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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:57:25 UTC
Update Date2018-03-12 21:54:33 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
Thumb
Synonyms
ValueSource
Amyl butanoateChEBI
Amyl butyrateChEBI
N-Amyl butyrateChEBI
Amyl butanoic acidGenerator
Pentyl butanoic acidGenerator
Amyl butyric acidGenerator
N-Amyl butyric 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
DescriptionThis compound 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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-73.2 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.06 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dl-9000000000-6fa919338a6659829346View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9000000000-9983d3bae455366d38f6View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9000000000-937c8363d4b8c7c59575View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dl-9000000000-6fa919338a6659829346View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9000000000-9983d3bae455366d38f6View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9000000000-937c8363d4b8c7c59575View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9000000000-f03a71b8badf2de6ff09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-7900000000-a07a966ce3fe708e9b0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9100000000-5b2cf24f2417113b34acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-3e82e7f1166f8ec2d0d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aor-9700000000-6350c49e277c764cff2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-9100000000-49191276c743fb72a2cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-9000000000-83de45fae189d8de11f8View in MoNA
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
FoodDB 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
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.