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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:32:41 UTC
Update Date2022-03-07 02:55:41 UTC
HMDB IDHMDB0038259
Secondary Accession Numbers
  • HMDB38259
Metabolite Identification
Common NameNeryl butyrate
DescriptionGeranyl butyrate is found in citrus. Geranyl butyrate is found in citrus peel oils, kumquat peel oil, celery leaves/stalks, tomato, yellow passion fruit, lavender oil and other essential oils. Geranyl butyrate is a flavouring agent.
Structure
Data?1563863167
Synonyms
ValueSource
Neryl butyric acidGenerator
(Z)-3,7-Dimethyl-2,6-octadienyl butanoateHMDB
(Z)-3,7-Dimethyl-2,6-octadienyl butyrateHMDB
3,7-Dimethyl-2,6-octadienyl ester(Z)-butanoic acidHMDB
3,7-Dimethyl-2,6-octadienyl ester(Z)-butyric acidHMDB
3,7-Dimethyl-2,6-octadienyl esterz)-butanoic acidHMDB
Butanoic acid, (2Z)-3,7-dimethyl-2,6-octadien-1-yl esterHMDB
Butanoic acid, (2Z)-3,7-dimethyl-2,6-octadienyl esterHMDB
cis-3,7-Dimethyl-2,6-octadienyl butanoateHMDB
FEMA 2774HMDB
Neryl butanoateHMDB
Nonyl N-butyrateHMDB
(Z)-3,7-Dimethyl-2,6-octadienyl butyric acidGenerator
Geranyl butyric acidGenerator
Chemical FormulaC14H24O2
Average Molecular Weight224.3392
Monoisotopic Molecular Weight224.177630012
IUPAC Name(2Z)-3,7-dimethylocta-2,6-dien-1-yl butanoate
Traditional Name(2Z)-3,7-dimethylocta-2,6-dien-1-yl butanoate
CAS Registry Number999-40-6
SMILES
CCCC(=O)OC\C=C(\C)CCC=C(C)C
InChI Identifier
InChI=1S/C14H24O2/c1-5-7-14(15)16-11-10-13(4)9-6-8-12(2)3/h8,10H,5-7,9,11H2,1-4H3/b13-10-
InChI KeyZSBOMYJPSRFZAL-RAXLEYEMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohol esters
Direct ParentFatty alcohol esters
Alternative Parents
Substituents
  • Fatty alcohol ester
  • Monoterpenoid
  • Acyclic monoterpenoid
  • Fatty acid ester
  • 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
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point239.00 to 240.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.71 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.923 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.06 g/LALOGPS
logP5.07ALOGPS
logP4.09ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity69.56 m³·mol⁻¹ChemAxon
Polarizability27.63 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+154.08531661259
DarkChem[M-H]-154.01631661259
DeepCCS[M+H]+156.60430932474
DeepCCS[M-H]-154.24630932474
DeepCCS[M-2H]-187.71830932474
DeepCCS[M+Na]+162.81130932474
AllCCS[M+H]+159.432859911
AllCCS[M+H-H2O]+156.032859911
AllCCS[M+NH4]+162.632859911
AllCCS[M+Na]+163.532859911
AllCCS[M-H]-159.832859911
AllCCS[M+Na-2H]-160.932859911
AllCCS[M+HCOO]-162.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Neryl butyrateCCCC(=O)OC\C=C(\C)CCC=C(C)C1852.8Standard polar33892256
Neryl butyrateCCCC(=O)OC\C=C(\C)CCC=C(C)C1503.9Standard non polar33892256
Neryl butyrateCCCC(=O)OC\C=C(\C)CCC=C(C)C1584.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Neryl butyrate EI-B (Non-derivatized)splash10-014l-9100000000-0bc04e3a6c520f0cfadd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Neryl butyrate EI-B (Non-derivatized)splash10-014l-9100000000-0bc04e3a6c520f0cfadd2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neryl butyrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-060c-9700000000-f17b16d0d76dc338c0892017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neryl butyrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neryl butyrate 10V, Positive-QTOFsplash10-004r-5960000000-5b753b26564fadc84dd62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neryl butyrate 20V, Positive-QTOFsplash10-0079-9600000000-9746fc341340ae0eca4f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neryl butyrate 40V, Positive-QTOFsplash10-0gbc-9100000000-40e406f728e794d88c522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neryl butyrate 10V, Negative-QTOFsplash10-00y0-9470000000-302dfcd1a756ed78a4d92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neryl butyrate 20V, Negative-QTOFsplash10-00kr-9200000000-50eeec28209003ce0bdd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neryl butyrate 40V, Negative-QTOFsplash10-00ko-9300000000-a79607bd760573fee44b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neryl butyrate 10V, Positive-QTOFsplash10-001i-9400000000-b75572ea773801a9bb222021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neryl butyrate 20V, Positive-QTOFsplash10-001i-9100000000-8e70f8f7070d443f55352021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neryl butyrate 40V, Positive-QTOFsplash10-0006-9100000000-1ee9f7115b0d598da89a2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neryl butyrate 10V, Negative-QTOFsplash10-00dr-8290000000-194292342db985cc328a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neryl butyrate 20V, Negative-QTOFsplash10-000i-9100000000-b6a318fb443d044e2e0e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neryl butyrate 40V, Negative-QTOFsplash10-014i-9000000000-9f2867696f737c8488c72021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB018005
KNApSAcK IDNot Available
Chemspider ID4509113
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5352162
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1033141
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.