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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

2012-09-11 17:43:52 UTC

Update Date

2023-02-21 17:20:45 UTC

HMDB ID

HMDB0031528

Secondary Accession Numbers

HMDB31528

Metabolite Identification

Common Name

Isopentyl acetate

Description

Isopentyl acetate, also known as isoamyl acetate or amylacetic ester, 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). Isopentyl acetate is an ester formed from isoamyl alcohol and acetic acid. It is a colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. Isopentyl acetate has a sweet, fruity banana odor and similar sweet, fruity banana taste. Isopentyl acetate is used to confer banana flavor in foods. Isopentyl 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. Outside of the human body, Isopentyl acetate is found, on average, in the highest concentration within a few different foods, such as red wines, white wines, and beers. Isopentyl acetate has also been detected, but not quantified in, several different foods, such as blackberries (Rubus), figs (Ficus carica), red teas, bananas (Musa acuminata), and black elderberries (Sambucus nigra). This could make isopentyl acetate a potential biomarker for the consumption of these foods. Isopentyl acetate occurs naturally in the banana plant and it is also produced synthetically. Based on a literature review a significant number of articles have been published on Isopentyl acetate. Pure isopentyl acetate, or mixtures of isopentyl acetate, amyl acetate, and other flavors may be referred to as banana oil. Because of its intense, pleasant odor and its low toxicity, isopentyl acetate is used to test the effectiveness of respirators or gas masks. Isopentyl acetate is released by a honey bee's sting where it serves as a pheromone beacon to attract other bees and provoke them to sting.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Methyl-1-butanol acetate	ChEBI
3-Methyl-1-butyl acetate	ChEBI
3-Methyl-but-1-yl acetate	ChEBI
3-Methylbutyl acetate	ChEBI
3-Methylbutyl ethanoate	ChEBI
Acetate d'isoamyle	ChEBI
Acetate d'isopentyle	ChEBI
Acetate de 3-methylbutyle	ChEBI
Acetic acid, 3-methylbutyl ester	ChEBI
Acetic acid, isopentyl ester	ChEBI
Amylacetic ester	ChEBI
beta-Methyl butyl acetate	ChEBI
CH3C(O)O(CH2)2ch(CH3)2	ChEBI
I-amyl acetate	ChEBI
Isoamyl ethanoate	ChEBI
Isoamylacetat	ChEBI
Isoamylazetat	ChEBI
Isopentyl ethanoate	ChEBI
3-Methyl-1-butanol acetic acid	Generator
3-Methyl-1-butyl acetic acid	Generator
3-Methyl-but-1-yl acetic acid	Generator
3-Methylbutyl acetic acid	Generator
3-Methylbutyl ethanoic acid	Generator
Acetic acid d'isoamyle	Generator
Acetic acid d'isopentyle	Generator
Acetic acid de 3-methylbutyle	Generator
Acetate, 3-methylbutyl ester	Generator
Acetate, isopentyl ester	Generator
b-Methyl butyl acetate	Generator
b-Methyl butyl acetic acid	Generator
beta-Methyl butyl acetic acid	Generator
Β-methyl butyl acetate	Generator
Β-methyl butyl acetic acid	Generator
I-amyl acetic acid	Generator
Isoamyl ethanoic acid	Generator
Isopentyl ethanoic acid	Generator
Isopentyl acetic acid	Generator
Isopentylacetate	MeSH
1-Butanol, 3-methyl-, 1-acetate	HMDB
1-Butanol, 3-methyl-, acetate	HMDB
3-Methyl butyl ester acetic acid	HMDB
3-Methyl-1-butanol, acetate	HMDB
3-Methyl-1-butanyl acetate	HMDB
FEMA 2055	HMDB
Isoamyl acetate	HMDB
Isopentyl acetate	ChEBI
Isoamyl acetic acid	Generator

Chemical Formula

C₇H₁₄O₂

Average Molecular Weight

130.1849

Monoisotopic Molecular Weight

130.099379692

IUPAC Name

3-methylbutyl acetate

Traditional Name

banana oil

CAS Registry Number

123-92-2

SMILES

CC(C)CCOC(C)=O

InChI Identifier

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

InChI Key

MLFHJEHSLIIPHL-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:31725 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0031528)
Cytoplasm (HMDB: HMDB0031528)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0031528)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031528)

Source

Endogenous

Endogenous (HMDB: HMDB0031528)

Plant

Plant (HMDB: HMDB0031528)

Exogenous

Food

Food (HMDB: HMDB0031528)

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

Tropical fruit

Banana (FooDB: FOOD00208)
Guava (FooDB: FOOD00150)
Papaya (FooDB: FOOD00041)

Other fruit

Fig (FooDB: FOOD00081)

Berry

Fruits (FooDB: FOOD00871)

Tea

Environmental

Tobacco Smoke (HMDB: HMDB0031528)

Process

Not Available

Role

Biological role

Irritant (HMDB: HMDB0031528)

Industrial application

Fragrance (HMDB: HMDB0031528)

Food and nutrition

Food and nutrition (HMDB: HMDB0031528)

