(4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol

• ChemBase ID: 153156
• Molecular Formular: C10H16O
• Molecular Mass: 152.23344
• Monoisotopic Mass: 152.12011513
• SMILES: CC(=C[C@H](CC(=C)C=C)O)C
• Canonical SMILES: C=CC(=C)C[C@@H](C=C(C)C)O
• InChI: InChI=1S/C10H16O/c1-5-9(4)7-10(11)6-8(2)3/h5-6,10-11H,1,4,7H2,2-3H3/t10-/m1/s1
• InChIKey: NHMKYUHMPXBMFI-SNVBAGLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol
• IUPAC Traditional name: (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol
• Synonyms: (S)-(+)-2-Methyl-6-methylene-2,7-octadien-4-ol; S-Ipsdienol

Database IDs

• CAS Number: 35628-00-3
• MDL Number: MFCD00065437
• PubChem SID: 162247296
• PubChem CID: 92301

CALCULATED PROPERTIES

• Acid pKa: 18.33107
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.306289
• LogD (pH = 7.4): 2.306289
• Log P: 2.306289
• Molar Refractivity: 49.8945 cm^3
• Polarizability: 19.08192 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 188.6 °F; 87 °C
• Optical Rotation: [α]/D +16±3°, c = 1 in methanol

Safety Information

• German water hazard class: 3
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H400
• GHS Precautionary statements: P273
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (HPLC)
• Empirical Formula (Hill Notation): C10H16O

DETAILS

Sigma Aldrich - 16817

Application
S-Ipsdienol has been used to study the genetic control of the enantiomeric composition of ipsdienol in the pine engraver, Ips pini. S-Ipsdienol has also been used to determine that myrcene hydroxylases do not determine enantiomeric composition of pheromonal ipsdienol in Ips spp.