Common Name(2e)-3-(3-hydroxyphenyl)prop-2-enoate
Descriptionm-Coumaric acid, also known as 3-coumarate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. m-Coumaric acid exists in all living organisms, ranging from bacteria to humans. m-Coumaric acid (CAS: 588-30-7) is a polyphenol metabolite from caffeic acid, formed by the gut microflora. Outside of the human body, m-Coumaric acid is found, on average, in the highest concentration within a few different foods, such as olives, corns, and beers. m-Coumaric acid has also been detected, but not quantified in several different foods, such as carrots, strawberries, grape wines, garden tomato, and bilberries. MCT-mediated absorption of phenolic compounds per se and their colonic metabolites would exert a significant impact on human health (PMID:16870009 , 15479001 , 15479001 ). m-Coumaric acid is transported by the monocarboxylic acid transporter (MCT). The amount of this compound in human biofluids is diet-dependant. m-Coumaric acid is detected after the consumption of whole grain.
Structure
Molecular FormulaC9H8O3
Average Mass164.15800
Monoisotopic Mass164.04734
IUPAC Name(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid
Traditional Name3-coumaric acid
CAS Registry Number14755-02-03
SMILESO=C([O-])/C=C/c1cccc(O)c1
InChI IdentifierInChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+
InChI KeyKKSDGJDHHZEWEP-SNAWJCMRSA-N
CHEBI IDCHEBI:47928
HMDB IDHMDB0001713
StateSolid
Water Solubility1.04e+00 g/l
logP1.71
logS-2.20
pKa (Strongest Acidic)4.01
pKa (Strongest Basic)-5.97
Hydrogen Acceptor Count3
Hydrogen Donor Count2
Polar Surface Area57.53 Ų
Rotatable Bond Count2
Physiological Charge-1
Formal Charge0
Refractivity45.04 m³·mol⁻¹
Polarizability16.37

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