2,3-Dihydroxycinnamic acid

2,3-Dihydroxycinnamic acid
Chemical structure of 2,3-dihydroxycinnamic acid
Names
Preferred IUPAC name
(2E)-3-(2,3-Dihydroxyphenyl)prop-2-enoic acid
Other names
trans-2,3-Dihydroxycinnamate
3-(2,3-Dihydroxyphenyl)acrylic acid
Identifiers
CAS Number
  • 31082-90-3 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 4445343
PubChem CID
  • 5282146
UNII
  • 8EU63XMR43 checkY
CompTox Dashboard (EPA)
  • DTXSID601030503 Edit this at Wikidata
InChI
  • InChI=1S/C9H8O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-5,10,13H,(H,11,12)/b5-4+
    Key: SIUKXCMDYPYCLH-SNAWJCMRSA-N
  • InChI=1/C9H8O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-5,10,13H,(H,11,12)/b5-4+
    Key: SIUKXCMDYPYCLH-SNAWJCMRBO
  • c1cc(c(c(c1)O)O)/C=C/C(=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

2,3-Dihydroxycinnamic acid is a hydroxycinnamic acid. It is an isomer of caffeic acid.

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

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.


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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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