(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

• ChemBase ID: 134449
• Molecular Formular: C10H14O
• Molecular Mass: 150.21756
• Monoisotopic Mass: 150.10446507
• SMILES: CC1([C@H]2CC=C([C@@H]1C2)C=O)C
• Canonical SMILES: O=CC1=CC[C@H]2C[C@@H]1C2(C)C
• InChI: InChI=1S/C10H14O/c1-10(2)8-4-3-7(6-11)9(10)5-8/h3,6,8-9H,4-5H2,1-2H3/t8-,9-/m0/s1
• InChIKey: KMRMUZKLFIEVAO-IUCAKERBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
• IUPAC Traditional name: (1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
• Synonyms: (1R)-2-Pinen-10-al; (1R)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-carboxaldehyde; (-)-Myrtenal; (-)-Myrtenal; (1R)-(-)-Myrtenal; (1R)-2-蒎烯-10-醛; (1R)-6,6-二甲基二环[3.1.1]庚-2-烯-2-甲醛; (-)-桃金娘烯醛; (-)-桃金娘烯醛; (1R)-(-)-桃金娘烯醛

Database IDs

• CAS Number: 18486-69-6
• MDL Number: MFCD00074768
• Beilstein Number: 2961587
• PubChem SID: 24901520; 162228725; 24886057; 24853054
• PubChem CID: 1201529
• FEMA ID: 3395
• Council of Europe Number: 10379

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.8347378
• LogD (pH = 7.4): 1.8347378
• Log P: 1.8347378
• Molar Refractivity: 45.5141 cm^3
• Polarizability: 17.524591 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 220-221 °C(lit.)
• Flash Point: 172.4 °F; 78 °C
• Density: 0.987 g/mL at 25 °C(lit.); 0.988 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.503(lit.); n20/D 1.504
• Optical Rotation: [α]20/D -14.6±1°, neat; [α]20/D -15°, neat; [α]22/D -15°, neat
• Organoleptic: berry; honey; lime; vanilla; pepper; minty; woody

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
• Storage Temperature: 2-8°C

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥97%; ≥97.0% (sum of enantiomers, GC); 98%
• Grade: Halal; Kosher; NI
• Empirical Formula (Hill Notation): C10H14O

DETAILS

Sigma Aldrich - 70125

Other Notes
Terpene used as chiral building block, e.g. prep. of thromboxanes1,2; Wittig and Wittig-Horner reactions3,4; Transformation to pinocarveol5

Sigma Aldrich - W339504

Biochem/physiol Actions
Taste at 30 ppm
Other Notes
Natural occurrence: Cumin seed, juniper berry, pepper, peppermint, scotch spearmint.
Packaging
1 kg in glass bottle
1 sample in glass bottle
100, 250 g in glass bottle

Sigma Aldrich - 218243

Packaging
10 g in glass bottle