Caftaric acid

Base Information

• Chemical Name: Caftaric acid
• CAS No.: 67879-58-7
• Deprecated CAS: 72880-50-3
• Molecular Formula: C13H12O9
• Molecular Weight: 312.233
• Hs Code.: 2918290000
• European Community (EC) Number: 614-155-2
• UNII: WCV7W3174L
• DSSTox Substance ID: DTXSID3036866
• Nikkaji Number: J404.659E,J323.016C,J909.755D
• Wikipedia: Caftaric_acid
• Wikidata: Q5017207
• Metabolomics Workbench ID: 42475
• ChEMBL ID: CHEMBL558557
• Mol file: 67879-58-7.mol

Synonyms:caftaric acid

Chemical Property of Caftaric acid

Chemical Property:

• Appearance/Colour: White Powder
• Vapor Pressure: 3.85E-16mmHg at 25°C
• Melting Point: 124-125 °C
• Refractive Index: 1.694
• Boiling Point: 618.2 °C at 760 mmHg
• PKA: 2.18±0.25(Predicted)
• Flash Point: 236.3 °C
• PSA: 161.59000
• Density: 1.694 g/cm³
• LogP: -0.44710
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly), Water (Slightly, Heated, Sonicated)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 312.04813196
• Heavy Atom Count: 22
• Complexity: 458

Purity/Quality:

95%-98% ^*data from raw suppliers

Caftaric acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C=CC(=O)OC(C(C(=O)O)O)C(=O)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1/C=C/C(=O)O[C@H]([C@H](C(=O)O)O)C(=O)O)O)O
• 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.
• 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.

Technology Process of Caftaric acid

There total 1 articles about Caftaric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

bis(diphenylmethyl) 2-(3,4-di(tert-butyldimethylsilyloxy)cinnamoyl)-3-hydroxy-L-tartrate → caftaric acid (67879-58-7,1234-09-9)

Guidance literature:

With acetic acid; for 10h; Reflux;

DOI:10.1021/jm1010594

Reference yield: 75.0%

3-mercapto-1-hexanol (90180-88-4,90180-90-8,51755-83-0) + caftaric acid (67879-58-7,1234-09-9) → 2'-(3''-sulfanylhexan-1''-ol)caftaric acid

Guidance literature:

With polyphenol oxidase; L-Tartaric acid; oxygen; In water; at 20 ℃; for 1h; pH=3.5; Enzymatic reaction;

DOI:10.1021/jf204295s

Reference yield:

caftaric acid (67879-58-7,1234-09-9) → L-Tartaric acid (87-69-4,138508-61-9) + caffeic acid (331-39-5,501-16-6)

Guidance literature:

With chlorogenate esterase; In aq. phosphate buffer; at 37 ℃; for 4h; pH=7; Reagent/catalyst; Enzymatic reaction;

Downstream raw materials:

L-Tartaric acid

caffeic acid

Refernces