(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid

• ChemBase ID: 119502
• Molecular Formular: C7H12O6
• Molecular Mass: 192.16658
• Monoisotopic Mass: 192.0633881
• SMILES: [C@@]1(C[C@H]([C@H]([C@@H](C1)O)O)O)(C(=O)O)O
• Canonical SMILES: O[C@@H]1[C@H](O)C[C@@](C[C@H]1O)(O)C(=O)O
• InChI: InChI=1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5-,7+/m1/s1
• InChIKey: AAWZDTNXLSGCEK-WYWMIBKRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
• IUPAC Traditional name: (-)-quinic acid
• Synonyms: 1,3,4,5-Tetrahydroxy-(1α,3R,4α,5R)-cyclohexanecarboxylic acid; D-(-)-Quinic acid; Quinic acid; (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid; D-(-)-奎宁酸; D-(-)-奎尼酸

Database IDs

• CAS Number: 77-95-2
• EC Number: 201-072-8
• MDL Number: MFCD00003864
• Beilstein Number: 2212412
• Merck Index: 148059
• PubChem SID: 162103189; 24853523; 24848361
• PubChem CID: 6508
• CHEBI ID: 17521
• CHEMBL: 465398
• Chemspider ID: 10246715
• Wikipedia Title: Quinic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.4612226
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -4.7242117
• LogD (pH = 7.4): -6.0818987
• Log P: -2.6952899
• Molar Refractivity: 39.7052 cm^3
• Polarizability: 16.201815 Å^3
• Polar Surface Area: 118.22 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 162-167°C; 165-170 °C; 168°C
• Density: 1.35 g/cm3
• Optical Rotation: [α]20/D -43.9°, c = 11.2 in H2O; [α]20/D -44±1°, c = 20% in H2O; -44 (c=20 in water)

Safety Information

• RTECS: GU8650000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38-43
• Safety Statements: 24-26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• NFPA704:
  

  0

  0

  0
• GHS Hazard statements: H315-H319-H317-H335
• GHS Precautionary statements: P280G-P262-P305+P351+P338
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (T); 98%
• Grade: purum
• Ignition Residue: ≤0.1%
• Empirical Formula (Hill Notation): C7H12O6
• Classification: Rare Genuine Natural Compounds

DETAILS

Sigma Aldrich - 138622

Packaging
25, 100 g in poly bottle

Sigma Aldrich - 22580

Other Notes
Use as chiral building block1,2; and references cited therein.

REFERENCES

• Chiral starting material, used for example in the synthesis of the angucycline antibiotics urdamycinone B and 104-2: J. Am. Chem. Soc., 117, 8472 (1995).