Isoamyl acetate
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| 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)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.004.240 |
| KEGG | |
| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C7H14O2 | |
| Molar mass | 130.187 g·mol−1 |
| Appearance | Colorless 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 (20 °C)[1] |
| Hazards | |
| NFPA 704 (fire diamond) | |
| Flash point | 25 °C (77 °F; 298 K) |
| Explosive limits | 1.0% (100 °C) - 7.5%[1] |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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7422 mg/kg (rabbit, oral) 16,600 mg/kg (rat, oral)[2] |
LCLo (lowest published)
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6470 ppm (cat)[2] |
| NIOSH (US health exposure limits): | |
PEL (Permissible)
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TWA 100 ppm (525 mg/m3)[1] |
REL (Recommended)
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TWA 100 ppm (525 mg/m3)[1] |
IDLH (Immediate danger)
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1000 ppm[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Isoamyl acetate, also known as isopentyl acetate, is an organic compound that is the 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. Isoamyl acetate has a strong odor which is also described as similar to both banana and pear.[3] Banana oil may be either pure isoamyl acetate, or flavorings that are mixtures of isoamyl acetate, amyl acetate, and other flavors.[4]
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. Alternately, an acidic ion exchange resin can be used as the catalyst.
Applications
Isoamyl acetate is used to confer banana flavor in foods. Pear oil commonly refers 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 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 are all-metal, such use is now mostly limited to historically accurate reproductions and scale models. In addition, isoamyl acetate serves as an alarm pheromone in honey bees.
Because of its intense, pleasant odor and its low toxicity, isoamyl acetate is used to test the effectiveness of respirators or gas masks. It is also used in thermometers
Occurrence in nature
Isoamyl acetate occurs naturally in the banana plant[5] and it is also produced synthetically.[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.[7]
References
- ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0347". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b "Isoamyl acetate". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ "Iso-amyl acetate". chemicalland21.com.
- ^ 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.
- ^ McGee, Harold (2003). On Food and Cooking. New York: Scribner.
- ^ Isoamyl Acetate, Occupational Safety and Health Administration
- ^ 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. doi:10.1038/1951018b0. PMID 13870346.