Raw Materials. New York: Pergamon
Press, 1979. 377]**PEER REVIEWED**
MUTAGENICITY OF EUGENOL IN AMES SALMONELLA TYPHIMURIUM
ASSAY WAS INCREASED BY ADDITION OF 3'-PHOSPHOADENOSINE-5'PHOSPHOSULFATE TO MICROSOMAL ASSAY.
[TO LP ET ALL; BULL ENVIRON CONTAM TOXICOL 28 (6): 647 (1982)]**PEER
REVIEWED**
Effects of topically applied betel leaf extract and its constituents, beta-carotene, alphatocopherol, eugenol and hydroxychavicol on 7,12-dimethylbenz(a)anthracene induced
skin tumors were evaluated in two strains of mice. Eugenol showed minimal protection
in both strains of mice. The mean latency period and survivors in betel leaf extract, betacarotene, alpha-tocopherol and hydroxychavicol treated groups were remarkably high as
compared to 7,12- dimethylbenz(a)anthracene alone treated group. Ip injection of betal
leaf constituents showed a significant effect on both glutathione and glutathione Stransferase levels in the Swiss mouse skin.
[Azuine MA et al; Indian J Exp Biol 29 (4): 346-51 (1991)]**PEER REVIEWED**
Environmental Fate & Exposure:
Probable Routes of Human Exposure:
... LIKELY TO OCCUR BY DIRECT CONTACT OF SKIN & EYES WITH OIL OR
SOLUTIONS OF OIL. EXCESSIVE EXPOSURE TO VAPORS DOES NOT SEEM
LIKELY IN VIEW OF LOW VOLATILITY & PUNGENT ODOR ... IN HIGH
CONCN.
[Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New
York: Interscience Publishers, 1963. 1691]**PEER REVIEWED**
Natural Pollution Sources:
... PRESENT IN OIL OF CAMPHOR, JAVA CITRONELLA, CALIFORNIA LAUREL
& ACACIA FLOWERS. ... REMARKABLE AMT ... IN OCIMUM SANCTUM (70%)
AND OCIMUM GRATISSIMUM (60%). EUGENOL IS ... FOUND IN OIL FROM
VIOLET FLOWERS (21%). IN SOME PLANTS PROBABLY OCCURS AS
GLUCOSIDE.
[Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by
T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975.
198]**PEER REVIEWED**
EUGENOL ... OCCURS IN CLOVE OIL (80-95%), PIMENTO OIL (80%),
CINNAMON LEAF OIL (95%), & BAY OIL (60%).
[Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New
York: Interscience Publishers, 1963. 1690]**PEER REVIEWED**
FOUND IN VOLATILE OILS FROM ... SASSAFRAS, MASSOY BARK, CANELLA,
CULILAWAN, & OTHER OILS.
[Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed.
Easton, Pennsylvania: Mack Publishing Co., 1975. 991]**PEER REVIEWED**
ESSENTIAL OIL FROM PIMENTA RACEMOSA (BAY OIL), AS WELL AS OILS
FROM OTHER MEMBERS OF MYRTACEAS FAMILY EXHIBIT
ANTIMICROBIAL EFFECT. MAIN CONSTITUENT OF THESE OILS WAS
EUGENOL.
[NADAL ET AL; COSMET PERFUM 88: 37 (1973)]**PEER REVIEWED**
Eugenol is the major active ingredient in cloves.
[Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of
Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988.
920]**PEER REVIEWED**
The Flavor and Extract Manufacturers' Association of the United States (1978) has
reported the occurrence of eugenol, without specific concentrations, in the following
food sources: cocoa, Japanese ginger oil, loganberries, mace essential oil, sweet
marjoram dried mushrooms, nutmeg, yellow passion fruit, black pepper, peppermint,
pimento berry oil and tomatoes. Additional reported occurrences of eugenol are as
follows: allspice tincture; Alpinia galanga oil; Apium graveolens seed essential oil;
Artemisia glacialis (glacier wood worm) essential oil; Bupleurum chinense D.C. essential
oil; Capsicum spp. (red pepper); Castanea creata Sieb et Zucc (chestnut) flower;
Cinnamomum pauciflorum Nees leaf essential oil; corn silage; curcumalonga; Cytisus
scoparius Link flower essential oil; fermented plum juice; Homalomena occulta oil;
Jasminium odoratissimum oil; Juglans regia leaf oil; Laurus nobilis L. leaf; Ligustrum
obtusifolium Sieb et Zucc flower essential oil; Ligustrum ovalifolium Hassk flower
essential oil; Lonicera japonica flower essential oil; Magnolia salicifolia Maxim. bud;
Mexalis accuminata bulb essential oil; Menyantes triforiata essential oils; Trachycarpus
excelsa and T. fortune; and Vetiveria zizamioides G. root essential oil.
