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2-Methoxycinnamic acid

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CAS:6099-03-2
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  • 2025-08-08
  • CAS:6099-03-2
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  • Purity: 99%
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  • 2-Methoxycinnamic acid
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  • 2025-06-27
  • CAS:6099-03-2
  • Min. Order: 1KG
  • Purity: 99%
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2-Methoxycinnamic acid Basic information
Product Name:2-Methoxycinnamic acid
Synonyms:Cinnamic acid, o-methoxy-;RARECHEM BK HC T255;O-METHOXYCINNAMIC ACID;TRANS-O-METHYL-O-COUMARIC ACID;TRANS-O-METHYL-O-CUMARIC ACID;TRANS-2-METHOXYCINNAMIC ACID;TRANS-3-(2-METHOXYPHENYL)ACRYLIC ACID;METHOXYCINNAMIC ACID,2-
CAS:6099-03-2
MF:C10H10O3
MW:178.18
EINECS:228-047-4
Product Categories:C10;Carbonyl Compounds;Carboxylic Acids;Aromatic Cinnamic Acids, Esters and Derivatives;11
Mol File:6099-03-2.mol
2-Methoxycinnamic acid Structure
2-Methoxycinnamic acid Chemical Properties
Melting point 182-186 °C
Boiling point 250.41°C (rough estimate)
density 1.1479 (rough estimate)
refractive index 1.5088 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form powder
pkapK1:4.462 (25°C)
color White
BRN 2209714
InChIInChI=1S/C10H10O3/c1-13-9-5-3-2-4-8(9)6-7-10(11)12/h2-7H,1H3,(H,11,12)
InChIKeyFEGVSPGUHMGGBO-UHFFFAOYSA-N
SMILESC(O)(=O)C=CC1=CC=CC=C1OC
LogP2.418 (est)
CAS DataBase Reference6099-03-2(CAS DataBase Reference)
NIST Chemistry Reference2-Propenoic acid, 3-(2-methoxyphenyl)-(6099-03-2)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-37/39-36
WGK Germany 3
HazardClass IRRITANT
HS Code 29189900
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
2-Methoxycinnamic acid Usage And Synthesis
Chemical Propertieslight yellow crystalline powder
Uses(E)-3-(2-Methoxyphenyl)acrylic Acid is a noncompetitive inhibitor of tyrosinase.
DefinitionChEBI: (E)-2-methoxycinnamic acid is a member of the class of cinnamic acids that is trans-cinnamic acid carrying a methoxy substituent at position 2 on the benzene ring. It has a role as a Brassica napus metabolite and an EC 1.14.18.1 (tyrosinase) inhibitor. It is a member of cinnamic acids and a monomethoxybenzene. It is functionally related to a trans-cinnamic acid.
Synthesis
Malonic acid

141-82-2

o-Anisaldehyde

135-02-4

2-Methoxycinnamic acid

6099-03-2

To a 500 mL three-necked round-bottomed flask was added o-methoxybenzaldehyde (20 g, 146.90 mmol, 1.00 eq.), pyridine (250 mL), malonic acid (18.3 g, 175.86 mmol, 1.20 eq.) and piperidine (2.5 g, 29.36 mmol, 0.20 eq.). The reaction mixture was stirred at 85°C overnight. Upon completion of the reaction, most of the solvent was removed by distillation under reduced pressure, followed by adjusting the pH of the remaining solution with aqueous hydrochloric acid to 3.0. The precipitated solid was collected by filtration to afford 25.6 g (98% yield) of 2-methoxycinnamic acid as a white solid.

References[1] Patent: WO2014/182950, 2014, A1. Location in patent: Paragraph 00322; 00323
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 336 - 343
[3] Journal of the Indian Chemical Society, 1988, vol. 65, # 3, p. 187 - 191
[4] Molecules, 2009, vol. 14, # 10, p. 4166 - 4179
[5] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 15, p. 4513 - 4519
2-Methoxycinnamic acid Preparation Products And Raw materials
Raw materialsAcetic acid-->Malonic acid-->o-Anisaldehyde-->Piperidine-->Pyridine
Preparation Products3-(2-METHOXY-PHENYL)-PROPIONALDEHYDE
Tag:2-Methoxycinnamic acid(6099-03-2) Related Product Information
Ethyl 2-(Chlorosulfonyl)acetate trans-Cinnamic acid alpha-Methylcinnamic acid N-BUTYL CINNAMATE Ethyl cinnamate 4-Hydroxycinnamic acid Folic acid Methyl cinnamate Acrylic acid Cinnamic acid o-Anisic acid o-Anisaldehyde Citric acid Ascoric Acid 3,4-Dimethoxycinnamonitrile 3,4,5-Trimethoxycinnamic acid 3-BROMO-4-HYDROXY-5-METHOXYCINNAMIC ACID 3-HYDROXY-4-METHOXYCINNAMIC ACID

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