Hydroxycinnamic acid

Class of chemical compounds

Hydroxycinnamic acids (hydroxycinnamates) are a class of aromatic acids or phenylpropanoids having a C6–C3 skeleton. These compounds are hydroxy derivatives of cinnamic acid.

In the category of phytochemicals that can be found in food, there are :

  • α-Cyano-4-hydroxycinnamic acid
  • Caffeic acid – burdock, hawthorn, artichoke, pear, basil, thyme, oregano, apple
  • Cichoric acid
  • Cinnamic acid – aloe
  • Chlorogenic acid – echinacea, strawberries, pineapple, coffee, sunflower, blueberries
  • Diferulic acids
  • Coumaric acid
  • Ferulic acid (3-methoxy-4-hydroxycinnamic acid) – oats, rice, artichoke, orange, pineapple, apple, peanut
  • Sinapinic acid (3,5-dimethoxy-4-hydroxycinnamic acid or sinapic acid)

Hydroxycinnamoyltartaric acids

  • Caftaric acid – grapes and wine,[1] mainly the trans isomer[2]
  • Coutaric acid – grapes and wine, both trans and cis isomers[2]
  • Fertaric acid – grapes and wine, mainly the trans isomer[2]

References

  1. ^ Vallverdú-Queralt, Anna; Verbaere, Arnaud; Meudec, Emmanuelle; Cheynier, Véronique; Sommerer, Nicolas (2015). "Straightforward Method To Quantify GSH, GSSG, GRP, and Hydroxycinnamic Acids in Wines by UPLC-MRM-MS". J. Agric. Food Chem. 63 (1): 142–149. doi:10.1021/jf504383g. PMID 25457918.
  2. ^ a b c Vrhovsek, U. (1998). "Extraction of Hydroxycinnamoyltartaric Acids from Berries of Different Grape Varieties". J. Agric. Food Chem. 46 (10): 4203–8. doi:10.1021/jf980461s.
  • v
  • t
  • e
Types of phenylpropanoids
Classes of phenylpropanoidsExamples
  • v
  • t
  • e
Types of hydroxycinnamic acids
Aglycones
Precursor
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)
  • v
  • t
  • e
Phenolic acids
Monohydroxybenzoic acids
Aglycones
Glycosides
Dihydroxybenzoic acids
Trihydroxybenzoic acids
Other phenolic acids
Hydroxycinnamic acids
Aromatic amino acids
Stub icon

This article about an aromatic compound is a stub. You can help Wikipedia by expanding it.

  • v
  • t
  • e