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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:47:14 UTC

Update Date

2023-02-21 17:28:02 UTC

HMDB ID

HMDB0040251

Secondary Accession Numbers

HMDB40251

Metabolite Identification

Common Name

Butyl isobutyrate

Description

Butyl isobutyrate, also known as fema 2188, belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Butyl isobutyrate is a sweet, apple, and banana tasting compound. Butyl isobutyrate has been detected, but not quantified, in several different foods, such as alcoholic beverages, fruits, milk and milk products, and pomes.

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 isobutyric acid	Generator
Butyl ester OF 2-methylpropanoic acid	HMDB
Butyl isobutanoate	HMDB
FEMA 2188	HMDB
Isobutyric acid N-butyl ester	HMDB
Isobutyric acid, butyl ester	HMDB
Isobutyric acid, butyl ester (6ci,7ci,8ci)	HMDB
N-Butyl isobutyrate	HMDB
Propanoic acid, 2-methyl-, butyl ester	HMDB
Butyl 2-methylpropanoic acid	Generator

Chemical Formula

C₈H₁₆O₂

Average Molecular Weight

144.2114

Monoisotopic Molecular Weight

144.115029756

IUPAC Name

butyl 2-methylpropanoate

Traditional Name

butyl 2-methylpropanoate

CAS Registry Number

97-87-0

SMILES

CCCCOC(=O)C(C)C

InChI Identifier

InChI=1S/C8H16O2/c1-4-5-6-10-8(9)7(2)3/h7H,4-6H2,1-3H3

InChI Key

JSLCOZYBKYHZNL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic acid esters

Alternative Parents

Substituents

Carboxylic acid ester
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0040251)
Cell membrane (HMDB: HMDB0040251)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040251)

Source

Exogenous

Exogenous (HMDB: HMDB0040251)

Food

Food (HMDB: HMDB0040251)

Fruit

Pome

Pomes (FooDB: FOOD00856)

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Endogenous

Plant

Plant (HMDB: HMDB0040251)

Animal

Animal (HMDB: HMDB0040251)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040251)

Biological role

Nutrient (HMDB: HMDB0040251)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	156.00 to 158.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	356.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.667 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.68 g/L	ALOGPS
logP	2.82	ALOGPS
logP	2.49	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	40.49 m³·mol⁻¹	ChemAxon
Polarizability	17.37 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	133.306	31661259
DarkChem	[M-H]-	129.152	31661259
DeepCCS	[M+H]+	139.873	30932474
DeepCCS	[M-H]-	136.992	30932474
DeepCCS	[M-2H]-	174.053	30932474
DeepCCS	[M+Na]+	149.156	30932474
AllCCS	[M+H]+	135.3	32859911
AllCCS	[M+H-H2O]+	131.3	32859911
AllCCS	[M+NH4]+	138.9	32859911
AllCCS	[M+Na]+	140.0	32859911
AllCCS	[M-H]-	136.4	32859911
AllCCS	[M+Na-2H]-	138.9	32859911
AllCCS	[M+HCOO]-	141.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Butyl isobutyrate	CCCCOC(=O)C(C)C	1173.5	Standard polar	33892256
Butyl isobutyrate	CCCCOC(=O)C(C)C	914.8	Standard non polar	33892256
Butyl isobutyrate	CCCCOC(=O)C(C)C	968.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Butyl isobutyrate EI-B (Non-derivatized)	splash10-059f-9000000000-9688cae9c61bb66ddb0c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl isobutyrate EI-B (Non-derivatized)	splash10-0abl-9000000000-c63b585334d9efe57448	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl isobutyrate CI-B (Non-derivatized)	splash10-0079-9000000000-daacd4b011914e28155d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl isobutyrate EI-B (Non-derivatized)	splash10-052f-9000000000-ddfd71ef6bb2b00f9175	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl isobutyrate EI-B (Non-derivatized)	splash10-059f-9000000000-9688cae9c61bb66ddb0c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl isobutyrate EI-B (Non-derivatized)	splash10-0abl-9000000000-c63b585334d9efe57448	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl isobutyrate CI-B (Non-derivatized)	splash10-0079-9000000000-daacd4b011914e28155d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl isobutyrate EI-B (Non-derivatized)	splash10-052f-9000000000-ddfd71ef6bb2b00f9175	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butyl isobutyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fu-9000000000-b2c694eef8f103b1cea3	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butyl isobutyrate 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 isobutyrate 10V, Positive-QTOF	splash10-0002-6900000000-18ee3f32bc7facbd8d57	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl isobutyrate 20V, Positive-QTOF	splash10-0a4i-9100000000-8b81251c356eb6e9ee83	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl isobutyrate 40V, Positive-QTOF	splash10-0abc-9000000000-8b9fbf85679f1af8c092	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl isobutyrate 10V, Negative-QTOF	splash10-0006-4900000000-defaa4b67aa46d8230ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl isobutyrate 20V, Negative-QTOF	splash10-000i-9200000000-108745d6d6d7870ace4a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl isobutyrate 40V, Negative-QTOF	splash10-000i-9000000000-b4542384fc8980c56e0a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl isobutyrate 10V, Positive-QTOF	splash10-0a4i-9000000000-cd98d2bcb980a6f21bba	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl isobutyrate 20V, Positive-QTOF	splash10-05fu-9000000000-88bd0d135085e554c99e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl isobutyrate 40V, Positive-QTOF	splash10-052f-9000000000-d5731443cec39fbdd84e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl isobutyrate 10V, Negative-QTOF	splash10-00dl-9600000000-0bda4a2ae0fb81f854d5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl isobutyrate 20V, Negative-QTOF	splash10-000l-9500000000-a772993fe1f022cdf94a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl isobutyrate 40V, Negative-QTOF	splash10-000i-9000000000-13bd10b260d2e523f27d	2021-09-25	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

Membrane

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

FDB019968

KNApSAcK ID

C00035117

Chemspider ID

7075

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7353

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1028651

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 isobutyrate (HMDB0040251)

MOL for HMDB0040251 (Butyl isobutyrate)

3D MOL for HMDB0040251 (Butyl isobutyrate)

3D SDF for HMDB0040251 (Butyl isobutyrate)

3D-SDF for HMDB0040251 (Butyl isobutyrate)

PDB for HMDB0040251 (Butyl isobutyrate)

3D PDB for HMDB0040251 (Butyl isobutyrate)

SMILES for HMDB0040251 (Butyl isobutyrate)

INCHI for HMDB0040251 (Butyl isobutyrate)

Structure for HMDB0040251 (Butyl isobutyrate)

3D Structure for HMDB0040251 (Butyl isobutyrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra