3-Methoxy-4-hydroxycinnamic acid,

The decarboxylation of 4-hydroxycinnamic acid to 4-hydroxystyrene, and of fernlic acid (3-methoxy-4-hydroxycinnamic acid) to 4-vinylgnaiacol by several strains of Haf-nia alvei and H. protea, and by single strains of Enterobacter cloacae and K. aerogenes (Fignre 2.7d) (Findsay and Priest 1975). The decarboxylase has been pnrihed from Bacillus pumilis (Degrassi et al. 1995). 

The metabolism of ferulic acid (3-methoxy-4-hydroxycinnamic acid) by Ent. cloacae to a nnmber of products including phenylpropionate and benzoate (Fignre 2.8) (Grbic-Galic 1986). 

FIGURE 8.32 Decarboxylation of ferulic acid (3-methoxy-4-hydroxycinnamic acid). 

Hydroxycinnamic acids 1057—see also trans-3,5-Dimethoxy-4-hydroxycinnamic acid, tratts-3-Methoxy-4-hydroxycinnamic acid mass spectra of 285... 

Megaphones, synthesis of 1250, 1252 Mercaptocalix[4]arenes, synthesis of 1402 [l.l.l.l]Metacyclophane framework 322 [l ]Metacyclophanes 1370 Metalation, directed 677 Metathesis reactions 1432 trarw-3-Methoxy-4-hydroxycinnamic acid, as MALDl matrix 323 Methoxylation 1167... 

Norwood et al. (1980) chlorinated a considerable number of phenolic acids of both benzoic and cinnamic acid types and looked for haloform production. Concentrations were from 0.5-6 mM and approximately a twofold excess of chlorine was added. For most of the acids tested, except those with 1,3-dihydroxy (resorcinol-type) substituents, chloroform yields were low (0-4 7o) except in the case of 3-methoxy-4-hydroxycinnamic acid (ferulic acid, 10), where about an 11% yield was... 

CAS 1135-24-6 EINECS/ELINCS 214-490-0 Synonyms Cinnamic acid, 4-hydroxy-3-methoxy- Coniferic acid trans-Ferulic acid 4-Hydroxy-3-methoxycinnamic acid 3-(4-Hydroxy)-3-methoxyphenyl)-2-propenoic acid 3-Methoxy-4-hydroxy-trans-cinnamate 3-Methoxy-4-hydroxycinnamic acid 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-Classification Organic compd. 

Methoxy-4-hydroxy-trans-ci nnamate 3-Methoxy-4-hydroxycinnamic acid. See Ferulic acid... 

Hydroxide ions open the lactone ring of coumarin forming the dianion of the (Z)-o-hydroxycinnamic acid 3 (coumarinic acid) which recylizes to coumarin when acid is added. The dianion 3 can be stabilized as the (2)-methoxy ester 5 by methylation with dimethyl sulfate. However, in prolonged reaction, it changes into the -compound 4 ... 

The intermediacy of o-hydroxycinnamic acid esters (5) in the Pechmann condensation was first proposed by Pechmann in 1884. In 1932, Robertson and co-workers provided support for this proposal through their examination of the reactions of w-methylanisole and dimethylresorcinol with ethyl acetoacetate under the conditions of the Pechmann condensation. Allowing these anisoles to stand with ethyl acetoacetate in sulfuric acid resulted in the formation of 4,7-dimethylcoumarin and 7-methoxy-4-methylcoumarin, respectively. 3 -(2-Methoxy-4-methylphenyl)-2-butenoic acid could likewise be converted to 4,7-dimethylcoumarin under similar conditions. These observations revealed cinnamate intermediates such as 5 to be viable intermediates in the Pechmann condensation and demonstrated that the formation of aryl acetoacetate intermediates such as 4 is not required for coumarin formation. 

Seven chlorogenic and hydroxycinnamic acids (caffeic, p- and o-coumeric, ferulic, 4-methoxy-, 3,4-dimethoxy-, 3,4,5-trimethoxycinnamic) were extracted from green coffee and baseline resolved on a Cjg colunm (A = 320 nm) using a complex 47-min 15/85 - 80/20 methanol/water (1% acetic acid) gradient [374]. Peak shapes were excellent. Linear ranges of 4—400 pg/mL with detection limits of 0.1 pg/mL were reported. 

Table 11.1 Overview of studies for profiling human pathogens with MALDI-TOF MS at the strain level Examples of strain categorization (A), strain differentiation (B), and strain identification (C). MRSA methicillin-resistant Staphylococcus aureus, MSSA methicillin-sensitive S. aureus, L library-based approach, P proteomics-based approach, CHCA a-cyano-4-hydroxycinnamic acid, CMBT 5-chloro-2-mercaptobenzothiazole, DHB 2-hydroxy-5-methoxy benzoic acid, FA ferulic acid, HABA 2,4-hydroxyphenylazobenzoic acid, SA 3,5-dimethoxy-4-hydroxycinnamic acid (sinapinic acid), THAP 2,4,6-trihydroxyacetophenon. Adapted and modified from Sandrin et al. (2013)... 

The most common unsaturated aromatic carboxylic acid is cinnamic acid (8-73). In cinnamon and other spices the (E)-isomer predominates. Cinnamic acid oxidation products are 4-hydroxycinnamic acid (also known as 4-coumaric or p-coumaric acid) and 3,4-dihydroxycinnamic acids, which is called caffeic acid. A 3-methoxy derivative of caffeic acid is feruhc acid and the 3,5-dimethoxy derivative is known as sinapic acid. 

Hydroxyl-functionalized cinnamic acid derivatives such as p-coumaric acid (p-hydroxycinnamic acid), ferulic acid, and sinapinic acid are attractive monomers for syntheses of high-performance polyesters. The obtained polyesters are also expected to be biodegradable in the case of copolymerization with aliphatic hydroxy acids such as lactic acid. Tanaka et al reported the thermal polycondensation of p-coumaric acid at 550 °C without any catalyst under high pressure up to 80 kbar (in the solid state) in 1975. They obtained red or brownish-red hard solids insoluble in conventional organic solvents. Higashi and his co-workers synthesized copolyesters of p-coumaric acid and 4-hydroxybenzoic acid or their methoxy substitutions (ferulic acid, vanillic acid, or syringic acid) by polycondensation using hexachlorocyclotri(phosphazene) in pyridine in 1981. The obtained polymers that exhibited UV spectra different... 

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