41014-93-1

Basic information

• Product Name: (S)-2-hydroxyvaleric acid
• Synonyms: (S)-2-hydroxyvaleric acid;(S)-2-Hydroxypentanoic acid;s-2-Hydroxyvaleric a
• CAS NO: 41014-93-1
• Molecular Formula: C₅H₁₀O₃
• Molecular Weight: 118.1311
• EINECS: 255-175-8
• Mol File: 41014-93-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 52-55 °C(Solv: carbon tetrachloride (56-23-5))
• Boiling Point: 248 °C at 760 mmHg
• Flash Point: 118 °C
• Appearance: /
• Density: 1.14 g/cm³
• Vapor Pressure: 0.00405mmHg at 25°C
• Refractive Index: 1.458
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 3.85±0.20(Predicted)
• CAS DataBase Reference: (S)-2-hydroxyvaleric acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-hydroxyvaleric acid(41014-93-1)
• EPA Substance Registry System: (S)-2-hydroxyvaleric acid(41014-93-1)

Safety Data

• Hazardous Substances Data: 41014-93-1(Hazardous Substances Data)

Usage

General Description

(S)-2-hydroxyvaleric acid, also known as (S)-2-hydroxypentanoic acid, is a specific isomer of 2-hydroxyvaleric acid, distinguished by the spatial orientation of its molecular structure. It is an organic compound and a type of beta-hydroxy acid. This chemical features a carboxylic acid group (-COOH) and a hydroxyl group (-OH), with the hydroxyl group attached to the second carbon atom in the pentanoic acid chain, hence the '2' in its name. Generally, 2-hydroxyvaleric acid may be utilized in a variety of scientific and manufacturing processes, including being a building block in the production of other complex organic compounds.

InChI:InChI=1/C5H10O3/c1-2-3-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)/t4-/m0/s1

Upstream product

• 6600-40-4 L-Norvaline 
• 617-31-2 2-hydroxyvaleric acid 
• 123-91-1 1,4-dioxane 
• 584-93-0 2-Bromovaleric acid 
• 207223-21-0 (2S,5S,6R)-2-propyl-2-hydroxy-4,5-dimethyl-6-phenylmorpholin-3-one 
• 207223-39-0 (2S,5S,6R)-4,5-Dimethyl-6-phenyl-2-propyl-morpholin-3-one 
• 207223-31-2 (5S,6R)-4,5-Dimethyl-6-phenyl-2-prop-(Z)-ylidene-morpholin-3-one 
• 219598-62-6 8a(S)-3-propyl-3-hydroxy-4-oxohexahydro-1H-pyrrolo<2,1-c><1,4>oxazine 
• 207223-17-4 2-oxopentanoyl chloride 
• 1821-02-9 2-oxopentanoic acid 
• 219598-66-0 (2S)-(2-hydroxymethyl)-1-[(2R)-2-hydroxypentanoyl]pyrrolidine 
• 133964-76-8 (S)-2-Hydroxy-pentanoic acid methylamide 
• 157733-17-0 (2S,5S)-2-tert-butyl-5-propyl-<1,3>dioxolan-4-one 
• 89426-81-3 (1S,2S,6R,7R)-4-(1-Methoxymethoxy-butyl)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 

Downstream Products

• 29117-54-2 (S)-(-)-1,2-pentanediol 
• 108340-61-0 (R)-1,2-pentanediol 
• 123731-60-2 Methanesulfonic acid (S)-1-(2-bromo-3,4,5-trimethoxy-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-heptyl ester 
• 123731-57-7 1-<(4S)-4-t-butyldimethylsilyloxy-1-phenylthioheptyl>-3,4,5-trimethoxybenzene 
• 123731-58-8 Acetic acid (S)-1-(2-bromo-3,4,5-trimethoxy-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-heptyl ester 
• 123731-59-9 (4S)-1-(2-bromo-3,4,5-trimethoxyphenyl)-4-t-butyldimethylsilyloxy-1-heptanol 
• 123808-04-8 2-bromo-1-<(1E,4S)-4-t-butyldimethylsilyloxy-1-heptenyl>-3,4,5-trimethoxybenzene 
• 123731-65-7 6-((2S,3R,5S)-3-Hydroxy-5-propyl-tetrahydro-furan-2-yl)-2,3,4-trimethoxy-benzoic acid 
• 123808-07-1 (2S,3R,5S)-2-(2-bromo-3,4,5-trimethoxyphenyl)-5-propyltetrahydrofuran-3-ol 
• 28890-33-7 monocerin 
• 28890-33-7 (2S,3aS,9bS)-6-Hydroxy-7,8-dimethoxy-2-propyl-2,3,3a,9b-tetrahydro-furo[3,2-c]isochromen-5-one 
• 123731-55-5 Toluene-4-sulfonic acid (S)-3-(tert-butyl-dimethyl-silanyloxy)-hexyl ester 
• 30263-96-8 (2S,3R,5S)-5-Propyl-2-(3,4,5-trimethoxy-phenyl)-tetrahydro-furan-3-ol 
• 123808-05-9 (1E,4S)-1-(2-bromo-3,4,5-trimethoxyphenyl)-1-hepten-4-ol 

Relevant articles and documents

Enzymatic Resolution by a d-Lactate Oxidase Catalyzed Reaction for (S)-2-Hydroxycarboxylic Acids

Oxidase-catalyzed kinetic resolution is important for the production of enantiopure 2-hydroxycarboxylic acids (2-HAs), which are versatile building blocks for the synthesis of many significant compounds. However, in contrast to that of (R)-2-HAs, the production of (S)-2-HA is challenging because of the lack of related oxidases. Herein, suitable enzymes were screened systematically through the analysis of numerous putative d-lactate oxidase sequences and identification of several required properties. Finally, a d-lactate oxidase from Gluconobacter oxydans 621H with advantageous characteristics, such as good solubility, broad substrate spectrum, and high stereoselectivity, was selected to resolve 2-HAs into (S)-2-HAs. A variety of (S)-2-HAs was produced successfully using this d-lactate oxidase with excellent enantiomeric excess values (>99 %). The presented screening criteria and approach for target biocatalysis suggested a guideline for the production of optically active chemicals such as (S)-2-HAs.

Efficient intramolecular asymmetric reductions of α-, β-, and γ-keto acids with diisopinocampheylborane1

(equation presented) α-, β-, and γ-Keto acids are reduced with diisopinocampheylborane at room temperature to the corresponding hydroxy acids with predictable stereochemistry in very high ee. The γ-hydroxy acids produced were conveniently cyclized to the corresponding lactones. This provides a simple synthesis of 4-hexanolide, a component of the pheromone secreted by the female dermestid beetle Trogoderma glabrum.

Asymmetric reactions of α-ketoacid-derived hemiacetals: Stereoselective synthesis of α-hydroxy acids

N-Acylation of prolinol with α-ketoacid chlorides results in concomitant hemiacetalization of the α-keto amide by the prolinol hydroxyl group. (R) or (S) α-hydroxy acids are obtained with good enantiomeric excess by stereodivergent reduction of these hemiacetals. Reaction with Grignard reagents at ambient temperature furnishes (R) α-alkyl mandelic acids with good stereoselectivity.