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Ethyl acetoxy butanoate

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(Redirected from Ethyl-4-acetoxybutanoate)
Ethyl acetoxy butanoate
Names
Preferred IUPAC name Ethyl 4-(acetyloxy)butanoate
Other names Ethyl 4-acetoxybutanoate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H14O4/c1-3-11-8(10)5-4-6-12-7(2)9/h3-6H2,1-2H3Key: KMPQIYXXLIFPKA-UHFFFAOYSA-N
SMILES
  • CCOC(=O)CCCOC(=O)C
Properties
Chemical formula C8H14O4
Molar mass 174.196 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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. 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.

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
GABA receptor modulators
Ionotropic
GABAATooltip γ-Aminobutyric acid A receptor
GABAATooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABABTooltip γ-Aminobutyric acid B receptor
See also
Receptor/signaling modulators
GABAA receptor positive modulators
GABA metabolism/transport modulators
GHB receptor modulators
Receptor
(ligands)
GHBRTooltip GHB receptor
GABABTooltip γ-Aminobutyric acid B receptor
Transporter
(blockers)
MCTsTooltip Monocarboxylate transporters
SMCTsTooltip Sodium-coupled monocarboxylate transporters
VIATTTooltip Vesicular inhibitory amino acid transporter
Enzyme
(inhibitors)
SSRTooltip Succinic semialdehyde reductase
GHBDHTooltip 4-Hydroxybutyrate dehydrogenase
HOTTooltip Hydroxyacid-oxoacid transhydrogenase
ADHTooltip Alcohol dehydrogenase
ALDHTooltip Aldehyde dehydrogenase
See also
Receptor/signaling modulators
GABA receptor modulators
Glutamate receptor modulators
Glycine receptor modulators


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