gamma-Hydroxybutyraldehyde

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

γ-Hydroxybutyraldehyde
Names
Preferred IUPAC name
4-Hydroxybutanal
Other names
GHBAL, γ-hydroxybutaldehyde, γ-hydroxybutanal
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.042.900
PubChem CID
UNII
InChI
  • 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
SMILES
  • C(CC=O)CO
Properties
Chemical formula
 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).
Infobox references

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.

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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