7-Methyl-3-methylene-1,6-octadiene (T3D3204)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-07-30 17:56:23 UTC
Update Date2014-12-24 20:26:00 UTC
Accession NumberT3D3204
Identification
Common Name7-Methyl-3-methylene-1,6-octadiene
ClassSmall Molecule
Description7-Methyl-3-methylene-1,6-octadiene is found in allspice. 7-Methyl-3-methylene-1,6-octadiene is found in many essential oils, e.g. hop oil. 7-Methyl-3-methylene-1,6-octadiene is a flavouring agent.
Compound Type
  • Food Toxin
  • Fragrance Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
2-Methyl-6-methylene-2,7-octadiene
3-Methylene-7-methyl-1, 6-octadiene
3-Methylene-7-methyl-1,6-octadiene
7-Methyl-3-methylene-1,6-octadiene (beta -myrcene)
7-Methyl-3-methylene-1,6-octadiene (myrcene)
7-Methyl-3-methylene-octa-1,6-diene
7-Methyl-3-methyleneocta-1,6-diene
7-Methyl-3-methyleneoctadiene-(1,6)
7-Methyl-3-methylideneocta-1,6-diene
B-Geraniolene
b-Myrcene
beta -mircene
beta -myrcene
beta-Myrcene
FEMA 2762
Myrcene
Chemical FormulaC10H16
Average Molecular Mass136.234 g/mol
Monoisotopic Mass136.125 g/mol
CAS Registry Number123-35-3
IUPAC Name7-methyl-3-methylideneocta-1,6-diene
Traditional Nameα-myrcene
SMILESCC(C)=CCCC(=C)C=C
InChI IdentifierInChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H3
InChI KeyInChIKey=UAHWPYUMFXYFJY-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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceYellow, oily liquid (6).
Experimental Properties
PropertyValue
Melting Point< -10°C
Boiling Point166-168°C
Solubility0.0056 mg/mL at 25°C
LogP4.17
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-94249d5850d02862868d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-078927c5db5ba8691e122017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-94249d5850d02862868d2018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-078927c5db5ba8691e122018-05-18View Spectrum
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-0006-9000000000-4934a34348f1966a1b572020-07-08View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gbc-9100000000-3140926424077f6fe8212016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-3900000000-3c559009ab39d35fd4932016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-9600000000-a02add9ea097612128742016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-c2cf7f8831e68542008b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-6882dc5ecf3f017e65842016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-c44cd1555bbebb14f1772016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9700000000-b1c0f8495736a8fba5102016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-ff2818480f196b4f58022021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05q9-9000000000-62442276cecbb1e6975b2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v00-9000000000-671d242601a78647a09d2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-7b99763f2098a29c1bd62021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-9815af0088c9d73412b62021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-24167ae6962b4d56019f2021-09-24View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-0044238938af2a6746702014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureDermal ; inhalation
Mechanism of ToxicityMyrcene exhibits tyrosinase inhibitory activities, which plays an important role in neuromelanin formation (3).
MetabolismNot Available
Toxicity ValuesLD50: >5000.00 mg/kg (Oral, Rat) (9) LD50: >5000.00 mg/kg (Dermal, Rabbit) (9)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesPerfume chemicals and flavoring. Myrcene is the major constituent of oil of bay and hop which are used in the manufacture of alcoholic beverages. Myrcene is also present in lemon grass (Cymbopogon citratus), a plant widely used in Brazilian folk medicine. Recently, it was shown that myrcene is a very potent analgesic substance and might be an alternative to the already available analgesic drugs (6, 2).
Minimum Risk LevelNot Available
Health EffectsHealth effects may include dermatitis (1).
SymptomsSneezing, itching, and increased nasal congestion (1).
TreatmentMonitor for respiratory distress in case of inhalation exposure. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. Administer symptomatic treatment as necessary. (5)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB38169
PubChem Compound ID31253
ChEMBL IDCHEMBL455491
ChemSpider ID28993
KEGG IDC06074
UniProt IDNot Available
OMIM ID
ChEBI ID17221
BioCyc IDCPD-4888
CTD IDNot Available
Stitch IDMyrcene
PDB IDNot Available
ACToR ID3633
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3204.pdf
General References
  1. Newmark FM: Hops allergy and terpene sensitivity: an occupational disease. Ann Allergy. 1978 Nov;41(5):311-2. [717854 ]
  2. Kauderer B, Zamith H, Paumgartten FJ, Speit G: Evaluation of the mutagenicity of beta-myrcene in mammalian cells in vitro. Environ Mol Mutagen. 1991;18(1):28-34. [1864266 ]
  3. Matsuura R, Ukeda H, Sawamura M: Tyrosinase inhibitory activity of citrus essential oils. J Agric Food Chem. 2006 Mar 22;54(6):2309-13. [16536612 ]
  4. 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. [21950166 ]
  5. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  6. Lewis RJ Sr. (ed) (1993). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co.
  7. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  8. Wikipedia. Myrcene. Last Updated 7 August 2009. [Link]
  9. The Good Scents Company (2009). Material Safety Data Sheet for Myrcene. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Tyrosinase
General Function:
Protein homodimerization activity
Specific Function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
P14679
Molecular Weight:
60392.69 Da
References
  1. Matsuura R, Ukeda H, Sawamura M: Tyrosinase inhibitory activity of citrus essential oils. J Agric Food Chem. 2006 Mar 22;54(6):2309-13. [16536612 ]