2-Hydroxycinnamic acid (583-17-5, 614-60-8)

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Suppliers

• Sigma-Aldrich - 2-Hydroxycinnamic acid
  27.20 - 96.00 USD
• Fisher Scientific - Search for 2-Hydroxycinnamic acid
• TCI - 2-Hydroxycinnamic acid
  22.00 - 63.00 USD

Most-cited Publications

• Characterization of hydroxycinnamic acid glucuronide and sulfate conjugates by HPLCDADMS2: Enhancing chromatographic quantification and application in Caco-2 cell metabolism (Journal of Pharmaceutical and Biomedical Analysis, 2011)
• The effect of temperature on the stability of compounds used as UV-MALDI-MS matrix: 2,5-dihydroxybenzoic acid, 2,4,6-trihydroxyacetophenone, -cyano-4-hydroxycinnamic acid, 3,5-dimethoxy-4-hydroxycinnamic acid, nor-harmane and harmane (Journal of Mass Spectrometry, 2009)
• Unsaturated polyamides and polyesters prepared from 1,4bis(2carboxyvinyl)benzene and 4hydroxycinnamic acid (Journal of Polymer Science Part A, 1996)
• Molecular and crystal structures of two matrices for MALDI-TOF-MS : 2-(4-hydroxyphenylazo)benzoic acid and 3,5-dimethoxy-4-hydroxycinnamic acid (Journal of Molecular Structure, 2005)
• 2,5-Dihydroxybenzoic acid instead of -cyano-4-hydroxycinnamic acid as matrix in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry for analyses of in-gel digests of silver-stained proteins (Analytical Biochemistry, 2007)
• Bioactivities of caffeic acid methyl ester (methyl-(E)-3-(3,4-dihydroxyphenyl)prop-2-enoate): a hydroxycinnamic acid derivative from Solanum melongena L. fruits (Journal of Pest Science, 2013)

Safety

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Trends

Alternate Names

• 2-hydroxycinnamic acid, (Z)-isomer
• 2-hydroxycinnamic acid, (E)-isomer
• ortho-hydroxycinnamic acid
• SMILES
  C1=CC=C(C(=C1)C=CC(=O)O)O
• InChIKey
  PMOWTIHVNWZYFI-UHFFFAOYSA-N

External Links

• Pubchem - 2-Hydroxycinnamic acid
• Wikipedia - (2E)-2-hydroxycinnamic acid
  o-Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers of coumaric acids - o-coumaric acid, m-coumaric acid, and p-coumaric acid- that differ by the position of the hydroxy substitution of the phenyl group.

Synthesis

glyoxylic acid  +  o-Hydroxybenzylchloride (Wittig)

SALICYLALDEHYDE  +  ACETIC ANHYDRIDE (Perkin reaction)

Vinylphenol  +  Chloroformic acid (Heck terminal vinyl)

(Z)-3-BROMOACRYLIC ACID  +  2-CHLOROPHENOL (Stille)

Reactant  +  dimethyl sulfide (Corey-Kim oxidation of secondary alcohols)

Synthesis of 2-Hydroxycinnamic acid ›

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2-Hydroxycinnamic acid

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