(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexan-1-ol

• ChemBase ID: 147724
• Molecular Formular: C16H24O
• Molecular Mass: 232.36116
• Monoisotopic Mass: 232.18271539
• SMILES: C[C@@H]1CC[C@H]([C@@H](C1)O)C(C)(C)c1ccccc1
• Canonical SMILES: C[C@@H]1CC[C@H]([C@@H](C1)O)C(c1ccccc1)(C)C
• InChI: InChI=1S/C16H24O/c1-12-9-10-14(15(17)11-12)16(2,3)13-7-5-4-6-8-13/h4-8,12,14-15,17H,9-11H2,1-3H3/t12-,14-,15-/m1/s1
• InChIKey: WTQIZFCJMGWUGZ-BPLDGKMQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexan-1-ol
• IUPAC Traditional name: (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexan-1-ol
• Synonyms: (-)-Phenmenthol; (-)-8-Phenylmenthol; (-)-8-苯基薄荷醇

Database IDs

• CAS Number: 65253-04-5
• MDL Number: MFCD00010501
• Beilstein Number: 3651167
• PubChem SID: 162241908; 24859793; 24887371
• PubChem CID: 2725001

CALCULATED PROPERTIES

• Acid pKa: 14.914905
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 4.098124
• LogD (pH = 7.4): 4.098124
• Log P: 4.098124
• Molar Refractivity: 72.0154 cm^3
• Polarizability: 28.595251 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 113 °C; 235.4 °F
• Density: 0.999 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.53(lit.); n20/D 1.531
• Optical Rotation: [α]20/D -26±1.5°, c = 2% in ethanol; [α]20/D -26°, c = 2 in ethanol

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (sum of enantiomers, HPLC); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C16H24O

DETAILS

Sigma Aldrich - 329487

Packaging
1 g in glass bottle
250 mg in glass bottle

Sigma Aldrich - 78805

Other Notes
Important chiral auxiliary. Used as chiral directing group in many types of reactions, e.g. DA-cycloadditions1,2; Ene reactions of glyoxylate ester3; 1,4-Addition to enoates4; Reduction of or Grignard addition to glyoxylate ester5