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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
  • 25714-71-0 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 84042
ECHA InfoCard 100.042.900
  • 93093
UNII
  • 8T59P1Q6NO Y
  • DTXSID1067128
  • 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).

Occurrence edit

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 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.



gamma, hydroxybutyraldehyde, hydroxybutyraldehyde, organic, compound, with, formula, hoch2ch2ch2cho, colorless, liquid, compound, occurs, nature, produced, commercially, hydroxybutyraldehyde, namespreferred, iupac, name, hydroxybutanalother, names, ghbal, hydr. g Hydroxybutyraldehyde is the organic compound with the formula HOCH2CH2CH2CHO It is a colorless liquid The compound occurs in nature and is produced commercially 1 g Hydroxybutyraldehyde NamesPreferred IUPAC name 4 HydroxybutanalOther names GHBAL g hydroxybutaldehyde g hydroxybutanalIdentifiersCAS Number 25714 71 0 Y3D model JSmol Interactive imageChemSpider 84042ECHA InfoCard 100 042 900PubChem CID 93093UNII 8T59P1Q6NO YCompTox Dashboard EPA DTXSID1067128InChI InChI 1S C4H8O2 c5 3 1 2 4 6 h3 6H 1 2 4H2Key PIAOXUVIBAKVSP UHFFFAOYSA NInChI 1 C4H8O2 c5 3 1 2 4 6 h3 6H 1 2 4H2Key PIAOXUVIBAKVSP UHFFFAOYAVSMILES C CC O COPropertiesChemical formula C 4H 8O 2Molar mass 88 106 g mol 1Appearance colorless liquidDensity 1 109 g cm3 at 12 C Boiling point 65 68 C 149 154 F 338 341 K 10 TorrExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesOccurrence editIt is a chemical intermediate in the biosynthesis of the neurotransmitter g 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 g 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 nbsp Metabolic pathway of GHB See also edit1 6 Dioxecane 2 7 dione 3 Hydroxybutanal Aceburic acid Ethyl acetoxy butanoateReferences edit 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 Thomas L Lemke David A Williams 24 January 2012 Foye s Principles of Medicinal Chemistry Lippincott Williams amp Wilkins pp 413 ISBN 978 1 60913 345 0 nbsp This article about an organic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Gamma Hydroxybutyraldehyde amp oldid 1165953380, wikipedia, wiki, book, books, library,

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