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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:28:09 UTC
Update Date2022-03-07 02:55:14 UTC
HMDB IDHMDB0037227
Secondary Accession Numbers
  • HMDB37227
Metabolite Identification
Common NameCitronellyl butyrate
DescriptionCitronellyl butyrate belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Based on a literature review a small amount of articles have been published on Citronellyl butyrate.
Structure
Data?1563862996
Synonyms
ValueSource
Citronellyl butyric acidGenerator
(1)-3,7-Dimethyloct-6-enyl butyrateHMDB
3,7-Dimethyl-6-octen-1-yl butyrateHMDB
3,7-Dimethyl-6-octenyl butanoateHMDB
Butanoic acid, 3,7-dimethyl-6-octen-1-yl esterHMDB
Butanoic acid, 3,7-dimethyl-6-octenyl esterHMDB
Butyric acid, 3,7-dimethyl-6-octenyl ester (8ci)HMDB
Butyric acid, ester with citronellolHMDB
e275HMDB
FEMA 2312HMDB
Chemical FormulaC14H26O2
Average Molecular Weight226.355
Monoisotopic Molecular Weight226.193280076
IUPAC Name3,7-dimethyloct-6-en-1-yl butanoate
Traditional Name3,7-dimethyloct-6-en-1-yl butanoate
CAS Registry Number141-16-2
SMILES
CCCC(=O)OCCC(C)CCC=C(C)C
InChI Identifier
InChI=1S/C14H26O2/c1-5-7-14(15)16-11-10-13(4)9-6-8-12(2)3/h8,13H,5-7,9-11H2,1-4H3
InChI KeyXQPZQXTWYZAXAK-UHFFFAOYSA-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 DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point245.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.59 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.224 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP4.93ALOGPS
logP4.34ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity68.87 m³·mol⁻¹ChemAxon
Polarizability28.23 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]+154.2431661259
DarkChem[M-H]-153.20831661259
DeepCCS[M+H]+159.0230932474
DeepCCS[M-H]-156.66230932474
DeepCCS[M-2H]-191.40730932474
DeepCCS[M+Na]+166.46630932474
AllCCS[M+H]+161.332859911
AllCCS[M+H-H2O]+158.032859911
AllCCS[M+NH4]+164.532859911
AllCCS[M+Na]+165.332859911
AllCCS[M-H]-161.132859911
AllCCS[M+Na-2H]-162.432859911
AllCCS[M+HCOO]-164.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Citronellyl butyrateCCCC(=O)OCCC(C)CCC=C(C)C1791.5Standard polar33892256
Citronellyl butyrateCCCC(=O)OCCC(C)CCC=C(C)C1479.0Standard non polar33892256
Citronellyl butyrateCCCC(=O)OCCC(C)CCC=C(C)C1539.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Citronellyl butyrate EI-B (Non-derivatized)splash10-00rx-9100000000-adf929332f117b653cc72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Citronellyl butyrate EI-B (Non-derivatized)splash10-008a-9300000000-5190c6b3c8ba0a74d8642017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Citronellyl butyrate EI-B (Non-derivatized)splash10-00rx-9100000000-adf929332f117b653cc72018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Citronellyl butyrate EI-B (Non-derivatized)splash10-008a-9300000000-5190c6b3c8ba0a74d8642018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citronellyl butyrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-08ml-9700000000-7d5d14e3eb0c9f976b012017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citronellyl butyrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citronellyl butyrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00rx-9100000000-a242f53795353291cf702015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl butyrate 10V, Positive-QTOFsplash10-004i-6790000000-64129f846c392693a12f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl butyrate 20V, Positive-QTOFsplash10-0079-9400000000-c87498cf8b86d83caebb2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl butyrate 40V, Positive-QTOFsplash10-066u-9100000000-d179c931bebfdf1013e42016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl butyrate 10V, Negative-QTOFsplash10-00or-8390000000-589cf0d48808257d75032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl butyrate 20V, Negative-QTOFsplash10-00kr-9210000000-ceef9b887d1536dede0d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl butyrate 40V, Negative-QTOFsplash10-00ko-9200000000-6b5f1d9d65f23e6a02182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl butyrate 10V, Positive-QTOFsplash10-001i-9410000000-cf68e31282a3c420cb062021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl butyrate 20V, Positive-QTOFsplash10-053r-9100000000-3bfc83fa7e692db013272021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl butyrate 40V, Positive-QTOFsplash10-0006-9000000000-1a9af3c97dee98985f832021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl butyrate 10V, Negative-QTOFsplash10-002r-9150000000-14a29cdcc773cd6cae932021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl butyrate 20V, Negative-QTOFsplash10-000i-9100000000-8a81ee75687704f5fabb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl butyrate 40V, Negative-QTOFsplash10-014i-9100000000-3afdaf99261e44f0258a2021-09-25Wishart 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 IDFDB016234
KNApSAcK IDNot Available
Chemspider ID8503
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8835
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1017851
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.