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7-Methyl-3-methylene-1,6-octadiene (FDB017400)

Record Information
Version1.0
Creation date2010-04-08 22:13:04 UTC
Update date2020-09-17 15:34:51 UTC
Primary IDFDB017400
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name7-Methyl-3-methylene-1,6-octadiene
Descriptionβ-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-eritritol-phosphate (MEP) pathway in the plastids. β-Myrcene is a significant component of the essential oil of several plants, including allspice, bay, 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. β-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.
CAS Number123-35-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot 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
Chemical FormulaC10H16
IUPAC name7-methyl-3-methylideneocta-1,6-diene
InChI IdentifierInChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H3
InChI KeyUAHWPYUMFXYFJY-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CCCC(=C)C=C
Average Molecular Weight136.238
Monoisotopic Molecular Weight136.125200515
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 88.16%; H 11.84%DFC
Melting Point<-10 oC
Boiling PointBp8.5 51-51.5°DFC
Experimental Water Solubility0.0056 mg/mL at 25 oCCHEMICALS INSPECTION AND TESTING INSTITU (1992)
Experimental logP4.17CHEMICALS INSPECTION AND TESTING INSTITU (
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[neutral] lmax 226 (e 16100) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-0044238938af2a6746702014-09-20View Spectrum
GC-MS7-Methyl-3-methylene-1,6-octadiene, non-derivatized, GC-MS Spectrumsplash10-00kf-9000000000-94249d5850d02862868dSpectrum
GC-MS7-Methyl-3-methylene-1,6-octadiene, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-078927c5db5ba8691e12Spectrum
GC-MS7-Methyl-3-methylene-1,6-octadiene, non-derivatized, GC-MS Spectrumsplash10-00kf-9000000000-94249d5850d02862868dSpectrum
GC-MS7-Methyl-3-methylene-1,6-octadiene, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-078927c5db5ba8691e12Spectrum
GC-MS7-Methyl-3-methylene-1,6-octadiene, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-4934a34348f1966a1b57Spectrum
Predicted GC-MS7-Methyl-3-methylene-1,6-octadiene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0gbc-9100000000-3140926424077f6fe821Spectrum
Predicted GC-MS7-Methyl-3-methylene-1,6-octadiene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Methyl-3-methylene-1,6-octadiene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-3900000000-3c559009ab39d35fd4932016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-9600000000-a02add9ea097612128742016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-c2cf7f8831e68542008b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-6882dc5ecf3f017e65842016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-c44cd1555bbebb14f1772016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9700000000-b1c0f8495736a8fba5102016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-ff2818480f196b4f58022021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05q9-9000000000-62442276cecbb1e6975b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v00-9000000000-671d242601a78647a09d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-7b99763f2098a29c1bd62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-9815af0088c9d73412b62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-24167ae6962b4d56019f2021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 22.53 MHz, CDCl3, experimental)Spectrum
ChemSpider ID28993
ChEMBL IDCHEMBL455491
KEGG Compound IDC06074
Pubchem Compound ID31253
Pubchem Substance IDNot Available
ChEBI ID17221
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB38169
CRC / DFC (Dictionary of Food Compounds) IDKXM92-T:KXM92-T
EAFUS ID2622
Dr. Duke IDMYRCENE|BETA-MYRCENE
BIGG IDNot Available
KNApSAcK IDC00000853
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID123-35-3
GoodScent IDrw1016531
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
angiotensin converting enzyme inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti convulsant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti mutagenicDUKE
anti nitrosaminicDUKE
anti nociceptive35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hypothermicDUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
irritantDUKE
myorelaxantDUKE
cytochrome-P450-2B1 inhibitor50183 An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
balsamic
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
must
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
spice
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
peppery
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
terpene
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsam
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
plastic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.