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γ-Hydroxybutyraldehyde

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(Redirected fromΓ-hydroxybutyraldehyde)
γ-Hydroxybutyraldehyde
Names
Preferred IUPAC name
4-Hydroxybutanal
Other names
γ-Hydroxybutanal, γ-Hydroxybutyraldehyde
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.042.900Edit this at Wikidata
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 mass88.106 g·mol−1
Appearancecolorless liquid
Density1.109 g/cm3 (at 12 °C)
Boiling point65–68 °C (149–154 °F; 338–341 K) 10 Torr
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

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

Occurrence

[edit]

It is achemical intermediate in thebiosynthesis of theneurotransmitterγ-hydroxybutyric acid (GHB) from1,4-butanediol (1,4-BD).[2] Like 1,4-BD, it also behaves as aprodrug to GHB when takenexogenously. However, as with allaliphaticaldehydes, γ-hydroxybutaldehyde iscaustic and is strong-smelling and foul-tasting; thus, actual ingestion of this compound is likely to be unpleasant and result in severenausea andvomiting.

Metabolic pathway of GHB.

See also

[edit]

References

[edit]
  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.


Catecholamines
Anabolism
Catabolism
Dopamine
Norepinephrine
Epinephrine
TryptophanSerotonin
Anabolism
Catabolism
SerotoninMelatonin
Trace amines
Histamine
GABA
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
Ionotropic
GABAATooltip γ-Aminobutyric acid A receptor
GABAATooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABABTooltip γ-Aminobutyric acid B receptor
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