Γ-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 γ-Hydroxybutanal, γ-Hydroxybutyraldehyde
Identifiers
CAS Number	25714-71-0 Y
3D model (JSmol)	Interactive image
ChemSpider	84042
ECHA InfoCard	100.042.900
PubChem CID	93093
UNII	8T59P1Q6NO Y
CompTox Dashboard (EPA)	DTXSID1067128
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

• γ-Aminobutyraldehyde
• 1,6-Dioxecane-2,7-dione
• 3-Hydroxybutanal
• Aceburic acid
• Ethyl acetoxy butanoate

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.