|Preferred IUPAC name
|Systematic IUPAC name
|3D model (Jmol)||Interactive image|
|Molar mass||130.19 g·mol−1|
|Melting point||−78 °C (−108 °F; 195 K)|
|Boiling point||142 °C (288 °F; 415 K)|
|0.3% (20 °C)|
|Vapor pressure||4 mmHg (20 °C)|
|Flash point||25 °C (77 °F; 298 K)|
|Explosive limits||1.0% (100 °C) - 7.5%|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|7422 mg/kg (rabbit, oral)
16,600 mg/kg (rat, oral)
LCLo (lowest published)
|6470 ppm (cat)|
|US health exposure limits (NIOSH):|
|TWA 100 ppm (525 mg/m3)|
|TWA 100 ppm (525 mg/m3)|
IDLH (Immediate danger)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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. Banana oil may be either pure isoamyl acetate, or flavorings that are mixtures of isoamyl acetate, amyl acetate, and other flavors.
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.
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.
Occurrence in nature
- "NIOSH Pocket Guide to Chemical Hazards #0347". National Institute for Occupational Safety and Health (NIOSH).
- "Isoamyl acetate". Immediately Dangerous to Life and Health. 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. England: Nature Publishing Group. 195 (4845): 1018–20. doi:10.1038/1951018b0. PMID 13870346.