3,5-Dihydroxycinnamic acid

Last updated
3,5-Dihydroxycinnamic acid
3,5-Dihydroxycinnamic acid.svg
Names
Preferred IUPAC name
(2E)-3-(2,4-Dihydroxyphenyl)prop-2-enoic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C9H8O4/c10-7-3-6(1-2-9(12)13)4-8(11)5-7/h1-5,10-11H,(H,12,13)/b2-1+
    Key: MFFCZSWTQMCKFP-OWOJBTEDSA-N
  • InChI=1/C9H8O4/c10-7-3-6(1-2-9(12)13)4-8(11)5-7/h1-5,10-11H,(H,12,13)/b2-1+
    Key: MFFCZSWTQMCKFP-OWOJBTEDBQ
  • c1c(cc(cc1O)O)/C=C/C(=O)O
Properties
C9H8O4
Molar mass 180.159 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3,5-Dihydroxycinnamic acid is a hydroxycinnamic acid. It is an isomer of caffeic acid.

It is a metabolite found in human urine. [1]

Related Research Articles

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Amino acid Organic compounds containing amine and carboxylic groups

Amino acids are organic compounds that contain amino and carboxylic acid functional groups, along with a side chain specific to each amino acid. The elements present in every amino acid are carbon (C), hydrogen (H), oxygen (O), and nitrogen (N) (CHON); in addition sulfur (S) is present in the side chains of cysteine and methionine, and selenium (Se) in the less common amino acid selenocysteine. More than 500 naturally occurring amino acids are known to constitute monomer units of peptides, including proteins, as of 2020 although only 22 appear in the genetic code, 20 of which have their own designated codons and 2 of which have special coding mechanisms: Selenocysteine which is present in all eukaryotes and pyrrolysine which is present in some prokaryotes.

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Carboxylic acid Organic compound

A carboxylic acid is an organic acid that contains a carboxyl group (C(=O)OH) attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

Ester Chemical compounds consisting of a carbonyl adjacent to an ether linkage

An ester is a chemical compound derived from an oxoacid in which at least one –OH hydroxyl group is replaced by an –O– alkyl (alkoxy) group, as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils.

Fatty acid Carboxylic acid

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Fat Esters of fatty acid or triglycerides

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Sulfuric acid Chemical compound

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Boric acid Weak acid of boron

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Lactic acid Group of stereoisomers

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Hydrochloric acid Strong mineral acid

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References

  1. Heindl, A; Rau, O; Spiteller, G (1985). "Identification of aromatic dihydroxy acids in biological fluids". Biomedical Mass Spectrometry. 12 (2): 59–66. doi:10.1002/bms.1200120203. PMID   3158357.