2-[(3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol

• ChemBase ID: 127623
• Molecular Formular: C15H26O
• Molecular Mass: 222.36634
• Monoisotopic Mass: 222.19836545
• SMILES: OC([C@H]1CC2=C([C@H](CC1)C)CC[C@@H]2C)(C)C
• Canonical SMILES: C[C@H]1CC[C@H](CC2=C1CC[C@@H]2C)C(O)(C)C
• InChI: InChI=1S/C15H26O/c1-10-5-7-12(15(3,4)16)9-14-11(2)6-8-13(10)14/h10-12,16H,5-9H2,1-4H3/t10-,11-,12+/m0/s1
• InChIKey: TWVJWDMOZJXUID-SDDRHHMPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol
• IUPAC Traditional name: guaiol
• Synonyms: (3R,6S,10S)-6,10,α,α-Tetramethylbicyclo[5.3.0]dec-1(7)-ene-3-methanol; (-)-Guaiol; Champacol; Guaiol; (3R,6S,10S)-6,10,α,α-四甲基二环[5.3.0]癸-1(7)-烯-3-甲醇; (-)-愈创醇

Database IDs

• CAS Number: 489-86-1
• EC Number: 207-702-8
• MDL Number: MFCD00043336
• Beilstein Number: 2047993
• PubChem SID: 24857585; 24868416; 162221941; 24873449
• PubChem CID: 227829
• CHEBI ID: 5552
• CHEMBL: 226915
• Chemspider ID: 198233
• Wikipedia Title: Guaiol

CALCULATED PROPERTIES

• Acid pKa: 19.36938
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 3.4171083
• LogD (pH = 7.4): 3.4171083
• Log P: 3.4171083
• Molar Refractivity: 69.2409 cm^3
• Polarizability: 27.301434 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 91-93 °C; 91-93 °C(lit.)
• Boiling Point: 92°C
• Density: 0.961 g/mL
• Optical Rotation: [α]20/D -28±2°, c = 4% in ethanol; [α]20/D -28°, c = 4 in ethanol; [α]20/D -30.0±2°, 4 hr in ethanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (sum of enantiomers, HPLC); ≥99.0% (HPLC); 97%
• Grade: analytical standard, for terpene analysis; purum
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C15H26O

DETAILS

Sigma Aldrich - 448575

Packaging
50 mg in glass bottle

Sigma Aldrich - 50900

Other Notes
Sesquiterpene alcohol found in the oil of Guaiac wood and the wood oil of other trees1,2; Dehydration with benzoyl chloride and oxidation with tert-butyl chromate leads to a dienone3