537-73-5

Basic information

• Product Name: 3-Hydroxy-4-methoxycinnamic acid
• Synonyms: ISOFERULIC ACID;HESPERETINIC ACID;HESPERETIC ACID;3-HYDROXY-4-METHOXYCINNAMIC ACID;AKOS BBS-00006960;(2E)-3-(3-HYDROXY-4-METHOXYPHENYL)ACRYLIC ACID;RARECHEM BK HW 0093;(2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid
• CAS NO: 537-73-5
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.18
• EINECS: 208-676-0
• Product Categories: Pharmaceutical Raw Materials;Aromatic Cinnamic Acids, Esters and Derivatives;Cinnamic acid;Aromatics Compounds;Aromatics;C10;Carbonyl Compounds;Carboxylic Acids;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 537-73-5.mol
• Article Data: 41

Chemical Properties

• Melting Point: 230 °C (dec.)(lit.)
• Boiling Point: 250.62°C (rough estimate)
• Flash Point: 167.6 °C
• Appearance: Off-white crystalline solid
• Density: 1.0583 (rough estimate)
• Vapor Pressure: 1.83E-07mmHg at 25°C
• Refractive Index: 1.5168 (estimate)
• Storage Temp.: -20?C Freezer
• Solubility: Soluble in ethanol and methanol.
• PKA: 4.53±0.10(Predicted)
• BRN: 2212760
• CAS DataBase Reference: 3-Hydroxy-4-methoxycinnamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxy-4-methoxycinnamic acid(537-73-5)
• EPA Substance Registry System: 3-Hydroxy-4-methoxycinnamic acid(537-73-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25
• WGK Germany: 2
• RTECS: UD3365400
• Hazardous Substances Data: 537-73-5(Hazardous Substances Data)

Usage

Description

3-Hydroxy-4-methoxycinnamic acid, also known as Isoferulic acid, is a bioactive metabolite predominantly found in its trans form as white crystals. It is isolated from the aerial part of the Chinese medicinal plant Artemisia capillaris and is a component of Chinese herbal medicine with various applications, including as a painkiller and stomachic. 3-Hydroxy-4-methoxycinnamic acid is also an efficient acetylcholine inhibitor and increases the resistance of low-density lipoprotein (LDL) to oxidation.

Uses

Used in Pharmaceutical Industry:
3-Hydroxy-4-methoxycinnamic acid is used as a hypoglycemic agent for managing blood sugar levels due to its hypoglycemic properties.
Used in Chemical Synthesis:
3-Hydroxy-4-methoxycinnamic acid is used as a key component in the synthesis of tranilast and various tranilast analogs (cinnamoyl anthranilates) by genetically engineered Saccharomyces cerevisiae yeast strain. It is also utilized in the synthesis of glycoside compounds through glycosidation.
Used in Nutraceutical and Health Supplements:
As an efficient acetylcholine inhibitor and a compound that increases LDL resistance to oxidation, 3-Hydroxy-4-methoxycinnamic acid can be used in the development of nutraceutical and health supplements to support cognitive function and cardiovascular health.
Used in Cosmetics:
Given its antioxidant properties and ability to increase LDL resistance to oxidation, 3-Hydroxy-4-methoxycinnamic acid can be employed in the cosmetics industry for the development of anti-aging and skin protection products.

InChI:InChI=1/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/p-1/b5-3+

Upstream product

• 621-59-0 isovanillin 
• 141-82-2 malonic acid 
• 58435-27-1 3-amino-4-methoxy-cinnamic acid 
• 97966-29-5 methyl (E)-3-(3-hydroxy-4-methoxyphenyl)-2-propenoate 
• 64-19-7 acetic acid 
• 520-26-3 hesperidin 
• 58435-22-6 4-methoxy-3-nitro-cinnamic acid 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 645386-79-4 isoferulic acid 3-O-β-4C1-glucopyranoside 
• 84428-15-9 3-(3-hydroxy-4-methoxyphenyl)acrylic acid ethyl ester 
• 103261-25-2 3-(3-iodo-4-methoxybenzene)acrylic acid 
• 331-39-5 caffeic acid 
• 485-80-3 S-adenosyl-L-methionine 

Downstream Products

• 97966-29-5 methyl (E)-3-(3-hydroxy-4-methoxyphenyl)-2-propenoate 
• 1135-15-5 dihydroisoferulic acid 
• 388566-84-5 (Z)-5-(2'-bromoethenyl)-2-methoxyphenol 
• 3207-31-6 3-(3-acetoxy-4-methoxyphenyl)acrylic acid 
• 30461-77-9 methyl 3,4-dimethoxycinnamate 
• 5396-64-5 methyl (E)-3-(3,4-dimethoxyphenyl)acrylate 
• 77261-98-4 2-(3-Hydroxy-4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 117292-80-5 2-phenylethyl (E)-3-(3-hydroxy-4-methoxyphenyl)acrylate 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 64-19-7 acetic acid 
• 388566-85-6 (E)-5-(2-bromoethenyl)-2-methoxyphenol 
• 916348-45-3 pentafluorophenyl 3-hydroxy-4-methoxycinnamate 
• 891188-86-6 (E)-N,N-diethyl-3-(3-hydroxy-4-methoxyphenyl)acrylamide 

Relevant articles and documents

New long-chained feruloyl ester from the bark of Cedrelinga catenaeformis

Tetradecyl ferulate and a new n-alkyl ester of 3-hydroxy-4-methoxy-trans- cinnamate (hexacosanylisoferulate) have been isolated from Cedrelinga catenaeformis Duke (Leguminoseae). The structures were determined by 1D- and 2D-NMR spectroscopy, mass spectrometry, chemical transformations and finally from unambiguous synthesis. This is the first report of long chained cinnamic acid ester derivative from the genus.

Copper and L-(?)-quebrachitol catalyzed hydroxylation and amination of aryl halides under air

L-(?)-Quebrachitol, a natural product obtained from waste water of the rubber industry, was utilized as an efficient ligand for the copper-catalyzed hydroxylation and amination of aryl halides to selectively give phenols and aryl amines in water or 95percent ethanol. In addition, the hydroxylation of 2-chloro-4-hydroxybenzoic acid was validated on a 100-g scale under air.

Regioselectivity of Cobalamin-Dependent Methyltransferase Can Be Tuned by Reaction Conditions and Substrate

Regioselective reactions represent a significant challenge for organic chemistry. Here the regioselective methylation of a single hydroxy group of 4-substituted catechols was investigated employing the cobalamin-dependent methyltransferase from Desulfitobacterium hafniense. Catechols substituted in position four were methylated either in meta- or para-position to the substituent depending whether the substituent was polar or apolar. While the biocatalytic cobalamin dependent methylation was meta-selective with 4-substituted catechols bearing hydrophilic groups, it was para-selective for hydrophobic substituents. Furthermore, the presence of water miscible co-solvents had a clear improving influence, whereby THF turned out to enable the formation of a single regioisomer in selected cases. Finally, it was found that also the pH led to an enhancement of regioselectivity for the cases investigated.