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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:57:25 UTC
Update Date2023-02-21 17:23:57 UTC
HMDB IDHMDB0034162
Secondary Accession Numbers
  • HMDB34162
Metabolite Identification
Common NamePentyl butanoate
DescriptionPentyl butanoate is found in apple. Pentyl butanoate is found in banana, apple and apricot fruits. Pentyl butanoate is used in food flavouring Pentyl butyrate, also known as pentyl butanoate or amyl butyrate, is an ester that is formed when pentanol is reacted with butyric acid, usually in the presence of sulfuric acid as a catalyst. This ester has a smell reminiscent of pear or apricot. This chemical is used as an additive in cigarettes.
Structure
Data?1677000237
Synonyms
ValueSource
Amyl butanoateChEBI
Amyl butyrateChEBI
N-Amyl butyrateChEBI
Amyl butanoic acidGenerator
Amyl butyric acidGenerator
N-Amyl butyric acidGenerator
Pentyl butanoic acidGenerator
1-Pentyl butyrateHMDB
Butanoic acid, pentyl esterHMDB
Butyric acid, pentyl esterHMDB
FEMA 2059HMDB
N-Amyl butyrate, 8ciHMDB
N-Amyl N-butyrateHMDB
N-Pentyl butanoateHMDB
N-Pentyl butyrateHMDB
N-Pentyl N-butyrateHMDB
Pentyl butanoate, 9ciHMDB
Pentyl butyrateHMDB
Chemical FormulaC9H18O2
Average Molecular Weight158.238
Monoisotopic Molecular Weight158.13067982
IUPAC Namepentyl butanoate
Traditional Namepentyl butyrate
CAS Registry Number540-18-1
SMILES
CCCCCOC(=O)CCC
InChI Identifier
InChI=1S/C9H18O2/c1-3-5-6-8-11-9(10)7-4-2/h3-8H2,1-2H3
InChI KeyCFNJLPHOBMVMNS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • 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
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-73.2 °CNot Available
Boiling Point185.00 to 187.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.06 mg/mL at 20 °CNot Available
LogP3.320The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.37 g/LALOGPS
logP3.32ALOGPS
logP2.84ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity45.12 m³·mol⁻¹ChemAxon
Polarizability19.43 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]+136.43931661259
DarkChem[M-H]-134.98831661259
DeepCCS[M+H]+140.99230932474
DeepCCS[M-H]-138.04430932474
DeepCCS[M-2H]-175.130932474
DeepCCS[M+Na]+150.3430932474
AllCCS[M+H]+140.832859911
AllCCS[M+H-H2O]+137.032859911
AllCCS[M+NH4]+144.432859911
AllCCS[M+Na]+145.432859911
AllCCS[M-H]-141.132859911
AllCCS[M+Na-2H]-143.232859911
AllCCS[M+HCOO]-145.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pentyl butanoateCCCCCOC(=O)CCC1308.7Standard polar33892256
Pentyl butanoateCCCCCOC(=O)CCC1076.5Standard non polar33892256
Pentyl butanoateCCCCCOC(=O)CCC1116.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Pentyl butanoate EI-B (Non-derivatized)splash10-00dl-9000000000-6fa919338a66598293462017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pentyl butanoate EI-B (Non-derivatized)splash10-00di-9000000000-9983d3bae455366d38f62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pentyl butanoate EI-B (Non-derivatized)splash10-006x-9000000000-937c8363d4b8c7c595752017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pentyl butanoate EI-B (Non-derivatized)splash10-00dl-9000000000-6fa919338a66598293462018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pentyl butanoate EI-B (Non-derivatized)splash10-00di-9000000000-9983d3bae455366d38f62018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pentyl butanoate EI-B (Non-derivatized)splash10-006x-9000000000-937c8363d4b8c7c595752018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentyl butanoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9000000000-f03a71b8badf2de6ff092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentyl butanoate 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 - Pentyl butanoate 10V, Positive-QTOFsplash10-0ab9-7900000000-a07a966ce3fe708e9b0e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentyl butanoate 20V, Positive-QTOFsplash10-00di-9100000000-5b2cf24f2417113b34ac2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentyl butanoate 40V, Positive-QTOFsplash10-006x-9000000000-3e82e7f1166f8ec2d0d82015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentyl butanoate 10V, Negative-QTOFsplash10-0aor-9700000000-6350c49e277c764cff2a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentyl butanoate 20V, Negative-QTOFsplash10-00kr-9100000000-49191276c743fb72a2cf2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentyl butanoate 40V, Negative-QTOFsplash10-014u-9000000000-83de45fae189d8de11f82015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentyl butanoate 10V, Negative-QTOFsplash10-052r-9400000000-4d66693cdb740c75bcd42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentyl butanoate 20V, Negative-QTOFsplash10-00kr-9000000000-f86bd3c639c9880fad5c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentyl butanoate 40V, Negative-QTOFsplash10-014i-9000000000-90c7f8891927530e440a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentyl butanoate 10V, Positive-QTOFsplash10-00dl-9000000000-648980b8cf460d26a8cf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentyl butanoate 20V, Positive-QTOFsplash10-006x-9000000000-4f6a68f6c4fc10f4466f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentyl butanoate 40V, Positive-QTOFsplash10-0006-9000000000-ef8c0ff132ee32d62a592021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 IDFDB012448
KNApSAcK IDNot Available
Chemspider ID10428
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPentyl butyrate
METLIN IDNot Available
PubChem Compound10890
PDB IDNot Available
ChEBI ID87684
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1004151
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.