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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:41:50 UTC

Update Date

2023-02-21 17:20:11 UTC

HMDB ID

HMDB0031246

Secondary Accession Numbers

HMDB31246

Metabolite Identification

Common Name

2-Methylpropyl acetate

Description

2-Methylpropyl acetate, also known as acetate d'isobutyle or essigsaeureisobutylester, 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). 2-Methylpropyl acetate is a sweet, apple, and banana tasting compound. 2-Methylpropyl acetate is found, on average, in the highest concentration within red wine and beer. 2-Methylpropyl acetate has also been detected, but not quantified in, several different foods, such as papayas (Carica papaya), muskmelons (Cucumis melo), apples (Malus pumila), asian pears (Pyrus pyrifolia), and fruits. This could make 2-methylpropyl acetate a potential biomarker for the consumption of these foods. 2-Methylpropyl acetate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on 2-Methylpropyl acetate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Methyl-1-propyl acetate	ChEBI
2-Methylpropyl ethanoate	ChEBI
Acetate d'isobutyle	ChEBI
Acetic acid, 2-methylpropyl ester	ChEBI
Acetic acid, isobutyl ester	ChEBI
beta-Methylpropyl ethanoate	ChEBI
Essigsaeureisobutylester	ChEBI
I-butyl acetate	ChEBI
Isobutyl ethanoate	ChEBI
Isobutylacetat	ChEBI
Isobutylazetat	ChEBI
2-Methyl-1-propyl acetic acid	Generator
2-Methylpropyl ethanoic acid	Generator
Acetic acid d'isobutyle	Generator
Acetate, 2-methylpropyl ester	Generator
Acetate, isobutyl ester	Generator
b-Methylpropyl ethanoate	Generator
b-Methylpropyl ethanoic acid	Generator
beta-Methylpropyl ethanoic acid	Generator
Β-methylpropyl ethanoate	Generator
Β-methylpropyl ethanoic acid	Generator
I-butyl acetic acid	Generator
Isobutyl ethanoic acid	Generator
2-Methylpropyl acetic acid	Generator
2-Methyl-1-propanol, acetate	HMDB
2-Methylpropyl acetate, 9ci	HMDB
beta -Methylpropyl ethanoate	HMDB
FEMA 2175	HMDB
Isobutyl acetate	HMDB
Isobutyl acetate FCC	HMDB
Isobutyl acetate, 8ci	HMDB
Isobutylester kyseliny octove	HMDB
Isobutyl acetic acid	Generator
Isobutylacetate	MeSH

Chemical Formula

C₆H₁₂O₂

Average Molecular Weight

116.1583

Monoisotopic Molecular Weight

116.083729628

IUPAC Name

2-methylpropyl acetate

Traditional Name

isobutyl acetate

CAS Registry Number

110-19-0

SMILES

CC(C)COC(C)=O

InChI Identifier

InChI=1S/C6H12O2/c1-5(2)4-8-6(3)7/h5H,4H2,1-3H3

InChI Key

GJRQTCIYDGXPES-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

acetate ester (CHEBI:50569 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0031246)
Cytoplasm (HMDB: HMDB0031246)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031246)

Source

Endogenous

Endogenous (HMDB: HMDB0031246)

Plant

Exogenous

Food

Food (HMDB: HMDB0031246)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)
Red wine (FooDB: FOOD00911)

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Fruit

Pome

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)
Asian pear (FooDB: FOOD00291)

Other fruit

Fig (FooDB: FOOD00081)

Tropical fruit

Papaya (FooDB: FOOD00041)
Pineapple (FooDB: FOOD00012)

Fruits (FooDB: FOOD00871)

Gourd

Muskmelon (FooDB: FOOD00064)

Herb and spice

Herb

Sweet bay (FooDB: FOOD00097)
Rosemary (FooDB: FOOD00159)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Not Available

Role

Industrial application

Opioid analgesic (HMDB: HMDB0031246)
Fragrance (HMDB: HMDB0031246)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031246)

