Physicochemical Properties
| Molecular Formula | C₁₅H₂₄ |
| Molecular Weight | 204.35 |
| Exact Mass | 204.188 |
| CAS # | 515-13-9 |
| Related CAS # | 515-13-9 |
| PubChem CID | 6918391 |
| Appearance | Colorless to light yellow liquid |
| Density | 0.862g/cm3 |
| Boiling Point | 252.1ºC at 760mmHg |
| Flash Point | 98.3ºC |
| Index of Refraction | 1.501 |
| LogP | 4.747 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 15 |
| Complexity | 284 |
| Defined Atom Stereocenter Count | 3 |
| SMILES | C=C[C@]1(C)CC[C@H](C[C@H]1C(=C)C)C(=C)C |
| InChi Key | OPFTUNCRGUEPRZ-QLFBSQMISA-N |
| InChi Code | InChI=1S/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,13-14H,1-2,4,8-10H2,3,5-6H3/t13-,14+,15-/m1/s1 |
| Chemical Name | (1S,2S,4R)-1-ethenyl-1-methyl-2,4-bis(prop-1-en-2-yl)cyclohexane |
| Synonyms | β-Elemene; (-)-β-Elemene; Levo-β-elemene |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | β-elemene (0 - 200 μg/mL; 24 hours) had IC50 values of 72.8 μg/mL; 47.4 against SV-HUC-1, T24, 5637, TCCSUP, J82, UMUC-3, RT4, and SW780 cells, respectively; 61.5 μg/mL; 3.661 μg/mL; 68 μg/mL; and 72.12 μg/mL[1]. β-elemene (0-75 μg/mL; 24 hours) caused a dose-dependent G1 workforce in T24 cells, significantly decreased the proportion of S phase, and started to diminish cell counts at 50 μg/ml with a considerable decrease at 75 μg/ml [1]. In T24 cells, β-elemene (50 μg/mL; 12 hours) upregulates the expression of p21 and p27 and duplicates the expression levels of p-STAT3 and cell cycle-related proteins, cyclin D1, CDK4, and CDK6 [1]. β-elemene readily increases cisplatin by triggering ROS-AMPK signaling (50 μg/mL; 24 hours). |
| Cell Assay |
Cell Viability Assay[2] Cell Types: T24, 5637, TCCSUP, J82, UM-UC-3, RT4 and SW780 cells Tested Concentrations: 0, 6.25, 12.5, 25, 50, 100 Induced cells are sterile[1]. , 150 and 200 µg/ml Incubation Duration: 24 hrs (hours) Experimental Results: Inhibits 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 Types: T24 and 5637 Cell Tested Concentrations: 0, 25, 50 and 75 µg/ml Incubation Duration: 24 hrs (hours) Experimental Results: The percentage of cells in S phase was induced in a dose-dependent manner. Western Blot Analysis[2] Cell Types: T24 Cell Tested Concentrations: 50 µg/ml Incubation Duration: 24 hrs (hours) Experimental Results: Downregulation of 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]. β-elemene enhances cisplatin-induced apoptosis in bladder cancer cells through the ROS-AMPK signaling pathway.Oncol Lett. 2020 Jan;19(1):291-300. |
| Additional Infomation |
(-)-beta-elemene is the (-)-enantiomer of beta-elemene that has (1S,2S,4R)-configuration. It has a role as an antineoplastic agent. beta-Elemene has been reported in Calypogeia muelleriana, Neolitsea aciculata, and other organisms with data available. Beta-elemene is one of the isomers of elemene, a lipid soluble sesquiterpene and the active component isolated from the Chinese medicinal herb Rhizoma zedoariae with potential antineoplastic and chemopreventive activities. Although the exact mechanism of action through which beta-elemene exerts its effect has yet to be fully elucidated, this agent appears to induce apoptosis through different mechanisms of action and induces cell cycle arrest at different stages based on the tumor cell type involved. Beta-elemene may sensitize cancer cells to other chemotherapeutic agents. See also: Cannabis sativa subsp. indica top (part of). |
Solubility Data
| Solubility (In Vitro) |
Ethanol: ~50 mg/mL (~244.68 mM) DMSO: ~50 mg/mL (~244.68 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.23 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (12.23 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (12.23 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.8936 mL | 24.4678 mL | 48.9356 mL | |
| 5 mM | 0.9787 mL | 4.8936 mL | 9.7871 mL | |
| 10 mM | 0.4894 mL | 2.4468 mL | 4.8936 mL |