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 80 (1985)]**PEER REVIEWED**
Food Survey Values:
REPORTED USED IN NON-ALCOHOLIC BEVERAGES 1.4 PPM; ICE CREAM,
ICES, ETC 3.1 PPM; CANDY 32 PPM; BAKED GOODS 33 PPM; GELATINS &
PUDDINGS 0.60 PPM; CHEWING GUM 500 PPM; CONDIMENTS 9.6-100 PPM;
MEATS 40-2000 PPM.
[Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by
T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975.
198]**PEER REVIEWED**
The Flavor and Extract Manufacturers' Association of the United States (1978) has
reported the occurrence of eugenol, without specific concentrations, in the following
food sources: cocoa, Japanese ginger oil, loganberries, mace essential oil, sweet
marjoram dried mushrooms, nutmeg, yellow passion fruit, black pepper, peppermint,
pimento berry oil and tomatoes.
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 80 (1985)]**PEER REVIEWED**
Environmental Standards & Regulations:
Acceptable Daily Intakes:
THE JOINT FAO/WHO EXPERT COMMITTEE ON FOOD ADDITIVE (1967) HAS
PUBLISHED A MONOGRAPH & SPECIFICATIONS FOR EUGENOL GIVING A
CONDITIONAL ADI /ACCEPTABLE DAILY INTAKE/ OF 0-5 MG/KG.
[Opdyke, D.L.J. (ed.). Monographs on Fragrance Raw Materials. New York: Pergamon
Press, 1979. 376]**PEER REVIEWED**
Chemical/Physical Properties:
Molecular Formula:
C10-H12-O2
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 612]**PEER REVIEWED**
Molecular Weight:
164.20
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 612]**PEER REVIEWED**
Color/Form:
COLORLESS OR PALE YELLOW LIQUID
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 612]**PEER REVIEWED**
CRYSTALS FROM HEXANE
[Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 73rd ed. Boca Raton, FL:
CRC Press Inc., 1992-1993.,p. 3-244]**PEER REVIEWED**
Odor:
ODOR OF CLOVES
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 612]**PEER REVIEWED**
Taste:
SPICY, PUNGENT TASTE
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 612]**PEER REVIEWED**
Boiling Point:
253.2 DEG C @ 760 MM HG
[Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 73rd ed. Boca Raton, FL:
CRC Press Inc., 1992-1993.,p. 3-244]**PEER REVIEWED**
Melting Point:
-9.2 TO -9.1 DEG C
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 612]**PEER REVIEWED**
Density/Specific Gravity:
1.0664 @ 20 DEG C/4 DEG C
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 612]**PEER REVIEWED**
Dissociation Constants:
pka = 10.19 @ 25 deg C
[Kortum G et al; Pure and Applied Chemistry, Vol. 1, No 2-3 (1961)]**QC
REVIEWED**
Octanol/Water Partition Coefficient:
] Log Kow = 2.27
[Sangster J; LOGKOW Databank. Sangster Res. Lab., Montreal Quebec, Canada
(1994)]**QC REVIEWED**
Solubilities:
PRACTICALLY INSOL IN WATER; SOL IN GLACIAL ACETIC ACID, 1 ML IN 2
ML 70% ALCOHOL, AQ FIXED ALKALI HYDROXIDE SOLUTIONS; MISCIBLE
WITH ALCOHOL, CHLOROFORM, ETHER, OILS
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 613]**PEER REVIEWED**
Water: 0.0398 moles/l
[Mueller M, Klein; Chemosphere 25: 769-82 (1992)]**PEER REVIEWED**
water solubility = 2.43X10+3 mg/l @ 25 deg C
[Yalkowsky SH, Dannenfelser RM; The AQUASOL dATAbASE of Aqueous Solubility.
Fifth ed, Tucson, AZ: Univ Az, College of Pharmacy (1992)]**QC REVIEWED**
Spectral Properties:
INDEX OF REFRACTION: 1.5416 @ 19.5 DEG C/D; 1.5380-1.5420 @ 20 DEG C/D;
SPECIFIC OPTICAL ROTATION: -1 DEG 30 MIN
[Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by
T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975.
