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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:10:05 UTC
Update Date2022-03-07 02:54:47 UTC
HMDB IDHMDB0036101
Secondary Accession Numbers
  • HMDB36101
Metabolite Identification
Common Name(R)-3,7-Dimethyl-1,6-octadien-3-ol
Description(R)-3,7-Dimethyl-1,6-octadien-3-ol, also known as (3S)-linalool, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Based on a literature review a significant number of articles have been published on (R)-3,7-Dimethyl-1,6-octadien-3-ol.
Structure
Data?1563862821
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 Weight154.2493
Monoisotopic Molecular Weight154.135765198
IUPAC Name(3S)-3,7-dimethylocta-1,6-dien-3-ol
Traditional Name(+)-linalool
CAS Registry Number126-91-0
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

Biological location

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point187.00 to 199.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility683.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.795 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.48 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.72931661259
DarkChem[M-H]-133.75631661259
DeepCCS[M+H]+135.07530932474
DeepCCS[M-H]-132.22530932474
DeepCCS[M-2H]-168.84530932474
DeepCCS[M+Na]+144.33630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-3,7-Dimethyl-1,6-octadien-3-olCC(C)=CCC[C@](C)(O)C=C1537.2Standard polar33892256
(R)-3,7-Dimethyl-1,6-octadien-3-olCC(C)=CCC[C@](C)(O)C=C1078.2Standard non polar33892256
(R)-3,7-Dimethyl-1,6-octadien-3-olCC(C)=CCC[C@](C)(O)C=C1098.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-3,7-Dimethyl-1,6-octadien-3-ol,1TMS,isomer #1C=C[C@](C)(CCC=C(C)C)O[Si](C)(C)C1221.7Semi standard non polar33892256
(R)-3,7-Dimethyl-1,6-octadien-3-ol,1TMS,isomer #1C=C[C@](C)(CCC=C(C)C)O[Si](C)(C)C1221.7Semi standard non polar33892256
(R)-3,7-Dimethyl-1,6-octadien-3-ol,1TBDMS,isomer #1C=C[C@](C)(CCC=C(C)C)O[Si](C)(C)C(C)(C)C1445.1Semi standard non polar33892256
(R)-3,7-Dimethyl-1,6-octadien-3-ol,1TBDMS,isomer #1C=C[C@](C)(CCC=C(C)C)O[Si](C)(C)C(C)(C)C1445.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xr-9100000000-ddd4389422ee0f3334df2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9810000000-fc748fa570a2ba2186852017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol Linear Ion Trap , negative-QTOFsplash10-052r-1900000000-8ca412f7f764aeb650602017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol Linear Ion Trap , positive-QTOFsplash10-000i-4900000000-656054d8175600557e752017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol Linear Ion Trap , positive-QTOFsplash10-053r-0900000000-7fca9e4a66d81b4355692017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol 10V, Positive-QTOFsplash10-052r-1900000000-b8dd7418c39ef6db8f402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol 20V, Positive-QTOFsplash10-05nr-9600000000-9d3208f5b352b9b9781c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol 40V, Positive-QTOFsplash10-0gb9-9100000000-4bc6e60fbc702ce661a52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol 10V, Negative-QTOFsplash10-0udi-0900000000-0405dd8fcdc66cf24c7a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol 20V, Negative-QTOFsplash10-0udi-1900000000-db461e62c034d983da232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol 40V, Negative-QTOFsplash10-0lei-9500000000-a32dadbfc03fff9b63f82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol 10V, Negative-QTOFsplash10-0udi-0900000000-221d2be472b40f055cb92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol 20V, Negative-QTOFsplash10-0udi-2900000000-d123b20dd29666c808092021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol 40V, Negative-QTOFsplash10-106r-9200000000-92641be024615f4e80782021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol 10V, Positive-QTOFsplash10-001i-9100000000-b50c7739963b598d98b62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol 20V, Positive-QTOFsplash10-001l-9000000000-9aee9265aa23930829f12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3,7-Dimethyl-1,6-octadien-3-ol 40V, Positive-QTOFsplash10-069r-9000000000-478f8a25d9f85574e0ac2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Nonalcoholic fatty liver disease
details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014941
KNApSAcK IDC00010301
Chemspider ID60523
KEGG Compound IDC11389
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound67179
PDB IDNot Available
ChEBI ID98
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1377001
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chanotiya CS, Yadav A: Enantiomeric composition of (3R)-(-)- and (3S)-(+)-linalool in various essential oils of Indian origin by enantioselective capillary gas chromatography-flame ionization and mass spectrometry detection methods. Nat Prod Commun. 2009 Apr;4(4):563-6. [PubMed:19476006 ]
  2. Bormann S, Etschmann MM, Mirata MA, Schrader J: Integrated bioprocess for the stereospecific production of linalool oxides from linalool with Corynespora cassiicola DSM 62475. J Ind Microbiol Biotechnol. 2012 Dec;39(12):1761-9. doi: 10.1007/s10295-012-1181-2. Epub 2012 Aug 18. [PubMed:22903341 ]
  3. 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. [PubMed:21950166 ]
  4. Silk PJ, Lemay MA, LeClair G, Sweeney J, MaGee D: Behavioral and electrophysiological responses of Tetropium fuscum (Coleoptera: Cerambycidae) to pheromone and spruce volatiles. Environ Entomol. 2010 Dec;39(6):1997-2005. doi: 10.1603/EN10156. [PubMed:22182567 ]
  5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  6. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  7. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  8. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  9. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  10. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.