Myrcene

Relevant Data

Food Additives Approved in the United States:

Food Additives Approved by WHO:

General Information

Chemical nameMyrcene
CAS number123-35-3
COE number2197
JECFA number1327
Flavouring typesubstances
FL No.01.008
MixtureNo
Purity of the named substance at least 95% unless otherwise specifiedAt least 90%; secondary components C15H24 terpene hydrocarbons (eg. valencene); Minimum assay value may include traces of limonene, alpha- and beta-pinene and other common C10H16 terpenes.

From webgate.ec.europa.eu

Computed Descriptors

Download SDF
2D Structure
CID31253
IUPAC Name7-methyl-3-methylideneocta-1,6-diene
InChIInChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H3
InChI KeyUAHWPYUMFXYFJY-UHFFFAOYSA-N
Canonical SMILESCC(=CCCC(=C)C=C)C
Molecular FormulaC10H16
Wikipediamyrcene

From Pubchem

Computed Properties

Property Name Property Value
Molecular Weight136.238
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count4
Complexity145.0
CACTVS Substructure Key Fingerprint A A A D c e B w A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G A A A A A A A D A C A A A A C A A A A A A C A A i B C A A A A A A A g A A A I C A A A A A g I A A I A A Q A A A A A A g A A I A A I A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area0.0
Monoisotopic Mass136.125
Exact Mass136.125
XLogP3None
XLogP3-AA4.3
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count10
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem

Food Additives Biosynthesis/Degradation

ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9478
Human Intestinal AbsorptionHIA+0.9538
Caco-2 PermeabilityCaco2+0.7228
P-glycoprotein SubstrateNon-substrate0.6521
P-glycoprotein InhibitorNon-inhibitor0.7010
Non-inhibitor0.8493
Renal Organic Cation TransporterNon-inhibitor0.8183
Distribution
Subcellular localizationNucleus0.5972
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8553
CYP450 2D6 SubstrateNon-substrate0.8223
CYP450 3A4 SubstrateNon-substrate0.5742
CYP450 1A2 InhibitorNon-inhibitor0.7790
CYP450 2C9 InhibitorNon-inhibitor0.9178
CYP450 2D6 InhibitorNon-inhibitor0.9341
CYP450 2C19 InhibitorNon-inhibitor0.8849
CYP450 3A4 InhibitorNon-inhibitor0.9747
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7215
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8650
Non-inhibitor0.9292
AMES ToxicityNon AMES toxic0.9227
CarcinogensCarcinogens 0.5684
Fish ToxicityHigh FHMT0.9448
Tetrahymena Pyriformis ToxicityHigh TPT0.5960
Honey Bee ToxicityHigh HBT0.8407
BiodegradationReady biodegradable0.7708
Acute Oral ToxicityIII0.8030
Carcinogenicity (Three-class)Non-required0.4589

From admetSAR

ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-3.4432LogS
Caco-2 Permeability1.5571LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.4040LD50, mol/kg
Fish Toxicity0.6786pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.6891pIGC50, ug/L

From admetSAR

Toxicity Profile

Route of ExposureDermal ; inhalation
Mechanism of ToxicityMyrcene exhibits tyrosinase inhibitory activities, which plays an important role in neuromelanin formation .
MetabolismNone
Toxicity ValuesLD50: >5000.00 mg/kg (Oral, Rat) LD50: >5000.00 mg/kg (Dermal, Rabbit)
Lethal DoseNone
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNone
Health EffectsHealth effects may include dermatitis (A334).
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.
Reference
  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 ]

From T3DB

Taxonomic Classification

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassPrenol lipids
SubclassMonoterpenoids
Intermediate Tree NodesNot available
Direct ParentAcyclic monoterpenoids
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsAcyclic monoterpenoid - Branched unsaturated hydrocarbon - Alkatriene - Unsaturated aliphatic hydrocarbon - Unsaturated hydrocarbon - Olefin - Acyclic olefin - Hydrocarbon - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.

From ClassyFire

Targets

Target Details

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 ]

From T3DB