3-Hydroxycinnamic acid (14755-02-3, 588-30-7)

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Suppliers

• Sigma-Aldrich - 3-Hydroxycinnamic acid
  21.10 - 326.00 USD
• Fisher Scientific - Search for 3-Hydroxycinnamic acid
• TCI - 3-Hydroxycinnamic acid
  32.00 - 94.00 USD

Most-cited Publications

• Peroxynitrite scavenging activity of sinapic acid (3,5-dimethoxy-4-hydroxycinnamic acid) isolated from Brassica juncea. (Journal of Agricultural and Food Chemistry, 2002)
• Preferential cytotoxicity to tumor cells of 3,5-diprenyl-4-hydroxycinnamic acid (artepillin C) isolated from propolis. (Anticancer Research, 1997)
• Browning capacity of grapes. 3. Changes and importance of hydroxycinnamic acid-tartaric acid esters during development and maturation of the fruit (Journal of Agricultural and Food Chemistry, 1983)
• Highly sensitive MALDI analyses of glycans by a new aminoquinoline-labeling method using 3-aminoquinoline/-cyano-4-hydroxycinnamic acid liquid matrix. (Analytical Chemistry, 2011)
• Effect of 4-coumaric and 3,4-dihydroxybenzoic acid on oxidative DNA damage in rat colonic mucosa (British Journal of Nutrition, 2003)
• Artepillin C (3,5-diprenyl-4-hydroxycinnamic acid) sensitizes LNCaP prostate cancer cells to TRAIL-induced apoptosis (International Journal of Oncology, 2012)

Areas of Application

Safety

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Trends

Alternate Names

• meta-coumaric acid
• 3-coumaric acid
• 3-coumaric acid, (E)-isomer
• m-coumaric acid
• SMILES
  C1=CC(=CC(=C1)O)C=CC(=O)O
• InChIKey
  KKSDGJDHHZEWEP-UHFFFAOYSA-N

External Links

• Pubchem - 3-Hydroxycinnamic acid
• Wikipedia - 3'-hydroxycinnamic acid
  m-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. m-Coumaric acid can be found in vinegar.

Synthesis

3-hydroxybenzaldehyde  +  ACETIC ANHYDRIDE (Perkin reaction)

glyoxylic acid  +  3-(chloromethyl)phenol (Wittig)

(Z)-3-BROMOACRYLIC ACID  +  3-Chlorophenol (Stille)

3-Vinylphenol  +  Chloroformic acid (Heck terminal vinyl)

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

Synthesis of 3-Hydroxycinnamic acid ›

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3-Hydroxycinnamic acid

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