(S)-(-)-PERILLIC ACID

Names

[ Name ]:
(S)-(-)-PERILLIC ACID

[Synonym ]:
(S)-(-)-perillyc acid
4-(1-methylethenyl)-1-cyclohexene-1-carboxylic acid
(4S)-[2-propenyl]-1-cyclohexene-1-carboxylic acid
4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid
MFCD02114258
4-Isopropenylcyclohex-1-enecarboxylic acid
(S)-(-)-perillic cid
(S)-4-(prop-1-en-2-yl)cyclohex-1-enecarboxylic acid
4-prop-1-en-2-ylcyclohexene-1-carboxylic acid
(S)-(-)-4-isopropenylcyclohexene-1-carboxylic acid
Perillic acid
EINECS 231-709-5
4-Isopropenyl-1-cyclohexene-1-carboxylic acid

Biological Activity

[Description]:

Perillic acid is the metabolite of Perillyl alcohol (HY-N7000). Perillic acid induces lung cancer cell cycle arrest and apoptosis. Perillic acid shows anti-HSV-1 and immunomodulatory activities[1][2][3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> Anti-infection >> HSV

Research Areas >> Infection

Research Areas >> Inflammation/Immunology

[Target]

HSV-1

[In Vitro]

Perillic acid (1-5 mM; 24 h) 以剂量依赖的方式降低 A549 细胞的存活率[1]。 Perillic acid (1 mM; 24 h) 诱导 A549 细胞 S 期阻滞，诱导 H520 细胞 G2/M 期阻滞[1]。 Perillic acid (2 mM; 24 h) 诱导 A549 和 H520 细胞凋亡[1]。 Perillic acid (0-50 μM; 24 h) 显示出主要针对 17syn+ HSV-1 的抗病毒活性 (EC50 KOS: 2.84 μM; 17syn+: 1.08 μM)[2]。 Cell Cytotoxicity Assay[1] Cell Line: A549 cells Concentration: 1, 2, 3, 4 and 5 mM Incubation Time: 24 h Result: Resulted in decreased survival in a dose-dependent manner with an IC50 of 3.6 mM. Cell Cycle Analysis[1] Cell Line: A549 and H520 cells Concentration: 1 mM Incubation Time: 24 h Result: Induced S-phase arrest in A549 cells and induced G2/M arrest in H520 cells. Apoptosis Analysis[1] Cell Line: A549 and H520 cells Concentration: 2 mM Incubation Time: 24 h Result: Increased apoptosis to 27% in A549 and to 18% in H520 cells compared to control (12%). Western Blot Analysis[1] Cell Line: H520 cells Concentration: 0.5 mM Incubation Time: 24 h Result: Increased Bax expression and decreased procaspase-3 levels.

[In Vivo]

Perillic acid (50 μM/kg; i.p.; daily for 5 days) 显示小鼠免疫调节活性[3]。 Animal Model: Balb/c mice[3] Dosage: 50 μM/kg Administration: Intraperitoneal injection, daily for 5 days Result: Increased the total white blood cells (WBC) count. Increased the total antibody production, antibody producing cells in spleen, bone marrow cellularity and α-esterase positive cells significantly compared to the normal animals.

[References]

[1]. 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.

[2]. Mello CP, et al. Perillyl alcohol and perillic acid exert efficient action upon HSV-1 maturation and release of infective virus. Antivir Ther. 2020;25(1):1-11.

[3]. Raphael TJ, et al. Immunomodulatory activity of naturally occurring monoterpenes carvone, limonene, and perillic acid. Immunopharmacol Immunotoxicol. 2003 May;25(2):285-94.

Chemical & Physical Properties

[ Density]:
1.068 g/cm3

[ Boiling Point ]:
284.9ºC at 760 mmHg

[ Melting Point ]:
129-131 °C(lit.)

[ Molecular Formula ]:
C₁₀H₁₄O₂

[ Molecular Weight ]:
166.21700

[ Flash Point ]:
134ºC

[ Exact Mass ]:
166.09900

[ PSA ]:
37.30000

[ LogP ]:
2.37360

[ Index of Refraction ]:
1.513

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
S26-S36

[ WGK Germany ]:
3

[ HS Code ]:
2916209090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2916209090

[ Summary ]:
2916209090 other cyclanic, cyclenic or cyclotherpenic monocarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:6.5% General tariff:30.0%