Record Information
Version1.0
Created at2020-03-18 23:24:21 UTC
Updated at2020-12-07 19:07:05 UTC
CannabisDB IDCDB000089
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameLinalool
DescriptionBeta-Linalool or 3,7-Dimethyl-1,6-octadien-3-ol, also known simply as linalool is a naturally occurring terpene alcohol. It belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Linalool has a role as a plant metabolite, a volatile oil component, an antimicrobial agent and a fragrance. There are two stereoisomers of Linalool – (S)-linalool and (R)-linalool. Linalool is used as a scent in 60% to 80% of perfumed hygiene products and cleaning agents including soaps, detergents, shampoos, and lotions. Linalool is also used by pest professionals as a flea, fruit fly, and cockroach insecticide. Linalool is found in more than 200 different species of plants, including many flowers and spice plants. (S)-linalool is found, for example, as a major constituent of the essential oils of coriander (Coriandrum sativum L.), cymbopogon (Cymbopogon martini var. martinii), and sweet orange (Citrus sinensis) flowers. (R)-linalool is present in lavender (Lavandula officinalis), bay laurel (Laurus nobilis), and sweet basil (Ocimum basilicum), among others. Linalool is also found in plants from the Lamiaceae family (mint and other herbs), Lauraceae (laurels, cinnamon, rosewood), Cinnamomum tamala, Solidago Meyen, Artemisia vulgaris (mugwort), Humulus lupulus. Linalool is also one of several monoterpenes that are found in cannabis plants (PMID: 6991645 ). There are more than 140 known terpenes in cannabis and the combination of these terepenoids produces the skunky, fruity odor characteristic of C. savita. Like the majority of monoterpenes, linalool starts with the condensation of dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP) to form geranyl pyrophosphate (GPP) (PMID: 7640522 ). Linalool is then synthesized with the aid of linalool synthase (LIS) (PMID: 12572612 ). Linalool has a citrus, floral, rose, woody aroma and a citrus, orange, waxy taste. Linalool is found in a few different foods and spices, such as spearmints, corianders, common thymes, limes, grapes, lemons, grapefruit, oranges, pineapples, blackcurrants, basil, and common oregano. This could make, Linalool a potential biomarker for the consumption of these foods. Linalool is also synthesized, de novo, by yeast (C. cerevisiae) and may contribute to the floral tones found in some wines (PMID: 15668008 ).
Structure
Thumb
Synonyms
ValueSource
(+)-LinaloolChEBI
(3S)-3,7-Dimethyl-1,6-octadien-3-olChEBI
(3S)-LinaloolChEBI
(S)-(+)-LinaloolChEBI
(S)-3,7-Dimethyl-1,6-octadien-3-olChEBI
(S)-LinalolChEBI
(-)-3,7-Dimethyl-1,6-octadien-3-olHMDB
(-)-LinaloolHMDB
(-)-R-LinaloolHMDB
(3R)-3,7-Dimethyl-1,6-octadien-3-olHMDB
(3R)-3,7-Dimethylocta-1,6-dien-3-olHMDB
(3R)-LinaloolHMDB
(R)-(-)-3,7-Dimethyl-1,6-octadien-3-olHMDB
(R)-(-)-LinaloolHMDB
(R)-LinalolHMDB
(R)-LinaloolHMDB
L-LinaloolHMDB
LicareolHMDB
Chemical FormulaC10H18O
Average Molecular Weight154.25
Monoisotopic Molecular Weight154.1358
IUPAC Name(3S)-3,7-dimethylocta-1,6-dien-3-ol
Traditional Name(+)-linalool
CAS Registry Number126-90-9
SMILES
CC(C)=CCC[C@](C)(O)C=C
InChI Identifier
InChI=1S/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3/t10-/m1/s1
InChI KeyCDOSHBSSFJOMGT-SNVBAGLBSA-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
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< −20 °CWikipedia
Boiling Point198 - 199 °CWikipedia
Water Solubility1.59 g/LWikipedia
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.68ALOGPS
logP2.65ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)18.46ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.21 m³·mol⁻¹ChemAxon
Polarizability18.97 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLinalool, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00xr-9100000000-ddd4389422ee0f3334dfSpectrum
