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ANTHRAQUINONE
CASRN: 84-65-1
For other data, click on the Table of Contents
Human Health Effects:
Human Toxicity Excerpts:
LOW SYSTEMIC TOXICITY, BUT MAY CAUSE SKIN IRRITATION,
SENSITIZATION.
[The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976. 94]**PEER
REVIEWED**
Chronic neurotoxic effects include vision disturbances. /From table/ /Quinones/
[O'Donoghue, J.L. (ed.). Neurotoxicity of Industrial and Commercial Chemicals. Volume
I. Boca Raton, FL: CRC Press, Inc., 1985. 129]**PEER REVIEWED**
Skin, Eye and Respiratory Irritations:
Irritates .. skin.
[ITII. Toxic and Hazardous Industrial Chemicals Safety Manual. Tokyo, Japan: The
International Technical Information Institute, 1988. 46]**PEER REVIEWED**
Probable Routes of Human Exposure:
Anthraquinone was detected in air samples collected in the potroom of an aluminum
reduction plant at 297 ng/cu m(1). NIOSH (NOES Survey 1981-1983) has statistically
estimated that 6188 workers (1603 of these are female) are potentially exposed to
anthraquinone in the USA(2).
[(1) Thrane KE, Stray H; Sci Total Environ 53: 111-31 (1986) (2) NIOSH; National
Occupational Exposure Survey (NOES) (1983)]**PEER REVIEWED**
Emergency Medical Treatment:
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The following Overview, *** ANTHRAQUINONES ***, 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
0.2.1.1 ACUTE EXPOSURE
A) These agents have an irritant cathartic action. Most
human cases are mild to moderate in severity, with
nausea, vomiting, diarrhea, abdominal cramps, and
palpitations as the primary symptoms. Severe poisonings
may produce kidney damage, gastrointestinal hemorrhage,
muscular seizures, dyspnea, and fluid depletion.
B) PLANT MATERIAL - There is a 6-hour delay in onset with
commercial cascara sagrada preparations that is not
seen in intoxications from fresh plant material, due to
other active ingredients in the plants.
1) Vomiting is also more prevalent with fresh plant
material.
0.2.4 HEENT
0.2.4.1 ACUTE EXPOSURE
A) DITHRANOL is an irritant to the eyes and mucous
membranes.
0.2.5 CARDIOVASCULAR
0.2.5.1 ACUTE EXPOSURE
A) Palpitations were seen in one case report of 6 women
who became toxic after ingesting an
anthraquinone-containing herbal tea.
0.2.6 RESPIRATORY
0.2.6.1 ACUTE EXPOSURE
A) Dyspnea is mentioned as a sign of severe poisoning.
0.2.7 NEUROLOGIC
0.2.7.1 ACUTE EXPOSURE
A) Muscular seizures are a rare sign of severe
intoxication. Dizziness is occasionally seen in severe
intoxications. CNS depression was seen in animals
tested with injections of emodin. Analgesia was also
noted with injection. These effects have not been noted
in human overdose.
0.2.8 GASTROINTESTINAL
0.2.8.1 ACUTE EXPOSURE
A) Nausea, vomiting, abdominal pain, and especially
diarrhea may be seen with both therapeutic doses and
overdose.
0.2.10 GENITOURINARY
0.2.10.1 ACUTE EXPOSURE
A) Oliguria and proteinuria may be seen in severe cases. A
red color is seen in alkaline urine, and yellow-brown
in acid urine. Large doses of anthraquinones may cause
nephritis.
0.2.12 FLUID-ELECTROLYTE
0.2.12.1 ACUTE EXPOSURE
A) If vomiting and diarrhea are extensive, excessive
fluids and electrolytes may be lost.
0.2.14 DERMATOLOGIC
0.2.14.1 ACUTE EXPOSURE
A) Some anthraquinones have been shown to be sensitizers.
Finger CLUBBING has been reported with abuse of senna.
The condition is reversible with discontinuation of the
drug. Dithranol may cause a burning sensation,
especially on perilesional skin.
0.2.20 REPRODUCTIVE HAZARDS
A) Casanthranol, danthron, senna, and cascara sagrada are
in pregnancy category C.
0.2.21 CARCINOGENICITY
0.2.21.2 HUMAN OVERVIEW
A) Various anthraquinones have been shown to have
carcinogenic potential.
0.2.22 GENOTOXICITY
A) Various anthraquinones have been shown to have mutagenic
potential. Many are frameshift mutagens.
Laboratory:
A) In cases where diarrhea and vomiting have been excessive,
fluid and electrolyte abnormalities might be seen. In
such cases monitor for electrolyte loss and/or
dehydration.
B) A red color is seen in alkaline urine, which turns a
yellow-brown in acid urine. The red urine should be
differentiated from hematuria.
Treatment Overview:
0.4.2 ORAL EXPOSURE
A) Emesis is not required. Since not all of the cathartic
would be removed with an emetic, vomiting and diarrhea
may be seen with overdose. Activated charcoal (without
cathartic) may be indicated.
B) GASTRIC LAVAGE: Consider after ingestion of a
potentially life-threatening amount of poison if it can
be performed soon after ingestion (generally within 1
hour). Protect airway by placement in Trendelenburg and
left lateral decubitus position or by endotracheal
intubation. Control any seizures first.
1) CONTRAINDICATIONS: Loss of airway protective reflexes
or decreased level of consciousness in unintubated
patients; following ingestion of corrosives;
hydrocarbons (high aspiration potential); patients at
risk of hemorrhage or gastrointestinal perforation; and
trivial or non-toxic ingestion.
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) Deaths of a 3-year-old and a 20-month-old after ingestion
of an unknown number of Rhamnus berries have been
reported.
B) Rhamnus fruits - In reports to Toxicology Centers
throughout Europe, there are exposures reported, but none
have resulted in serious symptoms.
C) Rheum species - Determination of a toxic dose is very
difficult when dealing with plant material. Various
species have different concentrations of anthraquinones.
[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:
Non-Human Toxicity Excerpts:
ANTHRAQUINONE...HAS BEEN NOTED ONLY IN EXPTL ANIMAL EYES TO
CAUSE IRRITATION & INFLAMMATION WHEN APPLIED TO THE EYE. ...IT IS
POSSIBLE THAT IRRITATION IS DUE TO MECH ACTION OF POWDER RATHER
THAN TO TOXIC EFFECT...
[Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas
Publisher, 1986. 109]**PEER REVIEWED**
SODIUM-POTASSIUM-ACTIVATED ATPASE FROM RABBIT RED CELL
MEMBRANE WAS INHIBITED BY ANTHRAQUINONE. THE INHIBITORY
ACTION OF ANTHRAQUINONE WAS DUE TO THE INHIBITION OF -SH GROUP
OR THE CARBOXYL GROUP OF THE ENZYME.
[KOH IS; TAEHAN SAENGRI HAKHOE CHI 11 (1): 1 (1977)]**PEER
REVIEWED**
ANTHRAQUINONE WAS MUTAGENIC FOR STRAINS TA1537, TA1538, & TA98,
IN THE ABSENCE OF RAT LIVER HOMOGENATE, IN THE
AMES/SALMONELLA MICROSOME ASSAY.
[LIBERMAN DF ET AL; APPL ENVIRON MICROBIOL 43 (6): 1354 (1982)]**PEER
REVIEWED**
ANTHRAQUINONE WAS NONMUTAGENIC, WITH OR WITHOUT METABOLIC
ACTIVATION, IN SALMONELLA TYPHIMURIUM STRAINS TA98, TA100, &
TA2637 BY THE PREINCUBATION METHOD.
[TIKKANEN L ET AL; MUTAT RES 116 (3-4): 297 (1983)]**PEER REVIEWED**
Acute neurotoxic effects reported in animals include convulsions; medullary paralysis.
