218359

(S)-(−)-Perillic acid

95%

• Synonym(s): 4-Isopropenylcyclohexene-1-carboxylic acid
• Empirical Formula (Hill Notation): C₁₀H₁₄O₂
• CAS Number: 23635-14-5
• Molecular Weight: 166.22
• MDL number: MFCD00062539
• UNSPSC Code: 12352002
• PubChem Substance ID: 24853062
• NACRES: NA.22

Properties

• assay: 95%
• form: flakes
• optical activity: [α]20/D −102°, c = 2 in methanol
• mp: 129-131 °C (lit.)
• functional group: carboxylic acid
• storage temp.: 2-8°C
• SMILES string: CC(=C)[C@H]1CCC(=CC1)C(O)=O
• 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
• InChI key: CDSMSBUVCWHORP-MRVPVSSYSA-N

Description

General description

(S)-(-)-Perillic acid is a perillyl derivative with potent antimicrobial and anticancer activity. It can be prepared via bio-oxidation of R-(+)-limonene.

Application

(S)-(−)-Perillic acid (PA) can be used as a starting material for the preparation of:,·        

• Aryl amides, 4-(prop-1-en-2-yl)-N-(3-(trifluoromethyl)phenyl)cyclohex-1-ene-1-carboxamide and N-(4-(4-amino-2-methylphenethyl)-3-methylphenyl)-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxamide, as in vitro antiproliferative active agents.
•  Machaeriols and cannabinoid-related compounds as antimalarial agents.   
• Tricyclic-β-lactone by treating with 1-chloro-N,N-2-trimethylpropenylamine and dimethylketomalonate, followed by addition of 9-azajulolidine.

Biochem/physiol Actions

Interferes with activity of p21^ras and other small G proteins by inhibiting post-translational cysteine isoprenylation.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves