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beta-elemene

Names

[ CAS No. ]:
515-13-9

[ Name ]:
beta-elemene

[Synonym ]:
(5S,7R,10S)-(-)-1-methyl-1-vinyl-2,4-diisopropenyl-cyclohexane
(1S,2S,4R)-1-methyl-1-vinyl-2,4-diisopropenylcyclohexane
C15 H24,Cyclohexan,1-ethenyl-1-methyl-2,4-bis(1-methylethenyl)
(1S,2S,4R)-1-Ethenyl-1-methyl-2,4-bis(1-methylethenyl)cyclohexane

Biological Activity

[Description]:

β-Elemene ((-)-β-Elemene; Levo-β-elemene) is isolated from natural plant Curcuma wenyujin with an antitumor activity. β-Elemene can induce cell apoptosis.

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer

[In Vitro]

β-Elemene (0-200 µg/ml; 24 hours) shows IC50 values of 72.8 µg/ml; 47.4 µg/ml; 61.5 µg/ml; 3.661 µg/ml; 68 µg/ml; 72.12 µg/ml; 37.894 µg/ml and 37.703 µg/ml for SV-HUC-1, T24, 5637, TCCSUP, J82,UMUC-3,RT4, and SW780 cells, respectively[1]. β-Elemene (0-75 µg/ml; 24 hours) decreases cell number from 50 µg/ml and is notably decreased at 75 µg/ml,  induces dose-dependent G1-phase arrest in T24cells and significantly reduces the percentage of cells in the S-phase [1]. β-Elemene (50 µg/ml; 12 hours) downregulates the expression levels of p-STAT3 and the cell cycle-related proteins cyclin D1, CDK4 and CDK6, and upregulates p21 and p27expression in T24 cells [1]. β-Elemene (50 µg/ml; 24 hours) enhances cisplatin-induced apoptosis by activating the ROS-AMPK signaling pathway[1]. Cell Viability Assay[2] Cell Line: T24, 5637, TCCSUP, J82, UM-UC-3, RT4 and SW780 cells Concentration: 0, 6.25, 12.5, 25, 50, 100, 150 and 200 µg/ml Incubation Time: 24 hours Result: Inhibited the proliferation of RT4, SW780, J82, UMUC-3, TCCSUP, 5637 and T24 human bladder cancer cells and SV-HUC-1 human urothelial cells.  Cell Cycle Analysis[2] Cell Line: T24 and 5637 cells Concentration: 0, 25, 50 and 75 µg/ml Incubation Time: 24 hours Result: Induced the percentage of cells in the S-phase as a dose-dependent manner. Western Blot Analysis[2] Cell Line: T24 cells Concentration: 50 µg/ml Incubation Time: 24 hours Result: Downregulated p-STAT3 and cell cycle-related proteins.

[References]

[1]. Ross, S.A., and ElSohly, M.A. The volatile oil composition of fresh and air-dried buds of Cannabis sativa. J. Nat. Prod. 59(1), 49-51 (1996).

[2]. Gan D, et al. β-elemene enhances cisplatin-induced apoptosis in bladder cancer cells through the ROS-AMPK signaling pathway.Oncol Lett. 2020 Jan;19(1):291-300.

Chemical & Physical Properties

[ Density]:
0.862g/cm3

[ Boiling Point ]:
252.1ºC at 760mmHg

[ Molecular Formula ]:
C15H24

[ Molecular Weight ]:
204.35100

[ Flash Point ]:
98.3ºC

[ Exact Mass ]:
204.18800

[ LogP ]:
4.74720

[ Index of Refraction ]:
1.501

[ Storage condition ]:
2-8°C

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GU9660000
CHEMICAL NAME :
Cyclohexane, 2,4-diisopropenyl-1-methyl-1-vinyl-, (1S,2R,4R)-(-)-
CAS REGISTRY NUMBER :
515-13-9
LAST UPDATED :
198303
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C15-H24
MOLECULAR WEIGHT :
204.39
WISWESSER LINE NOTATION :
L6TJ A1U1 A1 BY1&U1 DY1&U1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
279 mg/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
REFERENCE :
CYTPDT Zhongyao Tongbao. Bulletin of Chinese Materia Medica. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1-13, 1955-88 Suspended 1960-80(?). For Publisher information, see ZZZAE3 Volume(issue)/page/year: 6(6),32,1981

Safety Information

[ Supplemental HS ]:
Repeated exposure may cause skin dryness or cracking.

[ Risk Phrases ]:
66

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
GU9660000

[ HS Code ]:
2902199090

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2902199090

[ Summary ]:
2902199090 other cyclanes, cyclenes and cyclotherpenes。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:2.0%。General tariff:30.0%


Related Compounds

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