beta-elemene

Modify Date: 2024-01-01 21:34:28

beta-elemene Structure
beta-elemene structure
 Common Name beta-elemene
CAS Number 515-13-9 Molecular Weight 204.35100
Density 0.862g/cm3 Boiling Point 252.1ºC at 760mmHg
Molecular Formula C15H24 Melting Point N/A
MSDS USA Flash Point 98.3ºC

 Use of beta-elemene


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

 Names

Name β-ELEMENE 82%
Synonym More Synonyms

 beta-elemene 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
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

 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

1,3-dimethyl-2-(((1S,2S,3S,6S)-3-methyl-2,6-di(prop-1-en-2-yl)-3-vinylcyclohexyl)oxy)-1,3,2-diazaphospholidine 2-oxide structure

1,3-dimethyl-2-...

CAS#:873691-52-2

~94%

beta-elemene Structure

beta-elemene

CAS#:515-13-9

Literature: Huang, Lan Patent: US2006/14987 A1, 2006 ; Location in patent: Page/Page column 5; 10 ;
(-)-β-elemene-6-one structure

(-)-β-elemene-6-one

CAS#:38655-85-5

~%

beta-elemene Structure

beta-elemene

CAS#:515-13-9

Literature: Huang, Lan Patent: US2006/14987 A1, 2006 ; Location in patent: Page/Page column 4-5 ;
(+)-germacrene A structure

(+)-germacrene A

CAS#:28028-64-0

~99%

beta-elemene Structure

beta-elemene

CAS#:515-13-9

Literature: Faraldos, Juan A.; Wu, Shuiqin; Chappell, Joe; Coates, Robert M. Tetrahedron, 2007 , vol. 63, # 32 p. 7733 - 7742
Germacrone structure

Germacrone

CAS#:6902-91-6

~%

beta-elemene Structure

beta-elemene

CAS#:515-13-9

Literature: Barrero, Alejandro F.; Herrador, M. Mar; Quilez Del Moral, Jose F.; Arteaga, Pilar; Meine, Niklas; Perez-Morales, M. Carmen; Catalan, Julieta V. Organic and Biomolecular Chemistry, 2011 , vol. 9, # 4 p. 1118 - 1125
[4S,(+)]-2-Isopropylidene-4β-isopropenyl-5α-vinyl-5-methylcyclohexanone structure

[4S,(+)]-2-Isop...

CAS#:20303-60-0

~%

beta-elemene Structure

beta-elemene

CAS#:515-13-9

Literature: Barrero, Alejandro F.; Herrador, M. Mar; Quilez Del Moral, Jose F.; Arteaga, Pilar; Meine, Niklas; Perez-Morales, M. Carmen; Catalan, Julieta V. Organic and Biomolecular Chemistry, 2011 , vol. 9, # 4 p. 1118 - 1125
alpha-elemol structure

alpha-elemol

CAS#:639-99-6

~%

beta-elemene Structure

beta-elemene

CAS#:515-13-9

Literature: Ganter,C.; Keller-Wojtkiewicz,B. Helvetica Chimica Acta, 1971 , vol. 54, p. 183 - 205
(1S)-1r-methyl-4c-(α-benzoyloxy-isopropyl)-1-vinyl-2c-isopropenyl-cyclohexane structure

(1S)-1r-methyl-...

CAS#:83426-07-7

~%

beta-elemene Structure

beta-elemene

CAS#:515-13-9

Literature: Patil,L.J. et al. Indian Journal of Chemistry, 1966 , vol. 4, p. 400 - 402

 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%

 Synonyms

(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
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