(2R,3R)-2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

• ChemBase ID: 126324
• Molecular Formular: C13H12O9
• Molecular Mass: 312.22898
• Monoisotopic Mass: 312.04813196
• SMILES: O=C(O)[C@H](O)[C@@H](OC(=O)/C=C/c1cc(O)c(O)cc1)C(=O)O
• Canonical SMILES: O=C(O[C@H]([C@H](C(=O)O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O
• InChI: InChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/t10-,11-/m1/s1
• InChIKey: SWGKAHCIOQPKFW-GHMZBOCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid
• IUPAC Traditional name: (2R,3R)-2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid
• Synonyms: 2-Caffeoyl-L-tartaric acid; Caftaric acid; Monocaffeyltartaric acid; Butanedioic acid, 2-(3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)-3-hydroxy-, (R-(R*,R*-(E)))-; trans-caftaric acid; Caftaric acid

Database IDs

• CAS Number: 67879-58-7
• MDL Number: MFCD02094177
• PubChem SID: 162220662
• PubChem CID: 6440397
• CHEMBL: 558557
• Chemspider ID: 4944664
• MeSH Name: caftaric+acid
• Wikipedia Title: Caftaric_acid

CALCULATED PROPERTIES

• Acid pKa: 2.9580286
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -2.9574897
• LogD (pH = 7.4): -5.719278
• Log P: 0.5979602
• Molar Refractivity: 69.7429 cm^3
• Polarizability: 27.008837 Å^3
• Polar Surface Area: 161.59 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 618.2 °C at 760 mmHg
• Flash Point: 236.3 °C

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0%; ≥98.0% (HPLC)
• Grade: analytical standard
• Impurities: ≤10% water; ≤5.0% water
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C13H12O9

DETAILS

Sigma Aldrich - 15029

Application
Caftaric acid has been used in a study that evaluated the myelopoietic effect on bone marrow of rats treated with various Echinacea purpurea extracts. Caftaric acid has also been used in a study that identified (poly)phenolic compounds in concord grape juice and their metabolites in human plasma and urine after juice consumption.