Biological role

Irritant (HMDB: HMDB0031246)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-98.85 °C	Not Available
Boiling Point	116.50 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	6.3 mg/mL at 25 °C	Not Available
LogP	1.78	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.71 g/L	ALOGPS
logP	1.74	ALOGPS
logP	1.17	ChemAxon
logS	-1.2	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	3	ChemAxon
Refractivity	31.16 m³·mol⁻¹	ChemAxon
Polarizability	13.11 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]+	125.581	31661259
DarkChem	[M-H]-	119.741	31661259
DeepCCS	[M+H]+	129.989	30932474
DeepCCS	[M-H]-	128.04	30932474
DeepCCS	[M-2H]-	163.99	30932474
DeepCCS	[M+Na]+	138.513	30932474
AllCCS	[M+H]+	127.2	32859911
AllCCS	[M+H-H2O]+	123.0	32859911
AllCCS	[M+NH4]+	131.1	32859911
AllCCS	[M+Na]+	132.2	32859911
AllCCS	[M-H]-	128.8	32859911
AllCCS	[M+Na-2H]-	132.2	32859911
AllCCS	[M+HCOO]-	136.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methylpropyl acetate	CC(C)COC(C)=O	1059.4	Standard polar	33892256
2-Methylpropyl acetate	CC(C)COC(C)=O	714.4	Standard non polar	33892256
2-Methylpropyl acetate	CC(C)COC(C)=O	779.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-f217b5e6b92235a1dd71	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl acetate EI-B (Non-derivatized)	splash10-052f-9000000000-25cc25b3ba0651c0ba45	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-47909851abe2172156c6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-32ed7cd25a7cd585255a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl acetate EI-B (Non-derivatized)	splash10-052f-9000000000-497069f05d541433b66e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl acetate EI-B (Non-derivatized)	splash10-052f-9000000000-49585f528507ace5b393	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl acetate CI-B (Non-derivatized)	splash10-014i-1900000000-bb28c34b11812942773d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-ef6ece5c35a5dd154ad5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-f217b5e6b92235a1dd71	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl acetate EI-B (Non-derivatized)	splash10-052f-9000000000-25cc25b3ba0651c0ba45	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-47909851abe2172156c6	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-32ed7cd25a7cd585255a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl acetate EI-B (Non-derivatized)	splash10-052f-9000000000-497069f05d541433b66e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl acetate EI-B (Non-derivatized)	splash10-052f-9000000000-49585f528507ace5b393	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl acetate CI-B (Non-derivatized)	splash10-014i-1900000000-bb28c34b11812942773d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-ef6ece5c35a5dd154ad5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylpropyl acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-df6cefc23abcd1e80417	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylpropyl acetate 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 - 2-Methylpropyl acetate 10V, Positive-QTOF	splash10-066r-9700000000-a748f357862b1b998434	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl acetate 20V, Positive-QTOF	splash10-0a4i-9100000000-edefa0d353dff24eb16b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl acetate 40V, Positive-QTOF	splash10-0a4i-9000000000-f40694d799cd17a2cec4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl acetate 10V, Negative-QTOF	splash10-014i-7900000000-6534ebe4a3a380503d44	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl acetate 20V, Negative-QTOF	splash10-0aor-9200000000-fd7dc8a883948134a340	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl acetate 40V, Negative-QTOF	splash10-0a4l-9000000000-e0b525315cc093f0fd0c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl acetate 10V, Positive-QTOF	splash10-0a4i-9000000000-6eb8c377976b6fa47cd1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl acetate 20V, Positive-QTOF	splash10-0a4l-9000000000-75ca9d459a88c83adee2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl acetate 40V, Positive-QTOF	splash10-0006-9000000000-4531d1e7d918cb3881e5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl acetate 10V, Negative-QTOF	splash10-0600-9200000000-9d3e1ac44fb825b68474	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl acetate 20V, Negative-QTOF	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl acetate 40V, Negative-QTOF	splash10-0a4l-9000000000-e19c8390ed8f55d45a2d	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)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB003275

KNApSAcK ID

C00050471

Chemspider ID

7747

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isobutyl_acetate

METLIN ID

Not Available

PubChem Compound

8038

PDB ID

Not Available

ChEBI ID

50569

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1013631

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 2-Methylpropyl acetate (HMDB0031246)

MOL for HMDB0031246 (2-Methylpropyl acetate)

3D MOL for HMDB0031246 (2-Methylpropyl acetate)

3D SDF for HMDB0031246 (2-Methylpropyl acetate)

3D-SDF for HMDB0031246 (2-Methylpropyl acetate)

PDB for HMDB0031246 (2-Methylpropyl acetate)

3D PDB for HMDB0031246 (2-Methylpropyl acetate)

SMILES for HMDB0031246 (2-Methylpropyl acetate)

INCHI for HMDB0031246 (2-Methylpropyl acetate)

Structure for HMDB0031246 (2-Methylpropyl acetate)

3D Structure for HMDB0031246 (2-Methylpropyl acetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra