Ethyl acetoxy butanoate

Ethyl acetoxy butanoate (EAB) is a volatile chemical compound found as a minor component of the odour profile of ripe pineapples, though in its pure form it has a smell more similar to sour yoghurt.[1] It can be metabolized in humans into GHB, and thus can produce similar sedative effects.

Ethyl acetoxy butanoate
Names
Preferred IUPAC name
Ethyl 4-(acetyloxy)butanoate
Other names
Ethyl 4-acetoxybutanoate
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C8H14O4/c1-3-11-8(10)5-4-6-12-7(2)9/h3-6H2,1-2H3
    Key: KMPQIYXXLIFPKA-UHFFFAOYSA-N
  • CCOC(=O)CCCOC(=O)C
Properties
C8H14O4
Molar mass 174.196 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It is synthesised by the reaction of gamma-butyrolactone and ethyl acetate with sodium ethoxide.[2]

See also

References
  1. Umano RP, Hagi Y, Nakahara K, Shoji A, Shibamoto T. Volatile constituents of green and ripened pineapple (Ananas comosus). J Agric Food Chem 1992; 40:599-603. doi:10.1021/jf00016a014
  2. 常温下4-乙酰氧基丁酸乙酯的催化合成方法. 1994. CN1047589C


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