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CAFTARIC ACID

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CAFTARIC ACID Basic information

Product Name:
CAFTARIC ACID
Synonyms:
  • (2R,3R)-2-(((E)-3-(3,4-Dihydroxyphenyl)acryloyl)oxy)-3-hydroxysuccinic acid
  • MONO-(3,4-DIHYDROXYCINNAMOYL)-TARTARIC ACID
  • (2R,3R)-(-)-CAFTARIC ACID)
  • (2E,3R)-2-[[3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY]-3-HYDROXYBUTANEDIOIC ACID
  • CAFTARIC ACID
  • Cafftaric acid
  • 2-Caffeoyl-L-tartaric acid
  • (2R,3R)-2-[(3,4-Dihydroxy-trans-cinnamoyl)oxy]-3-hydroxybutanedioic acid
CAS:
67879-58-7
MF:
C13H12O9
MW:
312.23
Product Categories:
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Miscellaneous Natural Products
Mol File:
67879-58-7.mol
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CAFTARIC ACID Chemical Properties

Melting point:
124~125℃
Boiling point:
618.2±55.0 °C(Predicted)
Density 
1.694±0.06 g/cm3(Predicted)
storage temp. 
Sealed in dry,2-8°C
solubility 
Methanol (Slightly), Water (Slightly, Heated, Sonicated)
pka
2.18±0.25(Predicted)
form 
Solid
color 
White to Pale Beige
Odor
at 100.00?%. odorless
Stability:
Hygroscopic
LogP
1.147 (est)
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Safety Information

WGK Germany 
3
HS Code 
2918290000
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CAFTARIC ACID Usage And Synthesis

Description

Caftaric acid is a phenolic acid and a tartaric acid ester form of caffeic acid . It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) free radicals in a cell-free assay (EC50 = 20.4 μM) and inhibits oxidation of LDL isolated from human plasma by 97.6% compared to vehicle control in vitro when used at a concentration of 5 μM. Caftaric acid is the main phenolic compound in V. vinifera white, pink, and black table grapes as well as various wines. In vivo, caftaric acid content in dietary-administered red wine positively correlates with inhibition of protein carbonylation and decreased superoxide dismutase (SOD), glutathione peroxidase (Gpx), and catalase activities in mice.

Chemical Properties

Soluble in methanol, ethanol, DMSO and other organic solvents, derived from Echinacea purpurea.

Uses

Caftaric Acid is used in cancer therapy as an anticancer drug. Affecting the up regulation or down regulation of drug transporters or cytochrome p450 enzymes. Also provides antioxidant effects, found in wines.

Definition

ChEBI: Caftaric acid is a hydroxycinnamic acid.

target

LDL | NO

References

[1] C. RICE-EVANS G P N Miller. Antioxidant properties of phenolic compounds[J]. Trends in Plant Science, 1997, 2 1: 152-159. DOI: 10.1016/s1360-1385(97)01018-2
[2] D. VILLA?O . Radical scavenging ability of polyphenolic compounds towards DPPH free radical[J]. Talanta, 2007, 71 1: Pages 230-235. DOI: 10.1016/j.talanta.2006.03.050
[3] ANNE S. MEYER. Fruit Hydroxycinnamic Acids Inhibit Human Low-Density Lipoprotein Oxidation in Vitro[J]. Journal of Agricultural and Food Chemistry, 1998, 46 5: 1783-1787. DOI: 10.1021/jf9708960
[4] CHRISTOPHE AUBERT  Guillaume C. Chemical composition, bioactive compounds, and volatiles of six table grape varieties (Vitis vinifera L.)[J]. Food Chemistry, 2018, 240: Pages 524-533. DOI: 10.1016/j.foodchem.2017.07.152
[5] E.F. GRIS . Phenolic profile and effect of regular consumption of Brazilian red wines on in vivo antioxidant activity[C]//31 1. 2013: Pages 31-40. DOI: 10.1016/j.jfca.2013.03.002

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