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

Chemical Properties

Off-White Crystalline Solid

Uses

Different sources of media describe the Uses of 537-73-5 differently. You can refer to the following data:
1. 3-Hydroxy-4-methoxycinnamic Acid (Isoferulic acid) is a hypoglycemic agent.
2. 3-Hydroxy-4-methoxycinnamic acid exhibits hypoglycemic properties.
3. 3-Hydroxy-4-methoxycinnamic acid was used in the synthesis of tranilast and various tranilast analogs (cinnamoyl anthranilates) by genetically engineered Saccharomyces cerevisiae yeast strain. It was also used in the synthesis of glycoside compounds by undergoing glycosidation.

Definition

ChEBI: A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 4 and 3 respectively on the phenyl ring.

General Description

3-Hydroxy-4-methoxycinnamic acid, predominantly trans is available as white crystals. 3-Hydroxy-4-methoxycinnamic acid is isolated from the aerial part of Artemisia capillaris, Chinese medicinal plant. It is a component of chinese herbal medicine used for a pain killer and stomachic. It is an efficient acetylcholine inhibitor. 3-Hydroxy-4-methoxycinnamic acid is bioactive metabolite of Spilanthes acmella Murr. It increases the resistance of low-density lipoprotein (LDL) to oxidation.

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

• 331-39-5 caffeic acid 
• 485-80-3 S-adenosyl-L-methionine 
• 103261-25-2 3-iodo-4-methoxy-trans-cinnamic acid 
• 621-59-0 isovanillin 
• 108-59-8 malonic acid dimethyl ester 
• 773109-21-0 2-[(dimethylamino)methylene]malonate 
• 881-57-2 isovanillin acetate 
• 97966-29-5 methyl (E)-3-(3-hydroxy-4-methoxyphenyl)-2-propenoate 
• 134841-10-4 (2E)-3-[(3-acetyloxy)-4-methoxyphenyl]acrylic acid 
• 113953-02-9 leucosceptoside A 
• 331-39-5 caffeic acid 

Downstream Products

• 97966-29-5 methyl (E)-3-(3-hydroxy-4-methoxyphenyl)-2-propenoate 
• 30461-77-9 methyl 3,4-dimethoxycinnamate 
• 1135-15-5 dihydroisoferulic acid 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 64-19-7 acetic acid 
• 916348-45-3 pentafluorophenyl 3-hydroxy-4-methoxycinnamate 
• 129150-61-4 3-(3-hydroxy-4-methoxyphenyl)-propionic acid methyl ester 
• 143551-94-4 (Z)-3-<3-<4-(3-hydroxy-1-propenyl)phenoxy>-4-methoxyphenyl> propionic acid 
• 143551-93-3 methyl (Z)-3-<3-<4-(3-hydroxy-1-propenyl)phenoxy>-4-methoxyphenyl> propionate 
• 168135-09-9 methyl (Z)-3-<3-<4-(3-t-butyldimethylsilylether-1-propenyl)phenoxy>-4-methoxyphenyl> propionate 
• 168135-08-8 methyl-3-<3-<4-(3-t-butyldimethylsilylether-1-propynyl)phenoxy>-4-methoxyphenyl> propionate 
• 6305-53-9 3-(3-benzyloxy-4-methoxy-phenyl)-propionic acid methyl ester 
• 110037-35-9 3-hydroxyl-4-methoxycinnamic aldehyde 
• 194360-37-7 pentyl 4-methoxy-3-pentyloxycinnamate 

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.

Bioassay of ferulic acid derivatives as influenza neuraminidase inhibitors

Four series of ferulic acid derivatives were designed, synthesized, and evaluated for their neuraminidase (NA) inhibitory activities against influenza virus H1N1 in vitro. The pharmacological results showed that the majority of the target compounds exhibited moderate influenza NA inhibitory activity, which was also better than that of ferulic acid. The two most potent compounds were 1m and 4a with IC50 values of 12.77 ± 0.47 and 12.96 ± 1.34 μg/ml, respectively. On the basis of the biological results, a preliminary structure–activity relationship (SAR) was derived and discussed. Besides, molecular docking was performed to study the possible interactions of compounds 1p, 2d, 3b, and 4a with the active site of NA. It was found that the 4-OH-3-OMe group and the amide group (CON) of ferulic acid amide derivatives were two key pharmacophores for NA inhibitory activity. It is meaningful to further modify the natural product ferulic acid to improve its influenza NA inhibitory activity.

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.