198]**PEER REVIEWED**
INDEX OF REFRACTION: 1.5410 @ 20 DEG C/D
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 612]**PEER REVIEWED**
SADTLER REF NUMBER: 3880 (IR, PRISM)
[Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida:
CRC Press Inc., 1979.,p. C-303]**PEER REVIEWED**
IR: 5146 (Coblentz Society Spectral Collection)
[Weast, R.C. and M.J. Astle. CRC Handbook of Data on Organic Compounds. Volumes I
and II. Boca Raton, FL: CRC Press Inc. 1985.,p. V1 629]**PEER REVIEWED**
UV: 3-254 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New
York)
[Weast, R.C. and M.J. Astle. CRC Handbook of Data on Organic Compounds. Volumes I
and II. Boca Raton, FL: CRC Press Inc. 1985.,p. V1 629]**PEER REVIEWED**
NMR: 260 (Varian Associates NMR Spectra Catalogue)
[Weast, R.C. and M.J. Astle. CRC Handbook of Data on Organic Compounds. Volumes I
and II. Boca Raton, FL: CRC Press Inc. 1985.,p. V1 629]**PEER REVIEWED**
MASS: 1062 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
[Weast, R.C. and M.J. Astle. CRC Handbook of Data on Organic Compounds. Volumes I
and II. Boca Raton, FL: CRC Press Inc. 1985.,p. V1 629]**PEER REVIEWED**
Vapor Pressure:
1 MM HG @ 78.4 DEG C
[Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology:
Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982.
2497]**PEER REVIEWED**
Other Chemical/Physical Properties:
% IN SATURATED AIR: APPROX 0.004 AT 25 DEG C, 760 MM HG
[Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology:
Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982.
2497]**PEER REVIEWED**
DISTILLS BETWEEN 250 DEG C AND 255 DEG C
[Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed.
Easton, Pennsylvania: Mack Publishing Co., 1975. 991]**PEER REVIEWED**
OILY; BECOMES BROWN IN AIR; OPTICALLY INACTIVE
[Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York,
NY: Van Nostrand Rheinhold Co., 1993 501]**PEER REVIEWED**
Crystals; mp: 69-70 deg C; bp: 360 deg C; practically insol in water; freely sol in
benzene, chloroform, ether, hot alcohol. /Eugenol benzoate/
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 613]**PEER REVIEWED**
Chemical Safety & Handling:
Flash Point:
ABOUT 104 DEG C
[Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by
T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975.
198]**PEER REVIEWED**
Explosive Limits & Potential:
Combustible
[Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York,
NY: Van Nostrand Rheinhold Co., 1993 502]**PEER REVIEWED**
Stability/Shelf Life:
LOW VOLATILITY
[Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New
York: Interscience Publishers, 1963. 1691]**PEER REVIEWED**
STABILITY IS RATED AS FAIR WHEN USED AS FOOD ADDITIVE
[Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Cleveland: The Chemical
Rubber Co., 1972. 496]**PEER REVIEWED**
DARKENS & THICKENS ON EXPOSURE TO AIR
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 612]**PEER REVIEWED**
Occupational Exposure Standards:
Manufacturing/Use Information:
Major Uses:
IN PERFUMERY INSTEAD OF OIL OF CLOVES; MFR OF VANILLIN
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 613]**PEER REVIEWED**
RUBIFACIENT
[Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products.
5th ed. Baltimore: Williams and Wilkins, 1984.,p. II-257]**PEER REVIEWED**
CLOVE OIL SUBSTITUTE IN FOODS; GERMICIDE USED IN MEDICINE;
FLAVOR CHEMICAL; INT FOR 4-ALLYLVERATROLE & ISOEUGENOL
(PERFUME)
[SRI]**PEER REVIEWED**
Insect attractant. With phenylethyl butyrate as an adult Japanese beetle lure.
[Farm Chemicals Handbook 1993. Willoughby, OH: Meister Publishing Co., 1993.,p. C145]**PEER REVIEWED**
Denaturant for alcohol.
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 78 (1985)]**PEER REVIEWED**
Eugenol can be used as an antioxidant in inks, and it has been reported to be useful as a
fungicide in pharmaceuticals and cosmetics; no indication was found that eugenol is
being used commercially for such purposes at present /1985/. Eugenol was formerly used
internally in human medicine as an antiputrescent, but is no longer employed for this
purpose. It has been used in the treatment of flatulent colic.