Manufacturing industry

Laboratory chemical

Laboratory chemical (HMDB: HMDB0031528)

Environmental role

Air pollutant (HMDB: HMDB0031528)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-78.5 °C	Not Available
Boiling Point	142.00 to 143.00 °C. @ 756.00 mm Hg	The Good Scents Company Information System
Water Solubility	2 mg/mL at 25 °C	Not Available
LogP	2.25	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.06 g/L	ALOGPS
logP	2.36	ALOGPS
logP	1.53	ChemAxon
logS	-1.8	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	35.84 m³·mol⁻¹	ChemAxon
Polarizability	15.18 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]+	128.635	31661259
DarkChem	[M-H]-	124.768	31661259
DeepCCS	[M+H]+	133.549	30932474
DeepCCS	[M-H]-	131.342	30932474
DeepCCS	[M-2H]-	167.452	30932474
DeepCCS	[M+Na]+	142.306	30932474
AllCCS	[M+H]+	130.6	32859911
AllCCS	[M+H-H2O]+	126.5	32859911
AllCCS	[M+NH4]+	134.4	32859911
AllCCS	[M+Na]+	135.5	32859911
AllCCS	[M-H]-	132.5	32859911
AllCCS	[M+Na-2H]-	135.4	32859911
AllCCS	[M+HCOO]-	138.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isopentyl acetate	CC(C)CCOC(C)=O	1163.0	Standard polar	33892256
Isopentyl acetate	CC(C)CCOC(C)=O	858.6	Standard non polar	33892256
Isopentyl acetate	CC(C)CCOC(C)=O	894.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)	splash10-00kf-9000000000-b39e66ca9f24f516c159	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)	splash10-004i-9000000000-25e59405f21ad74bf82d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-712ec54497a1b720e6f4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)	splash10-006x-9000000000-8c50c23b8716d739a931	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)	splash10-00dl-9000000000-6eb9d62df8623ee92ac6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopentyl acetate CI-B (Non-derivatized)	splash10-001i-0900000000-21654613d581d7671bbc	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-fe72c0ec89d09374d63a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)	splash10-00kf-9000000000-b39e66ca9f24f516c159	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)	splash10-004i-9000000000-25e59405f21ad74bf82d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-712ec54497a1b720e6f4	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)	splash10-006x-9000000000-8c50c23b8716d739a931	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)	splash10-00dl-9000000000-6eb9d62df8623ee92ac6	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopentyl acetate CI-B (Non-derivatized)	splash10-001i-0900000000-21654613d581d7671bbc	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopentyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-fe72c0ec89d09374d63a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopentyl acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-5cec3842741b72d2888b	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopentyl acetate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-07a7afc7d858b6cfbcbd	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopentyl acetate 10V, Positive-QTOF	splash10-001i-5900000000-38618594a20a626349f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopentyl acetate 20V, Positive-QTOF	splash10-00di-9100000000-ed5c80c34661648c5359	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopentyl acetate 40V, Positive-QTOF	splash10-0abc-9000000000-8371bc765eaa9253dd3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopentyl acetate 10V, Negative-QTOF	splash10-004i-7900000000-d2baceb7d855f1c63083	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopentyl acetate 20V, Negative-QTOF	splash10-0a4i-9200000000-a0d1c48d52d2bcc8e9e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopentyl acetate 40V, Negative-QTOF	splash10-0a4l-9000000000-cfa80356b0c95bba654b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopentyl acetate 10V, Positive-QTOF	splash10-00dl-9000000000-94d22b8671a4b150f4da	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopentyl acetate 20V, Positive-QTOF	splash10-05fr-9000000000-8fdf0cfc29d75b55c993	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopentyl acetate 40V, Positive-QTOF	splash10-0006-9000000000-1a376d8c519c26546110	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopentyl acetate 10V, Negative-QTOF	splash10-052r-9000000000-313bea5d0d6a31ec5965	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopentyl acetate 20V, Negative-QTOF	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopentyl acetate 40V, Negative-QTOF	splash10-0a4i-9000000000-57efb85ba2c5a7c82d4c	2021-09-23	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]+)	2023-02-04	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

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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	26806034	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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohns disease	26806034	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	26806034	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 ]
Crohn's disease
Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Ulcerative colitis
Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]

Associated OMIM IDs

266600 (Crohn's disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isoamyl acetate

METLIN ID

Not Available

PubChem Compound

31276

PDB ID

Not Available

ChEBI ID

31725

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1006711

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 Isopentyl acetate (HMDB0031528)

MOL for HMDB0031528 (Isopentyl acetate)

3D MOL for HMDB0031528 (Isopentyl acetate)

3D SDF for HMDB0031528 (Isopentyl acetate)

3D-SDF for HMDB0031528 (Isopentyl acetate)

PDB for HMDB0031528 (Isopentyl acetate)

3D PDB for HMDB0031528 (Isopentyl acetate)

SMILES for HMDB0031528 (Isopentyl acetate)

INCHI for HMDB0031528 (Isopentyl acetate)

Structure for HMDB0031528 (Isopentyl acetate)

3D Structure for HMDB0031528 (Isopentyl acetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra