(-)-perillic acid

Names

[ Name ]:
(-)-perillic acid

[Synonym ]:
MFCD00062539
Lopac-P-7083
4-Isopropenylcyclohexene-1-carboxylic acid

Biological Activity

[Description]:

(S)-(-)-Perillic acid is a terpenoid plant extract with antimicrobial and anticancer activities. (S)-(-)-Perillic acid induces cell apoptosis and cell cycle arrest, and increases the levell of Bax, Bcl2, p21 and caspase-3 proteins. (S)-(-)-Perillic acid can be used for cancer and infection research[1][2][3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

(S)-(-)-Perillic acid (1.0-3.5 mM；24，48 和 72 小时) 时间和剂量依赖性地抑制动脉平滑肌细胞 (SMCs) 的生长[1]。 (S)-(-)-Perillic acid (1.0-3.5 mM；20 小时) 剂量依赖性地抑制大鼠动脉平滑肌细胞 (SMC) 胸腺嘧啶核内结合[1]。 (S)-(-)-Perillic acid (2.5 mM；24 小时) 阻滞 G0/G1 期细胞周期进程，诱导动脉平滑肌细胞凋亡[1]。 (S)-(-)-Perillic acid (1.0-3.5 mM；20小时) 剂量依赖性抑制 [3H]FOH 和[3H]GGOH 掺入特定低分子量蛋白[1]。 (S)-(-)-Perillic acid (0.5 mM；24小时) 提高 H520 细胞中 Bax，Bcl2，p21 和 caspase-3 蛋白水平[2]。 Cell Viability Assay[2] Cell Line: Human lung cancer A549 cell line Concentration: 0-5 mM Incubation Time: 24 hour Result: Inhibited long-term proliferation of A549 cells with an IC50 value of 3.6 mM.

[References]

[1]. Ferri N, et al. Effect of S(-) perillic acid on protein prenylation and arterial smooth muscle cell proliferation. Biochem Pharmacol. 2001 Dec 15;62(12):1637-45.

[2]. Yeruva L, et al. Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non small cell lung cancer cells. Cancer Lett. 2007 Nov 18;257(2):216-26.

[3]. Khandelia H, et al. Interaction of salicylate and a terpenoid plant extract with model membranes: reconciling experiments and simulations. Biophys J. 2010 Dec 15;99(12):3887-94.

Chemical & Physical Properties

[ Density]:
1.068g/cm3

[ Boiling Point ]:
284.9ºC at 760mmHg

[ Melting Point ]:
129-131ºC(lit.)

[ Molecular Formula ]:
C₁₀H₁₄O₂

[ Molecular Weight ]:
166.21700

[ Flash Point ]:
134ºC

[ Exact Mass ]:
166.09900

[ PSA ]:
37.30000

[ LogP ]:
2.37360

[ Vapour Pressure ]:
0.000746mmHg at 25°C

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
29162000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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