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

• ChemBase ID: 128564
• Molecular Formular: C16H18O9
• Molecular Mass: 354.30872
• Monoisotopic Mass: 354.09508216
• SMILES: O=C(O)[C@@]1(O)C[C@@H](O)[C@H](O)[C@H](OC(=O)/C=C/c2ccc(O)c(O)c2)C1
• Canonical SMILES: O=C(O[C@@H]1C[C@](O)(C[C@H]([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(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14+,16-/m1/s1
• InChIKey: CWVRJTMFETXNAD-NXLLHMKUSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 906-33-2
• EC Number: 212-997-1
• MDL Number: MFCD10566639
• PubChem SID: 162222871
• PubChem CID: 5280633
• CHEBI ID: 16384
• CHEMBL: 249450
• Chemspider ID: 4444237
• Wikipedia Title: Neochlorogenic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.3338532
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -2.4192955
• LogD (pH = 7.4): -3.6938899
• 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

• Apperance: Powder
• Optical Rotation: [α]/D +11.5±1.5°, c = 0.1 in methanol

Safety Information

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

Product Information

• Purity: ≥95.0% (HPLC); ≥98.0% (HPLC)
• Grade: analytical standard
• Impurities: ≤5.0% water
• Shelf Life: (limited shelf life, expiry date on the label)
• Loss on Drying: ≤3.0% loss on drying
• Empirical Formula (Hill Notation): C16H18O9

DETAILS

Sigma Aldrich - 94419

Biochem/physiol Actions
Neochlorogenic acid is an isomer of chlorogenic acid. Chlorogenic and neochlorogenic acid may function as chemopreventive compounds due to growth inhibition seen in breast cancer cell line MDA-MB-435.1