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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 23:27:07 UTC
Update Date2020-04-17 14:50:46 UTC
HMDB IDHMDB0038169
Secondary Accession Numbers
  • HMDB38169
Metabolite Identification
Common Namebeta-Myrcene
Descriptionbeta-Myrcene, also known as 7-methyl-3-methylene-1,6-octadiene, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, beta-myrcene is considered to be an isoprenoid lipid molecule. beta-Myrcene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. beta-Myrcene is found in allspice and many essential oils (e.g. hop oil). beta-Myrcene is a flavouring agent.
Structure
Data?1587135046
Synonyms
ValueSource
7-Methyl-3-methyleneocta-1,6-dieneChEBI
MyrceneChEBI
2-Methyl-6-methylene-2,7-octadieneHMDB
3-Methylene-7-methyl-1, 6-octadieneHMDB
3-Methylene-7-methyl-1,6-octadieneHMDB
7-Methyl-3-methylene-1,6-octadiene (beta -myrcene)HMDB
7-Methyl-3-methylene-1,6-octadiene (myrcene)HMDB
7-Methyl-3-methylene-octa-1,6-dieneHMDB
7-Methyl-3-methyleneoctadiene-(1,6)HMDB
7-Methyl-3-methylideneocta-1,6-dieneHMDB
b-GeranioleneHMDB
b-MyrceneHMDB, Generator
beta-MirceneHMDB
beta-MyrceneHMDB, KEGG
FEMA 2762HMDB
2-Methyl-6-methylene-1,7-octadieneMeSH, HMDB
β-MyrceneGenerator
7-Methyl-3-methylene-1,6-octadieneHMDB
beta-GeranioleneHMDB
β-GeranioleneHMDB
Chemical FormulaC10H16
Average Molecular Weight136.238
Monoisotopic Molecular Weight136.125200515
IUPAC Name7-methyl-3-methylideneocta-1,6-diene
Traditional Nameα-myrcene
CAS Registry Number123-35-3
SMILES
CC(C)=CCCC(=C)C=C
InChI Identifier
InChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H3
InChI KeyUAHWPYUMFXYFJY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
Substituents
  • Acyclic monoterpenoid
  • Branched unsaturated hydrocarbon
  • Alkatriene
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Acyclic olefin
  • Hydrocarbon
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point< -10 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0056 mg/mL at 25 °CNot Available
LogP4.17Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.078 g/LALOGPS
logP4.32ALOGPS
logP3.54ChemAxon
logS-3.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity48.38 m³·mol⁻¹ChemAxon
Polarizability17.53 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-94249d5850d02862868dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-078927c5db5ba8691e12Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-94249d5850d02862868dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-078927c5db5ba8691e12Spectrum
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-0006-9000000000-4934a34348f1966a1b57Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gbc-9100000000-3140926424077f6fe821Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-3900000000-3c559009ab39d35fd493Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-9600000000-a02add9ea09761212874Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-c2cf7f8831e68542008bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-6882dc5ecf3f017e6584Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-c44cd1555bbebb14f177Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9700000000-b1c0f8495736a8fba510Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-0044238938af2a674670Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Nonalcoholic fatty liver disease
details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB017400
KNApSAcK IDC00000853
Chemspider ID28993
KEGG Compound IDC06074
BioCyc IDCPD-4888
BiGG IDNot Available
Wikipedia LinkMyrcene
METLIN IDNot Available
PubChem Compound31253
PDB IDNot Available
ChEBI ID17221
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Luddeke F, Harder J: Enantiospecific (S)-(+)-linalool formation from beta-myrcene by linalool dehydratase-isomerase. Z Naturforsch C. 2011 Jul-Aug;66(7-8):409-12. [PubMed:21950166 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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. [PubMed:16902246 ]
  4. 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. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.