2-Methyl-1-butanol explained

2-Methyl-1-butanol (IUPAC name, also called active amyl alcohol) is an organic compound with the formula CH₃CH₂CH(CH₃)CH₂OH. It is one of several isomers of amyl alcohol. This colorless liquid occurs naturally in trace amounts and has attracted some attention as a potential biofuel, exploiting its hydrophobic (gasoline-like) and branched structure. It is chiral.^[1]

Occurrence

2-Methyl-1-butanol is a component of many mixtures of commercial amyl alcohols.

2M1B also occurs naturally. For example, fusel alcohols like 2M1B are grain fermentation byproducts, and therefore trace amounts of 2M1B are present in many alcoholic beverages. Also, it is one of the many components of the aroma of various fungi and fruit, e.g., the summer truffle, tomato,^[2] and cantaloupe.^{[3] [4]}

Production and reactions

2-Methyl-1-butanol has been produced from glucose by genetically modified E. coli. 2-Keto-3-methylvalerate, a precursor to threonine, is converted to the target alcohol by the sequential action of 2-keto acid decarboxylase and dehydrogenase.^[5] It can be derived from fusel oil (because it occurs naturally in fruits such as grapes) or manufactured by either the oxo process or via the halogenation of pentane.

See also

• 2-Methyl-2-butanol

Notes and References

1. 10.1002/1521-3773(20011203)40:23<4422::AID-ANIE4422>3.0.CO;2-G. Enantioseparation of Racemic Organic Molecules by a Zeolite Analogue. 2001. Xiong. Ren-Gen. You. Xiao-Zeng. Abrahams. Brendan F.. Xue. Ziling. Che. Chi-Ming. Angewandte Chemie International Edition. 40. 23. 4422–4425. 12404434.
2. 10.1021/jf00076a025. Fresh tomato aroma volatiles: A quantitative study. 1987. Buttery. Ron G.. Teranishi. Roy. Ling. Louisa C.. Journal of Agricultural and Food Chemistry. 35. 4. 540–544.
3. 10.1016/j.chroma.2003.08.016. Truffle Aroma Characterization by Headspace solid-phase microextraction. 2003. Dı́Az. P.. Ibáñez. E.. Señoráns. F.J. Reglero. G.. Journal of Chromatography A. 1017. 1–2. 207–214. 14584705.
4. 10.1021/jf0005768. Identification of Volatile Compounds in Cantaloupe at Various Developmental Stages Using Solid Phase Microextraction. 2001. Beaulieu. John C.. Grimm. Casey C.. Journal of Agricultural and Food Chemistry. 49. 3. 1345–1352. 11312862.
5. 10.1038/nature06450. Non-Fermentative Pathways for Synthesis of Branched-Chain Higher Alcohols as Biofuels. 2008. Atsumi. Shota. Hanai. Taizo. Liao. James C.. Nature. 451. 7174. 86–89. 18172501. 2008Natur.451...86A. 4413113.