Showing Compound Card for Linalyl acetate (CDB000621)

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Record Information
Version1.0
Created at2020-03-19 00:47:05 UTC
Updated at2020-12-07 19:07:35 UTC
CannabisDB IDCDB000621
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameLinalyl acetate
DescriptionLinalyl acetate belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of monoterpenes. Linalyl acetate occurs naturally and is found in many flowers and spices. It can be isolated from numerous plants and essential oils, such as clary sage, lavender, lemon, cardamom. It is also one of the principal components of the essential oils of bergamot and lavender. Chemically, it is the acetate ester of linalool, and the two often occur in conjunction. Linalyl acetate is a flavouring ingredient and it tastes similar to how it smells, with a pleasant fruity odor reminiscent of bergamot mint oil. It is found in Eau de Cologne mint. As a volatile terpene, linalyl acetate is also combustible. Linalyl acetate has been detected as a volatile component in cannabis plant samples (PMID: 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-3,7-Dimethylocta-1,6-dien-3-yl acetateChEBI
Acetic acid linalool esterChEBI
BergamiolChEBI
Bergamot mint oilChEBI
(+-)-3,7-Dimethylocta-1,6-dien-3-yl acetic acidGenerator
Acetate linalool esterGenerator
Linalyl acetic acidGenerator
(-)-Linalyl acetateChEBI
(-)-Linalyl acetic acidGenerator
(R)-Linalyl acetic acidGenerator
R-(-)-Linalyl acetatePhytoBank
R-Linalyl acetatePhytoBank
l-Linalyl acetatePhytoBank
(-)-(R)-3-Acetoxy-3,7-dimethylocta-1,6-dienePhytoBank
Linalool acetatePhytoBank
(±)-Linaloyl acetatePhytoBank
(±)-Linalyl acetatePhytoBank
1,5-Dimethyl-1-vinyl-4-hexenyl acetatePhytoBank
3,7-Dimethyl-1,6-octadien-3-yl acetatePhytoBank
3,7-Dimethylocta-1,6-dien-3-yl acetatePhytoBank
3-Acetoxy-3,7-dimethyl-1,6-octadienePhytoBank
BergamolPhytoBank
dl-Linalool acetatePhytoBank
Chemical FormulaC12H20O2
Average Molecular Weight196.29
Monoisotopic Molecular Weight196.1463
IUPAC Name(3R)-3,7-dimethylocta-1,6-dien-3-yl acetate
Traditional Name(+-)-linalyl acetate
CAS Registry Number16509-46-9
SMILES
CC(C)=CCC[C@@](C)(OC(C)=O)C=C
InChI Identifier
InChI=1S/C12H20O2/c1-6-12(5,14-11(4)13)9-7-8-10(2)3/h6,8H,1,7,9H2,2-5H3/t12-/m0/s1
InChI KeyUWKAYLJWKGQEPM-LBPRGKRZSA-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
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point220 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.03ALOGPS
logP3.09ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity59.36 m³·mol⁻¹ChemAxon
Polarizability23.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-0f6c80cf6386280605792016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-7900000000-c24d96c54b634a5ce01e2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-edecc6807b28c4e59a9d2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-e20da33a45dcd63c61052016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfs-3900000000-f698e30236a468ad6ab92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0553-9800000000-80dff10f3d6586f64ec22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9300000000-db6bdfd0a5edf9f3864c2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-9200000000-7cd15204eb37717e97262021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-91362b0817199d37003e2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9400000000-fe0af33cbf0db86bab7b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9200000000-f337ba0b5012d00f9c122021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-9ddd9f6b6037597d56172021-10-21View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0302749
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006042
KNApSAcK IDC00003048
Chemspider ID390908
KEGG Compound IDC09863
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLinalyl_acetate
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID6469
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]