/From table/ /Quinones/
[O'Donoghue, J.L. (ed.). Neurotoxicity of Industrial and Commercial Chemicals. Volume
I. Boca Raton, FL: CRC Press, Inc., 1985. 129]**PEER REVIEWED**
Ongoing Test Status:
The NTP Toxicology Research and Testing Program releases a Management Status
Report on a quarterly basis. This report gives the status of chemicals studied, under study,
or proposed for study by NTP. The 07/11/2001 issue indicates that anthraquinone is on
the list of post peer review technical reports in progress. Route: dosed-feed; Species: rats
and mice. NTP TR No 494.
[NTP; Division of Toxicology Research and Testing; Management Status Report;
07/11/2001; p.24]**QC REVIEWED**
Metabolism/Pharmacokinetics:
Metabolism/Metabolites:
YIELDS ANTHRONE, 9,10-DIHYDROXYANTHRACENE, & 2HYDROXYANTHRAQUINONE IN RATS. /FROM TABLE/
[Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New
York: Wiley, 1976.,p. A-62]**PEER REVIEWED**
Quinones (ie, 6,12-dione) have been shown to undergo oxidation-reduction cycles
involving quinone, hydroquinone, and molecular oxygen, resulting in the formation of
oxygen radicals and semiquinone radicals. /Quinones/
[Dean, J.H., M.I. Luster, A.E. Munson, I. Kimber. Immunotoxicology and
Immunopharmacology. 2nd ed. New York, NY: Raven Press, Ltd., 1994. 577]**PEER
REVIEWED**
Mechanism of Action:
THE QUINONES ARE ALPHA-BETA-UNSATURATED KETONES & REACT
WITH SULFHYDRYL (-SH) GROUPS. THIS REACTION HAS BEEN SUGGESTED
AS THE CRITICAL BIOCHEMICAL LESION INVOLVING THE -SH GROUPS OF
ENZYMES SUCH AS AMYLASE & CARBOXYLASE WHICH ARE INHIBITED BY
QUINONES. ... OVERALL /FUNGICIDAL/ MECHANISM MAY INVOLVE
BINDING OF ENZYME TO QUINONE NUCLEUS BY SUBSTITUTION OR ADDN
@ THE DOUBLE BOND, OXIDATIVE REACTION WITH -SH GROUP, & CHANGE
IN REDOX POTENTIAL. /QUINONES/
[White-Stevens, R. (ed.). Pesticides in the Environment: Volume 1, Part 1, Part 2. New
York: Marcel Dekker, Inc., 1971. 9]**PEER REVIEWED**
Pharmacology:
Environmental Fate & Exposure:
Environmental Fate/Exposure Summary:
Anthraquinone's production and subsequent use as an additive in the paper pulping
industry,as a bird repellent for seeds, and as the basis for the production of a large
number of dyes may result in its release to the environment through various waste
streams. Anthraquinone is also produced from anthracene in the environment through
photolytic and biodegradation processes. If released to the atmosphere, anthraquinone
will exist in both the vapor-phase and the particulate phase based on an experimental
vapor pressure of 1.16X10-7 mm Hg. In the vapor-phase, it should react with hydroxyl
radicals with an estimated half-life of 11 days. Particulate phase anthraquinone may be
physically removed from air by wet and dry deposition. Anthraquinone should have
slight to low mobility in soil based on estimated Koc values of 1664 and 3702. This
compound is expected to biodegrade fairly rapidly with 68% degradation reported in 12
weeks by a mixed soil population. In water, anthraquinone is expected to adsorb to
particulate matter and sediment in the water column based on its Koc values.
Biodegradation is a major fate process in water; over a three day period, 82% of the
added anthraquinone (at 10 mg/L) was degraded by river water, 91% was degraded by
sea water. Anthraquinone is also readily biodegraded by natural bacterial populations in
groundwater and by activated sludge. A photolysis half-life of 2.8 hours was measured
when anthraquinone was exposed to incident light (295-500 nm). Anthraquinone may
bioconcentrate in aquatic organisms based on estimated BCF values of 222 and 522; this
compound has been detected in fish. Monitoring data indicate that exposure to
anthraquinone by the general population is through the ingestion of drinking water.
Exposure to anthraquinone may occur occupationally during its use as a dye
intermediate or as a catalytic agent in the paperpulping process. (SRC)
**PEER REVIEWED**
Probable Routes of Human Exposure:
Anthraquinone was detected in air samples collected in the potroom of an aluminum
reduction plant at 297 ng/cu m(1). NIOSH (NOES Survey 1981-1983) has statistically
estimated that 6188 workers (1603 of these are female) are potentially exposed to
anthraquinone in the USA(2).
[(1) Thrane KE, Stray H; Sci Total Environ 53: 111-31 (1986) (2) NIOSH; National
Occupational Exposure Survey (NOES) (1983)]**PEER REVIEWED**
Artificial Pollution Sources:
Anthraquinone's production and subsequent use as an additive in the soda and kraft
chemical alkaline pulping processes in the paper pulping industry(1) and as the basis for
the production of a large number of acid and base dyes, vat dyes, disperse dyes, and
reactive dyes(2) may result in its release to the environment through various waste
streams(SRC). Anthracene, which is frequently detected in the environment probably due
to its pyrogenic origin, is known to yield anthraquinone upon direct photooxidation in
aqueous media(3). The biodegradation of anthracene by white rot fungi results in
anthraquinone as a major degradation intermediate(4). Soil samples contaminated with
diesel oil and originally not containing anthraquinone were found to contain
anthraquinone following 25 weeks(5). Aqueous chlorination products of standard
PAH's include anthraquinone; this process works via oxidation of the PAH using
hypochlorite(6).
[(1) Appleton HT et al; Technical Support Document 9,10-Anthraquinone. SRC TR-85105. USEPA Doc#: 40-8580018. Syracuse, NY (1985) (2) Vogel A; Ullman's Encyl
Indus Chem. Gerhartz W (ed). VCH Publishers, Deerfield Beach, FL VA2: 353 (1985)
(3) Rontani JF et al; Chemosphere 14: 1909-912 (1985) (4) Field JA et al; Appl Environ
Microbiol 58: 2219-2226 (1992) (5) Langbehn A, Steinhart H; Chemosphere 30: 855-868
(1995) (6) Alben K; Anal Chem 52: 1825-828 (1980)]**PEER REVIEWED**
Environmental Fate:
TERRESTRIAL FATE: Estimated Koc values of 1664 and 3702(1,SRC), based on
experimental values for log Kow(2) and water solubility(3), indicate that anthraquinone
will have low to slight mobility in soil using a soil mobility classification(4).
Anthraquinone is not expected to volatilize from dry surfaces based on an experimental
vapor pressure of 1.16X10-7 mm Hg(5) or to volatilize from moist soil surfaces given an
estimated Henry's Law constant of 3.18X10-9 atm-cu/mole(1,SRC) from the water
solubility(3) and vapor pressure(5). Biodegradation of anthraquinone is expected to be a
major fate process for this compound in soil; 68% of added anthraquinone was
biodegraded by a mixed soil population within 12 weeks(6). A mixed bacterial
population, isolated from a coal-tar contaminated soil, biodegraded anthraquinone even
faster with only 6.5% of the initial concentration of anthraquinone remaining after 3
days(7).
[(1) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington
DC: Amer Chem Soc pp. 4-9, 15-1 to 15-29 (1990) (2) Hansch C et al; Exploring QSAR.
Hydrophobic, Electronic, and Steric Constants. Chihara H et al, eds; ACS Prof Ref Book,
Washington,DC: Amer Chem Soc p. 118 (1995) (3) Yalkowsky SH, Dannenfelser RM;
Aquasol Database of Aqueous Solubility. Ver 5. Coll Pharm, Univ Arizona-Tucson, AZ.
PC Version (1992) (4) Swann RL et al; Res Rev 85: 23 (1983) (5) Shimizu T et al; J Soc
Dyers Colour 103: 132-7 (1987) (6) Mueller JG et al; Environ Sci Technol 25: 1045-55
(1991) (7) Mueller JG et al; Appl Environ Microbiol 55: 3085-90 (1989)]**PEER
REVIEWED**
AQUATIC FATE: Based on estimated Koc values of 1664 and 3702(1,SRC), determined
from experimental values for log Kow(2) and water solubility(3), anthraquinone may
adsorb to particulate matter and sediment in the water column(4); this may be a major
fate process for this compound(SRC). Photolysis of anthraquinone may occur in water.
