(1r,4r)-4-(propan-2-yl)cyclohexane-1-carboxylic acid

• ChemBase ID: 68068
• Molecular Formular: C10H18O2
• Molecular Mass: 170.24872
• Monoisotopic Mass: 170.13067982
• SMILES: [C@@H]1(CC[C@@H](CC1)C(C)C)C(=O)O
• Canonical SMILES: CC([C@@H]1CC[C@H](CC1)C(=O)O)C
• InChI: InChI=1S/C10H18O2/c1-7(2)8-3-5-9(6-4-8)10(11)12/h7-9H,3-6H2,1-2H3,(H,11,12)/t8-,9-
• InChIKey: YRQKWRUZZCBSIG-KYZUINATSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1r,4r)-4-(propan-2-yl)cyclohexane-1-carboxylic acid
• IUPAC Traditional name: (1r,4r)-4-isopropylcyclohexane-1-carboxylic acid
• Synonyms: trans-4-Isopropylcyclohexanecarboxylic acid; trans-4-(propan-2-yl)cyclohexane-1-carboxylic acid; trans-4-(1-Methylethyl)cyclohexanecarboxylic Acid; trans-p-Menthan-7-oic Acid

Database IDs

• CAS Number: 7077-05-6
• MDL Number: MFCD04004145
• PubChem SID: 162033800
• PubChem CID: 81526

CALCULATED PROPERTIES

• Acid pKa: 5.005544
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.2940385
• LogD (pH = 7.4): 0.54327315
• Log P: 2.9087634
• Molar Refractivity: 47.5441 cm^3
• Polarizability: 18.930742 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.284

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95%; 95+%

DETAILS

Toronto Research Chemicals - I824400

trans-4-Isopropylcyclohexanecarboxylic acid is an intermediate used in the process for the preparation of Nateglinide (N379375), a novel D-phenylalanine-derivative hypoglycemic agent.

REFERENCES

• Kletzien, R., et al.: Mol. Pharmacol., 41, 393 (1992)
• Amos, A., et al.: Diabet. Med., 14, S7 (1992)
• Henke, B., et al.: J. Med. Chem., 41, 5020 (1992)
• Wagman, A., et al.: Curr. Pharm. Des., 7, 417 (1992)