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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-12 01:07:30 UTC
Update Date2023-02-21 17:27:02 UTC
HMDB IDHMDB0039620
Secondary Accession Numbers
  • HMDB39620
Metabolite Identification
Common NameButyl butyrate
DescriptionButyl butyrate, or butyl butanoate, is an organic compound that is an ester formed by the condensation of butyric acid and n-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. Butyl 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 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.
Structure
Data?1677000422
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, MeSH
Butyric acid, butyl esterHMDB
FEMA 2186HMDB
N-Butyl N-butanoateHMDB, MeSH
N-Butyl N-butyrateHMDB, MeSH
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
Physiological effect
Disposition
Process
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-91.5 °CNot Available
Boiling Point166.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.5 mg/mL at 20 °CNot Available
LogP2.823 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.9631661259
DarkChem[M-H]-129.2731661259
DeepCCS[M+H]+137.0830932474
DeepCCS[M-H]-134.44230932474
DeepCCS[M-2H]-171.23530932474
DeepCCS[M+Na]+146.20230932474
AllCCS[M+H]+137.032859911
AllCCS[M+H-H2O]+133.032859911
AllCCS[M+NH4]+140.632859911
AllCCS[M+Na]+141.732859911
AllCCS[M-H]-136.832859911
AllCCS[M+Na-2H]-139.332859911
AllCCS[M+HCOO]-142.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Butyl butyrateCCCCOC(=O)CCC1219.1Standard polar33892256
Butyl butyrateCCCCOC(=O)CCC975.9Standard non polar33892256
Butyl butyrateCCCCOC(=O)CCC1012.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Butyl butyrate EI-B (Non-derivatized)splash10-0596-9000000000-d391cfb43ea3b2438e3d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butyl butyrate EI-B (Non-derivatized)splash10-05g3-9000000000-6475886c051aaeebd2f52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butyl butyrate EI-B (Non-derivatized)splash10-05g0-9000000000-909ad81987b43bcf251e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butyl butyrate EI-B (Non-derivatized)splash10-05bf-9000000000-0b6c3408eea71f00941f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butyl butyrate EI-B (Non-derivatized)splash10-0596-9000000000-d391cfb43ea3b2438e3d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butyl butyrate EI-B (Non-derivatized)splash10-05g3-9000000000-6475886c051aaeebd2f52018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butyl butyrate EI-B (Non-derivatized)splash10-05g0-9000000000-909ad81987b43bcf251e2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butyl butyrate EI-B (Non-derivatized)splash10-05bf-9000000000-0b6c3408eea71f00941f2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butyl butyrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-9100000000-f2ddcea30a5013f00c662016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butyl butyrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butyl 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 - Butyl butyrate 10V, Positive-QTOFsplash10-0002-6900000000-81e862955ac61e8740672016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl butyrate 20V, Positive-QTOFsplash10-0a4i-9100000000-fd89ba380bf05df525832016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl butyrate 40V, Positive-QTOFsplash10-0a4l-9000000000-fba91f33e8df2b7a62c32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl butyrate 10V, Negative-QTOFsplash10-00kf-9700000000-9c206aaf53a92583d5c52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl butyrate 20V, Negative-QTOFsplash10-00ku-9100000000-29b9b7fc42c82d1445f92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl butyrate 40V, Negative-QTOFsplash10-00ko-9000000000-952de79adebdbf91db942016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl butyrate 10V, Negative-QTOFsplash10-0006-4900000000-c68f4541a7c513bfdfe12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl butyrate 20V, Negative-QTOFsplash10-00kr-9000000000-3962f66d002cb36e47bb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl butyrate 40V, Negative-QTOFsplash10-014l-9000000000-d5753ce4a1aea9e8f5b82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl butyrate 10V, Positive-QTOFsplash10-0a4i-9000000000-c5b55e21e8f63d82657f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl butyrate 20V, Positive-QTOFsplash10-0a4l-9000000000-cf9087ec4564e94f78972021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl butyrate 40V, Positive-QTOFsplash10-052f-9000000000-2fde8ac0c28240eaba5e2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView

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 Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothAutism details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Nonalcoholic fatty liver disease
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB 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
MarkerDB IDNot Available
Good Scents IDrw1014091
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.