73349-08-3

Usage

Uses

Used in Food and Beverage Industry:
Methyl (S)-2-hydroxybutyrate is used as a flavoring agent for its fruity odor, enhancing the taste and aroma of various food products and beverages.
Used in Pharmaceutical Industry:
Methyl (S)-2-hydroxybutyrate is utilized as a precursor in the synthesis of pharmaceutical compounds, contributing to the development of new medications.
Used in Cosmetics Industry:
In the cosmetics industry, Methyl (S)-2-hydroxybutyrate is employed in the production of esters, which are integral to the formulation of various cosmetic products.
Used in Metabolic Disorders Treatment:
The (S)-enantiomer of Methyl (S)-2-hydroxybutyrate is studied for its potential therapeutic uses, particularly as a treatment for certain metabolic disorders, due to its biological activity.
Used in Chemical Synthesis:
Methyl (S)-2-hydroxybutyrate is used as a chemical intermediate in the synthesis of esters, which have a wide range of applications across different industries.

InChI:InChI=1/C5H10O3/c1-3-4(6)5(7)8-2/h4,6H,3H2,1-2H3/t4-/m1/s1

Upstream product

• 67-56-1 methanol 
• 3347-90-8 (2S)-2-hydroxybutanoic acid 
• 186581-53-3 diazomethane 
• 681-84-5 tetramethylorthosilicate 
• 3196-15-4 Methyl 2-bromobutyrate 

Downstream Products

• 73349-12-9 (S)-2-((S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-butyric acid methyl ester 
• 76905-00-5 (S)-2-O(MTPA)-butanoic acid methyl ester 
• 135423-72-2 (S)(-)-2-hydroxybutyric acid N-benzylamide 
• 110352-57-3 (S)-(-)-methyl 2-benzyloxybutyrate 
• 199679-83-9 (R)-2-(4-Chloro-phenylamino)-butyric acid methyl ester 
• 1113-58-2 (S)-2-hydroxy-butyric acid amide 

Relevant academic research and scientific papers

Role of the CAI-1 fatty acid tail in the Vibrio cholerae quorum sensing response

Quorum sensing is a mechanism of chemical communication among bacteria that enables collective behaviors. In V. cholerae, the etiological agent of the disease cholera, quorum sensing controls group behaviors including virulence factor production and biofilm formation. The major V. cholerae quorum-sensing system consists of the extracellular signal molecule called CAI-1 and its cognate membrane bound receptor called CqsS. Here, the ligand binding activity of CqsS is probed with structural analogues of the natural signal. Enabled by our discovery of a structurally simplified analogue of CAI-1, we prepared and analyzed a focused library. The molecules were designed to probe the effects of conformational and structural changes along the length of the fatty acid tail of CAI-1. Our results, combined with pharmacophore modeling, suggest a molecular basis for signal molecule recognition and receptor fidelity with respect to the fatty acid tail portion of CAI-1. These efforts provide novel probes to enhance discovery of antivirulence agents for the treatment of V. cholerae.

Enantioselectivity of haloalkane dehalogenases and its modulation by surface loop engineering

In the loop: Engineering of the surface loop in haloalkane dehalogenases affects their enantiodiscrimination behavior. The temperature dependence of the enantioselectivity (lnE versus 1/T) of β-bromoalkanes by haloalkane dehalogenases is reversed (red data points) by deletion of the surface loop; the selectivity switches back when an additional single-point mutation is made. This behavior is not observed for -bromoesters.

On the conversion of structural analogues of (S)-2-hydroxypropylphosphonic acid to epoxides by the final enzyme of fosfomycin biosynthesis in S. fradiae

2-Hydroxyethyl- and (S)-2-hydroxybutylphosphonic acid were prepared, starting in the latter case from (S)-2-aminobutyric acid. They were fed to cultures of Streptomyces fradiae producing fosfomycin. Only the latter (150 μg/mL of medium) was converted to the ethyl analogue of fosfomycin, isolated as 2-amino-1-hydroxybutylphosphonic acid (3%) in admixture with 2-amino-1-hydroxypropylphosphonic acid (97%) derived from fosfomycin.

On the interactions of alkyl 2-hydroxycarboxylic acids with alkoxysilanes: Selective esterification of simple 2-hydroxycarboxylic acids

The interactions of a range of monocarboxylic acids with tetramethoxysilane Si(OMe)4 (TMOS), in methanol (MeOH), have been investigated by using 1H, 13C and 29Si solution-phase NMR spectroscopy and electrospray mass spectrometry (ESMS). Si(OMe)4 acts as a catalyst/reagent in the selective methylation of 2-hydroxycarboxylic acids (2HOAs) in MeOH at room temperature: glycolic acid, lactic acid and 2-hydroxybutyric acid are esterified more than a hundred times faster in MeOH and Si(OMe)4 than in MeOH alone. No acceleration of methylation is observed for carboxylic acids lacking the 2-hydroxy group. Methylation of the 2HOAs is associated with the condensation of individual siloxane units to form oligomers. A mechanism is proposed in which 2HOAs attach to silicon via the alkoxy group, then subsequently via the carboxyl group in an intramolecular rearrangement to form an unstable and reactive cyclic intermediate. This intermediate may lead to accelerated methylation of the carboxylic acid via nucleophilic attack of MeOH at the carbonyl group, while a separate reaction pathway leads to condensation of silanols and/or alkoxysilanes leading to oligosiloxanes. The mechanism has implications for the use of 2HOAs as templates in sol-gel silica preparation.

Synthetic studies towards ptilomycalin A: total synthesis of crambescidin 359

A potentially biomimetic synthesis of the guanidine-containing marine natural product crambescidin 359 via a double Michael addition of guanidine to a suitably functionalised bis-enone is reported.

DIHYDROPTERIDINONES, METHOD FOR THE PRODUCTION AND USE THEREOF IN THE FORM OF DRUGS

The invention relates to novel dihydropteridinones of general formula (I), wherein rests L, R1-R5 have the significance indicated in claims and a specification, in the isomers thereof, in a method for producing and using said dihydropteridinones in the form of drugs.

A synthesis of crambescidin 359

A potentially biomimetic synthesis of the guanidine-containing marine natural product crambescidin 359 via a double Michael addition of guanidine to a suitably functionalised bis-enone is reported.

An unusual matrix of stereocomplementarity in the hydroxylation of monohydroxy fatty acids catalysed by cytochrome P450 from Bacillus megaterium with potential application in biotransformations

Cytochrome P450 from Bacillus megaterium catalyses the diastereoselective hydroxylations of 13-hydroxymyristic acid, to predominantly erythro-12,13-dihydroxymyristic acid, and of 12-hydroxymyristic acid to give predominantly threo-12,13-dihydroxymyristic acid, in reactions that are stereocomplementary and with considerable potential application in biotransformations.

Isosteres of chiral clofibric acid analogs: Synthesis, resolution, absolute configuration and HPLC detection of the optical purity

Both racemic and enantiomeric forms of some isosteres of chiral clofibric acid analogs have been synthesized. Also, the absolute configuration has been established by chemical correlation and the optical purity determined by a simple HPLC procedure. Moreover, these studies show that the isosteric substitution of the ether oxygen atom of α-aryloxy- alkanoic acids with sulfur, amino and methylene groups lead to compounds in which both biological activity and stereoselectivity regarding chloride channel are highly reduced.