γ-Hydroxybutyraldehyde

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γ-Hydroxybutyraldehyde
File:4-Hydroxybutanal.svg
Names
Preferred IUPAC name
4-Hydroxybutanal
Other names
GHBAL, γ-hydroxybutaldehyde, γ-hydroxybutanal
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C4H8O2/c5-3-1-2-4-6/h3,6H,1-2,4H2
    Key: PIAOXUVIBAKVSP-UHFFFAOYSA-N
  • InChI=1/C4H8O2/c5-3-1-2-4-6/h3,6H,1-2,4H2
    Key: PIAOXUVIBAKVSP-UHFFFAOYAV
  • C(CC=O)CO
Properties
C4H8O2
Molar mass 88.106 g·mol−1
Appearance colorless liquid
Density 1.109 g/cm3 (at 12 °C)
Boiling point 65–68 °C (149–154 °F; 338–341 K) 10 Torr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

γ-Hydroxybutyraldehyde (GHBAL) is the organic compound with the formula HOCH2CH2CH2CHO. It is a colorless liquid. The compound occurs in nature and is produced commercially.[1]

Occurrence

It is a chemical intermediate in the biosynthesis of the neurotransmitter γ-hydroxybutyric acid (GHB) from 1,4-butanediol (1,4-BD).[2] Like 1,4-BD, it also behaves as a prodrug to GHB when taken exogenously. However, as with all aliphatic aldehydes, γ-hydroxybutaldehyde is caustic and is strong-smelling and foul-tasting; thus, actual ingestion of this compound is likely to be unpleasant and result in severe nausea and vomiting.

File:GHB metabolic pathway.svg
Metabolic pathway of GHB.

See also

References

  1. ↑ Ahn, H. (1999). "Hydroformylation of olefins with formaldehyde in the presence of RhHCO(PPh3)3". Journal of Molecular Catalysis A: Chemical. 144 (2): 295–306. doi:10.1016/S1381-1169(99)00002-3.
  2. ↑ Thomas L. Lemke; David A. Williams (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 413–. ISBN 978-1-60913-345-0.
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