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MINYAK CENGKEH. KiMIA MINYAK ATSIRI. Cloves were used in China as early as 266 BC, and by the 4 th century, they were known in Europe, although very expensive. - PowerPoint PPT Presentation
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MINYAK CENGKEH
KiM
IA M
INYA
K AT
SIRI
Click icon to add picture
HISTORY OF CLOVECloves were used in China as early
as 266 BC, and by the 4th 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 FEATURESCloves 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 & PungentTaste: 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
CONSTITUENTS14-21% Volatile oils• Mainly eugenol & isoeugenol• Sitosterol• Stigmasterol• Campesterol
TanninsTriterpene acids & estersGlycosides
USES OF CLOVE
Stimulant aromaticSpiceFor the preparation of volatile oilSesquiterpenes: potential anti-carcinogenic
compounds
CLOVE OILOil 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 - CONSTITUENTSVolatile oils :PHENOLIC COMPOUNDS : mainly eugenolNON 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-septicAromaticStimulantFlavouring 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 DIDESTILASIEUGENOL nD = 1,5369; d = 1,053Lapisan kariofilena didestilasi ulang.
OCH3
OH
CH2CH=CH2
EUGENOL
KARIOFILENA
01234567PPM
IDENTIFIKASI EUGENOL SPEKTRUM H NMR EUGENOL
SPEKTRUM MASSA
DERIVATISASI EUGENOL1. SINTESIS EUGENIL METIL ETER
Eugenil Metil Eter sangat luas digunakan sebagai komposisi parfum , baunya lebi lunak dari eugenolPenarik lalat buah jantan (feromon)
OCH3
OH
CH2CH=CH2
CH3O-OCH3
O- Na+
CH2CH=CH2
Na++ CH3OH
CH3I
OCH3
OCH3
CH2CH=CH2
2. SINTESIS EUGENIL ASETAT EUGENIL ASETAT DIGUNAKAN SEBAGAI PENGHARUM SABUN DAN IMITATION SPICE OIL
OCH3
OH
CH2CH=CH2
+H3C O CH3
O O
CH3COONaOCH3
OCOCH3
CH2CH=CH2
+ CH3COOH
3. SINTESIS VANILIN
OCH3
OH
CH2CH=CH2
OH-OCH3
OH
CH=CHCH3
OCH3
OH
CHO
[O]
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
OCH3
OH
CH2CH=CH2
CH3O-OCH3
O- Na+
CH2CH=CH2
Na+ OCH3
OCH3
CH2CH=CH2
CH3OSO3CH3
HBr
OCH3
OCH3
CH2CHCH3
Br
OCH3
OCH3
CH2CHCH3
NH2
NH3
SINTESIS DOPADOPA OBAT PENYAKIT PARKINSON
OCH3
OH
CH2CH=CH2
CH3O-OCH3
O- Na+
CH2CH=CH2
Na+ OCH3
OCH3
CH2CH=CH2
CH3OSO3CH3
OCH3
OCH3
CH2CHCH3
OCH
O
OCH3
OCH3
CH2CHCH3
OH
HCOH
O
OH-OCH3
OCH3
CH2CCH3
O
PCCNH3
OCH3
OCH3
CH2CCH3
OH
NH2
NH4Cl, KCNOCH3
OCH3
CH2CCH3
CN
NH2
OCH3
OCH3
CH2CCH3
COOH
NH2
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