Caftaric Acid
Basic information
- CAS
67879-58-7- Standard SMILES
O=C(/C=C/c1ccc(O)c(O)c1)O[C@@H](C(=O)O)[C@@H](O)C(=O)O- InChIKey
SWGKAHCIOQPKFW-JTNORFRNSA-N- Molecular formula
- C13H12O9
- Average molar mass
- 312.23 g/mol
- Monoisotopic mass
- 312.04813196
Overview
Caftaric acid is a hydroxycinnamic acid.
Names & identifiers
- Preferred name
- Caftaric Acid
- IUPAC
- (2R,3R)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-hydroxybutanedioic acid
- English name
- Caftaric acid
- Molecular formula
- C13H12O9
- Molecular weight
- 312.23
Names & synonyms
caftaric acid67879-58-7(2R,3R)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-hydroxybutanedioic acidWCV7W3174LDTXSID3036866(2R,3R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acidButanedioic acid, 2-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-3-hydroxy-, (2R,3R)-(2R,3R)-2-(((2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy)-3-hydroxybutanedioic acid(2R,3R)-2-((E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy-3-hydroxybutanedioic acidRefChem:122671DTXCID50819886614-155-2
Show more names
CaftaricaciCafftaric acidCaftaric acid-RMCafeoyl tartaric acidtrans-Caffeoyl tartrateCAFTARIC ACID USP/EP/BP(2R,3R)-(-)-CAFTARIC ACID)
trans-caftaric acid2-Caffeoyl-L-tartaric acidmonocaffeoyltartaric acidCaffeoyltartaric acidCaftaric acid (Standard)MFCD02094177Caftaric acid , HPLC Grade(2R,3R)-2-(((E)-3-(3,4-Dihydroxyphenyl)acryloyl)oxy)-3-hydroxysuccinic acid
Database identifiers
- CAS
67879-58-7- PubChem CID
- 6440397
- DTXSID
DTXSID3036866- ChEMBL
CHEMBL499757、CHEMBL558557- ChEBI
CHEBI:174975- UNII
- WCV7W3174L
- EC Number
- 614-155-2
- Nikkaji
- J323.016C、J404.659E
Properties
Computed structural properties
- XLogP
- 0.1
- Topological polar surface area
- 162 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 7
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 458
Experimental & physicochemical properties
Boiling Point618.2 °C at 760 mmHg
Melting Point125 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 124 · 124~125℃
- Boiling point
- 618.2 · 618.2±55.0 °C(Predicted)
- Density
- 1.694 · 1.694±0.06 g/cm3(Predicted)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- Methanol (Slightly), Water (Slightly, Heated, Sonicated)
- form
- Solid
- pka
- 2.18 · 2.18±0.25(Predicted)
- color
- White to Pale Beige
- Odor
- 100 % · at 100.00%. odorless
- Stability
- Hygroscopic
- Major Application
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.
Not Classified
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- wgk
- 3
- hs_code
- 2918290000
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
DescriptionCaftaric 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.
UsesCaftaric 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.
Additional notes
DefinitionChEBI: Caftaric acid is a hydroxycinnamic acid.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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