o-Coumaric acid

o-Coumaric acid
Skeletal formula of o-coumaric acid
Skeletal formula of o-coumaric acid
Names
Preferred IUPAC name
(2E)-3-(2-Hydroxyphenyl)prop-2-enoic acid
Other names
ortho-Coumaric acid
2-Hydroxycinnamic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.009.444
UNII
  • InChI=1S/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5+
    Key: PMOWTIHVNWZYFI-AATRIKPKSA-N
  • InChI=1/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5+
    Key: PMOWTIHVNWZYFI-AATRIKPKBG
  • C1=CC=C(C(=C1)C=CC(=O)O)O
Properties
C9H8O3
Molar mass 164.16 g/mol
Hazards
GHS labelling:[1]
GHS06: ToxicGHS07: Exclamation mark
Danger
H301, H315, H319, H335
P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.

Natural occurrence

o-Coumaric acid can be found in vinegar.

Biosynthesis

In some plants such as Melilotus species, o-coumaric acid is produced directly from cinnamic acid by the enzyme trans-cinnamate 2-monooxygenase.[2]

2D representation of the chemical structure of cinnamic acid .
cinnamic acid
+ NADPH
 
 
O2 + H+
H2O
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 
2D representation of the chemical structure of O-Coumaric acid.
o-coumaric acid
+ NADP+
 

Metabolism

2-Coumarate reductase is an enzyme that converts o-coumaric acid to melilotic acid using reduced nicotinamide adenine dinucleotide (NADH).[3] This enzyme participates in phenylalanine metabolism.[4]

2D representation of the chemical structure of o-Coumaric acid.
o-coumaric acid
+ NADH
 
 
H+
 
Reversible left-right reaction arrow with minor forward substrate(s) from top left and minor reverse product(s) to bottom left
H+
 
 
2D representation of the chemical structure of Q11751633.
melilotic acid
+ NAD+
 

2-coumarate O-beta-glucosyltransferase forms a glucoside by transferring glucose from UDP-glucose:

o-Coumaric acid + UDP-glucose
 
 
 
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of Q27102443.
melilotoside

This occurs in Melilotus alba and gives uridine diphosphate (UDP) as byproduct.[5]

References

  1. ↑ GHS: PubChem
  2. ↑ Gestetner, Benjamin; Conn, Eric E. (1974). "The 2-hydroxylation of trans-cinnamic acid by chloroplasts from Melilotus alba desr". Archives of Biochemistry and Biophysics. 163 (2): 617–624. doi:10.1016/0003-9861(74)90522-0. PMID 4153528.
  3. ↑ Enzyme 1.3.1.11 at KEGG Pathway Database.
  4. ↑ Levy, Carl C.; Weinstein, Gerald D. (1964). "The Metabolism of Coumarin by a Microorganism. II. The Reduction of o-Coumaric Acid to Melilotic Acid". Biochemistry. 3 (12): 1944–7. doi:10.1021/bi00900a027. PMID 14269315.
  5. ↑ Poulton JE, McRee BE, Conn EE (1980). "Intracellular localization of two enzymes involved in coumarin biosynthesis in Melilotus alba". Plant Physiol. 65 (2): 171–175. doi:10.1104/pp.65.2.171. PMC 440292. PMID 16661155.


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