Isoamyl acetate

Last updated
Isoamyl acetate
Isoamyl acetate.svg
Isoamyl-acetate-3D-balls.png
Isopentyl acetate.jpg
Names
Preferred IUPAC name
3-Methylbutyl acetate
Systematic IUPAC name
3-Methylbutyl ethanoate
Other names
Isopentyl acetate
Isopentyl ethanoate
Isoamyl acetate
Banana oil
Pear essence
Identifiers
3D model (JSmol)
1744750
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.240 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-662-3
101452
KEGG
PubChem CID
RTECS number
  • NS9800000
UNII
UN number 1104 1993
  • InChI=1S/C7H14O2/c1-6(2)4-5-9-7(3)8/h6H,4-5H2,1-3H3 Yes check.svgY
    Key: MLFHJEHSLIIPHL-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C7H14O2/c1-6(2)4-5-9-7(3)8/h6H,4-5H2,1-3H3
    Key: MLFHJEHSLIIPHL-UHFFFAOYAI
  • O=C(OCCC(C)C)C
Properties
C7H14O2
Molar mass 130.187 g·mol−1
AppearanceColorless liquid
Odor Banana-like [1]
Density 0.876 g/cm3
Melting point −78 °C (−108 °F; 195 K)
Boiling point 142 °C (288 °F; 415 K)
0.3% (20 °C) [1]
Vapor pressure 4 mmHg or 0.533 kPa (20 °C) [1]
−89.4·10−6 cm3/mol
1.4020 at 20°
Hazards
GHS labelling:
GHS-pictogram-flamme.svg
Danger
H226, H315, H319, H335, H336, H372
P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P314, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
3
0
Flash point 25 °C (77 °F; 298 K)
Explosive limits 1.0% (100 °C) – 7.5% [1]
Lethal dose or concentration (LD, LC):
7422 mg/kg (rabbit, oral)
16,600 mg/kg (rat, oral) [2]
6470 ppm (cat) [2]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 100 ppm (525 mg/m3) [1]
REL (Recommended)
TWA 100 ppm (525 mg/m3) [1]
IDLH (Immediate danger)
1000 ppm [1]
Related compounds
Related compounds
 Isoamyl formate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Isoamyl acetate, also known as isopentyl acetate, is an ester formed from isoamyl alcohol and acetic acid, with the molecular formula C7H14O2. It is a colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. Isoamyl acetate has a strong odor which is described as similar to both banana and pear. [3] Pure isoamyl acetate, or mixtures of isoamyl acetate, amyl acetate, and other flavors in ethanol may be referred to as banana oil [4] or pear oil. [5]

Contents

Natural occurrence

Isoamyl acetate occurs naturally in many plants, including apple, banana, coffee, grape, guava, lychee, papaya, peach, pomegranate, and tomato. [6] [7] It is also released by fermentation processes, including those used for making beer, sake, cognac, and whisky. [6]

Isoamyl acetate is released by a honey bee's sting apparatus where it serves as a pheromone beacon to attract other bees and provoke them to sting. [8]

Production

Isoamyl acetate is prepared by the acid-catalyzed reaction (Fischer esterification) between isoamyl alcohol and glacial acetic acid as shown in the reaction equation below. Typically, sulfuric acid is used as the catalyst. Alternatively, p-toluenesulfonic acid or an acidic ion exchange resin can be used as the catalyst.

Essigsaureisopentylester Reaktionsschemata.svg

It is also produced synthetically by the rectification of amyl acetate. [9]

Applications

Isoamyl acetate is used to confer banana or pear flavor in foods such as circus peanuts, Juicy Fruit and pear drops. [10] Banana oil and pear oil commonly refer to a solution of isoamyl acetate in ethanol that is used as an artificial flavor.

It is also used as a solvent for some varnishes, oil paints, and nitrocellulose lacquers. As a solvent and carrier for materials such as nitrocellulose, it was extensively used in the aircraft industry for stiffening and wind-proofing fabric flying surfaces, where it and its derivatives were generally known as 'aircraft dope'. Now that most aircraft wings are made of metal, such use is mostly limited to historically accurate reproductions and scale models.

