218359

(S)-(−)-Perillic acid

95%

• Synonyme(s) : 4-Isopropenylcyclohexene-1-carboxylic acid
• Formule empirique (notation de Hill): C₁₀H₁₄O₂
• Numéro CAS: 23635-14-5
• Poids moléculaire : 166.22
• Numéro MDL: MFCD00062539
• Code UNSPSC : 12352002
• ID de substance PubChem : 24853062
• Nomenclature NACRES : NA.22

Propriétés

• Pureté: 95%
• Forme: flakes
• Activité optique: [α]20/D −102°, c = 2 in methanol
• Pf: 129-131 °C (lit.)
• Groupe fonctionnel: carboxylic acid
• Température de stockage: 2-8°C
• Chaîne SMILES: 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
• Clé InChI: CDSMSBUVCWHORP-MRVPVSSYSA-N

Description

Description générale

(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.

Actions biochimiques/physiologiques

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

Informations sur la sécurité

• Pictogrammes: GHS07
• Mention d'avertissement: Warning
• Mentions de danger: H315,H319,H335
• Conseils de prudence: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Classification des risques: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Organes cibles: Respiratory system
• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: dust mask type N95 (US), Eyeshields, Gloves