Showing Compound Card for Nerol (CDB000056)

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Record Information
Version1.0
Created at2020-03-18 23:23:09 UTC
Updated at2020-12-07 19:07:01 UTC
CannabisDB IDCDB000056
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameNerol
DescriptionNerol or (Z)-3,7-dimethyl-2,6-octadien-1-ol or cis-Geranial is formally classified as an alkylalcohol although it is biochemically a monoterpenoid synthesized from isoprene units. It is soluble in water and very soluble in alcohol. Nerol is a naturally occurring organic compound found in the essential oils of many plants and was originally found in neroli oil, from which its name was derived. The largest natural source is palmarosa oil and it is the primary constituent of rose oil, palmarosa oil, and citronella oil (Java type) with in small quantities found in geranium, lemon, and many other essential oils. Different foods contain nerol with the highest concentration found in common grapes, black walnuts, and common thymes and in lower concentrations in cardamoms, common oregano, and gingers. Nerol has also been detected in lemon verbena, oval-leaf huckleberries, common pea, sweet cherries, and nopals and in cannabis plants (PMID: 6991645 ) . Nerol has a sweet, citrus and floral flavor with a sweet rose-like odor. It is used to create flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. This alcohol is widely and frequently used in perfumery as it has a freshness to a rose base (PMID: 18640199 ). It is detected in small quantities in orange peel and together with other oils, was found to have antimicrobial properties (PMID: 27535797 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(2Z)-3,7-Dimethyl-2,6-octadien-1-olChEBI
(Z)-3,7-Dimethyl-2,6-octadien-1-olChEBI
(Z)-3,7-Dimethylocta-2,6-dien-1-olChEBI
(Z)-GeraniolChEBI
2-cis-3,7-Dimethyl-2,6-octadien-1-olChEBI
cis-3,7-Dimethyl-2,6-octadien-1-olChEBI
cis-GeraniolChEBI
Neryl alcoholChEBI
Geraniol, (e)-isomerMeSH
Geraniol, (Z)-isomerMeSH
Geraniol, 1-(14)C-labeled, (e)-isomerMeSH
Geraniol, 2-(14)C-labeled, (e)-isomerMeSH
Geraniol, titanium (4+) saltMeSH
(2E)3,7-Dimethyl-2,6-octadien-1-olHMDB
(2Z)3,7-Dimethyl-2,6-octadien-1-olHMDB
(cis)3,7-Dimethyl-2,6-octadien-1-olHMDB
(e)3,7-Dimethyl-2,6-octadien-1-olHMDB
(e)3,7-Dimethyl-octadien-1-olHMDB
(Z)3,7-Dimethyl-2,6-octadien-1-olHMDB
2,6-Dimethyl-trans-2,6-octadien-8-olHMDB
2-trans-3,7-Dimethyl-2,6-octadien-1-olHMDB
2-trans-3,7-Dimethyl-2,6-octadiene-1-olHMDB
2E-GeraniolHMDB
3,7-Dimethyl-2,6-octadien-1-olHMDB
3,7-Dimethyl-octane-1-ol tetrahydro derivativeHMDB
3,7-Dimethyl-trans-2, 6-octadien-1-olHMDB
3,7-Dimethylocta-2,6-dien-1-olHMDB
beta-GeraniolHMDB
Geraniol (natural)HMDB
Geraniol alcoholHMDB
Geranyl alcoholHMDB
GuaniolHMDB
LemonolHMDB
NerolHMDB
Nerol (natural)HMDB
Nerolidyl diphosphateHMDB
trans-3,7-Dimethyl-2,6-octadien-1-olHMDB
trans-GeraniolHMDB
VernolHMDB
GeraniolMeSH
(Z)-3,7-Dimethyl-2,6-octadienolPhytoBank
(Z)-3,7-Dimethyloct-2,6-diene-1-olPhytoBank
(Z)-NerolPhytoBank
3,7-Dimethyl-cis-2,6-octadien-1-olPhytoBank
cis-1-Hydroxy-3,7-dimethyl-2,6-octadienePhytoBank
beta-NerolPhytoBank
β-NerolPhytoBank
Chemical FormulaC10H18O
Average Molecular Weight154.25
Monoisotopic Molecular Weight154.1358
IUPAC Name(2Z)-3,7-dimethylocta-2,6-dien-1-ol
Traditional Namenerol
CAS Registry Number106-25-2
SMILES
CC(C)=CCC\C(C)=C/CO
InChI Identifier
InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7-
InChI KeyGLZPCOQZEFWAFX-YFHOEESVSA-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
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< -15 °CNot Available
Boiling Point224 - 225 °C at 745 mmHgWikipedia
Water Solubility0.53 mg/mL at 25 °CNot Available
logP3.47GRIFFIN,S ET AL. (1999)
Predicted Properties
PropertyValueSource
logP2.89ALOGPS
logP2.5ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)16.33ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.18 m³·mol⁻¹ChemAxon
