26543-05-5

Basic information

• Product Name: (S)-3-HYDROXY-2-METHYL-PROPIONIC ACID
• Synonyms: Sodium (S)-3-hydroxy-2-methylpropionate;Sodium (S)-β-hydroxyisobutyrate;(2S)-3-hydroxy-2-methylpropanoic acid;(S)-3-Hydroxy-2-Methylpropanoic acid;(S)-3-Hydroxy-2-methylpropionic acid sodium salt;(S)-β-Hydroxy-isobutyric acid sodium salt;S-HIBA
• CAS NO: 26543-05-5
• Molecular Formula: C₄H₈O₃
• Molecular Weight: 104.1
• Mol File: 26543-05-5.mol

Chemical Properties

• Boiling Point: 252.9°Cat760mmHg
• Flash Point: 121°C
• Appearance: /
• Density: 1.195g/cm³
• Vapor Pressure: 0.00292mmHg at 25°C
• Refractive Index: 1.455
• Storage Temp.: 2-8°C
• PKA: 4.46±0.10(Predicted)
• CAS DataBase Reference: (S)-3-HYDROXY-2-METHYL-PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-HYDROXY-2-METHYL-PROPIONIC ACID(26543-05-5)
• EPA Substance Registry System: (S)-3-HYDROXY-2-METHYL-PROPIONIC ACID(26543-05-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 26543-05-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-3-Hydroxy-2-methyl-propionic acid is used as an active pharmaceutical ingredient for its potential therapeutic properties, such as lowering cholesterol levels. It is valued for its role in energy metabolism, which can contribute to the development of treatments for metabolic disorders.
Used in Chemical Intermediates:
In the chemical industry, (S)-3-HIBA serves as a crucial intermediate in the synthesis of various compounds. Its unique structure and functional groups make it a versatile building block for creating a range of chemical products, including specialty chemicals and performance materials.
Used in Food Industry:
Although not explicitly mentioned in the provided materials, given its natural occurrence in certain foods, (S)-3-Hydroxy-2-methyl-propionic acid could potentially be used as a natural preservative or flavor enhancer in the food industry, leveraging its inherent properties to improve food quality or extend shelf life.

InChI:InChI=1/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1

Upstream product

• 535-11-5 Ethyl 2-bromopropionate 
• 909803-25-4 kaempferol 3-O-β-D-(6-O-3-hydroxyisobutyryl)glucopyranosyl-(1->4)-α-L-rhamnopyaranosyl-7-O-β-D-glucopyranoside 
• 67-56-1 methanol 
• 2163-42-0 2-methyl-1.3-propanediol 
• 89534-52-1 3-hydroxy-2-methyl-propionic acid ethyl ester 
• 56850-57-8 3-benzyloxy-2-methylpropionic acid 

Downstream Products

• 53009-01-1 β-phenylcarbamoyloxy-isobutyric acid 
• 80657-57-4 3-hydroxy-(2S)-methylpropionate 
• 72657-23-9 methyl (R)-3-hydroxy-2-methylpropionate 
• 79-41-4 poly(methacrylic acid) 
• 7623-10-1 2-methyl-3-chloropropionyl chloride 
• 91796-44-0 Benzyl 3-(phenylmethoxy)-2-methylpropanoate 
• 63930-49-4 (R)-3-(benzyloxy)-2-methylpropan-1-ol 
• 1360106-01-9 methyl (S)-3-(3-(4-chlorobenzyl)-4-(ethylthio)-2,6-dioxo-3,6-dihydro-1,3,5-triazin-1(2H)-yl)-2-methylpropanoate 
• 59965-08-1 (S)-(+)-3-N-Phenylcarbamoyloxy-2-methyl-propansaeure 
• 16837-14-2 2,2,5-trimethyl-1,3-dioxane-5-carboxylic acid 

Relevant articles and documents

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Solvent effect and reactivity trend in the aerobic oxidation of 1,3-propanediols over gold supported on titania: Nmr diffusion and relaxation studies

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Oxidative esterification of homologous 1,3-propanediols

The oxidative esterification of a homologous series of diols (1,3-propanediol,2-methyl-propanediol and 2,2-dimethyl-1,3-propanediol) with methanol has been investigated using titania-supported gold, palladium and gold-palladium catalysts using molecular oxygen. The gold-palladium catalysts showed the highest activity and 1,3-propanediol was the most reactive while the additional methyl groups decreased the reactivity. However, it is possible to achieve high selectivity to methyl 3-hydroxypropionate and 2-methyl-3- hydroxyisobutyrate by mono-oxidations. Graphical Abstract: [Figure not available: see fulltext.]

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In the presence of a Cu(I) catalyst and a pyridine oxide, alkynyl oxiranes and oxetanes can be converted into functionalized five- or six-membered α,β-unsaturated lactones or dihydrofuranaldehydes. This new oxidative cyclization is proposed to proceed via an unusual allenyloxypyridinium intermediate.

Bioactive constituents from chinese natural medicines. XXXI.1 hepatoprotective principles from sinocrassula indica: Structures of sinocrassosides A8, A9, A10, A11, and A12

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Gluconobacter were found to be capable of oxidizing prochiral diols such as 2-substituted propane-1,3-diols 1 and 3-substituted pentane-1,5-diols 4 with distinction of pro-R and pro-S sites of the molecules, in that (-)-(R)-α-substituted β-hydroxypropionic acids 2 and (+)-(3S)-3-substituted δ-valerolactones 5 were obtained, respectively.Oxidation of 3-methylpentane-1,3,5-triol 11 afforded unnatural (+)-(S)-mevalonolactone 12.The steric bulkiness of the substituents on the prochiral center and the distance from the hydroxy group greatly affected the rate and the enantioselectivity of the reaction.