Methyl (S)-(+)-3-hydroxybutyrate

Base Information

• Chemical Name: Methyl (S)-(+)-3-hydroxybutyrate
• CAS No.: 53562-86-0
• Molecular Formula: C5H10O3
• Molecular Weight: 118.133
• Hs Code.: 29181990
• European Community (EC) Number: 258-628-8
• UNII: G10281A5AH
• Nikkaji Number: J57.250K
• Mol file: 53562-86-0.mol

Synonyms:(+)-(3S)-3-Hydroxybutanoic acid methylester;(3S)-3-Hydroxybutanoic acid methyl ester;(S)-3-Hydroxybutanoic acidmethyl ester;(S)-Methyl3-hydroxybutanoate;Methyl (+)-3-hydroxybutanoate;Methyl (S)-3-hydroxybutyrate;

Chemical Property of Methyl (S)-(+)-3-hydroxybutyrate

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 0.768mmHg at 25°C
• Refractive Index: n20/D 1.422
• Boiling Point: 161.9 °C at 760 mmHg
• PKA: 13.95±0.20(Predicted)
• Flash Point: 71.7 °C
• PSA: 46.53000
• Density: 1.05 g/cm³
• LogP: -0.06970
• Storage Temp.: 0-6°C
• Water Solubility.: Miscible with alcohol. Immiscible with water.
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 118.062994177
• Heavy Atom Count: 8
• Complexity: 79.7

Purity/Quality:

99% ^*data from raw suppliers

Methyl (S)-(+)-3-hydroxybutyrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 38-41:
• Hazard Codes: 38-41:
• Statements: 38-41
• Safety Statements: 23-24/25

MSDS Files:

Useful:

• Canonical SMILES: CC(CC(=O)OC)O
• Isomeric SMILES: C[C@@H](CC(=O)OC)O
• Uses: Methyl (S)-(+)-3-hydroxybutyrate serves as an optically active starting material used in organic synthesis. It is also used in the preparation of (-)-methyl elenolate. Methyl (S)-(+)-3-hydroxybutyrate may be used as an intermediate in the synthesis of (-)-methyl elenolate.

Technology Process of Methyl (S)-(+)-3-hydroxybutyrate

There total 40 articles about Methyl (S)-(+)-3-hydroxybutyrate 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: 100.0%

acetoacetic acid methyl ester (105-45-3) → (S)-3-hydroxybutyric acid methyl ester (53562-86-0)

Guidance literature:

With cat; hydrogen; In methanol; dichloromethane; at 25 ℃; for 48h; under 77572.2 Torr;

DOI:10.1016/S0957-4166(00)86109-1

Reference yield: 100.0%

acetoacetic acid methyl ester (105-45-3) → (S)-3-hydroxybutyric acid methyl ester (53562-86-0) + Methyl (R)-3-hydroxybutyrate (3976-69-0)

Guidance literature:

With Ru₂Cl₄-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2*NEt₃; hydrogen; In methanol; at 35 ℃; for 48h; under 76000.1 Torr; Title compound not separated from byproducts;

DOI:10.1016/0022-328X(92)83466-U

Reference yield: 97.0%

acetoacetic acid methyl ester (105-45-3) → (S)-3-hydroxybutyric acid methyl ester (53562-86-0) + Methyl (R)-3-hydroxybutyrate (3976-69-0) + 3,3-bismethoxybutyric acid methyl ester (29267-46-7)

Guidance literature:

With hydrogen; {RuI((R)-2,2'-bis(diphenylphospino)-1,1'-binaphthyl)(p-cymene)}I; In methanol; at 30 ℃; for 35h; under 76000 Torr; Product distribution; other: catalysts, solvents, time, pressure, temperatures;

DOI:10.1021/jo00090a026

upstream raw materials:

diazomethane

(S)-3-Hydroxybutanoic Acid

l-menthyl (2R,6S)-6-methyl-4-oxo-2-phenyl-1,3-dioxane-2-carboxylate

methyl (2R,3S)-2-bromo-3-hydroxy butanoate

Downstream raw materials:

(3S)-methyl 3-(p-toluenesulfonyl)butyrate

(2S,3S)-2-Benzyloxymethyl-3-hydroxy-butyric acid methyl ester

acetoacetic acid methyl ester

Methyl (2RS,3S)-nilate

Refernces

• 1、 North, Michael. "Baker's yeast reduction of β-keto esters in petrol". . p. 1699 - 1702. Retrieved 1996.
• 2、 Knepper, Janosch,Lüddecke, Tim,Prei?ler, Kathleen,Vences, Miguel,Schulz, Stefan. "Isolation and Identification of Alkaloids from Poisons of Fire Salamanders (Salamandra salamandra)". . p. 1319 - 1324. Retrieved 2019.
• 3、 Lee, Jung Hwan. "Synthesis of Hantsch 1,4-dihydropyridines by fermenting bakers' yeast". . p. 7329 - 7330. Retrieved 2005.
• 4、 Li, Aipeng,Wang, Ting,Tian, Qing,Yang, Xiaohong,Yin, Dongming,Qin, Yong,Zhang, Lianbing. "Single-Point Mutant Inverts the Stereoselectivity of a Carbonyl Reductase toward β-Ketoesters with Enhanced Activity". . p. 6283 - 6294. Retrieved 2021/03/16.
• 5、 Arrigo, Rosa,Gallarati, Simone,Schuster, Manfred E.,Seymour, Jake M.,Gianolio, Diego,da Silva, Ivan,Callison, June,Feng, Haosheng,Proctor, John E.,Ferrer, Pilar,Venturini, Federica,Grinter, David,Held, Georg. "Influence of Synthesis Conditions on the Structure of Nickel Nanoparticles and their Reactivity in Selective Asymmetric Hydrogenation". . p. 1491 - 1503. Retrieved 2020/01/25.