3-Hydroxybutyric acid

Base Information

• Chemical Name: 3-Hydroxybutyric acid
• CAS No.: 26063-00-3
• Deprecated CAS: 625-71-8,2392893-69-3
• Molecular Formula: C₄H₈O₃
• Molecular Weight: 104.106
• Hs Code.: 2918199090
• 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: 26063-00-3.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:

• Appearance/Colour: YELLOW/WHITE SOLID
• Vapor Pressure: 0.000979mmHg at 25°C
• Melting Point: ~170°C
• Boiling Point: 269.2 °C at 760 mmHg
• Flash Point: 121 °C
• PSA: 57.53000
• Density: 1.195 g/cm³
• LogP: -0.15810
• 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:

99%, ^*data from raw suppliers

Poly(3-hydroxybutyric acid) natural origin, average Mn ~500,000 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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

Technology Process of 3-Hydroxybutyric acid

There total 189 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: 71.0%

(S)-(-)-β-methyl-β-propiolactone (65058-82-4) → (S)-3-Hydroxybutanoic Acid (6168-83-8,26063-00-3,29435-48-1)

Guidance literature:

With sodium hydroxide; In water; at 0 ℃; for 0.333333h;

DOI:10.1002/hlca.19870700513

Reference yield: 53.0%

(S)-3-hydroxybutyric acid methyl ester (53562-86-0) → (S)-3-Hydroxybutanoic Acid (6168-83-8,26063-00-3,29435-48-1)

Guidance literature:

With sodium hydroxide; In water; for 36h;

DOI:10.1002/(SICI)1522-2675(19981216)81:12<2430::AID-HLCA2430>3.0.CO;2-W

Reference yield: 47.0%

(S)-(-)-β-methyl-β-propiolactone (65058-82-4) → (S)-3-Hydroxybutanoic Acid (6168-83-8,26063-00-3,29435-48-1) + (R)-3-Mercaptobuttersaeure (115395-16-9)

Guidance literature:

With sodium hydrogensulfide; In water; Yields of byproduct given; 0 deg C, 1 h, then room temp., 24 h;

DOI:10.1002/hlca.19870700514

upstream raw materials:

pyridine

diethyl ether

malonic acid

acetaldehyde

Downstream raw materials:

2-isopropyl-5-methylcyclohexyl 3-hydroxybutyrate

acetaldehyde

acetone

3(R)-(4-Carboxy-2-nitrophenoxy)butyric acid

Refernces

• 1、 Ng,A.S. et al.. "-". . p. 1223 - 1227. Retrieved 1969.
• 2、 Seebach, Dieter,Zueger, Max. "Ueber die Depolymerisierung von Poly-(R)-3-hydroxy-buttersaeureester (PHB)". . p. 495 - 503. Retrieved 1982.
• 3、 Clarke. "". . p. 1610. Retrieved 1959.
• 4、 Knirel,Vinogradov,Shashkov,Kochetkov,L'vov,Dmitriev. "Identification of 5-acetamido-3,5,7,9-tetradeoxy-7-[(R)-3-hydroxybutyramido]-L- glycero-L-manno-nonulosonic acid as a component of bacterial polysaccharides.". . p. C1 - C3,C1-3. Retrieved 1985.
• 5、 Lian, Huiling,Whitman, Christian P.. "Stereochemical and isotopic labeling studies of 4-oxalocrotonate decarboxylase and vinylpyruvate hydratase: Analysis and mechanistic implications". . p. 10403 - 10411. Retrieved 1994.
• 6、 Lemoigne,Delaporte,Croson. "-". . p. 819. Retrieved 1943.
• 7、 Ganguly, Bishwajit,Kesharwani, Manoj K.,Matkovic, Marija,Basaric, Nikola,Singh, Ajeet,Mlinaric-Majerski, Kata. "Hydrolysis and retro-aldol cleavage of ethyl threo-2-(1-adamantyl)-3- hydroxybutyrate: Competing reactions". . p. 578 - 587. Retrieved 2011.
• 8、 Lemoigne et al.. "-". . p. 90. Retrieved 1945.
• 9、 -. "SYNTHESIS OF 3-HYDROXYBUTYRYL 3-HYDROXYBUTYRATE AND RELATED COMPOUNDS". Paragraph 0308; 0320-0324. . Retrieved 2021/04/02.
• 10、 Coady, Tracey M.,Coffey, Lee,Kinsella, Michael,Lennon, Claire M.,Mareya, Tatenda M.,O'Reilly, Catherine. "Process Optimisation Studies and Aminonitrile Substrate Evaluation of Rhodococcus erythropolis SET1, A Nitrile Hydrolyzing Bacterium". . p. 512 - 520. Retrieved 2020/10/02.