|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||88.148 g/mol|
|Appearance||Clear, colorless liquid|
|Density||0.8104 g/cm3 at 20 °C|
|Melting point||−117 °C (−179 °F; 156 K)|
|Boiling point||131.1 °C (268.0 °F; 404.2 K)|
|slightly soluble, 28 g/L|
|Solubility||very soluble in acetone, diethyl ether, ethanol|
|Vapor pressure||28 mmHg (20°C)|
Heat capacity (C)
Std enthalpy of
|-356.4 kJ·mol−1 (liquid) |
-300.7 kJ·mol−1 (gas)
|Flash point||43 °C (109 °F; 316 K)|
|350 °C (662 °F; 623 K)|
|Explosive limits||1.2 – 9%|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|3438 mg/kg (rabbit, oral)|
1300 mg/kg (rat, oral)
|NIOSH (US health exposure limits):|
|TWA 100 ppm (360 mg/m3)|
|TWA 100 ppm (360 mg/m3) ST 125 ppm (450 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 alcohol is a colorless liquid with the formula C
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.
Isoamyl alcohol is an ingredient in the production of banana oil, an ester found in nature and also produced as a flavouring in industry. It is a common fusel alcohol, produced as a major by-product of ethanol fermentation.
Isoamyl alcohol is one of the components of the aroma of Tuber melanosporum, the black truffle.
Isoamyl acetate is a component of the natural aroma of bananas, especially the Gros Michel variety.
Extraction from fusel oil
Isoamyl alcohol can be separated from fusel oil by either of two methods: shaking with strong brine solution and separating the oily layer from the brine layer; distilling it and collecting the fraction that boils between 125 and 140 °C. Further purification is possible with this procedure: shaking the product with hot limewater, separating the oily layer, drying the product with calcium chloride, and distilling it, collecting the fraction boiling between 128 and 132 °C.
Isoamyl alcohol can be synthesized from isobutanol by conversion into isovaleraldehyde, which is subsequently reduced to isobutyl carbinol by means of sodium amalgam. It is a colourless liquid of density 0.8247 g/cm3 (0 °C), boiling at 131.6 °C, slightly soluble in water, and easily dissolved in organic solvents. It has a characteristic strong smell and a sharp burning taste. Amyl alcohol has an oral LD50 of 200 mg/kg in mice, suggesting that it is significantly more toxic than ethanol. On passing the vapour through a red-hot tube, it decomposes into acetylene, ethylene, propylene, and other compounds. It is oxidized by chromic acid to isovaleraldehyde, and it forms addition compounds crystals with calcium chloride and tin(IV) chloride.
- Lide, David R., ed. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, Florida: CRC Press. pp. 3–374, 5–42, 6–188, 8–102, 15–22. ISBN 0-8493-0487-3.
- Straka, M.; van Genderen, A.; Růžička, K.; Růžička, V. Heat Capacities in the Solid and in the Liquid Phase of Isomeric Pentanols. J. Chem. Eng. Data 2007, 52, 794-802.
- NIOSH Pocket Guide to Chemical Hazards. "#0348". National Institute for Occupational Safety and Health (NIOSH).
- "Isoamyl alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- One or more of the preceding sentences incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). "Amyl Alcohols". Encyclopædia Britannica. 1 (11th ed.). Cambridge University Press. p. 900.
- Wilson, Calum & Davies, Noel & Corkrey, Ross & J. Wilson, Annabel & M. Mathews, Alison & C. Westmore, Guy. (2017). Receiver Operating Characteristic curve analysis determines association of individual potato foliage volatiles with onion thrips preference, cultivar and plant age. PLOS ONE. 12. e0181831. 10.1371/journal.pone.0181831.
- Zumbo, P. "Phenol-chloroform Extraction" (PDF). WEILL CORNELL MEDICAL COLLEGE P. ZUMBO LABORATORY OF CHRISTOPHER E. MASON, PH.D. Retrieved 19 June 2014.
- Green, Michael; Sambrook, Joseph. "Purification of Nucleic Acids: Extraction with Phenol-Chloroform". Molecular Cloning: A Laboratory Manual. Cold Spring Harbor Laboratory Press. ISBN 1936113422.