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

• 621-59-0 isovanillin 
• 141-82-2 malonic acid 
• 64-19-7 acetic acid 
• 331-39-5 caffeic acid 
• 485-80-3 S-adenosyl-L-methionine 
• 90-05-1 2-methoxy-phenol 
• 331-39-5 caffeic acid 
• 74-88-4 methyl iodide 
• 134841-10-4 (2E)-3-[(3-acetyloxy)-4-methoxyphenyl]acrylic acid 
• 520-26-3 hesperidin 
• 103261-25-2 3-iodo-4-methoxy-trans-cinnamic acid 
• 108-59-8 malonic acid dimethyl ester 
• 773109-21-0 2-[(dimethylamino)methylene]malonate 
• 881-57-2 isovanillin acetate 

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 
• 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 
• 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 

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.

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.

Structural features and antioxidant activities of Chinese quince (Chaenomeles sinensis) fruits lignin during auto-catalyzed ethanol organosolv pretreatment

Chinese quince fruits (Chaenomeles sinensis) have an abundance of lignins with antioxidant activities. To facilitate the utilization of Chinese quince fruits, lignin was isolated from it by auto-catalyzed ethanol organosolv pretreatment. The effects of three processing conditions (temperature, time, and ethanol concentration) on yield, structural features and antioxidant activities of the auto-catalyzed ethanol organosolv lignin samples were assessed individually. Results showed the pretreatment temperature was the most significant factor; it affected the molecular weight, S/G ratio, number of β-O-4′ linkages, thermal stability, and antioxidant activities of lignin samples. According to the GPC analyses, the molecular weight of lignin samples had a negative correlation with pretreatment temperature. 2D-HSQC NMR and Py-GC/MS results revealed that the S/G ratios of lignin samples increased with temperature, while total phenolic hydroxyl content of lignin samples decreased. The structural characterization clearly indicated that the various pretreatment conditions affected the structures of organosolv lignin, which further resulted in differences in the antioxidant activities of the lignin samples. These results can be helpful for controlling and optimizing delignification during auto-catalyzed ethanol organosolv pretreatment, and they provide theoretical support for the potential applications of Chinese quince fruits lignin as a natural antioxidant in the food industry.