MINYAK CENGKEH

HISTORY OF CLOVE

Cloves were used in China as early as 266 BC, and by the 4 Europe, although very expensive. th century, they were known in 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 CH3O Na+ 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 CH3O Na+ 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 CH3O Na+ 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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