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

• ChemBase ID: 126588
• Molecular Formular: C22H18O12
• Molecular Mass: 474.37112
• Monoisotopic Mass: 474.07982602
• SMILES: O=C(O)[C@H](OC(=O)/C=C/c1ccc(O)c(O)c1)[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)OC(=O)/C=C/c1ccc(c(c1)O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O
• InChI: InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/t19-,20-/m1/s1
• InChIKey: YDDGKXBLOXEEMN-WOJBJXKFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})butanedioic acid
• IUPAC Traditional name: (2R,3R)-2,3-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})butanedioic acid
• Synonyms: Cichoric acid; (2R,3R)-2,3-Bis{[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy}butanedioic acid; 2,3-Di-trans-caffeoyltartaric acid; no translation; ( -)-Chicoric acid

Database IDs

• CAS Number: 70831-56-0; 6537-80-0
• PubChem SID: 162220918
• PubChem CID: 5281764
• CHEMBL: 282731
• Chemspider ID: 4445078
• KEGG ID: C10437
• Wikipedia Title: Cichoric_acid

CALCULATED PROPERTIES

• Acid pKa: 2.7169409
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -0.564064
• LogD (pH = 7.4): -3.1466255
• Log P: 3.0247202
• Molar Refractivity: 113.2724 cm^3
• Polarizability: 43.271923 Å^3
• Polar Surface Area: 208.12 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Safety Statements: R
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC)
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C22H18O12