3-Hydroxybutyric acid

Base Information

• Chemical Name: 3-Hydroxybutyric acid
• CAS No.: 625-71-8
• Deprecated CAS: 625-71-8,2392893-69-3
• Molecular Formula: C₄H₈O₃
• Molecular Weight: 104.106
• European Community (EC) Number: 206-099-9,210-908-0
• NSC Number: 3806
• UNII: TZP1275679
• DSSTox Substance ID: DTXSID60859511
• Nikkaji Number: J4.451B,J507J
• Wikipedia: Beta-Hydroxybutyric_acid
• Wikidata: Q223092
• Metabolomics Workbench ID: 1282
• ChEMBL ID: CHEMBL1162496
• Mol file: 625-71-8.mol

Synonyms:(+ -)-3-Hydroxybutyric Acid;3 Hydroxybutyrate;3 Hydroxybutyric Acid;3-Hydroxybutyrate;3-Hydroxybutyric Acid;beta Hydroxybutyrate;beta Hydroxybutyric Acid;beta-Hydroxybutyrate;beta-Hydroxybutyric Acid

Chemical Property of 3-Hydroxybutyric acid

Chemical Property:

• Vapor Pressure: 0.000979mmHg at 25°C
• Melting Point: 49°C
• Refractive Index: n20/D 1.443(lit.)
• Boiling Point: 269.216 °C at 760 mmHg
• PKA: 4.70(at 25℃)
• Flash Point: 121.011 °C
• PSA: 57.53000
• Density: 1.196g/cm³
• LogP: -0.15810
• Storage Temp.: 0-6°C
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 104.047344113
• Heavy Atom Count: 7
• Complexity: 69.3

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Hydroxybutyric acid 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CC(CC(=O)O)O
• Recent ClinicalTrials: Brain Ketone Metabolism in Type 1 Diabetes
• Description: In human, 3-hydroxylbutyric acid (?-Hydroxybutyric acid or 3-hydrobutanoic acid) is one of the two primary endogenous agonists of hydroxycarboxylic acid receptor 2 (HCA2), a Gi/o-coupled G protein-coupled receptor (GPCR).1 It can be used for synthesis of biodegradable polymer, polyhydroxybutyrate.2
• Uses: 3-Hydroxybutyric acid was used in enantioselective synthesis of D-(-)-3-hydroxybutyric acid by Escherichia coli.

Technology Process of 3-Hydroxybutyric acid

There total 85 articles about 3-Hydroxybutyric 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: 95.0%

3-hydroxybutyric acid methyl ester (1487-49-6) → 3-Hydroxybutyric acid (300-85-6,625-71-8,26063-00-3,29435-48-1)

Guidance literature:

With water; potassium hydroxide; at 45 ℃; for 24h; Reagent/catalyst; Temperature;

Reference yield: 2.0%

but-3-yn-2-ol (2028-63-9) → propene (187737-37-7,13987-01-4,15220-87-8,9003-07-0,676-63-1,25085-53-4) + (E)-but-2-enoic acid (107-93-7) + 3-hydroxy-2-butanon (513-86-0,52217-02-4,51555-24-9) + 3-Hydroxybutyric acid (300-85-6,625-71-8,26063-00-3,29435-48-1)

Guidance literature:

With water; ruthenium tetrasulfophthalocyanine; at 80 ℃; for 24h; Further Variations:; Catalysts; Product distribution;

DOI:10.1002/ejic.200300562

Reference yield:

(E)-but-2-enoic acid (107-93-7) → propene (187737-37-7,13987-01-4,15220-87-8,9003-07-0,676-63-1,25085-53-4) + crotonic acid isopropyl ester (6284-46-4,17377-84-3,18060-77-0) + isopropyl alcohol (67-63-0,8013-70-5) + 3-Hydroxybutyric acid (300-85-6,625-71-8,26063-00-3,29435-48-1)

Guidance literature:

With water; at 230 ℃; for 1h; Product distribution; 1M Solution of acid.;

upstream raw materials:

pyridine

diethyl ether

malonic acid

acetaldehyde

Downstream raw materials:

3-hydroxybutyric acid methyl ester

citric acid

ethyl 3-hydroxybutyrate

2-isopropyl-5-methylcyclohexyl 3-hydroxybutyrate

Refernces

• 1、 Faria, Jimmy,Komarneni, Mallik R.,Li, Gengnan,Pham, Tu,Resasco, Daniel E.,Ruiz, Maria P.,Santhanaraj, Daniel. "Synthesis of α,β- and β-Unsaturated Acids and Hydroxy Acids by Tandem Oxidation, Epoxidation, and Hydrolysis/Hydrogenation of Bioethanol Derivatives". supporting information. p. 7456 - 7460. Retrieved 2020/03/23.
• 2、 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.