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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-12 01:07:27 UTC

Update Date

2023-02-21 17:27:02 UTC

HMDB ID

HMDB0039619

Secondary Accession Numbers

HMDB39619

Metabolite Identification

Common Name

Isopropyl butyrate

Description

Isopropyl butyrate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Based on a literature review a small amount of articles have been published on Isopropyl butyrate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Isopropyl butyric acid	Generator
1-Methylethyl butanoate	HMDB
2-Propyl butanoate	HMDB
Butanoic acid, 1-methylethyl ester	HMDB
Butanoic acid, 2-methylethyl ester	HMDB
Butyric acid, isopropyl ester	HMDB
FEMA 2935	HMDB
Isopropyl butanoate	HMDB
Isopropyl N-butyrate	HMDB
N-Butyric acid isopropyl ester	HMDB
N-C3H7C(O)OCH(CH3)2	HMDB

Chemical Formula

C₇H₁₄O₂

Average Molecular Weight

130.1849

Monoisotopic Molecular Weight

130.099379692

IUPAC Name

propan-2-yl butanoate

Traditional Name

isopropyl butanoate

CAS Registry Number

638-11-9

SMILES

CCCC(=O)OC(C)C

InChI Identifier

InChI=1S/C7H14O2/c1-4-5-7(8)9-6(2)3/h6H,4-5H2,1-3H3

InChI Key

FFOPEPMHKILNIT-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty 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 Framework

Aliphatic acyclic compounds

External Descriptors

Wax monoesters (LMFA07010673 )

Ontology

Cellular substructure

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0039619)
Urine (HMDB: HMDB0039619)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039619)

Source

Endogenous

Endogenous (HMDB: HMDB0039619)

Plant

Plant (HMDB: HMDB0039619)

Animal

Animal (HMDB: HMDB0039619)

Exogenous

Food

Food (HMDB: HMDB0039619)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0039619)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0039619)

Cellular process

Cell signaling (HMDB: HMDB0039619)

Biochemical process

Lipid transport (HMDB: HMDB0039619)

Role

Biological role

Energy storage (HMDB: HMDB0039619)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039619)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0039619)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	130.00 to 131.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	2.158 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.36 g/L	ALOGPS
logP	2.23	ALOGPS
logP	1.84	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Basic)	-7	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	4	ChemAxon
Refractivity	35.81 m³·mol⁻¹	ChemAxon
Polarizability	15.09 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]+	128.73	31661259
DarkChem	[M-H]-	125.954	31661259
DeepCCS	[M+H]+	130.499	30932474
DeepCCS	[M-H]-	128.251	30932474
DeepCCS	[M-2H]-	164.521	30932474
DeepCCS	[M+Na]+	139.412	30932474
AllCCS	[M+H]+	133.0	32859911
AllCCS	[M+H-H2O]+	129.0	32859911
AllCCS	[M+NH4]+	136.8	32859911
AllCCS	[M+Na]+	137.9	32859911
AllCCS	[M-H]-	132.7	32859911
AllCCS	[M+Na-2H]-	135.6	32859911
AllCCS	[M+HCOO]-	138.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isopropyl butyrate	CCCC(=O)OC(C)C	1038.8	Standard polar	33892256
Isopropyl butyrate	CCCC(=O)OC(C)C	825.9	Standard non polar	33892256
Isopropyl butyrate	CCCC(=O)OC(C)C	837.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Isopropyl butyrate EI-B (Non-derivatized)	splash10-006x-9000000000-b1225eb54077c992b141	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopropyl butyrate EI-B (Non-derivatized)	splash10-0076-9000000000-724f87ca3dc7590d6469	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopropyl butyrate EI-B (Non-derivatized)	splash10-0006-9000000000-6cf9a61263b7ec9813f9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopropyl butyrate EI-B (Non-derivatized)	splash10-006x-9000000000-b1225eb54077c992b141	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopropyl butyrate EI-B (Non-derivatized)	splash10-0076-9000000000-724f87ca3dc7590d6469	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopropyl butyrate EI-B (Non-derivatized)	splash10-0006-9000000000-6cf9a61263b7ec9813f9	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopropyl butyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-b65b885d4857e8056cd6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopropyl butyrate 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 - Isopropyl butyrate 10V, Positive-QTOF	splash10-0089-9700000000-2943a605eb3b3fce2f05	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl butyrate 20V, Positive-QTOF	splash10-022c-9000000000-793a47b7d49a3b643aef	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl butyrate 40V, Positive-QTOF	splash10-0006-9000000000-a0c621aa932712676adf	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl butyrate 10V, Negative-QTOF	splash10-004i-5900000000-3701171185b724b38a5e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl butyrate 20V, Negative-QTOF	splash10-0a4i-9200000000-106651cb9165902f14a9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl butyrate 40V, Negative-QTOF	splash10-0a4i-9000000000-498673646fa305162c21	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl butyrate 10V, Positive-QTOF	splash10-00du-9000000000-7cd4cdcb60f164033c72	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl butyrate 20V, Positive-QTOF	splash10-006x-9000000000-b59eddf36d1a53c82360	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl butyrate 40V, Positive-QTOF	splash10-0006-9000000000-1f20620f0e77d4109503	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl butyrate 10V, Negative-QTOF	splash10-0a4i-9100000000-09a7c4acf71580ee0bc1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl butyrate 20V, Negative-QTOF	splash10-0a4l-9000000000-96328ebb3589ab52fa90	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl butyrate 40V, Negative-QTOF	splash10-0a4l-9000000000-b7449696540a58231251	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23454028	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	details

Associated Disorders and Diseases

Disease References

Nonalcoholic fatty liver disease
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 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB019247

KNApSAcK ID

Not Available

Chemspider ID

55130

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61184

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1034021

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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 ]
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 ]
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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Isopropyl butyrate (HMDB0039619)

MOL for HMDB0039619 (Isopropyl butyrate)

3D MOL for HMDB0039619 (Isopropyl butyrate)

3D SDF for HMDB0039619 (Isopropyl butyrate)

3D-SDF for HMDB0039619 (Isopropyl butyrate)

PDB for HMDB0039619 (Isopropyl butyrate)

3D PDB for HMDB0039619 (Isopropyl butyrate)

SMILES for HMDB0039619 (Isopropyl butyrate)

INCHI for HMDB0039619 (Isopropyl butyrate)

Structure for HMDB0039619 (Isopropyl butyrate)

3D Structure for HMDB0039619 (Isopropyl butyrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra