Cinnamyl cinnamate

Phenyl-2-propenoic acid [621 -82-9] commonly referred to as cinnamic acid, is a white crystalline soHd having a low intensity sweet, honeylike aroma. It has been identified as a principal constituent in the botanical exudates from Styrax IJquidamber orientalis) Benzoin Styrax ben in Pern Balsam [Myroxylon pereirae and Tolu Balsam (]Ayro>ylon balsamum) (4,5). In these, as well as numerous other natural products, it exists both as the free acid and in the form of one or more of its esters, as for example, methyl cinnamate, ben2yl cinnamate [103 1 -3] and cinnamyl cinnamate. 

Upon treatment with aluminum ethoxide, the aldehyde is converted to cinnamyl cinnamate [122-69-0] (Tishchenko reaction), a valuable perfumery ingredient. 

Manufacture. A limited, amount of natural cinnamyl alcohol is produced by the alkaline hydrolysis of the cinnamyl cinnamate present in Styrax Oil. Thus treatment of the essential oil with alcohoHc potassium hydroxide Hberates cinnamyl alcohol of reasonable purity which is then subjected to distillation. This product is sometimes preferred in fine fragrance perfumery because it contains trace impurities that have a rounding effect in finished formulations. 

Health and Safety. Cinnamyl alcohol has been evaluated by FEMA and given GRAS status (FEMA No. 2294). Two of its esters, cinnamyl cinnamate (FEMA No. 2298) and cinnamyl acetate (FEMA No. 2293), ate also used extensively in flavor and fragrance compositions. Cinnamyl alcohol has also been tested by RIFM (48) and found to be safe for use. There have been reported cases of irritation and several manufacturers market a desensitized alcohol for use in fragrance appHcations. 

Cinnamyl Cinnamate.—Tbis ester is known as styracin, and is found in storax and other balsamic products, and possibly also in oil of hyacinths. It has the constitution... 

Storax resin is extracted from Liquidambar orientalis (Hammamelidiaceae) and Altingia and its major components are cinnamyl cinnamate and 3-phenylpropanyl cinnamate, with significant amounts of benzoic and cinnamic acids, and 3-phenylpropanol and cinnamyl alcohols [130,131]. The volatile content is very low and triterpenes (oleanonic and 3-epioleanolic acids and liquid ambronovic acid) have also been observed [130,132]. 

Styrax tonkinensis Pierre. S. benzoin Dryand An Xi Xian (Styrax) (leaf) Sumaresinolic acid, coniferyl cinnamate, styracin, vanillin, alpha-phenylpropyl cinnamyl cinnamate, balsamic acid.33-50 As an aromatic stimulant, for aphrodisiac, an astringent. 

N.A. Liquidambar orientalis Mill. L. styraciflua L. Levant storax cinnamic acid, cinnamyl cinnamate, phenylprepyl cinnamate, triterpene acid.99 Internally for strokes, infantile convulsions, coma, heart disease, and pruritus. 

Cinnamon Leaf Oil, 102, 579 Cinnamon Oil, 93 Cinnamyl Acetate, 468, 612 Cinnamyl Alcohol, 470, 612 Cinnamyl Anthranilate, xiv, xxxii Cinnamyl Butyrate, 470, 612 Cinnamyl Cinnamate, 470, 613 Cinnamyl Formate, 470, 613 Cinnamyl Isobutyrate, 470, 613 Cinnamyl Isovalerate, 470, 613, (Sl)64... 

The order of reactivity of this Ru/silane combination to various functional groups differs greatly from that of its Pd/silane/ZnCh analog. While the latter is very useful for allylic reductions and essentially useless for unsaturated esters, the Ru-based system exhibits opposite reactivity. This complementary che-moselectivity is illustrated by the reduction of cinnamyl cinnamate (Scheme 59), a substrate containing both an allylic carboxylate and an a, -unsaturated ester.Each of these can be reduced separately by silicon hydride and the appropriate transition metal catalyst. 

C18H11CI 10 Chloro-1,2-benzanthracene 20268-52-4 25.00 1 2144 2 30627 C18H1602 cinnamyl cinnamate 122-69-0 -figs 3-... 

There has been much interest in the synthesis of lignan lactones of the aryl tetralin type, induced by the antitumour activity of podophyllotoxin relatives, and some short oxidative routes into the series have been pursued. In a typical reaction, in which both Cp—Cp and Cp—Car couplings occur, the cinnamyl cinnamate (297) was treated for 30 s with chromium trioxide-fluoroboric acid in acetonitrile. Three tetracyclic products were obtained, the lactones (298 19%) and (299 7%), and ( )-isopodophyllotoxone... 

The commercial product contains esters benzyl cinnamate (cinnamein), benzyl benzoate, and cinnamyl cinnamate (styracin). The drug usually contains from 56 to 66% of these esters. Balsam of Peru is used as an antiseptic dressing for wounds (haemorrhoids). 

AI3-02445 CCRIS 904 Cinnamic acid, cinnamyl ester Cinnamyl p-phenylacryiate Cinnamyl alcohol, cinnamate Cinnamyl cinnamate Cinnamylester kyseliny skoricove EINECS 204-566-1 FEMA No. 2298 NSC 46161 Phenylallyl cinnamate 3-Phenylallyl cinnamate ... 

Propenoic acid, 3-phenyI-, 3-phenyI-2-propenyl ester cinnamyl cinnamate 3219, 3224, 3308, 3485, 4249 172a, 174b, 1053, 3266, 3370 ... 

Anisyl phenylacetate 78 Cinnamyl cinnamate 126 Ethyl acetoacetate... 

Propenoic acid, 3-phenyl-, 3-phenyl-2-propenyl ester cinnamyl cinnamate V.A-3... 

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