Predicted GC-MSLinalool, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9810000000-fc748fa570a2ba218685Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-052r-1900000000-8ca412f7f764aeb65060Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-4900000000-656054d8175600557e75Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-053r-0900000000-7fca9e4a66d81b435569Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-1900000000-b8dd7418c39ef6db8f40Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05nr-9600000000-9d3208f5b352b9b9781cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-4bc6e60fbc702ce661a5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-0405dd8fcdc66cf24c7aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-db461e62c034d983da23Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0lei-9500000000-a32dadbfc03fff9b63f8Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
8-Ball KushDetected and Quantified0.837 mg/g dry wt details
9 Lb HammerDetected and Quantified0.694 mg/g dry wt details
97 SageDetected and Quantified0.425 mg/g dry wt details
AdonisDetected and Quantified1.509 mg/g dry wt details
Alien DawgDetected and Quantified0.11 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Alien Dawg (Indica dominant)Detected and Quantified0.19 +/- 0.02 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Alien Sour AppleDetected and Quantified0.222 mg/g dry wt details
Animal CookiesDetected and Quantified1.6 +/- 0.4 mg/g dry wt details
Black BossDetected and Quantified0.491 mg/g dry wt details
Blue CookiesDetected and Quantified0.9 +/- 0.3 mg/g dry wt details
Blue DreamDetected and Quantified0.216 mg/g dry wt details
Blue DreamDetected and Quantified0.289 mg/g dry wt details
Blue DreamDetected and Quantified0.301 mg/g dry wt details
Blue DreamDetected and Quantified0.328 mg/g dry wt details
Blue DreamDetected and Quantified0.7 +/- 0.3 mg/g dry wt details
Bob MarleyDetected and Quantified0.737 mg/g dry wt details
Bubba KushDetected and Quantified0.7 +/- 0.4 mg/g dry wt details
ChemdawgDetected and Quantified0.308 mg/g dry wt details
Chemdawg #4Detected and Quantified0.288 mg/g dry wt details
Chemdawg #4Detected and Quantified0.528 mg/g dry wt details
ChemdogDetected and Quantified0.9 +/- 0.2 mg/g dry wt details
Cookies and CreamDetected and Quantified1.1 mg/g dry wt details
Crown OgDetected and Quantified1.7 +/- 0.3 mg/g dry wt details
Dairy QueenDetected and Quantified0.23 mg/g dry wt details
Dark Shadow HazeDetected and Quantified0.499 mg/g dry wt details
FLODetected and Quantified0.174 mg/g dry wt details
Fortune CookiesDetected and Quantified1.8 +/- 0.4 mg/g dry wt details
GabriolaDetected and Quantified0.7 mg/g dry wt
    • Jiamin Zheng, Yil...
details
GasDetected and Quantified2 +/- 0.3 mg/g dry wt details
GelatoDetected and Quantified3.1 +/- 0.9 mg/g dry wt details
Girl Scout CookiesDetected and Quantified1.5 +/- 0.6 mg/g dry wt details
GodfatherDetected and Quantified0.9 +/- 0.4 mg/g dry wt details
Goji OGDetected and Quantified0.915 mg/g dry wt details
Golden CobraDetected and Quantified0.324 mg/g dry wt details
Golden SageDetected and Quantified0.428 mg/g dry wt details
Gorilla GlueDetected and Quantified0.476 mg/g dry wt details
Gorilla Glue #4Detected and Quantified0.244 mg/g dry wt details
Gorilla Glue #4Detected and Quantified0.9 +/- 0.3 mg/g dry wt details
Grape ApeDetected and Quantified1.1 +/- 0.4 mg/g dry wt details
Grape StomperDetected and Quantified0.29 mg/g dry wt details
Grape StomperDetected and Quantified0.378 mg/g dry wt details
Grizzly KushDetected and Quantified0.309 mg/g dry wt details
Hash PlantDetected and Quantified0.772 mg/g dry wt details
HemlockDetected and Quantified0.16 mg/g dry wt details
Island HoneyDetected and Quantified0.19 mg/g dry wt
    • Jiamin Zheng, Yil...
