Eugenol, derivatives

Sell AB, Carlini EA. (1976). Anesthetic action of methyleugenol and other eugenol derivatives. Pharmacology. 14(4) 367-77. 

It is an oily liquid eugenol derivative and less potent than thiopentone. It is a very short acting intravenous anaesthetic and specially used for very short outpatient operations and dental procedures. 

According to Ref 2, camphor oil is a col, natural oil with characteristic odor, d 0.870 -1.040, nD 1.465-1.481 at 20° sol in eth, chlf insol in ale its chief constituents are pinene, camphor, cineol, phellandrene, dipentene, safrol eugenol. Derived by distg the wood of the Cinamonum camphora and separating the oil from solid camphor. Used as substitute for turpentine oil in varnishes, cheap soaps, shoe polishes, etc... 

Antiplatelet effect (bilberry leaf, evening primrose, garlic, ginger, gingko biloba, ginseng). Clove contains eugenol derivatives, which inhibit platelets... 

Merchan Arenas, D.R., A.M. Acevedo, L.Y. Vargas Mendez, and V.V. Kouznetsov. 2011. Scavenger activity evaluation of the clove bud essential oils Eugenia caryophyllus) and eugenol derivatives employing ABTS decolorization. Sci. Pharm., 79(4) 779-791. 

Dallmeier K, Carlini EA 1981 Anesthetic, hypothermic, myorelaxant and anticonvulsant effects of synthetic eugenol derivatives and natural analogues. Pharmacology 22 113-127... 

Eugenol yields a characteristic benzoyl derivative when treated with benzoyl chloride in the presence of caustic potash. Benzoyl-eugenol melts at 69° to 70°. 

The diphenylurethane melts at 107° to 108°. By treatment with methyl iodide in the presence of caustic alkali, eugenol is converted into methyl-eugenol, which is characterised by its monobromo derivative melting at 79° to 80°. 

The principal derivative for identification purposes is veratric acid, C H.,(C00H)(0CH3)2, which is obtained by oxidising 6 grams of methyl-eugenol with a solution of 18 grams of potassium permanganate in 400 c.c. of water. When recrystallised from alcohol, veratric acid melts at 179° to 180°. 

Bodell, W. J. Ye, Q. Pathak, D. N. Pongracz, K. Oxidation of eugenol to form DNA adducts and 8-hydroxy-2 -deoxyguanosine role of quinone methide derivative in DNA adduct formation. Carcinogenesis 1998, 19, 437 143. 

Individual compounds can be isolated from essential oils containing one or only a few major components by distillation or crystallization. Examples are eugenol from clove oil, menthol from commint oil, citronellal from Eucalyptus citriodora oil and citral from Litsea cubeba oil. These compounds are used as such or serve as starting materials for the synthesis of derivatives, which are also used as flavor and fragrance substances. However, the importance of some of these oils has decreased substantially because of the development of selective synthetic processes for their components. 

Pimento oils (allspice oil) are derived from pimento fruits and leaves. Pimento berry oil is obtained by steam distillation of the dried, fully grown, unripe, berrylike fruits of the pimento shrub, Pimenta dioica (L.) Merrill. (Myrtaceae), growing in the islands of the West Indies and Central America. It is a pale yellow to brown liquid with a spicy odor, reminiscent of eugenol. 

In this chapter chemical conversions of natural precursors resulting in flavour chemicals are discussed. The main groups of natural precursors are terpenes for all kinds of terpene derivatives, vanillin precursors like lignin and eugenol, sugars for Maillard-associated flavour chemicals, amino acids and molecules obtained by fermentation or available as residual streams of renewable resources. 

Green notes Floral cinnamic derivatives Eugenol cA-3-Hexenyl acetate Violet leaf absolute c/.s-3-Hexenyl benzoate Isoeugenol... 

The mellis accord, which makes up an important part of the fragrance here incorporates amyl salicylate in addition to benzyl salicylate, with the patchouli and woody aspect being accentuated, using cedryl acetate rather than the more traditional products derived from vetiver. Vertofix had yet to be discovered. The dominant spices, in combination with eugenol, are clove and cinnamon. 

Eugenol (4-allyl-2-methoxyphenol) Eugenol is not actually derived from a terpene molecule (as opposed to carvacrol and thymol) but it is a phenol and is found in essential oils of clove, cinnamon leaf, pimento, ylang ylang and rose. It has a spicy, pungent odour typical of clove. 

Phenylpropanoids have an aromatic ring with a three-carbon substituent. Caffeic acid (308) and eugenol (309) are known examples of this class of compounds. Phenylpropanoids are formed via the shikimic acid biosynthetic pathway via phenylalanine or tyrosine with cinnamic acid as an important intermediate. Phenylpropanoids are a diverse group of secondary plant compounds and include the flavonoids (plant-derived dyes), lignin, coumarins, and many small phenolic molecules. They are known to act as feeding deterrents, contributing bitter or astringent properties to plants such as lemons and tea. 

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