(1S,3R,4S,5R)-4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,3,5-trihydroxycyclohexane-1-carboxylic acid

• ChemBase ID: 154794
• Molecular Formular: C16H18O9
• Molecular Mass: 354.30872
• Monoisotopic Mass: 354.09508216
• SMILES: c1c(cc(c(c1)O)O)/C=C/C(=O)O[C@H]1[C@@H](C[C@](C[C@H]1O)(O)C(=O)O)O
• Canonical SMILES: O=C(O[C@@H]1[C@H](O)C[C@@](C[C@H]1O)(O)C(=O)O)/C=C/c1ccc(c(c1)O)O
• InChI: InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-14-11(19)6-16(24,15(22)23)7-12(14)20/h1-5,11-12,14,17-20,24H,6-7H2,(H,22,23)/t11-,12-,14-,16+/m1/s1
• InChIKey: GYFFKZTYYAFCTR-NCZKRNLISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,4S,5R)-4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,3,5-trihydroxycyclohexane-1-carboxylic acid
• IUPAC Traditional name: (1S,3R,4S,5R)-4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,3,5-trihydroxycyclohexane-1-carboxylic acid
• Synonyms: 4-O-(3,4-Dihydroxycinnamoyl)-D-quinic acid; Cryptochlorogenic acid; 4-O-Caffeoylquinic acid; 4-O-Caffeoylquinic acid; Cryptochlorogenic acid

Database IDs

• CAS Number: 905-99-7
• MDL Number: MFCD10566638
• PubChem SID: 162248932
• PubChem CID: 9798666

CALCULATED PROPERTIES

• Acid pKa: 3.3907294
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -2.3650498
• LogD (pH = 7.4): -3.680422
• Log P: -0.26852977
• Molar Refractivity: 83.2347 cm^3
• Polarizability: 32.441044 Å^3
• Polar Surface Area: 164.75 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Optical Rotation: [α]/D -76.0±5.0°, c = 0.5 in H2O

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥95.0%; ≥98.0%
• Grade: analytical standard
• Impurities: ≤5.0% residual solvents (GC-HS); ≤5.0% water
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C16H18O9

DETAILS

Sigma Aldrich - 65969

Biochem/physiol Actions
4-O-Caffeoylquinic acid, also known as cryptochlorogenic acid, is an isomer of chlorogenic acid and possesses antioxidant properties.