Because of its intense, pleasant odor and its low toxicity, isoamyl acetate is used to test the effectiveness of respirators or gas masks. [11]

Related Research Articles

<span class="mw-page-title-main">Ethyl acetate</span> Organic compound (CH₃CO₂CH₂CH₃)

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

<span class="mw-page-title-main">Methyl acetate</span> Chemical compound

Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or aqueous acids. Methyl acetate is not considered a VOC in the USA.

<span class="mw-page-title-main">Acetic anhydride</span> Organic compound with formula (CH₃CO)₂O

Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.

<span class="mw-page-title-main">Amyl acetate</span> Chemical compound

Amyl acetate (pentyl acetate) is an organic compound and an ester with the chemical formula CH3COO[CH2]4CH3 and the molecular weight 130.19 g/mol. It is colorless and has a scent similar to bananas and apples. The compound is the condensation product of acetic acid and 1-pentanol. However, esters formed from other pentanol isomers (amyl alcohols), or mixtures of pentanols, are often referred to as amyl acetate. The symptoms of exposure to amyl acetate in humans are dermatitis, central nervous system depression, narcosis and irritation to the eyes and nose.

Tributyl phosphate, known commonly as TBP, is an organophosphorus compound with the chemical formula (CH3CH2CH2CH2O)3PO. This colourless, odorless liquid finds some applications as an extractant and a plasticizer. It is an ester of phosphoric acid with n-butanol.

<span class="mw-page-title-main">Butyl acetate</span> Chemical compound

n-Butyl acetate is an organic compound with the formula CH3CO2(CH2)3CH3. A colorless, flammable liquid, it is the ester derived from n-butanol and acetic acid. It is found in many types of fruit, where it imparts characteristic flavors and has a sweet smell of banana or apple. It is used as an industrial solvent.

<span class="mw-page-title-main">Isobutyl acetate</span> Chemical compound

The chemical compound isobutyl acetate, also known as 2-methylpropyl ethanoate or β-methylpropyl acetate, is a common solvent. It is produced from the esterification of isobutanol with acetic acid. It is used as a solvent for lacquer and nitrocellulose. Like many esters it has a fruity or floral smell at low concentrations and occurs naturally in raspberries, pears and other plants. At higher concentrations the odor can be unpleasant and may cause symptoms of central nervous system depression such as nausea, dizziness and headache.

<span class="mw-page-title-main">Propyl acetate</span> Chemical compound

Propyl acetate, also known as propyl ethanoate, is an organic compound. Nearly 20,000 tons are produced annually for use as a solvent. This colorless liquid is known by its characteristic odor of pears. Due to this fact, it is commonly used in fragrances and as a flavor additive. It is formed by the esterification of acetic acid and propan-1-ol, often via Fischer–Speier esterification, with sulfuric acid as a catalyst and water produced as a byproduct.

<span class="mw-page-title-main">Benzyl acetate</span> Chemical compound

Benzyl acetate is an organic ester with the molecular formula CH3C(O)OCH2C6H5. It is formed by the condensation of benzyl alcohol and acetic acid.

<span class="mw-page-title-main">Isopropyl acetate</span> Chemical compound

Isopropyl acetate is an ester, an organic compound which is the product of esterification of acetic acid and isopropanol. It is a clear, colorless liquid with a characteristic fruity odor.

<i>sec</i>-Butyl acetate Chemical compound

sec-Butyl acetate, or s-butyl acetate, is an ester commonly used as a solvent in lacquers and enamels, where it is used in the production of acyclic polymers, vinyl resins, and nitrocellulose. It is a clear flammable liquid with a sweet smell.

<span class="mw-page-title-main">Octyl acetate</span> Chemical compound

Octyl acetate, or octyl ethanoate, is an organic compound with the formula CH3(CH2)7O2CCH3. It is classified as an ester that is formed from 1-octanol (octyl alcohol) and acetic acid. It is found in oranges, grapefruits, and other citrus products.

