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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 23:27:07 UTC
Update Date2021-10-13 07:11:13 UTC
HMDB IDHMDB0038169
Secondary Accession Numbers
  • HMDB38169
Metabolite Identification
Common Namebeta-Myrcene
Description7-Methyl-3-methylene-1,6-octadiene, also known as beta-Myrcene or myrcene is an acyclic monoterpene. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids. beta-Myrcene is a significant component of the essential oil of several plants, including allspice, bay, cannabis, hops, houttuynia, lemon grass, mango, myrcia, verbena, west indian bay tree, and cardamom. It is also the main component of wild thyme, the leaves of which contain up to 40% by weight of myrcene. Industrially, it is produced mainly semi-synthetically from myrcia, from which it gets its name. Myrcene has been detected as a volatile component in cannabis plant samples (PMID:26657499 ) and its essential oils (PMID:6991645 ). beta-Myrcene is the most abundant monoterpene in Cannabis and it has analgesic, anti-inflammatory, antibiotic, and antimutagenic activities. beta-Myrcene is a flavouring agent and it is used in the perfumery industry. It has a pleasant odor but is rarely used directly. It is a key intermediate in the production of several fragrances such as menthol, citral, citronellol, citronellal, geraniol, nerol, and linalool.
Structure
Data?1587135046
Synonyms
ValueSource
7-Methyl-3-methylene-1,6-octadieneChEBI
7-Methyl-3-methyleneocta-1,6-dieneChEBI
MyrceneChEBI
b-MyrceneGenerator
Β-myrceneGenerator
2-Methyl-6-methylene-1,7-octadieneMeSH
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
beta-MirceneHMDB
beta-MyrceneHMDB, KEGG
FEMA 2762HMDB
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

Biological location

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point< -10 °CNot Available
Boiling Point166.00 to 167.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.0056 mg/mL at 25 °CNot Available
LogP4.17Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.078 g/LALOGPS
logP10(4.32) g/LALOGPS
logP10(3.54) g/LChemAxon
logS10(-3.2) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.70131661259
DarkChem[M-H]-128.95831661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - beta-Myrcene EI-B (Non-derivatized)splash10-00kf-9000000000-94249d5850d02862868d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Myrcene EI-B (Non-derivatized)splash10-0006-9000000000-078927c5db5ba8691e122017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Myrcene EI-B (Non-derivatized)splash10-00kf-9000000000-94249d5850d02862868d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Myrcene EI-B (Non-derivatized)splash10-0006-9000000000-078927c5db5ba8691e122018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Myrcene GC-EI-Q (Non-derivatized)splash10-0006-9000000000-4934a34348f1966a1b572020-07-08HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Myrcene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gbc-9100000000-3140926424077f6fe8212016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Myrcene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Myrcene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-0044238938af2a6746702014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Myrcene 10V, Positive-QTOFsplash10-000i-3900000000-3c559009ab39d35fd4932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Myrcene 20V, Positive-QTOFsplash10-0019-9600000000-a02add9ea097612128742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Myrcene 40V, Positive-QTOFsplash10-0udi-9000000000-c2cf7f8831e68542008b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Myrcene 10V, Negative-QTOFsplash10-000i-0900000000-6882dc5ecf3f017e65842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Myrcene 20V, Negative-QTOFsplash10-000i-0900000000-c44cd1555bbebb14f1772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Myrcene 40V, Negative-QTOFsplash10-014i-9700000000-b1c0f8495736a8fba5102016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Myrcene 10V, Positive-QTOFsplash10-001i-9000000000-ff2818480f196b4f58022021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Myrcene 20V, Positive-QTOFsplash10-05q9-9000000000-62442276cecbb1e6975b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Myrcene 40V, Positive-QTOFsplash10-0v00-9000000000-671d242601a78647a09d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Myrcene 10V, Negative-QTOFsplash10-000i-0900000000-7b99763f2098a29c1bd62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Myrcene 20V, Negative-QTOFsplash10-000i-0900000000-9815af0088c9d73412b62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Myrcene 40V, Negative-QTOFsplash10-014i-9000000000-24167ae6962b4d56019f2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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 IDNot Available
Good Scents IDrw1016531
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.