Clove Oil
MINYAK CENGKEH
HISTORY OF CLOVE
Cloves were used in China as early as 266 BC, and by the 4 th century, they were known in
Europe, although very expensive.
Same as with nutmeg, the Dutch also destroyed all trees from surrounding native islands to secure a monopoly, and cultivated them only in a small group of islands.
In 1770, the French managed to introduce clove trees to
Mauritius, and started cultivating them there, as well as in Zanzibar, Penang and
Sumatra.
COLLECTION & PREPARATION
The flower buds are collected when the lower part turns green-crimson. The cloves are dried in the open air on mats & separated from their peduncles (forming clove stalks which are also sold commercially).
If left on the tree for too long, the buds open & the petals fall, leaving “brown cloves”.
Later the fruits (“mother cloves”) are produced.
MACROSCOPICAL FEATURES
Cloves are 10-17.5 mm long.
The head consists of 4 slightly projecting calyx teeth, 4 membranous petals and numerous incurved stamens around a large style.
Odour: Spicy & Pungent
Taste: Aromatic
MICROSCOPICAL FEATURES
Heavy cuticularized epidermis
Numerous oil cells (shizolysigenous)
Calcium oxalates (cluster crystals & prisms)
Stomata (epidermis of sepals)
Starch (Fruit – “mother cloves”)
Lignified sclereids
CONSTITUENTS
14-21% Volatile oils
• Mainly eugenol & isoeugenol
• Sitosterol
• Stigmasterol
• Campesterol
Tannins
Triterpene acids & esters
Glycosides
USES OF CLOVE
Stimulant aromatic
Spice
For the preparation of volatile oil
Sesquiterpenes: potential anti-carcinogenic compounds
CLOVE OIL
Oil distilled in Europe and the
US normally does not need purification, while oil distilled in other areas (e.g.
Madagascar) does. After purification the oil is sold with varying eugenol contents.
Oil of cloves is yellow or colourless, is slightly heavier than water.
CLOVE OIL - CONSTITUENTS
Volatile oils :
PHENOLIC COMPOUNDS : mainly eugenol
NON PHENOLIC COMPOUNDS : Sesquiterpenes (α and β caryophyllene, a-kubeben, a-kopaen, d, kadinen, kadina-1,3,5-trien)
Oil of clove – like other volatile/essential oils – should be stored in a well-fitted, air-tight container, & should be protected from light & heat.
CLOVE OIL - USES
Anti-septic
Aromatic
Stimulant
Flavouring Agent
ISOLASI EUGENOL DAN KARIOFILEN
MINYAK DAUN CENGKEH DIDESTILASI
BERTINGKAT DENGAN PENGURANGAN
TEKANAN.
DESTILAT DENGAN TITIK DIDIH 65-110Oc PADA
5 mmHg, PADA KROMATOGRAFI GAS
MEMPUNYAI DUA PUNCAK UTAMA, YAITU b-KARIOFILEN (28.0%) DAN EUGENOL (71,5%).
Sifat fisik : nD = 1,530, massa jenis pada 30oC =
0,9994
ISOLASI EUGENOL :
DItambahkan DENGAN NaOH , FASA AIR
DIASAMKAN, DAN FASA EUGENOL DIDESTILASI
EUGENOL nD = 1,5369; d = 1,053
Lapisan kariofilena didestilasi ulang.
OH
OCH
3
CH
2
CH=CH
2
EUGENOL
KARIOFILENA
IDENTIFIKASI EUGENOL
SPEKTRUM H NMR EUGENOL
7 6 5 4
PPM
3 2 1 0
SPEKTRUM MASSA
DERIVATISASI EUGENOL
1. SINTESIS EUGENIL METIL ETER
Eugenil Metil Eter sangat luas digunakan sebagai komposisi parfum , baunya lebi lunak dari eugenol
Penarik lalat buah jantan (feromon)
OH
OCH
3
CH3ONa+
CH
2
CH=CH
2
O
-
Na
+
OCH
3
+ CH3OH
CH
2
CH=CH
2
CH
3
I
OCH
3
OCH
3
CH
2
CH=CH
2
2
. SINTESIS EUGENIL ASETAT
EUGENIL ASETAT DIGUNAKAN SEBAGAI PENGHARUM SABUN DAN
IMITATION SPICE OIL
OH
OCH
3
+
H
3
C
O
CH
2
CH=CH
2
O
O
CH
3
CH
3
COONa
OCOCH
3
OCH
3
+ CH3COOH
CH
2
CH=CH
2
3. SINTESIS VANILIN
OH
OCH
3
OH-
OH
OCH
3
[O]
OH
OCH
3
CH
2
CH=CH
2
CH=CHCH
3
CHO
Isoeugenol , senyawa yang digunakan jenis pewangi floral dan fancy bonqouets, anyelir.
SINTESIS AMFETAMIN
• Amfetamin adalah psikostimulan, obat-obatan yang menstimulir dan menaikkan kepercayaan diri .
• Digunakan juga untuk perangsang psikomotor agar tidak mengantuk
• Penekan nafsu makan
• antiobesitas
OH
OCH
3
CH3ONa+
O
-
Na
+
OCH
3
CH
3
OSO
3
CH
3
OCH
3
OCH
3
CH
2
CH=CH
2 CH
2
CH=CH
2 CH
2
CH=CH
2
HBr
OCH
3
OCH
3 NH
3
OCH
3
OCH
3
CH
2
CHCH
3
NH
2
CH
2
CHCH
3
Br
SINTESIS DOPA
DOPA OBAT PENYAKIT PARKINSON
OH
OCH
3
CH3ONa+
O
-
Na
+
OCH
3
CH
3
OSO
3
CH
3
CH
2
CH=CH
2 CH
2
CH=CH
2
NH3
OCH
3
OCH
3
PCC
OCH
3
OCH
3
OH
-
OCH
3
OCH
3
CH
2
CH=CH
2
O
HCOH
OCH
3
OCH
3
CH
2
CCH
3
O
OCH
3
OCH
3
NH4Cl, KCN
NH
2
CH
2
CCH
3
OH
CH
2
CHCH
3
OH
OCH
3
OCH
3
NH
2
CH
2
CCH
3
CN
CH
2
CHCH
3
OCH
O
OCH
3
OCH
3
NH
2
CH
2
CCH
3
COOH
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