(4S)-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid

• ChemBase ID: 149701
• Molecular Formular: C10H14O2
• Molecular Mass: 166.21696
• Monoisotopic Mass: 166.09937969
• SMILES: CC(=C)[C@H]1CCC(=CC1)C(=O)O
• Canonical SMILES: CC(=C)[C@H]1CCC(=CC1)C(=O)O
• InChI: InChI=1S/C10H14O2/c1-7(2)8-3-5-9(6-4-8)10(11)12/h5,8H,1,3-4,6H2,2H3,(H,11,12)/t8-/m1/s1
• InChIKey: CDSMSBUVCWHORP-MRVPVSSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid
• IUPAC Traditional name: (4S)-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid
• Synonyms: 4-Isopropenylcyclohexene-1-carboxylic acid; (S)-(-)-Perillic acid; 4-异丙烯基环己烯-1-羧酸; (S)-(-)-紫苏酸

Database IDs

• CAS Number: 23635-14-5
• MDL Number: MFCD00062539
• PubChem SID: 162243863; 24853062
• PubChem CID: 2724160

CALCULATED PROPERTIES

• Acid pKa: 4.9914436
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.7860719
• LogD (pH = 7.4): 0.03294759
• Log P: 2.4115052
• Molar Refractivity: 48.1975 cm^3
• Polarizability: 18.445261 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 129-131 °C(lit.)
• Optical Rotation: [α]20/D -102°, c = 2 in methanol

Safety Information

• 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: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C10H14O2

DETAILS

Sigma Aldrich - 218359

Biochem/physiol Actions
Interferes with activity of p21ras and other small G proteins by inhibiting post-translational cysteine isoprenylation.
Packaging
1 g in glass bottle