(S)-2-Hydroxybutyric acid

Base Information

• Chemical Name: (S)-2-Hydroxybutyric acid
• CAS No.: 3347-90-8
• Molecular Formula: C4H8O3
• Molecular Weight: 104.106
• Hs Code.: 2918199090
• European Community (EC) Number: 628-477-6
• UNII: 8X9IM06H49
• DSSTox Substance ID: DTXSID001312294
• Nikkaji Number: J57.683B
• Wikidata: Q27887417
• NCI Thesaurus Code: C120002
• Metabolomics Workbench ID: 1478
• Mol file: 3347-90-8.mol

Synonyms:3347-90-8;(S)-2-Hydroxybutyric acid;(S)-2-hydroxybutanoic acid;(2S)-2-hydroxybutanoic acid;2-Hydroxybutyrate;L-2-hydroxybutyric acid;S-2-hydroxybutyric acid;Butanoic acid, 2-hydroxy-, (2S)-;2-Hydroxybutyric acid, (+)-;a-Hydroxybutyric acid;2S-Hydroxybutanoic acid;(S)-(+)-2-Hydroxybutanoic acid;2S-hydroxy-butanoic acid;UNII-8X9IM06H49;8X9IM06H49;MFCD01318568;Hydroxybutyric acid;alpha-hydroxybutanoic acid;DL-2-Hydroxybutanoic acid;(RS)-2-Hydroxybutyric acid;alpha-Hydroxybutanoate;a-Hydroxybutyrate;a-Hydroxybutanoate;2-hydroxy-Butanoate;DL-a-Hydroxybutyrate;a-Hydroxy-n-butyrate;2-Hydroxy-n-butyrate;a-Hydroxybutanoic acid;DL-2-Hydroxybutanoate;2-hydroxy-DL-Butyrate;alpha-hydroxy-n-butyrate;DL-alpha-Hydroxybutyrate;(RS)-2-Hydroxybutyrate;DL-a-Hydroxybutyric acid;a-Hydroxy-n-butyric acid;L-2-hydroxybutanoic acid;2-Hydroxy-n-butyric acid;(S)-2-hydroxybutanoicacid;2-hydroxy-DL-Butyric acid;L-alpha-hydroxybutyric acid;(+)-2-hydroxybutyric acid;L-alpha-hydroxybutanoic acid;DL-alpha-Hydroxybutyric acid;SCHEMBL193026;CHEBI:50613;DTXSID001312294;BBL103624;LMFA01050342;STL557434;AKOS015995014;CS-W019285;HY-W018499;DS-12665;C05984;EN300-115522;H-3956;A875281;Q27887417;(S)-2-Hydroxybutyric acid, for chiral derivatization, >=97.0%

Chemical Property of (S)-2-Hydroxybutyric acid

Chemical Property:

• Vapor Pressure: 0.00759mmHg at 25°C
• Melting Point: 50-54 °C
• Refractive Index: 1.455
• Boiling Point: 238.279 °C at 760 mmHg
• PKA: 3.83±0.10(Predicted)
• Flash Point: 112.177 °C
• PSA: 57.53000
• Density: 1.196 g/cm³
• LogP: -0.15810
• Storage Temp.: 2-8°C
• XLogP3: 0.1
• 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

(S)-2-HydroxybutanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C(=O)O)O
• Isomeric SMILES: CC[C@@H](C(=O)O)O
• Uses: (S)-2-Hydroxybutanoic acid is used in method for preparing Cationic Electrodeposition coating compounds.

Technology Process of (S)-2-Hydroxybutyric acid

There total 19 articles about (S)-2-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: 99.0%

2-Oxobutyric acid (600-18-0) → (2S)-2-hydroxybutanoic acid (3347-90-8)

Guidance literature:

With potassium hydroxide; mercaptoethyl alcohol; sodium formate; 2-amino-2-hydroxymethyl-1,3-propanediol; NAD; In water; for 115.2h;

DOI:10.1021/ja00217a044

Reference yield: 99.0%

2-phenylpropan-2-yl 2-hydroxybutanoate → (2S)-2-hydroxybutanoic acid (3347-90-8)

Guidance literature:

With hydrogenchloride; In methanol; for 4h; Reflux; Schlenk technique; Cooling with ethanol-dry ice; Glovebox;

DOI:10.1021/jacs.0c04532

Reference yield: 97.0%

L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) → (2S)-2-hydroxybutanoic acid (3347-90-8)

Guidance literature:

With NAD; sodium formate; In aq. phosphate buffer; at 30 ℃; for 24h; enantioselective reaction; Microbiological reaction;

DOI:10.1002/adsc.201600468

upstream raw materials:

L-2-aminobutyric acid

ethyl (2S)-2-acetoxybutanoate

2-Hydroxybutanoic acid

(S)-2-Amino-3-methyl-butyric acid (S)-1-carboxy-propyl ester

Downstream raw materials:

methyl (S)-2-hydroxybutyrate

(S)-2-chlorobutyric acid

(2R)-2-bromobutanoic acid

ethyl (2S)-2-hydroxybutanoate

Refernces

• 1、 Ahmed, Farjad,Al-Mutairi, Eiman H.,Avery, Kathryn L.,Cullis, Paul M.,Primrose, William U.,Roberts, Gordon C. K.,Willis, Christine L.. "An unusual matrix of stereocomplementarity in the hydroxylation of monohydroxy fatty acids catalysed by cytochrome P450 from Bacillus megaterium with potential application in biotransformations". . p. 2049 - 2050. Retrieved 1999.
• 2、 Yao, Peiyuan,Cui, Yunfeng,Yu, Shanshan,Du, Yuncheng,Feng, Jinhui,Wu, Qiaqing,Zhu, Dunming. "Efficient Biosynthesis of (R)- or (S)-2-Hydroxybutyrate from l-Threonine through a Synthetic Biology Approach". . p. 2923 - 2928. Retrieved 2016.
• 3、 Gunasekera, Sarath P.,Meyer, Julie L.,Ding, Yousong,Abboud, Khalil A.,Luo, Danmeng,Campbell, Justin E.,Angerhofer, Alexander,Goodsell, Justin L.,Raymundo, Laurie J.,Liu, Junyang,Ye, Tao,Luesch, Hendrik,Teplitski, Max,Paul, Valerie J.. "Chemical and Metagenomic Studies of the Lethal Black Band Disease of Corals Reveal Two Broadly Distributed, Redox-Sensitive Mixed Polyketide/Peptide Macrocycles". . p. 111 - 121. Retrieved 2019/01/21.