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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-12 01:07:30 UTC
Update Date2019-07-23 06:30:09 UTC
HMDB IDHMDB0039620
Secondary Accession Numbers
  • HMDB39620
Metabolite Identification
Common NameButyl butyrate
DescriptionButyl butyrate is found in alcoholic beverages. Butyl butyrate is present in many fruits, e.g. banana, cherry, melon, plum, also present in gruyere de comte cheese, cider, soybean etc. Butyl butyrate is used in fruit flavour compositions Butyl butyrate, or butyl butanoate, is an organic compound which is an ester formed by the condensation of butyric acid and butanol. It is a clear, colorless liquid that is insoluble in water, but miscible with ethanol and diethyl ether. Its refractive index is 1.406 at 20 °C.
Structure
Data?1563863409
Synonyms
ValueSource
N-Butyl butanoateChEBI
N-Butyl butyrateChEBI
N-Butyric N-butyl esterChEBI
N-Butyl butanoic acidGenerator
N-Butyl butyric acidGenerator
Butyl butyric acidGenerator
1-Butyl butyrateHMDB
Butanoic acid, butyl esterHMDB
Butyl butanoateHMDB
Butyl butylateHMDB
Butyl ester OF butanoic acidHMDB
Butyl N-butyrateHMDB
Butyric acid, butyl esterHMDB
FEMA 2186HMDB
N-Butyl N-butanoateHMDB
N-Butyl N-butyrateHMDB
N-Butyl-N-butyrateHMDB
N-Butyric acid N-butyl esterHMDB
Butryl butyric acidGenerator
Butyl butyrateMeSH
Chemical FormulaC8H16O2
Average Molecular Weight144.2114
Monoisotopic Molecular Weight144.115029756
IUPAC Namebutyl butanoate
Traditional Namebutyl butyrate
CAS Registry Number109-21-7
SMILES
CCCCOC(=O)CCC
InChI Identifier
InChI=1S/C8H16O2/c1-3-5-7-10-8(9)6-4-2/h3-7H2,1-2H3
InChI KeyXUPYJHCZDLZNFP-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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-91.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.5 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP2.82ALOGPS
logP2.39ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity40.51 m³·mol⁻¹ChemAxon
Polarizability17.34 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0596-9000000000-d391cfb43ea3b2438e3dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05g3-9000000000-6475886c051aaeebd2f5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05g0-9000000000-909ad81987b43bcf251eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05bf-9000000000-0b6c3408eea71f00941fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0596-9000000000-d391cfb43ea3b2438e3dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05g3-9000000000-6475886c051aaeebd2f5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05g0-9000000000-909ad81987b43bcf251eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05bf-9000000000-0b6c3408eea71f00941fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-9100000000-f2ddcea30a5013f00c66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-6900000000-81e862955ac61e874067Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-fd89ba380bf05df52583Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-fba91f33e8df2b7a62c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kf-9700000000-9c206aaf53a92583d5c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ku-9100000000-29b9b7fc42c82d1445f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ko-9000000000-952de79adebdbf91db94Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Children (1-13 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Female
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not Quantified Children (1-13 years old)BothAutism details
FecesDetected but not Quantified Children (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not Quantified Adult (>18 years old)Female
Nonalcoholic fatty liver disease
details
FecesDetected but not Quantified Adult (>18 years old)Both
Diarrhea-predominant IBS
details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Diarrhoea predominant irritable bowel syndrome
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019248
KNApSAcK IDC00035546
Chemspider ID7694
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkButyl butyrate
METLIN IDNot Available
PubChem Compound7983
PDB IDNot Available
ChEBI ID87429
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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.