Polarizability19.29 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSNerol, non-derivatized, GC-MS Spectrumsplash10-014l-9000000000-8132ea67e057a3dd9c80Spectrum
GC-MSNerol, non-derivatized, GC-MS Spectrumsplash10-014l-9100000000-a5bdece739d0cb5bf629Spectrum
GC-MSNerol, non-derivatized, GC-MS Spectrumsplash10-015c-9200000000-eea073073c86ea4d9a38Spectrum
GC-MSNerol, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-0625da1bcd5a7d1938a6Spectrum
GC-MSNerol, non-derivatized, GC-MS Spectrumsplash10-014l-9000000000-41e0055b618413366b81Spectrum
GC-MSNerol, non-derivatized, GC-MS Spectrumsplash10-014l-9000000000-8132ea67e057a3dd9c80Spectrum
GC-MSNerol, non-derivatized, GC-MS Spectrumsplash10-014l-9100000000-a5bdece739d0cb5bf629Spectrum
GC-MSNerol, non-derivatized, GC-MS Spectrumsplash10-015c-9200000000-eea073073c86ea4d9a38Spectrum
GC-MSNerol, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-0625da1bcd5a7d1938a6Spectrum
GC-MSNerol, non-derivatized, GC-MS Spectrumsplash10-014l-9000000000-41e0055b618413366b81Spectrum
GC-MSNerol, non-derivatized, GC-MS Spectrumsplash10-014l-9000000000-2ab93357dd27a7c07eb7Spectrum
Predicted GC-MSNerol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014u-9300000000-c85bc4c928fbf7d824e8Spectrum
Predicted GC-MSNerol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-030c-9520000000-69b7fbbb25764f7b612eSpectrum
Predicted GC-MSNerol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001r-9600000000-69c0de28e07b8b530c9a2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9100000000-0ee3622152359826448f2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-003r-9000000000-d5bb693fadd752735f312012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-014l-9000000000-8132ea67e057a3dd9c802012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-014l-9100000000-a5bdece739d0cb5bf6292012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-015c-9200000000-eea073073c86ea4d9a382012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positivesplash10-0006-9000000000-0625da1bcd5a7d1938a62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-014l-9000000000-7b5a5cfbbe0b42fdd23e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-0a4i-0900000000-73a127efb4137eb425802020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-1900000000-3d437630e5bec67a7e072016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-8900000000-0e505c85cec6344cab5c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-c7400df359a9559bd5942016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-113756054eed13d33ee42016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0900000000-dea43b41c5b791cef9d22016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aou-9800000000-c028a2bd6550260942512016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-9100000000-6e205fbbb6213cf2eb8c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-a55b9b951ba285782da92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-29f4b3188008e31f7b9f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-d3a143bdeacdf3ef0e942021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-f29389e574ed8f84a6832021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9100000000-1a426588f258e723527c2021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0005812
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014945
KNApSAcK IDC00000855
Chemspider ID558917
KEGG Compound IDC09871
BioCyc IDCPD-7978
BiGG IDNot Available
Wikipedia LinkNerol
METLIN IDNot Available
PubChem Compound643820
PDB IDNot Available
ChEBI ID29452
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. Lapczynski A, Foxenberg RJ, Bhatia SP, Letizia CS, Api AM: Fragrance material review on nerol. Food Chem Toxicol. 2008 Nov;46 Suppl 11:S241-4. doi: 10.1016/j.fct.2008.06.062. Epub 2008 Jul 2. [PubMed:18640199 ]
  3. Geraci A, Di Stefano V, Di Martino E, Schillaci D, Schicchi R: Essential oil components of orange peels and antimicrobial activity. Nat Prod Res. 2017 Mar;31(6):653-659. doi: 10.1080/14786419.2016.1219860. Epub 2016 Aug 18. [PubMed:27535797 ]