Coniferyl cinnamate

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. 

The major constituents of Sumatra benzoin are p-coumaryl cinnamate, cinnamic acid, cinnamyl cinnamate (styracin), p-coumaryl benzoate, pinoresinol, benzoic acid, coniferyl cinnamate, and coniferyl benzoate. The major constituents of Siam benzoin are p-coumaryl benzoate, benzoic acid, pinoresinol, cinnamic... 

Benzoe resin (also known as benzoin) comes from Styrax spp. (Styraceae family). In the Sty rax genus the only species that occurs in the Mediterranean is Styrax officinalis, so this was probably the source of the resin in ancient times in that area. Benzoe mainly contains free cinnamic and benzoic acids, and their corresponding esters with cinnamyl, p-coumaryl and coniferyl alcohols. The amounts of these compounds are quite variable and depend on which species the resin was obtained from [129]. 

Lignin has a complex structure that varies with the source, growing conditions, etc. This complex and varied structure is typical of many plant-derived macromolecules. Lignin is generally considered as being formed from three different phenylpropanoid alcohols— coniferyl, coumaryl, and sinapyl alcohols, which are synthesized from phenylalanine via various cinnamic acid derivatives and commercially is sometimes treated as being composed of a Cg repeat unit where the superstructure contains aromatic and aliphatic alcohols and ethers, and aliphatic aldehydes and vinyl units. 

Coniferol (Coniferyl Alcohol or 4-Oxy-3-methoxy cinnamic Alcohol), HO.CH2CH CH.C6H3(OH)-. O.CH3 mw 180. 20, O 26.64% col prisms, mp 73-74° v sol in eth sol in ale alkalies dife sol in hot w, almost insol in cold w prepn other props are given in Beil (Ref 1). It is supposed that four moles of coniferol condense to form Lignin, a cellulose-like substance Refs l)Beil 6, 1131 [ 1093] 2)Hackhs (1944), 221 3)Clift Fedoroff 4 (1946), 17... 

This lactone derives from the shikimic acid-cinnamic acid pathway, via oxidative dimerization of coniferyl alcohol. Whereas the presence of yatein itself was not detected in the plants producing steganes, presteganes A and B were isolated in Steganotaenia araliaceae and constitute therefore viable biogenetic precursors [82,83]. 

Fig. 4-2. Simplified reaction route illustrating the formation of lignin precursors. 1, 5-Dehydroquinic acid 2, shikimic acid 3, phenylpyruvic acid 4, phenylalanine 5, cinnamic acid 6, ferulic acid (Ri=H and R2=OCH3), sinapic acid (R,= R2=OCH3), and p-coumaric acid (R1=R2 = H) 7, coniferyl alcohol (Ri = H and R2=OCH3), sinapyl alcohol (Rj = R2=OCH3), and p-coumaryl alcohol (R =R2=H) 8, the corresponding glucosides of 7.

The alcohols formed from some cinnamic acid derivatives, namely /7-coumaryl alcohol, coniferyl alcohol (LI), and sinapyl alcohol (L2), commonly known as monolignols, undergo dimerization reactions that yield lignans such as (-l-)-pinoresinol (L3), (-l-)-sesamin (L4), (-)-matairesinol (L5), and podophyllotoxin (L6) (Fig. 13). Several thousand lignans are found to occur in nature. Lignins, the structural components of plant cell walls, are polymers of monolignols and/or lignans. 

Benzoin, or gum benzoin, is a resinous secretion obtained from cuts made in the trunk or branches of the Styrax benzoin tree. It contains coniferyl benzoate, benzoic acid, benzyl cinnamate, vanillin (a phenol aldehyde) and a number of triterpenes. ... 

Coniferyl Alcohol, 4-(3-Hydroxy l-propenyl -2-mthoxyphetfOl 3 (4 hydroxy 3 methoxyphenyt)-2-propen-1 -of 4-hydroxy-3-methoxy cinnamic alcohol y-hydroxyisoeu-eenol. Ci8H.2Oj mol wt 180.20. C 66.65%, H 6.7 l%> O 26.64%. In benzoin, especially Siam benzoin, as coniferyl benzoate (up to 78%) Reinitzer, Arch. Pharm. 264, 131... 

