p-Coumaric acid

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P-coumaric acid
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p-Coumaric acid
Skeletal formula of p-coumaric acid
Ball-and-stick model of p-coumaric acid
Names
Preferred IUPAC name
(2E)-3-(4-Hydroxyphenyl)prop-2-enoic acid
Other names
(E)-3-(4-Hydroxyphenyl)-2-propenoic acid
(E)-3-(4-Hydroxyphenyl)acrylic acid
para-Coumaric acid
4-Hydroxycinnamic acid
β-(4-Hydroxyphenyl)acrylic acid
Identifiers
3D model (
JSmol
)
2207383
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
 100.116.210 Edit this at Wikidata
EC Number
  • 231-000-0
2245630
IUPHAR/BPS
KEGG
UNII
  • InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+ checkY
    Key: NGSWKAQJJWESNS-ZZXKWVIFSA-N checkY
  • InChI=1/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11, 12)/b6-3+/f/h11H
  • InChI=1/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
    Key: NGSWKAQJJWESNS-ZZXKWVIFBJ
  • C1=CC(=CC=C1\C=C\C(=O)O)O
  • c1cc(ccc1/C=C/C(=O)O)O
Properties
C9H8O3
Molar mass 164.160 g·mol−1
Melting point 210 to 213 °C (410 to 415 °F; 483 to 486 K)
Hazards
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Danger
H301, H302, H311, H314, H315, H317, H319, H335
P260, P261, P264, P270, P271, P272, P280, P301+P310, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P333+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

p-Coumaric acid is an organic compound with the formula HOC6H4CH=CHCO2H. It is one of the three isomers of hydroxycinnamic acid. It is a white solid that is only slightly soluble in water but very soluble in ethanol and diethyl ether.

Natural occurrences

It is a precursor to many natural products, especially lignols, precursors to the woody mass that comprise many plants.[1] Of the myriad occurrences, p-coumaric acid can be found in Gnetum cleistostachyum.[2]

In food

p-Coumaric acid can be found in a wide variety of edible plants and fungi such as peanuts, navy beans, tomatoes, carrots, basil and garlic.[citation needed] It is found in wine and vinegar.[3] It is also found in barley grain.[4]

p-Coumaric acid from pollen is a constituent of honey.[5]

Derivatives

flaxseed.[6] Diesters of p-coumaric acid can be found in carnauba wax
.

Biosynthesis

It is biosynthesized from

4-cinnamic acid hydroxylase
(C4H).

cinnamic acid   para-coumaric acid

It is also produced from L-

tyrosine ammonia lyase
(TAL).

L-Tyrosine   para-coumaric acid + NH3 + H+

Biosynthetic building block

p-Coumaric acid is the precursor of

Vinyl phenol reductase then catalyzes the reduction of 4-vinylphenol to 4-ethylphenol. Coumaric acid is sometimes added to microbiological media
, enabling the positive identification of Brettanomyces by smell.

The conversion of p-coumaric acid to 4-ethyphenol by Brettanomyces

4′-O-β-D-glucosyl-cis-p-coumarate and uridine diphosphate (UDP). This enzyme belongs to the family of glycosyltransferases, specifically the hexosyltransferases.[8]

Phloretic acid, found in the rumen of sheep fed with dried grass, is produced by hydrogenation of the 2-propenoic side chain of p-coumaric acid.[9]

The enzyme,

resveratrol synthase, also known as stilbene synthase, catalyzes the synthesis of resveratrol ultimately from a tetraketide derived from 4-coumaroyl CoA.[10]

p-Coumaric acid is a cofactor of photoactive yellow proteins (PYP), a homologous group of proteins found in many eubacteria.[11]

See also

References

  1. doi:10.1146/annurev.arplant.54.031902.134938
  2. S2CID 37661785
    .
  3. S2CID 91784893
    .
  4. PMID 17177530
    .
  5. PMID 23630255
    .
  6. PMID 26047292
    .
  7. ^ "Brettanomyces Monitoring by Analysis of 4-ethylphenol and 4-ethylguaiacol". etslabs.com. Archived from the original on 2008-02-19.
  8. doi:10.1016/S0031-9422(97)00337-3
    .
  9. PMID 16346090
    .
  10. PMID 28168876
    .
  11. PMID 7947803
    .
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