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218359

Sigma-Aldrich

(S)-(−)-Perillic acid

95%

Synonym(s):

4-Isopropenylcyclohexene-1-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C10H14O2
CAS Number:
Molecular Weight:
166.22
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22

Assay

95%

form

flakes

optical activity

[α]20/D −102°, c = 2 in methanol

mp

129-131 °C (lit.)

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

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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 p21ras and other small G proteins by inhibiting post-translational cysteine isoprenylation.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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