When exposed to incident light (295-500 nm), a photolysis half-life of 2.8 hours was
measured(5). Anthraquinone may bioconcentrate in aquatic organisms based on
estimated BCF values of 222 and 522(1,SRC) determined from experimental values of
log Kow(2) and water solubility(3), respectively; this compound has been detected in
fish(6).
[(1) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington
DC: Amer Chem Soc pp. 4-9, 5-4, 5-10 (1990) (2) Hansch C et al; Exploring QSAR.
Hydrophobic, Electronic, and Steric Constants. Chihara H et al, eds; ACS Prof Ref Book,
Washington,DC: Amer Chem Soc p. 118 (1995) (3) Yalkowsky SH, Dannenfelser RM;
Aquasol Database of Aqueous Solubility. Ver 5. Coll Pharm, Univ Arizona-Tucson, AZ.
PC Version (1992) (4) Swann RL et al; Res Rev 85: 23 (1983) (5) Svenson A, Bjorndahl
H; Chemosphere 17: 2397-2405 (1988) (6) Vassilaros DL et al; Anal Chem 54: 106-112
(1982)]**PEER REVIEWED**
AQUATIC FATE: Biodegradation of anthraquinone in the water column is expected to
be a major fate process. Over a three day period, 82% of the added anthraquinone (at 10
mg/l) was degraded by river water, 91% was degraded by sea water(1). Biodegradation
using mixed cultures from seawater degraded anthraquinone 50% over 10 days;
metabolite concentration was low but included mainly benzoic and phthalic acids(2).
Mixed bacterial populations from groundwater were able to completely degrade
anthraquinone within 5 days(3). From 50-100% degradation has been reported using
activated sludge as an inoculum and a three week incubation period(4-9).
[(1) Kondo M et al; Eisei Kagaku 34: 188-95 (1988) (2) Rontani JF et al; Chemosphere
14: 1909-912 (1985) (3) Mueller JG et al; Appl Environ Microbiol 57: 1277-285 (1991)
(4) Struijs J, Stoltenkamp J; Ecotoxicol Environ Safety 19: 204-211 (1990) (5) Chemicals
Inspection and Testing Institute; Biodegradation and Bioaccumulation Data of Existing
Chemicals Based on the CSCL Japan. Japan Chemical Industry Ecology-Toxicology and
Information Center. ISBN 4-89074-101-1 (1992) (6) De Morsier A et al; Chemosphere
16: 833-47 (1987) (7) Nyholm N; Chemosphere 21: 1477-87 (1990) (8) Kawasaki M;
Ecotoxic Environ Saf 4: 444-54 (1980) (9) Blok J, Booy M; Ecotox Environ Saf 8: 41022 (1984)]**PEER REVIEWED**
ATMOSPHERIC FATE: Based on an experimental vapor pressure of 1.16X10-7 mm Hg
at 25 deg C(1), anthraquinone will exist in both the vapor phase and the particulate
phase in the ambient atmosphere(2,SRC). Anthraquinone is expected to degrade fairly
quickly in the vapor phase by reaction with photochemically produced hydroxyl radicals
with an estimated half-life of 11 days(3,SRC). Particulate phase anthraquinone may be
removed physically from air by wet and dry deposition(SRC). Anthraquinone absorbed
to airborne wood soot particles and exposed to sunlight (3-4 hour period) was stable.
Under the same conditions but with 0.1 ppm NOx present a half-life of 2.5 hours was
reported indicating that ozone in the presence of sunlight promotes degradation reactions
for this compound(4). Anthraquinone has been detected in rain water from several storm
events(5).
[(1) Shimizu T et al; J Soc Dyers Colour 103: 132-7 (1987) (2) Bidleman TF; Environ Sci
Technol 22: 361-367 (1988) (3) Meylan WM, Howard PH; Chemosphere 26: 2293-2299
(1993) (4) Kamens RM et al; Environ Sci Technol 23: 801-06 (1989) (5) Ligocki MP et
al; Atmos Environ 19: 1609-617 (1985)]**PEER REVIEWED**
Environmental Biodegradation:
Anthraquinone (at 10 mg/l organic carbon), inoculated with activated sludge, reached
28% of the theoretical CO2 within 28 days(1). 52.3% of the initial concn of
anthraquinone (100 mg/l) was biodegraded by an activated sludge inoculum (time = 3
weeks)(2). Biodegradation of anthraquinone was measured using three standard tests
(each using activated sludge inocula)(3). Over a 20 day period, 51-91%, 81-93%, and
70% of the added anthraquinone was biodegraded in the Sturm test, MITI test, and the
RDA test, respectively(3). Anthraquinone (at 100 mg/l) was biodegraded by 46% over a
28 day period (UK-MITI test); a lag time of about 7 days was observed(4). From 30100% BODT was measured in the Japanese-MITI test over 14 days (anthraquinone =
100 mg/l)(5). Varying activated sludge inoculum sizes had little impact on the final
oxidation of anthraquinone; 40-60% oxidation at 56 days was seen for all inoculum
levels(6).
[(1) Struijs J, Stoltenkamp J; Ecotoxicol Environ Safety 19: 204- 211 (1990) (2)
Chemicals Inspection and Testing Institute; Biodegradation and Bioaccumulation Data of
Existing Chemicals Based on the CSCL Japan. Japan Chemical Industry EcologyToxicology and Information Center. ISBN 4-89074-101-1 (1992) (3) De Morsier A et al;
Chemosphere 16: 833-47 (1987) (4) Nyholm N; Chemosphere 21: 1477-87 (1990) (5)
Kawasaki M; Ecotoxic Environ Saf 4: 444-54 (1980) (6) Blok J, Booy M; Ecotox
Environ Saf 8: 410-22 (1984)]**PEER REVIEWED**
A mixed bacterial population (EM4) isolated from sea water foam biodegraded
anthraquinone (concentration = 1 g/l); 50% of the added compound was degraded over
10 days(1). Metabolites included benzoic and phthalic acids in low concentrations(1).
Over a three day period, 82% of the added anthraquinone (at 10 mg/l) was degraded by
river water, 91% was degraded by sea water(2). Anthraquinone was present in
groundwater at an initial concentration of 3.3 ug/ml; 1.9 ug/ml remained after 3 days, and
an undetectable amount was left following 5 days after inoculation with a mixed
population derived from creosote contaminated soil(3). Anthraquinone, using an
anaerobic digesting sludge inoculum, inhibited gas production for 4 weeks (lag phase >75
days) before limited net gas production began; the volume of gas produced during the
experiment (60-100 days) was not greater than that produced by the blanks. It was not
possible to say whether degradation of this compound occurred as this gas may have been
produced either by degradation of anthraquinone or by degradation of substrates in the
sludge which were not degraded during the inhibitory phase(4).
[(1) Rontani JF et al; Chemosphere 14: 1909-912 (1985) (2) Kondo M et al; Eisei Kagaku
34: 188-95 (1988) (3) Mueller JG et al; Appl Environ Microbiol 57: 1277-285 (1991) (4)
Battersby NS, Wilson V; Appl Environ Microbiol 55: 433-39 (1989)]**PEER
REVIEWED**
White rot fungi of the genus Trametes degraded anthracene without any accumulation of
anthraquinone suggesting that either anthraquinone was not formed as a metabolite of
this process or that this genus can rapidly metabolize anthraquinone(1). Lignolytic
cultures of Phanerochaete chrysosporium metabolized anthraquinone(1).
Anthraquinone, initially present at 48.6 mg/3 kg soil, was biodegraded by the soil
bacterial population to 15.3 mg/3 kg soil following 12 weeks incubation(2).
