(1S,4R,5R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one

• ChemBase ID: 152477
• Molecular Formular: C10H16O
• Molecular Mass: 152.23344
• Monoisotopic Mass: 152.12011513
• SMILES: C[C@@H]1[C@H]2C[C@]2(CC1=O)C(C)C
• Canonical SMILES: O=C1C[C@]2([C@@H]([C@H]1C)C2)C(C)C
• InChI: InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8-,10+/m1/s1
• InChIKey: USMNOWBWPHYOEA-MRTMQBJTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4R,5R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one
• IUPAC Traditional name: thujone
• Synonyms: (-)-alpha-Thujone; (1S,4R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one; (-)-α-Thujone; (1S,4R)-1-异丙基-4-甲基双环[3.1.0]己-3-酮; (-)-α-侧柏酮

Database IDs

• CAS Number: 546-80-5
• EC Number: 208-912-2
• MDL Number: MFCD00001313
• Beilstein Number: 4660369
• PubChem SID: 24889199; 162246622
• PubChem CID: 261491

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.2839904
• LogD (pH = 7.4): 2.2839904
• Log P: 2.2839904
• Molar Refractivity: 44.5396 cm^3
• Polarizability: 17.763361 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 147.2 °F; 64 °C
• Density: 0.914 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.450
• Optical Rotation: [α]20/D -19.0±2.0°, neat

Safety Information

• RTECS: XO9625000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96.0% (GC)
• Empirical Formula (Hill Notation): C10H16O

DETAILS

Sigma Aldrich - 89231

Biochem/physiol Actions
GABAA receptor antagonist.
Other Notes
Chiral building block1,2,3
Packaging
1, 5 mL in glass bottle