2,5-Dihydroxycinnamic acid

2,5-Dihydroxycinnamic acid
Chemical structure of 2,5-dihydroxycinnamic acid
Names
Preferred IUPAC name
(2E)-3-(2,5-Dihydroxyphenyl)prop-2-enoic acid
Other names
(2E)-3-(2,5-Dihydroxyphenyl)acrylic acid, grevillic acid
Identifiers
CAS Number
  • 38489-67-7 checkY
  • 636-01-1 (non-specific) checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 6442618
PubChem CID
  • 181581
UNII
  • 6EHK92QE99 checkY
InChI
  • InChI=1S/C9H8O4/c10-7-2-3-8(11)6(5-7)1-4-9(12)13/h1-5,10-11H,(H,12,13)
    Key: JXIPYOZBOMUUCA-UHFFFAOYSA-N
  • C1=CC(=C(C=C1O)C=CC(=O)O)O
Properties
Chemical formula
 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).
Infobox references
Chemical compound

2,5-Dihydroxycinnamic acid is a hydroxycinnamic acid derivative. It is an isomer of caffeic acid.

Preparation

2,5-Dihydroxycinnamic acid is produced by Elbs persulfate oxidation of o-coumaric acid.[1][2]

See also

  • Homogentisic acid
  • Gentisic acid

References

  1. ^ Cain, J.C.; Greenaway, A.J. (1907). "Abstracts of Papers on Organic chemistry". Journal of the Chemical Society, Abstracts. 92: A741–A812. doi:10.1039/CA9079200741.
  2. ^ Otto, Neubauer; Flatow, L. (1907). "Synthesen von Alkaptonsäuren". Zeitschrift für Physiologische Chemie. 52 (3–4): 375–398. doi:10.1515/bchm2.1907.52.3-4.375.
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Types of hydroxycinnamic acids
Aglycones
Precursor
  • Cinnamic acid
Monohydroxycinnamic acids
(Coumaric acids)
  • p-Coumaric acid
  • o-Coumaric acid
  • m-Coumaric acid
Dihydroxycinnamic acids
Trihydroxycinnamic acids
O-methylated forms
others
Esters
glycoside-likes
Esters of
caffeic acid
with cyclitols
esters of
quinic acid
  • Chlorogenic acid (3-caffeoylquinic acid)
  • Cryptochlorogenic acid (4-O-caffeoylquinic acid)
  • Neochlorogenic acid (5-O-Caffeoylquinic acid)
  • Cynarine (1,5-dicaffeoylquinic acid)
  • 3,4-dicaffeoylquinic acid
  • 3,5-dicaffeoylquinic acid
esters of
shikimic acid
Glycosides
  • Ferulic acid glucoside
  • p-Coumaric acid glucoside
  • 1-Sinapoyl-D-glucose
Tartaric acid esters
Other esters
with caffeic acid
Caffeoyl phenylethanoid
glycoside (CPG)
  • Echinacoside
  • Calceolarioside A, B, C, F
  • Chiritoside A, B, C
  • Cistanoside A, B, C, D, E, F, G, H
  • Conandroside
  • Myconoside
  • Pauoifloside
  • Plantainoside A
  • Plantamajoside
  • Tubuloside B
  • Verbascoside (Isoverbascoside, 2′-Acetylverbascoside)
Oligomeric forms
Dimers
Trimers
Tetramers
  • Tetraferulic acids
Conjugates with
coenzyme A (CoA)
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