(4R)-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde

• ChemBase ID: 134476
• Molecular Formular: C10H14O
• Molecular Mass: 150.21756
• Monoisotopic Mass: 150.10446507
• SMILES: CC(=C)[C@@H]1CCC(=CC1)C=O
• Canonical SMILES: O=CC1=CC[C@@H](CC1)C(=C)C
• InChI: InChI=1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,7,10H,1,4-6H2,2H3/t10-/m0/s1
• InChIKey: RUMOYJJNUMEFDD-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde
• IUPAC Traditional name: (4R)-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde
• Synonyms: (4R)-4-(1-Methylethenyl)-1-cyclohexene-1-carboxaldehyde; (+)-Perillaldehyde; (R)-(+)-Perillaldehyde; (R)-4-(Prop-1-en-2-yl)cyclohex-1-ene-1-carboxaldehyde; (R)-Perillaldehyde; (R)-p-Mentha-1,8-dien-7-al; (R)-4-Isopropenylcyclohexene-1-carboxaldehyde; (+)-Perillaaldehyde; (R)-1,8-对孟二烯-7-醛; (R)-4-异丙烯基环己-1-烯-1-醛; (+)-紫苏醛

Database IDs

• CAS Number: 5503-12-8
• MDL Number: MFCD00067159
• Beilstein Number: 2413108
• PubChem SID: 162228752; 24887183
• PubChem CID: 1548901

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.252889
• LogD (pH = 7.4): 2.252889
• Log P: 2.252889
• Molar Refractivity: 47.2721 cm^3
• Polarizability: 18.023672 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ether
• Apperance: Pale Yellow Oil
• Density: 0.966 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.505
• Optical Rotation: [α]20/D +136.0±2°, c = 10% in ethanol

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥98.0% (sum of enantiomers, GC)
• Optical Purity: enantiomeric ratio: ≥99:1 (GC)
• Empirical Formula (Hill Notation): C10H14O

DETAILS

Sigma Aldrich - 77301

Other Notes
Highly purified (+)-perillaaldehyde useful as chiral building block1,2,3

Toronto Research Chemicals - P287400

An additive which contributes spiciness to foods. This compound is also often used as a regent in the preparation of its reduced alcohol, a compound commonly used in perfumery.

REFERENCES

• Hardcastle, I., et al.: Biochem. Pharmacol., 57, 801 (1999)
• Mookdasanit, J., et al.: Food Sci. Technol. Res., 8, 367 (1999)
• Jang, Y., et al.: J. Agric. Food Chem., 53, 7892 (1999)