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 78 (1985)]**PEER REVIEWED**
Eugenol is used principally as a fragrance and flavoring agent, as an analgesic in dental
materials and nonprescription drug products, as an insect attractant, and as a chemical
intermediate.
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 77 (1985)]**PEER REVIEWED**
A DENTAL OBTUNDENT & TOPICAL ANESTHETIC USED EXTENSIVELY TO
REPLACE CLOVE OIL, PRINCIPALLY BY DENTISTS, WHO ALSO EMPLOY IT
FOR ITS DISINFECTANT ACTION IN FILLING ROOT CANALS.
[Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed.
Easton, Pennsylvania: Mack Publishing Co., 1975. 991]**PEER REVIEWED**
IT IS USED AS A CHEMICAL INTERMEDIATE TO PRODUCE ISOEUGENOL ... .
[Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New
York: Interscience Publishers, 1963. 1691]**PEER REVIEWED**
/ZINC-EUGENOL CEMENT USP IS USED/ IN GENERAL DENTAL PRACTICE ...
AS A PULP CAPPING OR A TEMPORARY FILLING.
[Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed.
Easton, Pennsylvania: Mack Publishing Co., 1975. 1268]**PEER REVIEWED**
MEDICATION
**QC REVIEWED**
Manufacturers:
Firmenick Inc, Hq, PO Box 5880, Princeton, NJ 08543, (609) 452-1000; Firmenick
Chemical Manufacturing Center, 928-964 Doremus Ave, Port Newark, NJ 07114;
Production site: Port Newark, NJ 07114
[SRI. 1992 Directory of Chemical Producers-United States of America. Menlo Park, CA:
SRI International, 1992. 648]**PEER REVIEWED**
Givaudan Corp, Hq, 100 Delawanna Ave, Clifton, NJ 07014, (201) 365-8000; Chemicals
Div; Fritzsche Dodge & Olcott Div, 76 Ninth Ave, New York, NY 10011; Production
site: East Hanover, NJ 07936
[SRI. 1992 Directory of Chemical Producers-United States of America. Menlo Park, CA:
SRI International, 1992. 648]**PEER REVIEWED**
International Flavors & Fragrances Inc, Hq, 521 West 57th Street, New York, NY 10019,
(212) 765-5500; Production site: Union Beach, NJ 07735
[SRI. 1992 Directory of Chemical Producers-United States of America. Menlo Park, CA:
SRI International, 1992. 648]**PEER REVIEWED**
Ungerer & Co, Hq, 4 Bridgewater Lane, Lincoln Park, NJ 07035, (201) 628-0600;
Chemical Div, 110 N Commerce Way, Bethlehem, PA 18017; Production site:
Bethlehem, PA 18017
[SRI. 1992 Directory of Chemical Producers-United States of America. Menlo Park, CA:
SRI International, 1992. 648]**PEER REVIEWED**
Methods of Manufacturing:
OIL CONTAINING EUGENOL ... TREATED WITH 3% AQ SOLN OF NAOH;
NONACID COMPONENTS ... EXTRACTED WITH ETHER. ALKALINE SOLN IS
ACIDIFIED TO ISOLATE PHENOLS & ... FRACTIONALLY DISTILLED UNDER
REDUCED PRESSURE. TO AVOID FORMATION OF EMULSIONS,
PRETREATMENT OF OIL WITH TARTARIC ACID ... PREFERRED.
[Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by
T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975.
198]**PEER REVIEWED**
OBTAINED FROM MANY NATURAL SOURCES; FROM OIL OF CLOVES.
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 612]**PEER REVIEWED**
It can be extracted from clove oil with aqueous potassium hydroxide, followed by
liberation with an acid, and distillation in a stream of CO2. It can be synthesized by the
reaction of allyl chloride with guaiacol.
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 77 (1985)]**PEER REVIEWED**
General Manufacturing Information:
/INCOMPATIBLE WITH/ FERRIC CHLORIDE, POTASSIUM PERMANGANATE.