Anthraquinone initially present at 1229.7 mg/3 kg sediment was biodegraded by the
sediment bacterial population to 1122.9 mg/3 kg sediment following 12 weeks
incubation(2). A seven strain bacterial community isolated from a coal-tar contaminated
soil biodegraded anthraquinone with only 6.5% of the initial concentration remaining
after 3 days(3).
[(1) Field JA et al; Appl Environ Microbiol 58: 2219-2226 (1992) (2) Mueller JG et al;
Environ Sci Technol 25: 1045-1055 (1991) (3) Mueller JG et al; Appl Environ Microbiol
55: 3085-3090 (1989)]**PEER REVIEWED**
Environmental Abiotic Degradation:
Anthraquinone in aquatic media (ethanol(99%): water (1%)) exposed to incident light
from 295-500 nm resulted in a reported photolysis half-life of 2.8 hours(1).
Anthraquinone subjected to exhaustive photolysis (16 hr, 253.7 nm irradiation, in
ethanol) undergoes photochemical conversion to 9,10-dihydroxyanthracene and secondly
to 9-anthranol in the absence of oxygen(2). Anthraquinone deposited on silica gel and
exposed in the dark did not react to the presence of ozone at varying concentrations and
exposure times(3). Anthraquinone absorbed to airborne wood soot particles and exposed
to sunlight (3-4 hour period) was stable; under the same conditions but with 0.1 ppm
NOx present, a half-life of 2.5 hours was reported. This indicates that ozone in the
presence of sunlight promotes degradation reactions for this compound(4). The rate
constant for the vapor-phase reaction of anthraquinone with photochemically produced
hydroxyl radicals has been estimated as 1.498X10-12 cu cm/molecule-sec at 25 deg
C(5,SRC). This corresponds to an atmospheric half-life of about 11 days at an
atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(5,SRC).
[(1) Svenson A, Bjorndahl H; Chemosphere 17: 2397-2405 (1988) (2) Carlson SA,
Hercules DM; Anal Chem 45: 1794-99 (1973) (3) Grosjean D et al; Environ Sci Technol
21: 635-43 (1987) (4) Kamens RM et al; Environ Sci Technol 23: 801-06 (1989) (5)
Meylan WM, Howard PH; Chemosphere 26: 213-218 (1993)]**PEER REVIEWED**
Environmental Bioconcentration:
BCF values of 222 and 522 were calculated for anthraquinone, using an experimental
log Kow of 3.39(1) and an experimental water solubility of 1.353 mg/l(2), respectively,
and recommended regression-derived equations(3,SRC). This BCF value suggests that
anthraquinone may bioconcentrate in aquatic organisms(3). Anthraquinone was
detected in brown bullhead catfish from the Black River, Ohio(4) indicating that
bioconcentration may occur(SRC).
[(1) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants.
Chihara H et al, eds; ACS Prof Ref Book, Washington,DC: Amer Chem Soc p. 118
(1995) (2) Yalkowsky SH, Dannenfelser RM; Aquasol Database of Aqueous Solubility.
Ver 5. Coll Pharm, Univ Arizona-Tucson, AZ. PC Version (1992) (3) Lyman WJ et al;
Handbook of Chemical Property Estimation Methods. Washington DC: Amer Chem Soc
pp. 5-4, 5-10 (1990) (4) Vassilaros DL et al; Anal Chem 54: 106-112 (1982)]**PEER
REVIEWED**
Soil Adsorption/Mobility:
Based on an experimental log Kow of 3.39(1)and an experimental water solubility of
1.353 mg/l(2), Koc values of 1664 and 3702, respectively, for anthraquinone can be
calculated using regression-derived equations(3,SRC). According to a suggested
classification scheme(4), these Koc values suggest that anthraquinone has low to slight
mobility in soil(SRC).
[(1) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants.
Chihara H et al, eds; ACS Prof Ref Book, Washington,DC: Amer Chem Soc p. 118
(1995) (2) Yalkowsky SH, Dannenfelser RM; Aquasol Database of Aqueous Solubility.
Ver 5. Coll Pharm, Univ Arizona-Tucson, AZ. PC Version (1992) (3) Lyman WJ et al;
Handbook of Chemical Property Estimation Methods. Washington DC: Amer Chem Soc
pp. 4-9 (1990) (4) Swann RL et al; Res Rev 85: 23 (1983)]**PEER REVIEWED**
Volatilization from Water/Soil:
The Henry's Law constant for anthraquinone was determined from experimental values
of vapor pressure(1) and water solubility(2) as 2.35X10-8 atm-cu/mole(3,SRC). This
value indicates that volatilization of anthraquinone from water surfaces will be slow(3).
[(1) Shimizu T et al; J Soc Dyers Colour 103: 132-7 (1987) (2) Yalkowsky SH,
Dannenfelser RM; Aquasol Database of Aqueous Solubility. Ver 5. Coll Pharm, Univ
Arizona-Tucson, AZ. PC Version (1992) (3) Lyman WJ et al; Handbook of Chemical
Property Estimation Methods. Washington, DC: Amer Chem Soc p. 15-1 to 15-29
(1990)]**PEER REVIEWED**
Environmental Water Concentrations:
SURFACE WATER: Anthraquinone was detected in 2 of 79 samples of industrial
wastewater from either the timber products or organics and plastics industries(1). Surface
water from 2 sites and anoxic deep water from a single site in the Baltic Sea contained
anthraquinone at unreported concentrations(2). Anthraquinone was detected at
unreported concentrations in the Waal River, April 1974(3).
[(1) Bursey JT, Pellizzari ED; Analysis of Industrial Wastewater for Organic Pollutants
in Consent Degree Survey. Contract No. 68- 03-2867. Athens, GA: USEPA Environ Res
Lab pp 167 (1982) (2) Ehrhardt M et al; Marine Chem 11: 449-61 (1982) (3) Meijers AP,
Van der Leer RC; Water Res 10:697-604 (1976)]**PEER REVIEWED**
GROUNDWATER: Anthraquinone was present in groundwater down-gradient from an
abandoned wood-preserving plant at concentrations of 3.3 mg/25 ml; at 0.002 mg/l in
streamwater that flowed through the plant site(1).
[(1) Middaugh DP et al; Arch Environ Contam Toxicol 21: 233-44 (1991)]**PEER
REVIEWED**
DRINKING WATER: A tap water sample taken from Kitakyushu, Japan contained 5.2
ng/l anthraquinone(1). Tap water from Tsukuba, Japan contained anthraquinone at
unreported concentrations(2). Anthraquinone was detected in Ottawa's drinking water
supply, sampled in January and February 1978 (concn = 1.8-2.4 ng/l)(3). Twelve Great
Lakes municipal drinking water supplies in Canada contained anthraquinone with
concentrations ranging from not detected to 72 ng/l(4). Drinking water taken from 6
unspecified water treatment plants, was analyzed for the presence of anthraquinone in
June and October 1978; anthraquinone was detected at all sites in concentrations of 0.6
to 2.1 ng/l(5). Tap water from Athens, GA contained anthraquinone at concentrations of
20-100 ng/l(6).
[(1) Akiyama T et al; J UOEH 2: 285-300 (1980) (2) Shiraishi H et al; Environ Sci
Technol 19: 585-590 (1985) (3) Benoit FM et al; Intern J Environ Anal Chem 6: 277-87
(1979) (4) Williams DT et al; Chemosphere 11: 263-76 (1982) (5) Benoit FM et al; Bull
Environ Contam Toxicol 23: 774-78 (1979) (6) Thruston AD Jr.; J Chrom Sci 16: 254-59
(1978)]**PEER REVIEWED**
RAIN/SNOW: Anthraquinone was detected in eight of nine documented rain storms in
Oregon at concentrations of 2.2 to 16 ng/l for spring storms and 18-74 ng/l for fall
storms(1). Anthraquinone was detected in 7 of 7 rain storms in Portland, OR from
February to April, 1984 (concns = 1.5-3.6 ng/cu-m)(2). Anthraquinone was detected in
precipitation in Norway with a possible source of this chemical in Eastern Europe and
England(3).
