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Merck
모든 사진(2)

문서

218359

Sigma-Aldrich

(S)-(−)-Perillic acid

95%

동의어(들):

4-Isopropenylcyclohexene-1-carboxylic acid

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모든 사진(2)

About This Item

실험식(Hill 표기법):
C10H14O2
CAS Number:
23635-14-5
Molecular Weight:
166.22
MDL number:
MFCD00062539
UNSPSC 코드:
12352002
PubChem Substance ID:
24853062
NACRES:
NA.22

분석

95%

형태

flakes

광학 활성

[α]20/D −102°, c = 2 in methanol

mp

129-131 °C (lit.)

저장 온도

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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관련 카테고리

일반 설명

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

애플리케이션

(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.

생화학적/생리학적 작용

Interferes with activity of p21ras and other small G proteins by inhibiting post-translational cysteine isoprenylation.

픽토그램

Exclamation mark
GHS07

신호어

Warning

유해 및 위험 성명서

H315,H319,H335

Hazard Classifications

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

표적 기관

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

개인 보호 장비

dust mask type N95 (US), Eyeshields, Gloves

시험 성적서(COA)

제품의 로트/배치 번호를 입력하여 시험 성적서(COA)을 검색하십시오. 로트 및 배치 번호는 제품 라벨에 있는 ‘로트’ 또는 ‘배치’라는 용어 뒤에서 찾을 수 있습니다.

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문서 라이브러리 방문

Natural product derivatization with β -lactones, β -lactams and epoxides toward `infinite?binders
Jouanneau M, et al.
Tetrahedron, 75(24), 3348-3354 (2019)
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)
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

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