ChemFOnt: Showing chemical card for Isopentyl acetate (CFc000012714)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:00:52 UTC

Chemfont ID

CFc000012714

Molecule Identification

Common Name

Isopentyl acetate

Definition

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 SDF PDB SMILES InChI

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 )

Functional Ontology

Feces (PMID: 23454028)

Cellular substructure

Extracellular (HMDB: HMDB0031528)
Cytoplasm (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)

Exogenous (HMDB: HMDB0031528)

Process

Not Available

Role

Environmental role

Air pollutant (HMDB: HMDB0031528)

Industrial application

Food and nutrition

Food and nutrition (HMDB: HMDB0031528)

Manufacturing industry

Laboratory chemical

Laboratory chemical (HMDB: HMDB0031528)

Fragrance (HMDB: HMDB0031528)

Biological role

Irritant (HMDB: HMDB0031528)

Physical Properties

Predicted 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