[(1) Pankow JF et al; Environ Sci Technol 18: 310-18 (1984) (2) Ligocki MP et al;
Atmos Environ 19: 1609-617 (1985) (3) Lunde G; Ambio 5: 207-8 (1976)]**PEER
REVIEWED**
Effluent Concentrations:
Anthraquinone was emitted at concns of 24.3 and 4.4 ug/km during particulate emission
tests (simulating urban driving conditions) of tailpipes of non-catalyst (average of 1965
Mercury Monterey, 1969 Ford Mustang, 1970 Buick Skylark, 1972 Chevrolet Caprice,
1974 Ford Pinto, and 1976 Volkswagen Beetle) and catalyst cars (average of 1977
Chevrolet Vega, 1980 Honda Civic 150, 1980 Honda 1500, 1980 Toyota Corolla, Datsun
200 SX, 1983 Chevrolet Malibu CL, and 1983 Dodge Omni), respectively; at a concn of
23.5 ug/km from tailpipes of heavy-duty diesel trucks (average of a 1987 GMC truck,
two-axle, and a 1987 Ford Dump truck, three-axle)(1). Particulate samples obtained from
an automobile using a diesel engine contained anthraquinone at unreported concns(2).
Diesel emission particulates from a Volkswagen Rabbit contained anthraquinone(3).
Particulate emissions from a representative small aircraft gas turbine engine contained
detectable quantities of anthraquinone in 5 of 8 different sampling conditions (concns of
0.06-58.49 ng/cu-m; detection limit=0.01 ug)(4). Organic extracts of emissions from
burning cereal straw contained anthraquinone at 995 ug/kg fuel(5). Particulate samples
from the exhaust of a flame retention head residential oil burner combusting No. 2 fuel
oil contained anthraquinone(6).
[(1) Rogge WF et al; Environ Sci Technol 27: 636-651 (1993) (2) Yu ML, Hites RA;
Anal Chem 53: 951-54 (1981) (3) Choudhury DR; Environ Sci Technol 16: 102- 06
((1982) (4) Robertson DJ et al; J Air Pollut Control Assoc 30: 261-66 (1980) (5)
Ramdahl T, Becher G; Analytica Chimica Acta 144: 83-91 (1982) (6) Leary JA et al;
Environmental Health Perspectives. Washington,DC: US Dept Health and Human
Services 73: 223-34 (1987)]**PEER REVIEWED**
Anthraquinone was detected in 2 of 4 extracts of MM5 trains from 4 different municipal
waste incinerators (concn = 2.9-9.0 ug/ml)(1). Flyash extracts from municipal
incinerators contained anthraquinone in 3 of 5 sites(2). Anthraquinone was identified
in the flyash of an Ontario municipal incinerator at unreported concentrations(3).
Anthraquinone was not detected in tire wear particles and was present at concentrations
of 0.31 and 0.41 ug/g in brake lining particles and road dust particles, respectively(4).
[(1) James RH et al; Evaluation of Analytical Methods for the Determination of POHC in
Combustion Products. J Proc APCA 77th Ann Mtg, June 24-9, 1984. San Francisco, CA
Paper 84-18.5 pp. 1-25 (1984) (2) Eiceman GA et al; Anal Chem 51: 2343-350 (1979) (3)
Tong HY et al; J Chrom 285: 423-41 (1984) (4) Rogge WF et al; Environ Sci Technol
27: 1892-904 (1993)]**PEER REVIEWED**
Anthraquinone was detected in leachate (concentration=0.7 ug/l) from central Texas
lignite under conditions meant to replicate rainfall leaching of coal piles(1). Tap water
(pH=9) exposed to test panels coated with a commercial coal tar contained
anthraquinone(2). Anthraquinone was detected in pulping liquors from processes using
this compound as a catalyst for the delignification of wood; in black liquors n=14,
concentration=3.0-170 mg/l; in alkaline pulping liquors n=6, concentration=0.5-11.5
mg/l; in wash liquors n=5, concentration=0.13-0.75; in filtrates from bleaching n=5,
concentration=0.04-0.66(3). Anthraquinone was detected at concentrations of 49-110
ppb in the raw wastewater of a dye manufacturing plant; it was not detected in the final
effluent of the same plant(4). Anthraquinone was detected in 235 samples obtained from
superfund sites; data were compiled from CLP Analytical Results Database(5).
[(1) Stahl RG Jr. et al; Arch Environ Contam Toxicol 13: 179-90 (1984) (2) Alben K;
Anal Chem 52: 1825-828 (1980)(3) Nelson KH, Cietek DJ; J Chrom 281: 237-44 (1983)
(4) Games LM, Hites RA; Anal Chem 49: 433-40 (1977) (5) Eckel WP; Amer Chem Soc,
Div Environ Chem, Preprint Ext Abstr, 208th ACS Nat Meet, 34: 67-9 (1994)]**PEER
REVIEWED**
Sediment/Soil Concentrations:
Marine sediments from the sewage area of Marseilles, France contained anthraquinone
in 9 of 10 sites (concentration=2-400 ng/g)(1). Sediment from Dokai Bay contained
anthraquinone(2).
[(1) Milano JC, Vernet JL; Oceanis 14: 19-27 (1988) (2) Terashi A et al; Bull Environ
Contam Toxicol 50: 348-55 (1993)]**PEER REVIEWED**
Atmospheric Concentrations:
SOURCE DOMINATED: Anthraquinone was detected in one of eight air samples
(concn = 44.5 ng/cu m) near a chemical factory in Czechoslovakia(1). Anthraquinone
was detected in air samples collected in the potroom of an aluminum reduction plant at a
concn of 297 ng/cu m(2).
[(1) Holoubek I et al; Toxicol Environ Chem 29: 251-260 (1991) (2) Thrane KE, Stray H;
Sci Total Environ 53: 111-31 (1986)]**PEER REVIEWED**
URBAN/SUBURBAN: Organic extracts from airborne particulate matter collected in
Barcelona City contained anthraquinone at 9, not detected, 26, and 21 pg/cu m during
the spring, summer, fall, and winter, respectively(1). Atmospheric aerosol samples were
collected in Barcelona; anthraquinone was present in the summer sample at 82 pg/cu m
and in the winter sample at 75 pg/cu m(2). Anthraquinone was detected in airborne
particulate matter in Duisburg, Germany from February to April, 1982 (concn = 0.221.89 ng/cu m(3). Ambient air levels of anthraquinone in Toronto, Ontario were reported
as 0.9-1.3 pg/cu m(4). 2 of 7 sites in the US sampled for ambient air particulates (Upland,
CA; Lake Charles, LA) contained anthraquinone at unreported concentrations(5). Mean
gas and particulate-phase concentrations of anthraquinone were measured in Portland,
OR during February and April, 1984 and February and April, 1985 (gas concn = 2.5
ng/cu m; particulate concn = 0.59 ng/cu m)(6). Urban air particles from St. Louis, MO
contained anthraquinone at unreported concentrations(7).
[(1) Bayona JM et al; Chemosphere 29: 441-50 (1994) (2) Galceran MT, Moyano E;
Talanta 40: 615-21 (1993) (3) Konig J et al; Anal Chem 55: 599-603 (1983) (4) Harkov
R; J Environ Sci Health A21: 409-33 (1986) (5) Kolber A et al; In: Short-term Bioassays
in the Analysis of Complex Environmental Mixtures II, pp. 21-43, Mar 82, PB82-233198
(1982) (6) Ligocki MP, Pankow JF; Environ Sci Technol 23: 75-83 (1989) (7) Ramdahl
T et al; Environ Sci Technol 16: 861-865 (1982)]**PEER REVIEWED**
RURAL/REMOTE: Airborne particulate matter sampled near Chacaltaya, Bolivia
(remote location) and Antwerp, Belgium (urban location) contained anthraquinone in 6
of 6 samples (Bolivia, n = 2, concn = 0.064-0.065 ug/1000 cu m; Belgium, n = 4, concn =
0.57-1.0 ug/1000 cu m; detection limit = 0.02 ug/1000 cu m)(1).
