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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:47:18 UTC

Update Date

2023-02-21 17:28:03 UTC

HMDB ID

HMDB0040252

Secondary Accession Numbers

HMDB40252

Metabolite Identification

Common Name

Isobutyl isobutyrate

Description

Isobutyl isobutyrate 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). Isobutyl isobutyrate is a grape skin, pineapple, and tropical tasting compound. Isobutyl isobutyrate has been detected, but not quantified in, several different foods, such as alcoholic beverages, fruits, roman camomiles (Chamaemelum nobile), and sweet bays (Laurus nobilis). This could make isobutyl isobutyrate a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Isobutyl isobutyrate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Isobutyl isobutyric acid	Generator
2-Methyl-1-propyl 2-methylpropanoate	HMDB
2-Methylpropyl 2-methylpropionate	HMDB
2-Methylpropyl isobutyrate	HMDB
FEMA 2189	HMDB
Isobutyl 2-methylpropanoate	HMDB
Isobutyl ester OF 2-methylpropanoic acid	HMDB
Isobutyl isobutanoate	HMDB
Isobutyl isobutyrate	HMDB
Isobutylester kyseliny isomaselne	HMDB
Isobutyric acid, isobutyl ester	HMDB
Propanoic acid, 2-methyl-, 2-methylpropyl ester	HMDB
2-Methylpropyl 2-methylpropionic acid	Generator

Chemical Formula

C₈H₁₆O₂

Average Molecular Weight

144.2114

Monoisotopic Molecular Weight

144.115029756

IUPAC Name

2-methylpropyl 2-methylpropanoate

Traditional Name

isobutyl isobutyrate

CAS Registry Number

97-85-8

SMILES

CC(C)COC(=O)C(C)C

InChI Identifier

InChI=1S/C8H16O2/c1-6(2)5-10-8(9)7(3)4/h6-7H,5H2,1-4H3

InChI Key

RXGUIWHIADMCFC-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

Wax monoesters (LMFA07010566 )

Ontology

Cellular substructure

Membrane (HMDB: HMDB0040252)
Cell membrane (HMDB: HMDB0040252)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040252)

Source

Exogenous

Exogenous (HMDB: HMDB0040252)

Food

Food (HMDB: HMDB0040252)

Herb and spice

Herb

Sweet bay (FooDB: FOOD00097)
Roman camomile (FooDB: FOOD00046)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0040252)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040252)

