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

• ChemBase ID: 148727
• Molecular Formular: C20H32O2
• Molecular Mass: 304.46688
• Monoisotopic Mass: 304.24023026
• SMILES: C[C@@H]1[C@H]2C[C@]2(CC1=O)C(C)C.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.O=C1C[C@]2([C@@H]([C@H]1C)C2)C(C)C
• InChI: InChI=1S/2C10H16O/c2*1-6(2)10-4-8(10)7(3)9(11)5-10/h2*6-8H,4-5H2,1-3H3/t7-,8+,10-;7-,8-,10+/m01/s1
• InChIKey: AKPBIVZAUPVDMO-APEKEWONSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 76231-76-0
• MDL Number: MFCD00135597
• PubChem SID: 162242902; 24857084; 24889198
• PubChem CID: 45052294

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: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 84-86 °C/17 mmHg(lit.)
• Flash Point: 147.2 °F; 64 °C
• Density: 0.925 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.455(lit.); n20/D 1.46
• Optical Rotation: [α]20/D -15°, neat

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2810
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 23/24/25-36/37/38-42/43
• Safety Statements: 23-26-36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H317-H319-H331-H334-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2810 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ~10% β-thujone basis; ~70% α-thujone basis
• Grade: technical; technical grade
• Impurities: 1.2% limonene; 17.8% fenchone; 2.0% p-cymene
• Empirical Formula (Hill Notation): C10H16O

DETAILS

Sigma Aldrich - 89230

Packaging
10, 50 mL in glass bottle
Preparation Note
isolated from natural oil of cedar-leaves

Sigma Aldrich - 283118

Packaging
5 g in glass bottle