[(1) Cautreels W et al; Sci Total Environ 8: 79-88 (1977)]**PEER REVIEWED**
Plant Concentrations:
2 of 6 samples of mosses and 3 of 6 samples of needles contained anthraquinone
(mosses = 1756.8 to 4054.1 ng/g; needles = 459.5 to 1918.9 ng/g) near a chemical factory
in Czechoslovakia(1).
[(1) Holoubek I et al; Toxicol Environ Chem 29: 251-260 (1991)]**PEER
REVIEWED**
Fish/Seafood Concentrations:
42 ppb anthraquinone was detected in Black River (Ohio) bullhead catfish(1).
[(1) Vassilaros DL et al; Anal Chem 54: 106-112 (1982)]**PEER REVIEWED**
Animal Concentrations:
2 of 5 earthworm samples contained anthraquinone (concns = 473 to 4715.9 ng/g) near
a chemical factory in Czechoslovakia(1).
[(1) Holoubek I et al; Toxicol Environ Chem 29: 251-260 (1991)]**PEER
REVIEWED**
Environmental Standards & Regulations:
TSCA Requirements:
Section 8(a) of TSCA requires manufacturers of this chemical substance to report
preliminary assessment information concerned with production, use, and exposure to
EPA as cited in the preamble in 51 FR 41329.
[40 CFR 712.30 (7/1/94)]**PEER REVIEWED**
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data
Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and
processors of listed chemical substances and mixtures to submit to EPA copies and lists
of unpublished health and safety studies. Anthraquinone is included on this list.
[40 CFR 716.120 (7/1/94)]**PEER REVIEWED**
Manufacturers and processors of anthraquinone are required to conduct specific
chemical tests as required under TSCA section 4.
[40 CFR 799.500 (7/1/94)]**PEER REVIEWED**
Chemical/Physical Properties:
Molecular Formula:
C14-H8-O2
**PEER REVIEWED**
Molecular Weight:
208.20
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 109]**PEER REVIEWED**
Color/Form:
LIGHT YELLOW, SLENDER MONOCLINIC PRISMS BY SUBLIMATION IN
VACUO; ALMOST COLORLESS, ORTHORHOMBIC, BIPYRAMIDAL CRYSTALS
FROM SULFURIC ACID + WATER
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 109]**PEER REVIEWED**
YELLOW RHOMBIC NEEDLES FROM ALCOHOL, BENZENE
[Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida:
CRC Press Inc., 1979.,p. C-121]**PEER REVIEWED**
YELLOW-GREEN CRYSTALS
[Worthing, C. R. (ed.). Pesticide Manual. 6th ed. Worcestershire, England: British Crop
Protection Council, l979. 19]**PEER REVIEWED**
Boiling Point:
377 DEG C @ 760 MM HG
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 109]**PEER REVIEWED**
Melting Point:
286 DEG C
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 109]**PEER REVIEWED**
Density/Specific Gravity:
1.42-1.44 AT DEG 20 C/4 DEG C
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 109]**PEER REVIEWED**
Octanol/Water Partition Coefficient:
log Kow = 3.39
[Hansch, C. and A. Leo. The Log P Database. Claremont, CA: Pomona College,
1987.]**PEER REVIEWED**
Solubilities:
INSOL IN WATER; 0.44 G/100 G ALC @ 25 DEG C; 2.25 G/100 G BOILING ALC;
0.11 G/100 G ETHER @ 25 DEG C; 0.61 G/100 G CHLOROFORM @ 20 DEG C; 0.26
G/100 G BENZENE @ 20 DEG C; 0.30 G/100 G TOLUENE @ 25 DEG C
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 109]**PEER REVIEWED**
SOL IN CONCN SULFURIC ACID
[Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida:
CRC Press Inc., 1979.,p. C-121]**PEER REVIEWED**
SOL IN ACETONE
[Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York,
NY: Van Nostrand Rheinhold Co., 1993 84]**PEER REVIEWED**
Solubility in water = 1.353 mg/l
[Yalkowsky SH, Dannenfelser RM; Aquasol Database of Aqueous Solubility. Version 5.
College of Pharmacy, University of Arizona-Tucson, AZ. PC Version (1992)]**PEER
REVIEWED**
Spectral Properties:
MAX ABSORPTION (ALCOHOL): 252 NM (LOG E= 4.7), 278 NM (LOG E= 4.1),
330 NM (LOG E= 3.7); SADTLER REF NUMBER: 1815 (IR, PRISM); 508 (UV)
[Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida:
CRC Press Inc., 1979.,p. C-121]**PEER REVIEWED**
Intense mass spectral peaks: 208 m/z (100%), 180 m/z (96%), 152 m/z (75%), 151 m/z
(38%)
[Hites, R.A. Handbook of Mass Spectra of Environmental Contaminants. Boca Raton,
FL: CRC Press Inc., 1985. 44]**PEER REVIEWED**
IR: 279 (Sadtler Research Laboratories IR Grating 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 102]**PEER REVIEWED**
UV: 815 (Absorption Spectra in the UV and visible Regions, Academic Press, 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 102]**PEER REVIEWED**
MASS: 1478 (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 102]**PEER REVIEWED**
The UV spectrum exhibits four bands - 251 nm (Emax = 54000), 279 (Emax = 17600),
321 nm (Emax = 4800), 377 nm (Emax = 110)
[Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol
A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present.,p. VA2 347]**PEER
REVIEWED**
Vapor Density:
7.16 (AIR= 1)
[Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire
Protection Association, 1997. ,p. 325-16]**QC REVIEWED**
Vapor Pressure:
1.16X10-7 mm Hg @ 25 deg C
[Shimizu T et al; J Soc Dyers Colour 103: 132-7 (1987)]**PEER REVIEWED**
Other Chemical/Physical Properties:
VAPOR PRESSURE = 1 MM HG @ 190.0 DEG C
[Sax, N.I. Dangerous Properties of Industrial Materials. 4th ed. New York: Van Nostrand
Reinhold, 1975. 411]**PEER REVIEWED**
Liquid Molar Volume = 0.193625 cu m/kmol; IG Heat of Formation = -9.52X10+7
J/kmol; Heat Fusion at Melting Point = 3.2552X10+7 J/kmol
[Daubert, T.E., R.P. Danner. Physical and Thermodynamic Properties of Pure Chemicals
Data Compilation. Washington, D.C.: Taylor and Francis, 1989.]**PEER REVIEWED**
Flash point = 185 deg C
[Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York,
NY: Van Nostrand Rheinhold Co., 1993 84]**PEER REVIEWED**
Anthraquinone is sublimed easily without decomposition
[Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol
A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present.,p. VA2 348]**PEER
REVIEWED**
Anthraquinone dissolves in 90% sulfuric acid giving a yellow to orange solution, and in
oleum (20% SO3), giving a red solution.
[Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol
A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present.,p. VA2 348]**PEER
REVIEWED**
Chemical Safety & Handling:
Skin, Eye and Respiratory Irritations:
Irritates .. skin.
[ITII. Toxic and Hazardous Industrial Chemicals Safety Manual. Tokyo, Japan: The
International Technical Information Institute, 1988. 46]**PEER REVIEWED**
Fire Potential:
SLIGHT, WHEN EXPOSED TO HEAT OR FLAME. SPONTANEOUS HEATING: NO
[Sax, N.I. Dangerous Properties of Industrial Materials. 6th ed. New York, NY: Van
Nostrand Reinhold, 1984. 292]**PEER REVIEWED**
NFPA Hazard Classification:
Health: 0. 0= Materials that, on exposure under fire conditions, offer no hazard beyond
that of ordinary combustible material.
[Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire
Protection Association, 1997. ,p. 325-16]**QC REVIEWED**
Flammability: 1. 1= This degree includes materials that must be preheated before ignition
will occur, such as Class IIIB combustible liquids and solids and semi-solids whose flash
point exceeds 200 deg F (93.4 deg C), as well as most ordinary combustible materials.