Gum Benzoin. Resin benzoin resin benjamin gum benjamin. Balsamic resin from Styrax benzoin Dryand., known as Sumatra benzoin, or from S. tonkinensis (Pierre) Craib, Styracaceae, or other species of Styrax known as Siam benzoin. Habit. Thailand, Cambodia, S. Vietnam, Sumatra, Java, and Sunda Islands. Constit. Ethereal oil, free and combined benzoic and cinnamic acids up to 39%, vanillin, coniferyl benzoate, resin (a mixture of benzoresino] and ben-zoresinotannol) ester fled with benzoic acid, styrol, styradn. Not less than 90% of Siam and not less than 75% of Sumatra benzoic is sol in ale (U.S.F.), Ref Reinitzer, Arch. Pharm. 264, 131 (1926) Brans, Pharm. Weekbl. 73, 374 (1936) Freudenberg, Bittner, Ber. 83, 600 (1950). 

The main monolignols are coniferyl, sinapyl, and p-coumaryl alcohols. Cinnamic aldehydes and acids that are biogenetic precursors to the monolignol can also take part in the biosynthesis. This chapter is concerned with the topological aspects of the structnral organisation of lignin. 

Cross colophony, balsam Tolu, cinnamates, benzoates, styrax, benzoin, tiger balm, beeswax, benzaldehyde, benzylsalicylate, coniferyl alcohol, coumarin, eugenol, isoeugenol, farnesol, propanidid, propolis, diethylstilbestrol. May produce erythema-multiforme-like eruptions. PT. ICU, NICU. MYROXYLON PEREIRAE... 

Table 50. Formation of cinnamic alcohol glucosides used in the biosynthesis of lignins by UDP-glucose coniferyl alcohol glucosyltransferase...

The first step of phenylpropanoid biosynthesis is conversion of phenylalanine into cinnamic acid by cleavage of ammonium group by the enzyme phenylalanine ammonia-lyase (PAL). Reduction of carboxylic acid from the cinnamic acid leads to cinnamaldehyde, which is then acylated with acetate from acetyl-CoA to form coniferyl alcohol [14]. Reductive cleavage of coniferyl alcohol by eugenol synthase yields eugenol [15]. 

Lignans and lignins are both composed of the hydroxy cinnamic alcohols (monohgnols) />-cotmiaryl alcohol, coniferyl alcohol, and... 

Fig. 4 Branch of the phenylpropanoid pathway leading to isoeugenol/eugenol and their derivatives. CFAT, coniferyl alcohol acyltransferase C4H, cinnamate 4-hydroxylase 4CL, 4-hydroxycinnamoyl CoA ligase EGS, eugenol synthase lEMT, (iso)eugenol O-methyltransferase IGS, isoeugenol synthase PAL, phenylalanine ammonia lyase...

The biosynthesis of lignin (Fig. 101) starts from the cinnamic acids. / -Coumaric acid, ferulic acid, and sinapic acid are converted to the corresponding alcohols, /7-coumaryl, coniferyl, and sinapyl alcohols. The reduction which this conversion implies takes place with the help of NADPH -h... 

The building blocks of wood lignin are derived from carbohydrates metabolized via a so-called shikimic acid pathway and converted to phenylpropane amino acids (Figure 6.6). These amino acids supply precursors for the s Tithesis of lignin, plant proteins and flavonoids. The first step is the -elimination of ammonia from L-phenylalanine to form fra 5-cinnamic acid. Successive hydroxylation and methylation reactions convert cinnamic acid to />-coumaryl alcohol, caffeyl alcohol, coniferyl alcohol, 5-hydroxyconiferyl alcohol and sinapyl alcohol. Softwood mainly uses coniferyl alcohol with a small amount of p-cou-maryl alcohol. 

---