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

• ChemBase ID: 152052
• Molecular Formular: C32H38O19
• Molecular Mass: 726.63272
• Monoisotopic Mass: 726.200729
• SMILES: c1c(cc(c(c1)O)O)/C=C/C(=O)O[C@H]1[C@@H]([C@@H](C[C@@](C1)(O)C(=O)O)O)O.c1c(cc(c(c1)O)O)/C=C/C(=O)O[C@H]1[C@@H]([C@@H](C[C@@](C1)(O)C(=O)O)O)O.O
• 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.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.O
• InChI: InChI=1S/2C16H18O9.H2O/c2*17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21;/h2*1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23);1H2/t2*11-,12-,14-,16+;/m11./s1
• InChIKey: KMUJVRDSAIKKTF-QTTSOXPBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis((1S,3R,4R,5R)-3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid) hydrate
• IUPAC Traditional name: bis(chlorogenic acid) hydrate
• Synonyms: 3-O-(3,4-Dihydroxycinnamoyl)-D-quinic acid; Chlorogenic acid hemihydrate; 3-O-(3,4-二羟基肉桂酰)-D-奎宁酸; 氯原酸 半水合物

Database IDs

• CAS Number: 6001-76-9
• EC Number: 206-325-6
• MDL Number: MFCD02179353
• Beilstein Number: 3039251
• PubChem SID: 24855563; 162246197
• PubChem CID: 71306904

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: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 206-210 °C (dec.)
• Optical Rotation: [α]20/D -40.5±1°, c = 2.8% in ethanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: rat ... G6pc(25634)

Product Information

• Purity: ≥98.0% (T)
• Impurities: ≤4% water
• Empirical Formula (Hill Notation): C16H18O9 · 0.5H2O

DETAILS

Sigma Aldrich - 25700

Packaging
250 mg in glass bottle