Ethyl acetoxy butanoate

Ethyl acetoxy butanoate
Names
	Preferred IUPAC name Ethyl 4-(acetyloxy)butanoate
	Other names Ethyl 4-acetoxybutanoate
Identifiers
CAS Number	25560-91-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	3544989;
PubChem CID	4340980;
UNII	R622BPD8K6 ;
CompTox Dashboard (EPA)	DTXSID50402111 ;
	InChI InChI=1S/C8H14O4/c1-3-11-8(10)5-4-6-12-7(2)9/h3-6H2,1-2H3 Key: KMPQIYXXLIFPKA-UHFFFAOYSA-N;
	SMILES CCOC(=O)CCCOC(=O)C;
Properties
Chemical formula	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

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.

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

References

^ 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
^ 常温下4-乙酰氧基丁酸乙酯的催化合成方法. 1994. CN1047589C

[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

[1]

[2]

See also

References