<span class="mw-page-title-main">Isoamyl alcohol</span> Chemical compound

Isoamyl alcohol is a colorless liquid with the formula C
5H
12O, specifically (H3C–)2CH–CH2–CH2–OH. It is one of several isomers of amyl alcohol (pentanol). It is also known as isopentyl alcohol, isopentanol, or (in the IUPAC recommended nomenclature) 3-methyl-butan-1-ol. An obsolete name for it was isobutyl carbinol.

<span class="mw-page-title-main">2-Ethoxyethanol</span> Chemical compound

2-Ethoxyethanol, also known by the trademark Ethyl cellosolve, is a solvent used widely in commercial and industrial applications. It is a clear, colorless, nearly odorless liquid that is miscible with water, ethanol, diethyl ether, acetone, and ethyl acetate.

<span class="mw-page-title-main">2-Methoxyethanol</span> Chemical compound

2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula C
3H
8O
2 that is used mainly as a solvent. It is a clear, colorless liquid with an ether-like odor. It is in a class of solvents known as glycol ethers which are notable for their ability to dissolve a variety of different types of chemical compounds and for their miscibility with water and other solvents. It can be formed by the nucleophilic attack of methanol on protonated ethylene oxide followed by proton transfer:

<span class="mw-page-title-main">1-Butanol</span> Chemical compound

1-Butanol, also known as butan-1-ol or n-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and tert-butanol. The unmodified term butanol usually refers to the straight chain isomer.

<span class="mw-page-title-main">2-Heptanone</span> Chemical compound

2-Heptanone, also known as methyl n-amyl ketone, or Heptan-2-one, is a ketone with the molecular formula C7H14O. It is a colorless, water-like liquid with a banana-like, fruity odor. 2-Heptanone has a neutral formal charge, and is only slightly soluble in water. It is one of several compounds that contributes to the odor of sweaty clothing.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC. Acetic acid is also known as acetyl hydroxide (AcOH).

<i>sec</i>-Amyl acetate Chemical compound

sec-Amyl acetate is an organic compound and an ester. It is formed in an esterification reaction of sec-amyl alcohol (2-pentanol) and acetic acid. It is a colorless liquid.

Ethyl octanoate, also known as ethyl caprylate, is a fatty acid ester formed from caprylic acid and ethanol. A colorless liquid at room temperature, it has the semi-developed formula of CH3(CH2)6COOCH2CH3, and is used in food industries as a flavoring and in the perfume industry as a scent additive. It is present in many fruits and alcoholic beverages, and has a strong odor of fruit and flowers. It is used in the creation of synthetic fruity scents.

References

  1. 1 2 3 4 5 6 7 NIOSH Pocket Guide to Chemical Hazards. "#0347". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 "Isoamyl acetate". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. ↑ "Iso-amyl acetate". chemicalland21.com.
  4. ↑ Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi : 10.1002/14356007.a11_141.
  5. ↑ "T3DB: Isopentyl acetate". Toxin and Toxin Target Database (T3DB). Canadian Institutes of Health Research, Canada Foundation for Innovation, and by The Metabolomics Innovation Centre (TMIC). Retrieved 2 April 2023.
  6. 1 2 Technical Resources International, Inc (November 1994). "SUMMARY OF DATA FOR CHEMICAL SELECTION: Isoamyl Acetate" (PDF). National Toxicology Program. U.S. Department of Health and Human Services. Retrieved 2 April 2023.
  7. ↑ "Isoamyl acetate Taxonomy". PubChem. National Center for Biotechnology Information. Retrieved 2 April 2023.
  8. ↑ Boch R; Shearer DA; Stone BC (September 8, 1962). "Identification of isoamyl acetate as an active component in the sting pheromone of the honey bee". Nature. 195 (4845). England: Nature Publishing Group: 1018–20. Bibcode:1962Natur.195.1018B. doi:10.1038/1951018b0. PMID   13870346. S2CID   4224788.
  9. ↑ "Isoamyl acetate Methods of Manufacturing". PubChem. National Center for Biotechnology Information.
  10. ↑ "Isoamyl acetate". American Chemical Society. Retrieved 27 October 2022.
  11. ↑ "Fit Testing Procedures (Mandatory). - 1910.134 App A | Occupational Safety and Health Administration". www.osha.gov. Retrieved 2020-02-04.
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