Biological role

Nutrient (HMDB: HMDB0040252)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-81 °C	Not Available
Boiling Point	148.60 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1 mg/mL at 20 °C	Not Available
LogP	2.511 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.96 g/L	ALOGPS
logP	2.56	ALOGPS
logP	2.41	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	4	ChemAxon
Refractivity	40.36 m³·mol⁻¹	ChemAxon
Polarizability	17.12 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]+	134.265	31661259
DarkChem	[M-H]-	129.366	31661259
DeepCCS	[M+H]+	137.237	30932474
DeepCCS	[M-H]-	134.58	30932474
DeepCCS	[M-2H]-	171.272	30932474
DeepCCS	[M+Na]+	146.48	30932474
AllCCS	[M+H]+	133.2	32859911
AllCCS	[M+H-H2O]+	129.3	32859911
AllCCS	[M+NH4]+	136.8	32859911
AllCCS	[M+Na]+	137.8	32859911
AllCCS	[M-H]-	134.5	32859911
AllCCS	[M+Na-2H]-	137.1	32859911
AllCCS	[M+HCOO]-	140.0	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.	4.86 minutes	32390414
Predicted by Siyang on May 30, 2022	15.9791 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.38 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2197.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	576.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	190.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	337.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	108.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	642.2 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	741.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	148.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1140.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	497.4 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	1449.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	386.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	376.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	509.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	498.1 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	21.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isobutyl isobutyrate	CC(C)COC(=O)C(C)C	1125.5	Standard polar	33892256
Isobutyl isobutyrate	CC(C)COC(=O)C(C)C	851.7	Standard non polar	33892256
Isobutyl isobutyrate	CC(C)COC(=O)C(C)C	913.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Isobutyl isobutyrate EI-B (Non-derivatized)	splash10-0596-9000000000-fb563351fb63b4833e24	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isobutyl isobutyrate EI-B (Non-derivatized)	splash10-05fu-9000000000-5808ba7a72e3f14794fd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isobutyl isobutyrate CI-B (Non-derivatized)	splash10-00di-9000000000-074030ed9e891a78b12d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isobutyl isobutyrate EI-B (Non-derivatized)	splash10-0596-9000000000-cc0e2f654a9c0d39e1ad	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isobutyl isobutyrate EI-B (Non-derivatized)	splash10-0596-9000000000-fb563351fb63b4833e24	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isobutyl isobutyrate EI-B (Non-derivatized)	splash10-05fu-9000000000-5808ba7a72e3f14794fd	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isobutyl isobutyrate CI-B (Non-derivatized)	splash10-00di-9000000000-074030ed9e891a78b12d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isobutyl isobutyrate EI-B (Non-derivatized)	splash10-0596-9000000000-cc0e2f654a9c0d39e1ad	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isobutyl isobutyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0596-9000000000-03b197bc2c2ed4b44c64	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isobutyl 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 - Isobutyl isobutyrate 10V, Positive-QTOF	splash10-052b-9600000000-730896e3131a90d2ee16	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isobutyl isobutyrate 20V, Positive-QTOF	splash10-0a4i-9100000000-bde9bfffc19ea267c931	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isobutyl isobutyrate 40V, Positive-QTOF	splash10-0a4i-9000000000-efb977f0b56e97d23592	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isobutyl isobutyrate 10V, Negative-QTOF	splash10-0006-3900000000-878740376f9065e57a98	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isobutyl isobutyrate 20V, Negative-QTOF	splash10-000l-9300000000-1f2b6b9c863b0d9a4a5d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isobutyl isobutyrate 40V, Negative-QTOF	splash10-00kr-9000000000-c7400c1ac784b6337d52	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isobutyl isobutyrate 10V, Negative-QTOF	splash10-0006-0900000000-91a6d7eda80533c9e0fe	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isobutyl isobutyrate 20V, Negative-QTOF	splash10-000l-9300000000-a62b956a68fdf6326ad2	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isobutyl isobutyrate 40V, Negative-QTOF	splash10-000i-9000000000-e5ca3aa37766d93a9ea5	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isobutyl isobutyrate 10V, Positive-QTOF	splash10-0596-9000000000-d2446a05a51c544086f8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isobutyl isobutyrate 20V, Positive-QTOF	splash10-0596-9000000000-ec5e12fbef2cce4b882e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isobutyl isobutyrate 40V, Positive-QTOF	splash10-0006-9000000000-6b82393cb0e4fb319fe7	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

FDB019969

KNApSAcK ID

C00035117

Chemspider ID

7073

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7351

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1007601

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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

Showing metabocard for Isobutyl isobutyrate (HMDB0040252)

MOL for HMDB0040252 (Isobutyl isobutyrate)

3D MOL for HMDB0040252 (Isobutyl isobutyrate)

3D SDF for HMDB0040252 (Isobutyl isobutyrate)

3D-SDF for HMDB0040252 (Isobutyl isobutyrate)

PDB for HMDB0040252 (Isobutyl isobutyrate)

3D PDB for HMDB0040252 (Isobutyl isobutyrate)

SMILES for HMDB0040252 (Isobutyl isobutyrate)

INCHI for HMDB0040252 (Isobutyl isobutyrate)

Structure for HMDB0040252 (Isobutyl isobutyrate)

3D Structure for HMDB0040252 (Isobutyl isobutyrate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra