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Fertaric acid
(2S ,3S )-stereoisomer
Names
IUPAC name
2-Hydroxy-3-{[(2E )-3-(4-hydroxy-3methoxyphenyl)prop-2-enoyl]oxy}butandioic acid
Identifiers
ChEBI
ChemSpider
InChI=1S/C14H14O9/c1-22-9-6-7(2-4-8(9)15)3-5-10(16)23-12(14(20)21)11(17)13(18)19/h2-6,11-12,15,17H,1H3,(H,18,19)(H,20,21)/b5-3+
Key: XIWXUSFCUBAMFH-HWKANZROSA-N
Oc1ccc(cc1OC)/C=C/C(=O)OC(C(=O)O)C(O)C(=O)O
Properties
C 14 H 14 O 9
Molar mass
326.257 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Fertaric acid is a
hydroxycinnamic acid found in wine and grapes.
[1] It is an ester formed from
ferulic acid bound to
tartaric acid .
It is a metabolite of
caftaric acid after caftaric acid has been fed to rats. Fertaric acid is then found in plasma, kidney, and urine.
[2]
References
Aglycones
Precursor Monohydroxycinnamic acids (Coumaric acids)
Dihydroxycinnamic acids Trihydroxycinnamic acids O -methylated formsothers
Esters
glycoside-likes
Esters of caffeic acid with cyclitols
Glycosides
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
Diferulic acids (DiFA) :
5,5′-Diferulic acid ,
8-O -4′-Diferulic acid ,
8,5′-Diferulic acid ,
8,5′-DiFA (DC) ,
8,5′-DiFA (BF) ,
8,8′-Diferulic acid
Trimers Tetramers
Conjugates with
coenzyme A (CoA)