Coutaric acid

Coutaric acid
Names

IUPAC name (2R,3R)-2-Hydroxy-3-(((E)-3-(4-hydroxyphenyl)acryloyl)oxy)succinic acid
Other names trans-coutaric acid cis-coutaric acid trans-p-Coumaroyltartaric acid cis-p-coumaroyl-(+)-tartaric acid trans-p-coumaroyl-(+)-tartaric acid cis-Coumaroyl tartaric acidbr>trans-Coumaroyl tartaric acid
Identifiers
CAS Number	27174-07-8^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:77439^N
ChemSpider	26325199^N
InChI InChI=1S/C13H12O8/c14-8-4-1-7(2-5-8)3-6-9(15)21-11(13(19)20)10(16)12(17)18/h1-6,10-11,14,16H,(H,17,18)(H,19,20)/b6-3+/t10-,11-/m1/s1^N Key: INYJZRKTYXTZHP-NNPIPJJVSA-N^N InChI=1/C13H12O8/c14-8-4-1-7(2-5-8)3-6-9(15)21-11(13(19)20)10(16)12(17)18/h1-6,10-11,14,16H,(H,17,18)(H,19,20)/b6-3+/t10-,11-/m1/s1 Key: INYJZRKTYXTZHP-NNPIPJJVBX
SMILES c1cc(ccc1/C=C/C(=O)O[C@H]([C@H](C(=O)O)O)C(=O)O)O
Properties
Chemical formula	C₁₃H₁₂O₈
Molar mass	296.23 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

Coutaric acid is an hydroxycinnamoyltartaric acid found in wine, pomace^[1] and grape.^[2] It is an ester formed from coumaric acid and tartaric acid.

References

↑ Maier, T.; Sanzenbacher, S.; Kammerer, D. R.; Berardini, N.; Conrad, J. R.; Beifuss, U.; Carle, R.; Schieber, A. (2006). "Isolation of hydroxycinnamoyltartaric acids from grape pomace by high-speed counter-current chromatography". Journal of Chromatography A. 1128 (1–2): 61–67. doi:10.1016/j.chroma.2006.06.082. PMID 16860334.
↑ Singleton, V. L.; Zaya, J.; Trousdale, E. K. (1986). "Caftaric and coutaric acids in fruit of Vitis". Phytochemistry. 25 (9): 2127. doi:10.1016/0031-9422(86)80078-4.

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

Tartaric acid esters

Other esters
with caffeic acid

Caffeoyl phenylethanoid
glycoside (CPG)

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	Triferulic acids : 5-5',8'-O-4"-Triferulic acid

Tetramers	Tetraferulic acids

Conjugates with
coenzyme A (CoA)

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