(1S,2S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol

• ChemBase ID: 149391
• Molecular Formular: C10H16O
• Molecular Mass: 152.23344
• Monoisotopic Mass: 152.12011513
• SMILES: CC1=C[C@@H]([C@H]2C[C@@H]1C2(C)C)O
• Canonical SMILES: CC1=C[C@H](O)[C@H]2C[C@@H]1C2(C)C
• InChI: InChI=1S/C10H16O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-9,11H,5H2,1-3H3/t7-,8+,9-/m0/s1
• InChIKey: WONIGEXYPVIKFS-YIZRAAEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol
• IUPAC Traditional name: (1S,2S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol
• Synonyms: (1S,2S)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-ol; (S)-cis-Verbenol; (1S,2S)-4,6,6-三甲基双环[3.1.1]庚-3-烯-2-醇; (S)-顺式-马鞭草烯醇

Database IDs

• CAS Number: 18881-04-4
• EC Number: 242-645-2; 235-908-8
• MDL Number: MFCD00065444
• Beilstein Number: 2206582
• PubChem SID: 24854847; 162243557
• PubChem CID: 87839

CALCULATED PROPERTIES

• Acid pKa: 18.588343
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.6488041
• LogD (pH = 7.4): 1.6488041
• Log P: 1.6488041
• Molar Refractivity: 46.1608 cm^3
• Polarizability: 18.07373 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 62-65 °C; 62-65 °C(lit.)
• Optical Rotation: [α]20/D +10° in ethanol; [α]20/D -9° in chloroform

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: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95% (sum of enantiomers, GC); 95%
• Grade: technical
• Optical Purity: ee: ≥50% (GLC)
• Empirical Formula (Hill Notation): C10H16O

DETAILS

Sigma Aldrich - 247065

Packaging
5, 25 g in glass bottle

Sigma Aldrich - 94879

Analysis Note
α(D) + 10° (c=2 in ethanol) at 50% ee (opt. rotation depends on the solvent)