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 613]**PEER REVIEWED**
EUGENOL HAS THE FLAVOR OF SPICE & CLOVE WHEN USED AS A
SYNTHETIC FLAVORING. IN THE FINISHED FLAVORING IT ACTS AS A
FIXATIVE (REDUCES LOSS OF LIGHT VOLATILES), A TOP NOTE (GIVES
IDENTITY ON FIRST IMPRESSION), & A BODY (GIVES MAIN FLAVOR
CHARACTERISTICS). /FROM TABLE/
[Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Cleveland: The Chemical
Rubber Co., 1972. 496]**PEER REVIEWED**
REPORTED USED IN NON-ALCOHOLIC BEVERAGES 1.4 PPM; ICE CREAM,
ICES, ETC 3.1 PPM; CANDY 32 PPM; BAKED GOODS 33 PPM; GELATINS &
PUDDINGS 0.60 PPM; CHEWING GUM 500 PPM; CONDIMENTS 9.6-100 PPM;
MEATS 40-2000 PPM.
[Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by
T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975.
198]**PEER REVIEWED**
[IARC MONOGRAPHS 1972-PRESENT V36 p.76] Heavy metal content must not
exceed 0.004% max
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V 36 76 (1985)]**PEER REVIEWED**
Formulations/Preparations:
TECHNICAL PRODUCT CONTAINS 95-100% EUGENOL.
[Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by
T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975.
198]**PEER REVIEWED**
GRADES: TECHNICAL; UNITED STATES PHARMACOPEIA; "FOOD CHEMICAL
CODEX"
[Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York,
NY: Van Nostrand Rheinhold Co., 1993 501]**PEER REVIEWED**
Consumption Patterns:
Eugenol is used primarily as a fragrance and flavoring agent, as an analgesic in dental
materials and nonprescription drug products, as an insect attractant, and as a chemical
intermediate. Several other applications have been reported, the commercial status of
which is unknown. (1985)
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 77 (1985)]**PEER REVIEWED**
U. S. Production:
(1972) 2.15X10+8 g
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 77 (1985)]**PEER REVIEWED**
(1975) 1.45X10+8 g
[IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man.
Geneva: World Health Organization, International Agency for Research on Cancer, 1972PRESENT. (Multivolume work).p. V36 77 (1985)]**PEER REVIEWED**
(1984) 1.63X10+8 g
[USITC. SYN ORG CHEM-U.S. PROD/SALES 1984 p.119]**PEER REVIEWED**
U. S. Exports:
(1984) 1.51X10+9 g /Citronellal, Eugenol, Geraniol, Heliotropin, Hydroxycitronellal and
Isoeugenol/
[BUREAU OF THE CENSUS. U.S. EXPORTS, SCHEDULE E, 1984 p.2-83]**PEER
REVIEWED**
Laboratory Methods:
Clinical Laboratory Methods:
Sensitive HPLC assay used for the determination of eugenol in body fluids. Amt in the
range 0.02-100 ug of eugenol/ml of body fluid were determined with intra-assay
coefficients of variation <4% (1.13-3.72%).
[Fischer IU, Dengler HJ; J Chromatogr 525 (2): 369-77 (1990)]**PEER REVIEWED**
Analytic Laboratory Methods:
EUGENOL WAS DETERMINED BY HPLCON KONTRON RP-18 COLUMN OR ON
NUCLEOSIL COLUMN.
[GRACZA L; DTSCH APOTH-ZTG 120 (40): 1859 (1980)]**PEER REVIEWED**
... UV SPECTROPHOTOMETRY MAY BE USED TO YIELD RESULTS ACCURATE
TO CONCN /IN AIR/ AS SMALL AS 0.005 MG/ML.
[Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology:
Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982.
2533]**PEER REVIEWED**
EUGENOL WAS DETERMINED IN OIL FROM CINNAMON LEAVES & BARK
BY GLC USING A NONPOLAR STATIONARY PHASE.
[ANALYST (LONDON) 106 (1261): 456 (1981)]**PEER REVIEWED**
The analyte can be gas chromatographed as determined by Athen-ERL or S-Cubed.
[USEPA/SCC; Environmental Monitoring Methods Index p.264 (1992)]**PEER
REVIEWED**
Special References:
Special Reports:
DHHS/NTP; Toxicology & Carcinogenesis Studies of Eugenol in F344/N Rats and
B6C3F1 Mice (Feed Studies) Technical Report Series No. 223 (1983) NIH Publication
No. 84-1779
Maura A et al; Negative Evidence In-vivo of DNA-Damaging Mutagenic and
Chromosomal Effects of Eugenol. Negative evidence in-vivo of DNA-damaging
mutagenic and chromosamal effects of eugenol; Mutat Res 227 (2): 129-30 (1989). Rat
granuloma pouch assay bone marrow micronucleus test.
