MINYAK CENGKEH

KiM

IA M

INYA

K AT

SIRI

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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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