Eugenol, methoxy

The leaves of two other general varieties, either anise scented or lemon scented, have been reported to yield volatile oils with quite different proportions of the above components. The anise scented variety contains methyleugenol (43%) and methylchavicol (32%) as the major components, and the lemon scented variety contains mostly citral (>80%). The main constituents of the essential oil of the leaves of P. racemosa var. terebinthina (Burret) L. R. Landrum are 4-methoxy eugenol (12.6%), a-terpineol (20%), and a-terpineol acetate (27%), while in the essential oil of P. racemosa var. grisea (Kiaersk.) Fosberg, the major constituents are 4-methoxy eugenol (4.5%) and 4-meth-oxy-isoeugenol (75.2%). The leaves also contain abietic acid, a diterpene. Lupeol, a triterpene, was isolated from the leaves of P. racemosa var. ozua (Urban Ekman) L. R. Landrum. ... 

The methyl ether of eugenol, CjjHj 02, is found in calamus oil, cassie oU, betel oil, bay oil, and various other essential oils. It can be prepared artificially by the action of methyl iodide on eugenol sodium. Its constitution is identical with that of eugenol, except that the phenolic group, OH, has been replaced by the methoxy group, O. CHg. 

Eugenol, 4 allyl-2-methoxy phenol, is capable of forming cements with ZnO, CuO, MgO, CaO, CdO, PbO and HgO (Brauer, White Moshonas, 1958 Nielsen, 1963). Other 2-methoxy phenols are also capable of forming cements with metal oxides, provided the allyl group is not in a 3- or 6-position where it sterically hinders the reaction (Brauer, Argentar Durany, 1964). These include guaiacol, 2-methoxyphenol, and the allyl and propylene 2-methoxy phenols. 

All cements that contain eugenol inhibit the polymerization of acrylates, and those of EBA-eugenol are no exception. In order to remedy this and other defects, Brauer and his coworkers examined alternatives to eugenol (Figure 9.7). These included the esters of vanillic acid (3-methoxy-4-hydroxybenzoic acid, HV) and syringic acid (3,5-dimethoxy-4-hydroxy-benzoic acid). Both are 3-methoxy-4-hydroxy compounds and are thus chemically related to eugenol and guaiacol. Both are solids and have to be dissolved in EBA where they form satisfactory cements with EBA zinc oxide powder. The vanillate (EBA-HV) cements are the more important. 

Bolton, J. L. Comeau, E. Vukomanovic, V. The influence of 4-alkyl substituents on the formation and reactivity of 2-methoxy-quinone methides evidence that extended ji-conjugation dramatically stabilizes the quinone methide formed from eugenol. Chem.-Biol. Interact. 1995, 95, 279-290. 

Ethyl phenylacetate <60.5 Ethyl salicylate 103.5 Eugenol( 2-Methoxy-4-allylphenol)<59.5 Eugenol methyl ether <61.5... 

Exercise 26-12 Devise a reasonable sequence of synthetic steps for conversion of eugenol to the flavoring material vanillin, which is 3-methoxy-4-hydroxybenzene-carbaldehyde (Section 26-5). 

Another occasionally useful transformation of allylphenols is the isomerization to propenylphenols by strong alkali, as in the well-known isomerization of eugenol to isoeugenol. For example, 2-methoxy-6-allylphenol (LXXI) is changed to the propenyl compound LXXII by... 

Cikalo et al used TLC to establish the origins of cinnamons of commerce. Six different solvent systems were used in conjunction with silica plates to separate eugenol, cinnamyl alcohol, cinnamyl acetate, frans-cinnamil-aldehyde, 2-methoxy-cinnamylaldehyde, and coumarin [21]. 

It was reported that intraperitoneal injection of a single 450 mg/kg dose of 14C-methoxy labeled eugenol resulted in rapid distribution to all organs. Both ether- and water-soluble materials were recovered from most tissues and excretions. Only 0.2-1.0% of the dose was eliminated as expired 14C-... 

FEMA No. 2469 Aceteugenol Acetyl Eugenol 4-Allyl-2-methoxy-phenyl Acetate Eugenol Acetate... 

Eugenol (= Allylguaiacol, Caryophyllic acid, Eugenic acid 2-Methoxy-4-( 2-propenyl)phenol) (phenylpropanoid)... 

SYNS 4-ALLYLGUAtACOL 4-ALLYL-l-HYDROXY-2-METHOXYBENZENE 4-ALLYL-2-METHOXYPHENOL CARYOPHYLLIC ACID EUGENIC ACID Fa 100 FEMA No. 2467 1-HYDROXY-2-METHOXY-4-ALLYLBENZENE 4-HYDROXY-3-METHOXYALLYLBENZENE 1-HYDROXY-2-METHOXY-4-PROP-2-ENYLBENZENE 2-METHOXY-4-ALLYLPHENOL 2-METHOXY-4-PROP-2-ENYLPHENOL 2-METHOXY-4-(2-PROPENYL)PHENOL 2-METOKSY-4-ALULOFENOL (POUSH) NCI-C50453 SYNTHETIC EUGENOL... 

SYNS ACETEUGENOL 1-ACETOXY-2-METHOXY-4-ALLYLBENZENE ACETYLEUGENOL 4-ALLYL-2-METHOXYPHENOL ACETATE 1,3,4-EUGENOL ACETATE EUGENYL ACETATE FEMA No. 2469... 

Eiigenole and Safrole.—The chief constituent of a more common essential oil is eugenole which occurs in oil of cloves. It is the monomethyl ether of di-hydroxy 7-phenyl propene in which the methoxy group is meta and the hydroxyl group is para to the propene chain. It is thus a propene derivative of the mono-methyl ether of pyro-catechinol. The alpha isomer is known as iso-eugenole. 

Dimethoxy-4-hydroxycinnamaldehyde Phenol, 2,6-dimethoxy Eugenol 2-Methoxy-6-methylphenol Vanillin Phenol, 2-methoxy-4-(l-propenyl) S additional peaks 3, S-Dimethoxy-4-hydroxycinnamaldehyde... 

Eugenol (4-hydroxy-3-methoxy-allybenzene) Containing Botanicals... 

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