beta-Elemene (CHEM029696)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:20:50 UTC
Update Date2016-11-09 01:18:56 UTC
Accession NumberCHEM029696
Identification
Common Namebeta-Elemene
ClassSmall Molecule
DescriptionThe (-)-enantiomer of beta-elemene that has (1S,2S,4R)-configuration.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1S,2S,4R)-(-)-1-Methyl-1-vinyl-2,4-diisopropenylcyclohexaneChEBI
(1S,2S,4R)-1-Methyl-2,4-di(prop-1-en-2-yl)-1-vinylcyclohexaneChEBI
(1S,2S,4R)-2,4-Diisopropenyl-1-methyl-1-vinylcyclohexaneChEBI
2,4-Diisopropenyl-1-methyl-1-vinylcyclohexaneChEBI
beta-ElemenChEBI
Levo-beta-elemeneChEBI
b-ElemenGenerator
Β-elemenGenerator
Levo-b-elemeneGenerator
Levo-β-elemeneGenerator
b-ElemeneGenerator
Β-elemeneGenerator
(-)-b-ElemeneHMDB
(-)-beta-ElemeneHMDB
beta-ElemeneChEBI
(-)-β-ElemeneGenerator
(1S,2S,4R)-1-Ethenyl-1-methyl-2,4-bis(1-methylethenyl)cyclohexanePhytoBank
(±)-beta-ElemenePhytoBank
(±)-β-ElemenePhytoBank
Chemical FormulaC15H24
Average Molecular Mass204.351 g/mol
Monoisotopic Mass204.188 g/mol
CAS Registry Number33880-83-0
IUPAC Name(1S,2S,4R)-1-ethenyl-1-methyl-2,4-bis(prop-1-en-2-yl)cyclohexane
Traditional Nameβ-elemene
SMILESCC(=C)[C@@H]1CC[C@@](C)(C=C)[C@@H](C1)C(C)=C
InChI IdentifierInChI=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
InChI KeyOPFTUNCRGUEPRZ-QLFBSQMISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentElemane sesquiterpenoids
Alternative Parents
Substituents
  • Elemane sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.004 g/LALOGPS
logP5.4ALOGPS
logP4.74ChemAxon
logS-4.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity68.23 m³·mol⁻¹ChemAxon
Polarizability25.97 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-055f-9300000000-0289c8de75fe9d63ecbeSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a5c-9300000000-5b0ee4d8b7869c2f1150Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-055f-9300000000-0289c8de75fe9d63ecbeSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a5c-9300000000-5b0ee4d8b7869c2f1150Spectrum
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-00kf-9500000000-bf13cd3bd5550f5ba5c9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0080-5900000000-01235238c52dcbb6dd6bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1790000000-453c5a1555b65a45bbf6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ri-4910000000-01642b086e5ae7d47ddfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9300000000-8a8cfd7c816b632bb230Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-c96ee5d6723e9d3e562cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-650d4bfb37438f455f35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1900000000-0f6b74b8fa42644d3cd0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg0-0940000000-2cbeadbe4dfea2ed5383Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-059i-0910000000-4293e9b1be9fc1d09c27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05cr-9710000000-733055659972947a1171Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9300000000-b061378f98f19194e1c5Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0061848
FooDB IDFDB014577
Phenol Explorer IDNot Available
KNApSAcK IDC00007453
BiGG IDNot Available
BioCyc IDCPD-8232
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID5293588
ChEBI ID62855
PubChem Compound ID6918391
Kegg Compound IDC17094
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12058328
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15868411
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15868412
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19128976
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21246417
6. Li Z, Wang K, Chen YR, Wu XY, Su CY: [Studies on metabolite of beta-elemene in rat bile]. Yao Xue Xue Bao. 2000 Nov;35(11):829-31.
7. Wang K, Su CY: [Pharmacokinetics and disposition of beta-elemene in rats]. Yao Xue Xue Bao. 2000 Oct;35(10):725-8.
8. Zou L, Liu W, Yu L: [beta-elemene induces apoptosis of K562 leukemia cells]. Zhonghua Zhong Liu Za Zhi. 2001 May;23(3):196-8.
9. Chen SL, You J, Wang GJ: [Supercritical fluid extraction of beta-elemene under lower pressure]. Se Pu. 2001 Mar;19(2):179-81.
10. Wang K, Li Z, Chen YR, Wu XY, Li SY, Su CY: [Excretion of beta-elemene from rat respiratory tracts]. Yao Xue Xue Bao. 2005 Jan;40(1):54-6.
11. Zhang BJ, Li WC, Liu XP: [The pharmacokinetics of long-circulating beta-elemene liposomes]. Zhong Yao Cai. 2012 Sep;35(9):1464-8.
12. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
13. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
14. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
15. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
16. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
17. The lipid handbook with CD-ROM
18. YUREN CHEN, 'BETA-ELEMENE, METHOD TO PREPARE THE SAME AND USES THEREOF.' U.S. Patent US20020155522, issued October 24, 2002.: http://www.google.ca/patents/US20020155522
19. Yuren Chen, 'Beta-elemene, method to prepare the same and uses thereof.' U.S. Patent US20030216605, issued November 20, 2003.: http://www.google.ca/patents/US20030216605
20. Lan Huang, 'Synthesis of beta-elemene, intermediates thereto, analogues and uses thereof.' U.S. Patent US20060014987, issued January 19, 2006.: http://www.google.ca/patents/US20060014987