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

• ChemBase ID: 139112
• Molecular Formular: C10H14O
• Molecular Mass: 150.21756
• Monoisotopic Mass: 150.10446507
• SMILES: CC1=CC(=O)[C@H]2C[C@@H]1C2(C)C
• Canonical SMILES: CC1=CC(=O)[C@H]2C[C@@H]1C2(C)C
• InChI: InChI=1S/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3/t7-,8+/m0/s1
• InChIKey: DCSCXTJOXBUFGB-JGVFFNPUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one
• IUPAC Traditional name: levoverbenone
• Synonyms: (1S,5S)-2-Pinen-4-one; (1S,5S)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one; (1S)-(-)-Verbenone; (-)-4,6,6-三甲基二环[3.1.1]庚-3-烯-2-酮; 马鞭烯酮; 马鞭草烯醇

Database IDs

• CAS Number: 1196-01-6
• EC Number: 214-807-2
• MDL Number: MFCD00065445
• Beilstein Number: 1907623
• PubChem SID: 24902029; 24890073; 24853055; 162233362; 24881158
• PubChem CID: 92874

CALCULATED PROPERTIES

• Acid pKa: 19.843767
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.238156
• LogD (pH = 7.4): 2.238156
• Log P: 2.238156
• Molar Refractivity: 45.3663 cm^3
• Polarizability: 17.524591 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 227-228 °C(lit.)
• Flash Point: 185 °F; 85 °C
• Density: 0.975 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.496(lit.); n20/D 1.497
• Optical Rotation: [α]20/D -140°, c = 10 in ethanol; [α]20/D -142°, neat; [α]20/D -165±10°, neat; [α]20/D -185±25°, neat; [α]25/D -130°, c = 10 in ethanol
• Organoleptic: minty; spicy; vanilla

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: 2-8°C

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥93%; ≥96.0% (sum of enantiomers, GC); ≥99%; ≥99.0% (sum of enantiomers, GC); 94%
• Grade: analytical standard, for terpene analysis; Halal; Kosher; purum
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C10H14O

DETAILS

Sigma Aldrich - 218251

Packaging
10, 50 g in glass bottle

Sigma Aldrich - W506907

Packaging
1 kg in glass bottle
1 sample in glass bottle
100 g in glass bottle
5 kg in poly drum

Sigma Aldrich - 94882

Other Notes
Monoterpenoid chiral building block.; Isomerization to 2(10)-pinen-4-one1; Cyclopentannulation2; Oxidative cleavage to pinononic acid3