4-Hydroxybutanoic acid

Base Information

• Chemical Name: 4-Hydroxybutanoic acid
• CAS No.: 591-81-1
• Molecular Formula: C4H8O3
• Molecular Weight: 104.106
• European Community (EC) Number: 691-053-4
• UNII: 30IW36W5B2
• DSSTox Substance ID: DTXSID2074740
• Nikkaji Number: J2.691C
• Wikipedia: Gamma-Hydroxybutyric acid,Gamma-Hydroxybutyric_acid
• Wikidata: Q207920
• NCI Thesaurus Code: C61773
• RXCUI: 1546380,2387302
• Pharos Ligand ID: 18HB6484VTJ8
• Metabolomics Workbench ID: 1283
• ChEMBL ID: CHEMBL1342
• Mol file: 591-81-1.mol

Synonyms:4-hydroxybutyric acid;gamma-hydroxybutyric acid

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Chemical Property of 4-Hydroxybutanoic acid

Chemical Property:

• Vapor Pressure: 0.000156mmHg at 25°C
• Melting Point: 212℃
• Refractive Index: 1.4761 (estimate)
• Boiling Point: 295.6 °C at 760 mmHg
• PKA: 4.72(at 25℃)
• Flash Point: 146.8 °C
• PSA: 57.53000
• Density: 1.2 g/cm³
• LogP: -0.15650
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 104.047344113
• Heavy Atom Count: 7
• Complexity: 60

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Narcolepsy Agents
• Canonical SMILES: C(CC(=O)O)CO
• Recent ClinicalTrials: Towards a Post-exposition Pharmacological Prophylaxis for Post-traumatic Stress Disorder
• Recent EU Clinical Trials: Efficacy and safety of Sodium Oxybate in reducing alcohol consumption and maintaining abstinence in alcohol-dependent subjects with high and very high drinking risk level.
• Description: γ-Hydroxybutyric acid (GHB), also known as 4- hydroxybutanoic acid, is a naturally occurring substance found in the human central nervous system, as well as in wine, beef, small citrus fruits, and almost all animals in small amounts. It is also categorized as an illegal drug in many countries. It is currently regulated in Australia and New Zealand, Canada, most of Europe and in the US. GHB as the sodium salt, known as sodium oxybate (INN) or by the trade name Xyrem, is used to treat cataplexy and excessive daytime sleepiness in patients with narcolepsy.
• Uses: Anesthetic (intravenous). In treatment of narcolepsy; in treatment of alcoholism. This is a Schedule III controlled substance.
• Clinical Use: The only common medical applications for GHB today are in the treatment of narcolepsy and more rarely alcoholism. GHB is the active ingredient in the prescription medication sodium oxybate (Xyrem). Sodium oxybate is approved by the U.S. Food and Drug Administration (FDA) for the treatment of cataplexy associated with narcolepsy and Excessive Daytime Sleepiness (EDS) associated with narcolepsy.

Technology Process of 4-Hydroxybutanoic acid

There total 54 articles about 4-Hydroxybutanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

methyl hydrogen succinate (3878-55-5) → 4-hydroxybutanoic acid (591-81-1)

Guidance literature:

With sodium tetrahydroborate; In water; for 12h; Ambient temperature;

Reference yield: 69.2%

cyclobutanone (1191-95-3) → 4-butanolide (96-48-0) + 4-hydroxybutanoic acid (591-81-1)

Guidance literature:

With dihydrogen peroxide; In acetonitrile; at 55 - 60 ℃; for 4h;

Reference yield: 65.0%

4-butanolide (96-48-0) → 4-hydroxybutanoic acid (591-81-1)

Guidance literature:

With water; sodium hydroxide; at 100 ℃; Cooling with ice;

upstream raw materials:

succinic acid anhydride

4-phenyloxybutanoic acid

γ-chlorobutyric acid

4-hydroxybutyraldehyde

Downstream raw materials:

4-butanolide

4-phosphonooxy-butyric acid

C₁₀H₂₄O₃Si₂

2-methoxyethoxymethyl 4-(2-methoxyethoxymethoxy) butyrate

Refernces

• 1、 Kao, Lien-Chung,Sen, Ayusman. "Platinum(II) Catalysed Selective Remote Oxidation of Unactivated C-H Bonds in Aliphatic Carboxylic Acids". . p. 1242 - 1243. Retrieved 1991.
• 2、 Dafforn,G.A.,Koshland,D.E.. "-". . p. 7246 - 7257. Retrieved 1977.
• 3、 Janssen, Michiel,De Vos, Dirk E.. "PtII-Catalyzed Hydroxylation of Terminal Aliphatic C(sp3)?H Bonds with Molecular Oxygen". supporting information. p. 10724 - 10734. Retrieved 2019/07/15.