2,4,5-Trihydroxycinnamic acid

2,4,5-Trihydroxycinnamic acid
Chemical structure of 2,4,5-trihydroxycinnamic acid.
Names
Preferred IUPAC name
(2E)-3-(2,4,5-Trihydroxyphenyl)prop-2-enoic acid
Other names
2,4,5-THC
(Z)-2,4,5-Trihydroxycinnamic acid
Identifiers
CAS Number
  • 2631046-97-2 ☒N
  • 56437-15-1 (non-specific) checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1765652
ChemSpider
  • 14089396
PubChem CID
  • 25244000
UNII
  • JMT8N4J5PA checkY
InChI
  • InChI=1S/C9H8O5/c10-6-4-8(12)7(11)3-5(6)1-2-9(13)14/h1-4,10-12H,(H,13,14)/b2-1-
    Key: GUOJZFSYQUIYCN-UPHRSURJSA-N
  • OC(=O)\C=C\c(cc1O)c(O)cc1O
Properties
Chemical formula
 C9H8O5
Molar mass 196.158 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

2,4,5-Trihydroxycinnamic acid is a hydroxycinnamic acid found in rooibos tea.[1] cis-2,4,5-Trihydroxycinnamic acid can be isolated from seeds of Alisma orientale.[2]

References

  1. ^ Rabe, Charlene; Steenkamp, Jacobus A.; Joubert, Elizabeth; Burger, Johann F.W.; Ferreira, Daneel (1994). "Phenolic metabolites from rooibos tea (Aspalathus linearis)". Phytochemistry. 35 (6): 1559. doi:10.1016/S0031-9422(00)86894-6.
  2. ^ Zhao, M; Chen, J. Y.; Xu, L. J.; Goedecke, T; Zhang, X. Q.; Duan, J. A.; Che, C. T. (2012). "Cis-aconitic anhydride ethyl ester and phenolic compounds from the seeds of Alisma orientale". Natural Product Communications. 7 (6): 785–7. doi:10.1177/1934578X1200700624. PMID 22816308. S2CID 21479738.


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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
  • 2,4,5-Trihydroxycinnamic acid
  • 3,4,5-Trihydroxycinnamic acid
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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