Water may cause frothing if it sinks below the surface of the burning liquid and turns to
steam. However, a water fog that is gently applied to the surface of the liquid will cause
frothing that will extinguish the fire.
[Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire
Protection Association, 1997. ,p. 325-16]**QC REVIEWED**
Flash Point:
365 DEG F (185 DEG C) (CLOSED CUP)
[Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire
Protection Association, 1997. ,p. 325-16]**QC REVIEWED**
Fire Fighting Procedures:
WATER, FOAM, CARBON DIOXIDE, WATER SPRAY OR MIST, DRY CHEM
[Sax, N.I. Dangerous Properties of Industrial Materials. 6th ed. New York, NY: Van
Nostrand Reinhold, 1984. 292]**PEER REVIEWED**
Preventive Measures:
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The
benefit or detrimental effects of wearing contact lenses depend not only upon the
substance, but also on factors including the form of the substance, characteristics and
duration of the exposure, the uses of other eye protection equipment, and the hygiene of
the lenses. However, there may be individual substances whose irritating or corrosive
properties are such that the wearing of contact lenses would be harmful to the eye. In
those specific cases, contact lenses should not be worn. In any event, the usual eye
protection equipment should be worn even when contact lenses are in place.
**PEER REVIEWED**
Disposal Methods:
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill)
disposal practices are subject to significant revision. Prior to implementing land disposal
of waste residue (including waste sludge), consult with environmental regulatory
agencies for guidance on acceptable disposal practices.
**PEER REVIEWED**
Occupational Exposure Standards:
Manufacturing/Use Information:
Major Uses:
CHEM INT FOR VAT DYES, ACID DYES, MORDANT DYES, DISPERSE DYES,
SOLVENT DYES, & FOR PIGMENTS
[SRI]**PEER REVIEWED**
Anthraquinone serves as the basis for the production of a large number of acid and base
dyes, vat dyes, disperse dyes, and reactive dyes.
[Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol
A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present.,p. VA2 353]**PEER
REVIEWED**
As an additive in the soda and kraft chemical alkaline pulping processes in the paper
pulping industry.
[Appleton HT et al; Technical Support Document 9,10-Anthraquinone. SRC TR-85-105.
EPA Fiche # OTS0581336. Syracuse, NY (1985)]**PEER REVIEWED**
Anthraquinone is used as an intermediate in the manufacture of the laxative Danthron,
also as a major dyestuff intermediate, as a catalyst in the isomerization of linseed and
other vegetable oils, as an accelerant in nickel electroplating, and has a use in improving
adhesion and heat stability of tirecords.
[Appleton HT et al; Technical Support Document 9,10-Anthraquinone. SRC TR-85-105.
EPA Fiche # OTS0581336. Syracuse, NY (1985)]**PEER REVIEWED**
Intermediate for dyes and organics, organic inhibitor, bird repellent for seeds.
[Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York,
NY: Van Nostrand Rheinhold Co., 1993 84]**PEER REVIEWED**
Manufacturers:
James River Corp of Virginia. PO Box 2218 Tredegar Street Richmond, VA 23217 (804)
644-5411. James River Specialty Chemicals, 4th & Adams Street, Camas, WA 98607
(360) 834-8278. Production Site: Camas, WA 98607
[SRI. 1995 Directory of Chemical Producers-United States of America. Menlo Park, CA:
SRI International, 1995 460]**PEER REVIEWED**
Methods of Manufacturing:
Through the oxidation of naphthalene to naphthaquinone, which is condensed with
butadiene to yield tetrahydroanthraquinone; this is dehydrogenated to produce
anthraquinone.
[Appleton HT et al; Technical Support Document 9,10-Anthraquinone. SRC TR-85-105.
EPA Fiche # OTS0581336. Syracuse, NY (1985)]**PEER REVIEWED**
PRODUCED INDUSTRIALLY FROM PHTHALIC ANHYDRIDE & BENZENE IN
PRESENCE OF ALUMINUM CHLORIDE BY FRIEDEL-CRAFTS REACTION.
FROM ANTHRACENE WITH VANADIUM PENTOXIDE, SODIUM CHLORATE,
GLACIAL ACETIC & SULFURIC ACIDS. CONVENIENT LAB PROCEDURE.
[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 109]**PEER REVIEWED**
Anthracene + nitric acid, concentrated (nitric acid oxidation process); o-Benzoylbenzoic
acid (acid-catalyzed condensation)
[Ashford, R.D. Ashford's Dictionary of Industrial Chemicals. London, England:
Wavelength Publications Ltd., 1994.]**PEER REVIEWED**
General Manufacturing Information:
BASIC PRODUCERS: BAYER AG (WEST GERMANY) (CORBIT*, MORKIT*) JF
HENRY CHEM CO, INC, FINE CHEM DIV.
[Farm Chemicals Handbook 1981. Willoughby, Ohio: Meister, 1981.,p. C-20]**PEER
REVIEWED**
ANTHRAQUINONE DYE. A DYE WHOSE MOLECULAR STRUCTURE IS BASED
ON ANTHRAQUINONE. ... CI NUMBERS FROM 58000 TO 72999. THESE ARE
ACID OR MORDANT DYES WHEN OH OR HSO3 GROUPS RESPECTIVELY ARE
PRESENT. THOSE ANTHRAQUINONE DYES THAT CAN BE REDUCED TO
ALKALINE SOL LEUCO (VAT) DERIVATIVE THAT HAS AFFINITY FOR
FIBERS, & WHICH CAN BE REOXIDIZED TO THE DYE, ARE KNOWN AS
ANTHRAQUINONE VAT DYES. THEY ARE LARGELY USED ON COTTON,
RAYON, & SILK, & HAVE EXCELLENT PROPERTIES OF COLOR & FASTNESS,
& RELATIVELY LOW TOXICITY. /ANTHRAQUINONE DYE/
[Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York,
NY: Van Nostrand Rheinhold Co., 1993 84]**PEER REVIEWED**
...DISPERSE DYES (USED FOR ACETATE, RAYON & SYNTHETIC FIBERS)...
DISPERSE COLORS MAY BE ANTHRAQUINONE...DYES...
[International Labour Office. Encyclopedia of Occupational Health and Safety. Volumes
I and II. New York: McGraw-Hill Book Co., 1971. 426]**PEER REVIEWED**
FUNGICIDAL ACTIVITY IS FOUND IN VARIETY OF QUINONES IN GENERAL
ORDER 1,4-NAPHTHOQUINONE GREATER THAN PHENANTHROQUINONE
GREATER THAN P-BENZOQUINONE GREATER THAN ANTHRAQUINONE.
[White-Stevens, R. (ed.). Pesticides in the Environment: Volume 1, Part 1, Part 2. New
York: Marcel Dekker, Inc., 1971. 9]**PEER REVIEWED**
AS BIRD REPELLANT TREAT SEEDS OF CEREALS, VEGETABLES & LEGUMES
@ RATE OF ABOUT 1 LB (OF 25% FORMULATION)/500 LB SEED.
[Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication
1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada,
1982. 19]**PEER REVIEWED**
Formulations/Preparations:
GRADES: SUBLIMED; 30% PASTE (SOLD ON 100% BASIS); ELECTRICAL 99.5%.
[Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York,
NY: Van Nostrand Rheinhold Co., 1993 84]**PEER REVIEWED**
ANTHRAQUINONE CATHARTICS ALL CONTAIN CHARACTERISTIC DERIV
WHICH ARE PRESENT IN THE FREE STATE...OR IN GLYCOSIDIC
COMBINATION WITH GLUCOSE, ARABINOSE, OR RHAMNOSE. MAJOR
ACTIVE CONSTITUENTS.../INCL/ ANTHRAQUINONE...
[Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed.
Easton, Pennsylvania: Mack Publishing Co., 1975. 738]**PEER REVIEWED**
AS SEED DRESSINGS: 25% WP OR IN CONJUNCTION WITH OTHER SEED
PROTECTANTS.
[Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication
1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada,
1982. 19]**PEER REVIEWED**
Consumption Patterns:
ESSENTIALLY 100% AS A CHEMICAL INTERMEDIATE FOR THE
MANUFACTURE OF DYES (1976)
[SRI]**PEER REVIEWED**
U. S. Production:
(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS
[SRI]**PEER REVIEWED**
(1975) GREATER THAN 4.54X10+5 GRAMS
[SRI]**PEER REVIEWED**
U. S. Imports:
(1972) 3X10+7 GRAMS (PRINCPL CUSTMS DISTS)
[SRI]**PEER REVIEWED**
(1975) 1.03X10+8 GRAMS (PRINCPL CUSTMS DISTS)
[SRI]**PEER REVIEWED**
813,322 pounds (in 1983)
[Appleton HT et al; Technical Support Document 9,10-Anthraquinone. SRC TR-85-105.
Syracuse, NY (1985)]**PEER REVIEWED**
Laboratory Methods:
Analytic Laboratory Methods:
A CONVENIENT PROCEDURE IS DESCRIBED FOR QUANTITATION OF
POLYNUCLEAR AROMATIC HYDROCARBONS BY HPLC-GC IN WATER AT
THE NANOGRAM TO MICROGRAM PER LITER LEVEL. APPLICATION OF THIS
PROCEDURE TO THE STUDY OF AQ CHLORINATION REACTIONS OF
SEVERAL POLYNUCLEAR AROMATIC HYDROCARBONS IS DESCRIBED.
[OYLER AR ET AL; ANAL CHEM 50 (7): 837 (1978)]**PEER REVIEWED**
A METHOD WAS DEVELOPED FOR THE DETECTION OF 9,10ANTHRAQUINONE BIRD REPELLANT IN SEEDS, CROPS, & SOIL. THE
DETECTION WAS BY ELECTRON-CAPTURE DETECTOR. RECOVERIES WERE
94-106% @ 0.5-0.05 PPM, & THE MAX SENSITIVITY WAS 0.05 PPM.
[MAINI P; J CHROMATOGR 128 (1): 174 (1976)]**PEER REVIEWED**
ANTHRAQUINONE DETERMINATION IN AIRBONE PARTICULATE MATTER
BY CAPILLARY GAS CHROMATOGRAPHY & GAS CHROMATOGRAPHY/MASS
SPECTROMETRY.
[KOENIG J ET AL; ANAL CHEM 55 (4): 599 (1983)]**PEER REVIEWED**
POLAROGRAPHIC DETERMINATION OF ANTHRAQUINONE WITH DMF AS
SOLVENT, AMMONIUM ACETATE SOLN AS SUPPORTING ELECTROLYTE, &
GELATIN SOLN AS MAX SUPPRESSOR. RESULTS WERE REPRODUCIBLE &
ERRORS DID NOT EXCEED + OR - 3%.
[POPESCU S; ANAL LETT 12 (B15): 1565 (1979)]**PEER REVIEWED**
Anthraquinone was detected in rainwater using GC/MS (MDL = 0.05-0.10 ng/l).
[Pankow JF et al; Environ Sci Technol 18: 310-8 (1984)]**PEER REVIEWED**
Anthraquinone was detected in fish tissue using capillary gas chromatography followed
by GC/MS (detection limit = 0.2 ppb, average recovery = 72%).
[Vassilaros DL et al; Anal Chem 54: 106-12 (1982)]**PEER REVIEWED**
Anthraquinone was detected in tap water using GC/MS followed by mass
fragmentography.
[Shinohara R et al; Water Research 15: 535-42 (1981)]**PEER REVIEWED**
Special References:
Special Reports:
ZWAVING JH; RECENT DEVELOPMENTS IN THE ANALYSIS OF
ANTHRAQUINONE DERIVATIVES; PHARMACOLOGY 20(SUPPL 1) 65 (1980).
A REVIEW & DISCUSSION ON RECENT DEVELOPMENTS IN THE ANALYSIS
OF ANTHRAQUINONE DERIVATIVES.
FRIEDMANN CA; STRUCTURE-ACTIVITY RELATIONSHIPS OF
ANTHRAQUINONES IN SOME PATHOLOGICAL CONDITIONS;
PHARMACOLOGY 20(SUPPL 1) 113 (1980). A REVIEW ON THE STRUCTUREACTIVITY RELATIONSHIPS OF ANTHRAQUINONES IN SOME
PATHOLOGICAL CONDITIONS.
ANTON R ET AL; PHARMACOLOGY 20 (SUPPL 1): 104 (1980). A REVIEW &
DISCUSSION ON THE THERAPEUTIC USE OF NATURAL ANTHRAQUINONE
FOR OTHER THAN LAXATIVE ACTIONS.
Synonyms and Identifiers:
Synonyms:
ANTHRACENE, 9,10-DIHYDRO-9,10-DIOXO**PEER REVIEWED**
9,10-ANTHRACENEDIONE
**PEER REVIEWED**
ANTHRADIONE
**PEER REVIEWED**
9,10-ANTHRAQUINONE
**PEER REVIEWED**
CORBIT
**PEER REVIEWED**
9,10-DIOXOANTHRACENE
**PEER REVIEWED**
HOELITE
**PEER REVIEWED**
MORKIT
**PEER REVIEWED**
Formulations/Preparations:
GRADES: SUBLIMED; 30% PASTE (SOLD ON 100% BASIS); ELECTRICAL 99.5%.
[Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York,
NY: Van Nostrand Rheinhold Co., 1993 84]**PEER REVIEWED**
ANTHRAQUINONE CATHARTICS ALL CONTAIN CHARACTERISTIC DERIV
WHICH ARE PRESENT IN THE FREE STATE...OR IN GLYCOSIDIC
COMBINATION WITH GLUCOSE, ARABINOSE, OR RHAMNOSE. MAJOR
ACTIVE CONSTITUENTS.../INCL/ ANTHRAQUINONE...
[Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed.
Easton, Pennsylvania: Mack Publishing Co., 1975. 738]**PEER REVIEWED**
AS SEED DRESSINGS: 25% WP OR IN CONJUNCTION WITH OTHER SEED
PROTECTANTS.
[Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication
1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada,
1982. 19]**PEER REVIEWED**
Administrative Information:
Hazardous Substances Databank Number: 2074
Last Revision Date: 20020118
Last Review Date: Reviewed by SRP on 1/31/1996
Update History:
Complete Update on 01/18/2002, 4 fields added/edited/deleted.
Field Update on 01/14/2002, 1 field added/edited/deleted.
Complete Update on 09/07/2001, 1 field added/edited/deleted.
Complete Update on 08/09/2001, 1 field added/edited/deleted.
Complete Update on 03/03/2000, 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 09/02/1998, 1 field added/edited/deleted.
Complete Update on 06/02/1998, 1 field added/edited/deleted.
Complete Update on 02/27/1998, 1 field added/edited/deleted.
Complete Update on 10/26/1997, 1 field added/edited/deleted.
Complete Update on 02/24/1997, 1 field added/edited/deleted.
Complete Update on 08/07/1996, 56 fields added/edited/deleted.
Field Update on 05/10/1996, 1 field added/edited/deleted.
Field Update on 01/23/1996, 1 field added/edited/deleted.
Field Update on 10/19/1995, 1 field added/edited/deleted.
Field Update on 10/03/1995, 1 field added/edited/deleted.
Complete Update on 12/28/1994, 1 field added/edited/deleted.
Complete Update on 08/11/1994, 1 field added/edited/deleted.
Complete Update on 03/25/1994, 1 field added/edited/deleted.
Complete Update on 05/25/1993, 1 field added/edited/deleted.
Complete Update on 02/05/1993, 1 field added/edited/deleted.
Field update on 12/24/1992, 1 field added/edited/deleted.
Complete Update on 04/16/1990, 1 field added/edited/deleted.
Complete Update on 03/06/1990, 1 field added/edited/deleted.
Field update on 03/06/1990, 1 field added/edited/deleted.
Complete Update on 12/28/1984