potassium (1R,3R,4S)-1,3,4-trihydroxy-5-oxocyclohexane-1-carboxylate

• ChemBase ID: 156078
• Molecular Formular: C7H9KO6
• Molecular Mass: 228.24106
• Monoisotopic Mass: 228.00361969
• SMILES: C1[C@H]([C@@H](C(=O)C[C@]1(C(=O)[O-])O)O)O.[K+]
• Canonical SMILES: O[C@@H]1C[C@@](O)(CC(=O)[C@H]1O)C(=O)[O-].[K+]
• InChI: InChI=1S/C7H10O6.K/c8-3-1-7(13,6(11)12)2-4(9)5(3)10;/h3,5,8,10,13H,1-2H2,(H,11,12);/q;+1/p-1/t3-,5+,7-;/m1./s1
• InChIKey: XOXNBNMEMILWBJ-HOMRGJANSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: potassium (1R,3R,4S)-1,3,4-trihydroxy-5-oxocyclohexane-1-carboxylate
• IUPAC Traditional name: potassium (-)-3-dehydroquinate
• Synonyms: (1R,3R,4S)-1,3,4-Trihydroxy-5-oxocyclohexanecarboxylic acid potassium salt; 5-Dehydroquinic acid potassium salt; 3-Dehydroquinic acid potassium salt; (1R,3R,4S)-1,3,4-Trihydroxy-5-oxocyclohexanecarboxylic acid 钾盐; 3-Dehydroquinic acid 钾盐; 5-Dehydroquinic acid 钾盐

Database IDs

• CAS Number: 494211-79-9
• MDL Number: MFCD11045271
• PubChem SID: 162250216
• PubChem CID: 23679023

CALCULATED PROPERTIES

• Acid pKa: 3.3044891
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -4.233844
• LogD (pH = 7.4): -5.4804006
• Log P: -2.05525
• Molar Refractivity: 49.5345 cm^3
• Polarizability: 15.559651 Å^3
• Polar Surface Area: 117.89 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D -48±4°, c = 1.5 in H2O

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (TLC)
• Impurities: ~5% water
• Empirical Formula (Hill Notation): C7H9KO6

DETAILS

Sigma Aldrich - 40216

Biochem/physiol Actions
Metabolite of the shikimate pathway, which is required for the synthesis of aromatic compounds in microorganisms and plants.
Citation
Metabolite of the aromatic amino acids pathway; review1