details
JabberwockyDetected and Quantified0.451 mg/g dry wt details
JabberwockyDetected and Quantified1.435 mg/g dry wt details
Kandy KushDetected and Quantified0.198 mg/g dry wt details
Kush PuppyDetected and Quantified0.396 mg/g dry wt details
La ChocoDetected and Quantified0.774 mg/g dry wt details
Lemon BalmDetected and Quantified0.304 mg/g dry wt details
Lemon GojiDetected and Quantified0.676 mg/g dry wt details
Lemon OGDetected and Quantified0.283 mg/g dry wt details
Lemon SherbetDetected and Quantified0.08 mg/g dry wt details
Lemon SkunkDetected and Quantified0.37 mg/g dry wt details
Lemon SkunkDetected and Quantified2.211 mg/g dry wt details
Liberty HazeDetected and Quantified0.73 mg/g dry wt details
LohanDetected and Quantified0.087 mg/g dry wt details
Lucky CharmsDetected and Quantified0.381 mg/g dry wt details
Maui HazeDetected and Quantified0.792 mg/g dry wt details
Miami White KushDetected and Quantified1.7 +/- 0.6 mg/g dry wt details
Moby DickDetected and Quantified0.631 mg/g dry wt details
Moonshine Ghost Trane HazeDetected and Quantified1.053 mg/g dry wt details
Nightmare CookieDetected and Quantified0.964 mg/g dry wt details
Og KushDetected and Quantified1.8 +/- 1 mg/g dry wt details
Orange SkunkDetected and Quantified0.289 mg/g dry wt details
Pineapple SkunkDetected and Quantified0.259 mg/g dry wt details
Pipe DreamDetected and Quantified0.756 mg/g dry wt details
Platinum DelightDetected and Quantified1.343 mg/g dry wt details
Purple CreamDetected and Quantified1 +/- 0.2 mg/g dry wt details
Purple EclipseDetected and Quantified1.658 mg/g dry wt details
Purple PrincessDetected and Quantified1.2 +/- 0.2 mg/g dry wt details
Purple UrkleDetected and Quantified1.4 +/- 0.1 mg/g dry wt details
QuadraDetected and Quantified0.89 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Rocket FuelDetected and Quantified0.459 mg/g dry wt details
Rollex OGDetected and Quantified1.136 mg/g dry wt details
Rosetta StoneDetected and Quantified1.909 mg/g dry wt details
SatoriDetected and Quantified0.098 mg/g dry wt details
SherbertDetected and Quantified2 +/- 0.6 mg/g dry wt details
Skunk HazeDetected and Quantified0.304 mg/g dry wt details
Skywalker OGDetected and Quantified0.835 mg/g dry wt details
Skywalker Og KushDetected and Quantified2 +/- 0.6 mg/g dry wt details
Sour DieselDetected and Quantified1.1 +/- 0.3 mg/g dry wt details
Star BudDetected and Quantified0.485 mg/g dry wt details
Star KillerDetected and Quantified0.285 mg/g dry wt details
Strawberry FieldsDetected and Quantified0.34 mg/g dry wt details
Strawberry FieldsDetected and Quantified0.469 mg/g dry wt details
Strawberry HazeDetected and Quantified1.2 +/- 0.1 mg/g dry wt details
Sunset SherbetDetected and Quantified1.03 mg/g dry wt details
Sunset SherbetDetected and Quantified1.39 mg/g dry wt details
Superman Og KushDetected and Quantified1.8 +/- 0.3 mg/g dry wt details
Tahoe Og KushDetected and Quantified2.1 +/- 0.6 mg/g dry wt details
Tangerine DreamDetected and Quantified0.29 mg/g dry wt details
Tangerine Dream (Sativa dominant)Detected and Quantified0.35 +/- 0.02 mg/g dry wt
    • Jiamin Zheng, Yil...
details
The SauceDetected and Quantified0.44 mg/g dry wt details
Thin MintsDetected and Quantified1.5 +/- 0.7 mg/g dry wt details
TrainwreckDetected and Quantified0.4 +/- 0.4 mg/g dry wt details
Triple ODetected and Quantified2.2 +/- 0.4 mg/g dry wt details
Venom OGDetected and Quantified0.93 mg/g dry wt details
White WidowDetected and Quantified0.227 mg/g dry wt details
Wonder WomanDetected and Quantified0.479 mg/g dry wt details
HMDB IDHMDB0036101
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014941
KNApSAcK IDC00010301
Chemspider ID391430
KEGG Compound IDC11389
BioCyc IDCPD-8997
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound67179
PDB IDNot Available
ChEBI ID98
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  3. Cseke L, Dudareva N, Pichersky E: Structure and evolution of linalool synthase. Mol Biol Evol. 1998 Nov;15(11):1491-8. doi: 10.1093/oxfordjournals.molbev.a025876. [PubMed:12572612 ]
  4. Carrau FM, Medina K, Boido E, Farina L, Gaggero C, Dellacassa E, Versini G, Henschke PA: De novo synthesis of monoterpenes by Saccharomyces cerevisiae wine yeasts. FEMS Microbiol Lett. 2005 Feb 1;243(1):107-15. doi: 10.1016/j.femsle.2004.11.050. [PubMed:15668008 ]