Synonyms and Identifiers:
Synonyms:
ALLYLGUAIACOL
**PEER REVIEWED**
P-ALLYLGUAIACOL
**PEER REVIEWED**
4-ALLYLGUAIACOL
**PEER REVIEWED**
5-Allylguaiacol
**PEER REVIEWED**
4-ALLYL-1-HYDROXY-2-METHOXYBENZENE
**PEER REVIEWED**
4-ALLYL-2-METHOXYPHENOL
**PEER REVIEWED**
CARYOPHYLLIC ACID
**PEER REVIEWED**
EUGENIC ACID
**PEER REVIEWED**
P-EUGENOL
**PEER REVIEWED**
FEMA NUMBER 2467
**PEER REVIEWED**
1-HYDROXY-2-METHOXY-4-ALLYLBENZENE
**PEER REVIEWED**
4-HYDROXY-3-METHOXYALLYLBENZENE
**PEER REVIEWED**
1-HYDROXY-2-METHOXY-4-PROP-2-ENYLBENZENE
**PEER REVIEWED**
2-METHOXY-4-ALLYLPHENOL
**PEER REVIEWED**
2-METHOXY-1-HYDROXY-4-ALLYLBENZENE
**PEER REVIEWED**
2-METHOXY-4-PROP-2-ENYLPHENOL
**PEER REVIEWED**
NCI-C50453
**PEER REVIEWED**
PHENOL, 4-ALLYL-2-METHOXY**PEER REVIEWED**
PHENOL, 2-METHOXY-4-(2-PROPENYL)**PEER REVIEWED**
SYNTHETIC EUGENOL
**PEER REVIEWED**
Associated Chemicals:
Eugenol benzoate;531-26-0
Formulations/Preparations:
TECHNICAL PRODUCT CONTAINS 95-100% EUGENOL.
[Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by
T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975.
198]**PEER REVIEWED**
GRADES: TECHNICAL; UNITED STATES PHARMACOPEIA; "FOOD CHEMICAL
CODEX"
[Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York,
NY: Van Nostrand Rheinhold Co., 1993 501]**PEER REVIEWED**
Administrative Information:
Hazardous Substances Databank Number: 210
Last Revision Date: 20020114
Last Review Date: Reviewed by SRP on 12/10/1993
Update History:
Complete Update on 01/14/2002, 1 field added/edited/deleted.
Complete Update on 08/09/2001, 1 field added/edited/deleted.
Complete Update on 05/16/2001, 1 field added/edited/deleted.
Complete Update on 09/12/2000, 1 field added/edited/deleted.
Complete Update on 02/02/2000, 1 field added/edited/deleted.
Complete Update on 09/21/1999, 1 field added/edited/deleted.
Complete Update on 08/26/1999, 1 field added/edited/deleted.
Complete Update on 09/11/1998, 1 field added/edited/deleted.
Complete Update on 06/02/1998, 1 field added/edited/deleted.
Complete Update on 10/23/1997, 2 fields added/edited/deleted.
Complete Update on 10/17/1997, 1 field added/edited/deleted.
Complete Update on 03/27/1997, 1 field added/edited/deleted.
Complete Update on 03/11/1997, 3 fields added/edited/deleted.
Complete Update on 02/07/1997, 3 fields added/edited/deleted.
Complete Update on 01/24/1997, 1 field added/edited/deleted.
Complete Update on 01/18/1996, 1 field added/edited/deleted.
Complete Update on 12/19/1994, 1 field added/edited/deleted.
Complete Update on 04/16/1994, 52 fields added/edited/deleted.
Field Update on 11/01/1993, 1 field added/edited/deleted.
Field Update on 09/02/1993, 1 field added/edited/deleted.
Complete Update on 01/20/1993, 1 field added/edited/deleted.
Field update on 12/11/1992, 1 field added/edited/deleted.
Complete Update on 09/03/1992, 1 field added/edited/deleted.
Complete Update on 09/26/1991, 1 field added/edited/deleted.
Field update on 11/09/1990, 1 field added/edited/deleted.
Complete Update on 10/22/1990, 4 fields added/edited/deleted.
Field Update on 03/01/1989, 1 field added/edited/deleted.
Complete Update on 02/19/1988, 10 fields added/edited/deleted.
Complete Update on 12/14/1984