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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:59:20 UTC

Update Date

2023-02-21 17:28:17 UTC

HMDB ID

HMDB0040447

Secondary Accession Numbers

HMDB40447

Metabolite Identification

Common Name

Butyl acetoacetate

Description

Butyl acetoacetate belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom. Butyl acetoacetate is a sweet, brandy, and fermented tasting compound. Based on a literature review very few articles have been published on Butyl acetoacetate.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Butyl acetoacetic acid	Generator
Acetoacetic acid, butyl ester	HMDB
Butanoic acid, 3-oxo-, butyl ester	HMDB
Butyl 3-ketobutanoate	HMDB
Butyl 3-ketobutyrate	HMDB
Butyl 3-oxobutanoate	HMDB
Butyl 3-oxobutyrate	HMDB
Butylester kyseliny acetoctove	HMDB
FEMA 2176	HMDB
Butyl 3-oxobutanoic acid	Generator

Chemical Formula

C₈H₁₄O₃

Average Molecular Weight

158.195

Monoisotopic Molecular Weight

158.094294314

IUPAC Name

butyl 3-oxobutanoate

Traditional Name

butyl 3-oxobutanoate

CAS Registry Number

591-60-6

SMILES

CCCCOC(=O)CC(C)=O

InChI Identifier

InChI=1S/C8H14O3/c1-3-4-5-11-8(10)6-7(2)9/h3-6H2,1-2H3

InChI Key

REIYHFWZISXFKU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Beta-keto acids and derivatives

Direct Parent

Beta-keto acids and derivatives

Alternative Parents

Substituents

Fatty acid ester
Beta-keto acid
Fatty acyl
1,3-dicarbonyl compound
Ketone
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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Exogenous (HMDB: HMDB0040447)

Food

Food (HMDB: HMDB0040447)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040447)

Biological role

Nutrient (HMDB: HMDB0040447)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-35.6 °C	Not Available
Boiling Point	100.00 to 103.00 °C. @ 16.00 mm Hg	The Good Scents Company Information System
Water Solubility	15080 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.386 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.88 g/L	ALOGPS
logP	1.12	ALOGPS
logP	1.47	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.93	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	41.18 m³·mol⁻¹	ChemAxon
Polarizability	17.25 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.293	31661259
DarkChem	[M-H]-	133.117	31661259
DeepCCS	[M+H]+	141.684	30932474
DeepCCS	[M-H]-	138.633	30932474
DeepCCS	[M-2H]-	175.924	30932474
DeepCCS	[M+Na]+	150.912	30932474
AllCCS	[M+H]+	138.0	32859911
AllCCS	[M+H-H2O]+	134.2	32859911
AllCCS	[M+NH4]+	141.6	32859911
AllCCS	[M+Na]+	142.7	32859911
AllCCS	[M-H]-	137.4	32859911
AllCCS	[M+Na-2H]-	139.4	32859911
AllCCS	[M+HCOO]-	141.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.45 minutes	32390414
Predicted by Siyang on May 30, 2022	12.6481 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.2 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1844.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	395.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	149.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	241.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	152.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	483.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	554.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1042.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	374.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1165.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	339.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	350.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	363.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	337.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	26.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Butyl acetoacetate	CCCCOC(=O)CC(C)=O	1724.6	Standard polar	33892256
Butyl acetoacetate	CCCCOC(=O)CC(C)=O	1077.7	Standard non polar	33892256
Butyl acetoacetate	CCCCOC(=O)CC(C)=O	1154.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Butyl acetoacetate,1TMS,isomer #1	CCCCOC(=O)C=C(C)O[Si](C)(C)C	1342.7	Semi standard non polar	33892256
Butyl acetoacetate,1TMS,isomer #1	CCCCOC(=O)C=C(C)O[Si](C)(C)C	1304.3	Standard non polar	33892256
Butyl acetoacetate,1TMS,isomer #2	C=C(CC(=O)OCCCC)O[Si](C)(C)C	1291.1	Semi standard non polar	33892256
Butyl acetoacetate,1TMS,isomer #2	C=C(CC(=O)OCCCC)O[Si](C)(C)C	1304.1	Standard non polar	33892256
Butyl acetoacetate,1TBDMS,isomer #1	CCCCOC(=O)C=C(C)O[Si](C)(C)C(C)(C)C	1555.4	Semi standard non polar	33892256
Butyl acetoacetate,1TBDMS,isomer #1	CCCCOC(=O)C=C(C)O[Si](C)(C)C(C)(C)C	1505.1	Standard non polar	33892256
Butyl acetoacetate,1TBDMS,isomer #2	C=C(CC(=O)OCCCC)O[Si](C)(C)C(C)(C)C	1489.7	Semi standard non polar	33892256
Butyl acetoacetate,1TBDMS,isomer #2	C=C(CC(=O)OCCCC)O[Si](C)(C)C(C)(C)C	1491.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Butyl acetoacetate EI-B (Non-derivatized)	splash10-0006-9000000000-5e338755179443d54e95	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl acetoacetate EI-B (Non-derivatized)	splash10-0006-9000000000-5e338755179443d54e95	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butyl acetoacetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-052o-9000000000-4b9f9277618e63634cbd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butyl acetoacetate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl acetoacetate 10V, Positive-QTOF	splash10-0a4l-5900000000-ae93eb5ac7561513db15	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl acetoacetate 20V, Positive-QTOF	splash10-0a4i-9200000000-7faa734bafbcbd5de8a0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl acetoacetate 40V, Positive-QTOF	splash10-0a4l-9000000000-3b3c2f3b068787667b47	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl acetoacetate 10V, Negative-QTOF	splash10-0a59-8900000000-abd99597282483f1ea03	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl acetoacetate 20V, Negative-QTOF	splash10-0a59-9400000000-a4f2c1a9497414ae3339	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl acetoacetate 40V, Negative-QTOF	splash10-0a59-9000000000-08f70687efb728353ee3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl acetoacetate 10V, Negative-QTOF	splash10-05fr-9100000000-29b4f3d3b0a0996e1c49	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl acetoacetate 20V, Negative-QTOF	splash10-0a4i-9400000000-ac5633eb28b0b0f61018	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl acetoacetate 40V, Negative-QTOF	splash10-0a4i-9000000000-1f5c3f393aafeff74d7d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl acetoacetate 10V, Positive-QTOF	splash10-0a4l-9200000000-4b22daccd0054d4a39c5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl acetoacetate 20V, Positive-QTOF	splash10-0006-9000000000-176b6c846160958b7376	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl acetoacetate 40V, Positive-QTOF	splash10-052f-9000000000-a5f09d612ccf5bc42e55	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020199

KNApSAcK ID

Not Available

Chemspider ID

11088

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11576

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1013081

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Butyl acetoacetate (HMDB0040447)

MOL for HMDB0040447 (Butyl acetoacetate)

3D MOL for HMDB0040447 (Butyl acetoacetate)

3D SDF for HMDB0040447 (Butyl acetoacetate)

3D-SDF for HMDB0040447 (Butyl acetoacetate)

PDB for HMDB0040447 (Butyl acetoacetate)

3D PDB for HMDB0040447 (Butyl acetoacetate)

SMILES for HMDB0040447 (Butyl acetoacetate)

INCHI for HMDB0040447 (Butyl acetoacetate)

Structure for HMDB0040447 (Butyl acetoacetate)

3D Structure for HMDB0040447 (Butyl acetoacetate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra