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Showing Compound Nerol (FDB014945)

Record Information
Version1.0
Creation date2010-04-08 22:11:33 UTC
Update date2020-09-17 15:30:02 UTC
Primary IDFDB014945
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. 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).
CAS Number106-25-2
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(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
(2e)3,7-Dimethyl-2,6-octadien-1-olHMDB
(Z)-3,7-dimethyl-2,6-Octadien-1-olbiospider
2,6-Octadien-1-ol, 3,7-dimethyl-, (2Z)-biospider
2,6-Octadien-1-ol, 3,7-dimethyl-, (Z)-biospider
FEMA 2770db_source
Nerolidyl diateHMDB
Predicted Properties
PropertyValueSource
Water Solubility1.37 g/LALOGPS
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
Chemical FormulaC10H18O
IUPAC name(2Z)-3,7-dimethylocta-2,6-dien-1-ol
InChI IdentifierInChI=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
Isomeric SMILESCC(C)=CCC\C(C)=C/CO
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
Classification
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:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 77.87%; H 11.76%; O 10.37%DFC
Melting Point<-15 oC
Boiling PointBp 225-226°DFC
Experimental Water Solubility0.531 mg/mL at 25 oCMILLER,DJ & HAWTHORNE,SB (2000A)
Experimental logP3.47GRIFFIN,S ET AL. (1999)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn20D 1.4744DFC
Spectra
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
ChemSpider ID558917
ChEMBL IDCHEMBL452683
KEGG Compound IDC09871
Pubchem Compound ID643820
Pubchem Substance IDNot Available
ChEBI ID29452
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05812
CRC / DFC (Dictionary of Food Compounds) IDJVC33-F:JXL41-N
EAFUS ID2649
Dr. Duke IDNEROL
BIGG IDNot Available
KNApSAcK IDC00000855
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID106-25-2
GoodScent IDrw1008951
SuperScent IDNot Available
Wikipedia IDNerol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti helicobacter33282 A substance that kills or slows the growth of bacteria.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
estrogenicDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
trichomonicideDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sweet
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
natural
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
neroli
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
citrus
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
magnolia
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.