gamma-Hydroxybutyraldehyde

γ-Hydroxybutyraldehyde

Names
IUPAC name 4-Hydroxybutanal
Identifiers
CAS Number	25714-71-0
ChemSpider	84042
Jmol interactive 3D	Image
PubChem	93093
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	88.11 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

γ-Hydroxybutyraldehyde, also referred to as GHBAL, γ-hydroxybutaldehyde or γ-hydroxybutanal, is a chemical intermediate in the biosynthesis of the neurotransmitter γ-hydroxybutyric acid (GHB) from 1,4-butanediol (1,4-BD).^[1] 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

Metabolic pathway of GHB.

See also

• γ-Butyrolactone
• 3-Hydroxybutanal

References

1. 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.