Fertaric acid

Fertaric acid
Names
(2S,3S)-stereoisomer
IUPAC name 2-Hydroxy-3-{[(2E)-3-(4-hydroxy-3methoxyphenyl)prop-2-enoyl]oxy}butandioic acid
Identifiers
3D model (JSmol)	Interactive image
ChEBI	CHEBI:76120 2S,3S,trans CHEBI:76118 2S,3S,cis CHEBI:76116 2R,3R,trans CHEBI:76115 2R,3R,cis
ChemSpider	20058463^N
PubChem CID	22298372
InChI 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
SMILES Oc1ccc(cc1OC)/C=C/C(=O)OC(C(=O)O)C(O)C(=O)O
Properties
Chemical formula	C₁₄H₁₄O₉
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). N verify (what is ^YN ?) Infobox references

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

^ Branka Mozetič; Irma Tomažič; Andreja Škvarč; Polonca Trebše (2006). "Determination of Polyphenols in White grape Berries cv. Rebula" (PDF). Acta Chim. Slov. 53: 58–64. Archived from the original (PDF) on 2011-08-07.
^ Vanzo, A; Cecotti, R; Vrhovsek, U; Torres, AM; Mattivi, F; Passamonti, S (2007). "The fate of trans-caftaric acid administered into the rat stomach". Journal of Agricultural and Food Chemistry. 55 (4): 1604–11. doi:10.1021/jf0626819. PMID 17300159.

Aglycones

Precursor	Cinnamic acid
Monohydroxycinnamic acids (Coumaric acids)	p-Coumaric acid o-Coumaric acid m-Coumaric acid
Dihydroxycinnamic acids	Caffeic acid (3,4-dihydroxycinnamic acid) Umbellic acid (2,4-dihydroxycinnamic acid) 2,3-Dihydroxycinnamic acid 2,5-Dihydroxycinnamic acid 3,5-Dihydroxycinnamic acid
Trihydroxycinnamic acids	2,4,5-Trihydroxycinnamic acid 3,4,5-Trihydroxycinnamic acid
O-methylated forms	Ferulic acid 5-Hydroxyferulic acid Isoferulic acid Sinapinic acid
others	Plicatin A Plicatin B

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	Dactylifric acid (3-O-caffeoylshikimic acid)

Glycosides

Other esters
with caffeic acid

Caffeoyl phenylethanoid
glycoside (CPG)

Oligomeric forms

Dimers	Diferulic acids (DiFA) : 5,5′-Diferulic acid, 8-<i>O</i>-4′-Diferulic acid, 8,5′-Diferulic acid, 8,5′-DiFA (DC), 8,5′-DiFA (BF), 8,8′-Diferulic acid
Trimers	Triferulic acids : 5-5′,8′-<i>O</i>-4″-Triferulic acid
Tetramers	Tetraferulic acids

Conjugates with
coenzyme A (CoA)

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This page was last edited on 20 December 2023, at 19:58