218359
(S)-(−)-Perillic acid
95%
Synonym(s):
4-Isopropenylcyclohexene-1-carboxylic acid
Sign In to View Organizational & Contract Pricing.
Select a Size
About This Item
Empirical Formula (Hill Notation):
C10H14O2
CAS Number:
Molecular Weight:
166.22
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352002
MDL number:
Assay:
95%
Form:
flakes
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
SMILES string
CC(=C)[C@H]1CCC(=CC1)C(O)=O
InChI key
CDSMSBUVCWHORP-MRVPVSSYSA-N
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
Quality Level
Related Categories
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Bioconversion of R-(+)-limonene to perillic acid by the yeast Yarrowia lipolytica.
Ferrara MA, et al.
Brazilian Journal of Microbiology, 44(4), 1075-1080 (2013)
Felix Klotter et al.
Angewandte Chemie (International ed. in English), 54(29), 8547-8550 (2015-06-17)
Short and highly efficient stereoselective syntheses provide machaeriols and cannabinoids in a divergent approach starting from a common precursor, commercially available (S)-perillic acid. Key features of the novel strategy are a stereospecific palladium-catalyzed decarboxylative arylation and a one-pot sequence comprising
Novel N-arylamide derivatives of (S)-perillic acid ((S)-PA): in vitro and in vivo cytotoxicity and antitumor evaluation
Mukhtar YM, et al.
Royal Society of Chemistry Advances, 9(35), 19973-19982 (2019)
Natural product derivatization with β -lactones, β -lactams and epoxides toward `infinite?binders
Jouanneau M, et al.
Tetrahedron, 75(24), 3348-3354 (2019)
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service