Methoxy-cinnamic aldehyde

Ortho-methoxy-cinnamic aldehyde is present in small amount in cassia oil. It has the composition Cj( Hjq02, and its physical characters are as follows —... 

Para-methoxy-cinnamic aldehyde has been isolated from tarrago oU. It has the following characters —... 

An aldehyde was isolated from the oil of the root of a variety of Chlorocodon, by Goulding and Pelly,i which Friedlander has shown to be p-methoxy-cinnamic aldehyde. This aldehyde has been obtained artificially by Tiemann and Parrisius by acting with chloroform on an alkaline-solution of methylresorcmol. 

Table VIII shows the dramatic differences between fresh and dried leaves. In this case, as oj sed to peppermint, rosemary and thyme, trans-2-hexenal is more in the fresh than in the dried and aged. The same is true for phenyl ethyl alcohol. Interestingly, trans-cinnamic aldehyde constitutes 50% of the total living headspace volatiles, but it is still less than in the aged leaf and commercial oil. However, cinnaniyl alcohol represents 20% of the fresh volatiles but is only a trace conpcanent of the aged leaf and oil. 4-Methoxy cinnamic aldehyde, identified as a cassia constituent for the first time, also increases 3-fold on drying but has disappeared completely in the comtnercial oil. 2-Methoxy cinnamic aldehyde, sometimes called the character impact component of cassia oil, is present in the headspace of the leaves to only a minor extent but it is the second most abundant component of the oil.

Synonyms Methoxycinnamaldehyde 4-Methoxycinnamaldehyde p-Methoxy cinnamic aldehyde 3-(4-Methoxyphenyl)-2-propenal Propenal, 3-(4-methoxyphenyl)-... 

Pyruvic Acid Compounds.—Lubrzynska and Smedley have recently shown that a number of aldehydes such as heliotropin, anisic aldehyde, benzaldehyde, and cinnamic aldehyde, condense with pyruvic acid in slightly alkaline solution, with the formation of )8-unsaturated-a-ketonic acids. For example, if heliotropin and pyruvic acid in alkaline solution be left standing for about eight days at ordinary temperature, dihydroxy-methylene-benzal-pyruvic acid is formed. This body forms yellow needles, melting at 163° Similarly, anisic aldehyde yields methoxy-benzal-pyruvic acid, melting at 130° and cinnamic aldehyde yields cinnamal-pyruvic acid, melting at 73°. 

For the Cu(OTf)2-promoted reaction between ethyl diazoacetate and cinnam-aldehyde dimethyl acetal, products 143-145 account for only 35% the total yield. C/C and C/H insertion products 151 and 152 are obtained additionally in 49 and 14% yield, respectively154). It was assumed that the copper compound acts through Lewis-acid catalysis here, just as it is believed to do when orthoesters are used as substrates 160). According to this, catalyst-induced formation of a methoxy-... 

Among all these UV-B Sunscreen agents octyl methoxy cinnamate accounts for almost 90% of all the Sunscreen agents and has been occupying a pride of place. Besides, octyl methoxy cinnamate (OMC) also known as 2-ethyl-hexyl cinnamate is produced from p-cresol via p-anisic aldehyde and will be discussed here in some detail. 

Ethyl p-methoxy cinnamate from p-anisic aldehyde and ethyl acetate... 

Soon p-anisic aldehyde produced from p-cresol through the process of methylation of the hydroxy group and subsequent oxidation of the methyl group, turned out to be a very important organic chemical and an attractive outlet of p-cresol. p-Anisic aldehyde is effectively used for making octyl methoxy cinnamate (an UV-B sunscreen chemical) and dilitiazem (an antihypertension drug). Subsequently, a series of downstream derivatives of p-cresol have been synthesized and commercially produced. 

Pinene 2-8% pinene 1-4% myrcene 1-12% of-pheUandrene 1-25% Hmonene 8 30% fenchone 7-16% estragole 2-7% cw-anethole <0.5% rra/ii-anethole 15-40% anise ketone <0.05% tasmanian-type a -pinene 2-11% a-pheUandrene 1-8.5% hmonene 1 % fenchone 10-25% estragole 1.5-6% cis-anethole <0.5% trans-anethole 45-78% anisaldehyde <1% anisketone <0.05% /S-myrcene 0.1-1% hmonene 30-45% trans-dihydrocarvone max. 2.5% carvone 50-65% trans-casrveoh max. 2.5% trans-cinnamic aldehyde 70-90% cinnamyl acetate 1-6% eugenol <0.5% coumarin 1.5-4% rra s-2-methoxy-cinnamaldehyde 3-15%... 

Reactions of the anions (L) of Schiff bases from 5 -a-amino acids and cinnamic aldehyde or 4-methoxy or 2,4-dimethoxy benzaldehyde with [Cp RhCl2]2 gave the (N,0) chelate complexes ds/trans Cp RhCl(L). The complex Cp RhCl[02CCH(CHMe2)N=CH-CH=CHPh] 136 was formed with a high diastereoisomeric excess (9/1). ... 

The conversion of phenylalanine, a C-6—C-3 precursor, to the C-6—C-1 unit of the Amaryllidaceae alkaloids requires the formal loss of two carbon atoms from the side chain of the amino acid as well as the introduction of at least two oxygenated substituents into the aromatic ring. The results shown in the latter part of Table III emphasize the specificity of the C-6—C-1 precursor. Benzaldehyde, -hydroxybenzal-dehyde, isovanillin, and protocatechuic acid are not incorporated to any appreciable extent into the alkaloids, while cinnamic, -hydroxy-cinnamic and caffeic acids, protocatechuic aldehyde, and 3-hydroxy-4-methoxy-i C-A-methyl-i4( ., enzylamine readily become part of the C-6—C-1 unit. 

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