5405-40-3

Basic information

• Product Name: L-PANTOLACTONE
• Synonyms: S(+)-3,3-DIMETHYL-2-HYDROXY-GAMMA-BUTYROLACTONE;S(+)-2-HYDROXY-3,3-DIMETHYL-GAMMA-BUTYROLACTONE;(S)-(+)-DIHYDRO-3-HYDROXY-4,4-DIMETHYL-2(3H)-FURANONE;(S)-DIHYDRO-3-HYDROXY-4,4-DIMETHYL-2(3H)-FURANONE;(S)-(+)-PANTOLACTONE;L-PANTOLACTONE;L-(+)-PANTOYL LACTONE;L-(+)-2-HYDROXY-3,3-DIMETHYL-GAMMA-BUTYROLACTONE
• CAS NO: 5405-40-3
• Molecular Formula: C₆H₁₀O₃
• Molecular Weight: 130.14
• EINECS: 201-210-7
• Mol File: 5405-40-3.mol
• Article Data: 95

Chemical Properties

• Melting Point: 90-94 °C
• Boiling Point: 120-122 °C/15 mmHg(lit.)
• Flash Point: 98.957 °C
• Appearance: /
• Density: 1.1066 (rough estimate)
• Vapor Pressure: 0.018mmHg at 25°C
• Refractive Index: 1.4730 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 13.12±0.40(Predicted)
• Water Solubility: Soluble in water, hardly soluble in alcohol.
• BRN: 4659425
• CAS DataBase Reference: L-PANTOLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: L-PANTOLACTONE(5405-40-3)
• EPA Substance Registry System: L-PANTOLACTONE(5405-40-3)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 5405-40-3(Hazardous Substances Data)

Usage

Description

L-PANTOLACTONE, also known as (S)-(+)-Pantolactone, is a versatile cyclic ester compound that serves as a key reactant in various chemical and pharmaceutical applications. It is derived from the fermentation of microorganisms and is characterized by its unique chemical structure, which allows for a wide range of reactions and transformations.

Uses

Used in Asymmetric Catalysis:
L-PANTOLACTONE is used as a reactant for the preparation of tunable ligands, specifically carbohydrate-derived diarylphosphinites. These ligands are crucial in asymmetric catalysis, a field that focuses on the selective synthesis of chiral molecules with a single enantiomer, which is essential in the pharmaceutical industry for the development of more effective and safer drugs.
Used in Hydrovinylation of Styrene Derivatives:
L-PANTOLACTONE is also utilized in the hydrovinylation of styrene derivatives, a chemical reaction that involves the addition of a hydrogen atom and an alkyl group to a vinyl compound. This process is significant in the synthesis of various industrial chemicals and materials, such as polymers and pharmaceutical intermediates.

InChI:InChI=1/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3/t4-/m1/s1

Upstream product

• 79-50-5 pantolactone 
• 13031-04-4 ketopantolactone 
• 28227-35-2 (RS)-2-acetoxy-3,3-dimethyl-γ-butyrolactone 
• 1902-01-8 DL-sodium pantoate 
• 82118-78-3 (2S)-3,3-Dimethylbernsteinsaeure-4-methylester 
• 123355-74-8 (R,R)-(-)-trans-2,3-bis(diphenylhydroxymethyl)-1,4-dioxaspiro<4.5>decane * (S)-(-)-pantolactone 
• 157717-57-2 (3R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl trifluoromethanesulfonate 
• 599-04-2 (R)-Pantolacton 
• 28387-34-0 (S)-2-acetoxy-3,3-dimethyl-γ-butyrolactone 
• 250738-86-4 tert-butyl-(4,4-dimethyl-4,5-dihydro-furan-2-yloxy)-dimethyl-silane 
• 75-36-5 acetyl chloride 
• 259107-29-4 2S-3,3-dimethyl-2-hydroxy-4-methoxybutanoic acid N-methyl amide 
• 259107-28-3 2S,5S,6R-4,5-dimethyl-6-phenyl-2-(1,1-dimethyl-2-methoxy ethyl) morpholin-3-one 
• 696641-89-1 2-((2S,5S,6R)-4,5-Dimethyl-3-oxo-6-phenyl-morpholin-2-yl)-2-methyl-propionic acid ethyl ester 

Downstream Products

• 134734-33-1 O-(4-nitro-benzoyl)-L-pantolactone 
• 101776-81-2 N-phenethyl-L-pantamide 
• 20664-72-6 O-(toluene-4-sulfonyl)-L-pantolactone 
• 27979-04-0 (3aS)-1,3-dibenzyl-6c-((S)-4,4-dimethyl-2-oxo-(3ar,6ac)-tetrahydro-furan-3-yloxy)-tetrahydro-furo[3,4-d]imidazole-2,4-dione 
• 27979-04-0 (3aR)-1,3-dibenzyl-6t-((S)-4,4-dimethyl-2-oxo-(3ar,6ac)-tetrahydro-furan-3-yloxy)-tetrahydro-furo[3,4-d]imidazole-2,4-dione 
• 74561-18-5 dexpanthenol 
• 20374-33-8 (S)-3-(benzyloxy)-4,4-dimethyldihydrofuran-2(3H)-one 
• 86809-23-6 l-1-Phenoxy-2-hydroxy-3-ammoniumpropane-L-pantoate 
• 300578-08-9 (R)-4,4-Dimethyl-3-((2S,3R)-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-dihydro-furan-2-one 
• 300578-06-7 (R)-4,4-Dimethyl-3-((2R,3S)-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-dihydro-furan-2-one 
• 1112-32-9 L-pantoic acid 
• 924961-36-4 (2S)-2-tert-butyldiphenylsiloxy-3,3-dimethyl-4-butanolide 
• 668485-55-0 C₁₃H₁₃NO₇ 
• 924961-42-2 (2S)-3-tert-butyldiphenylsiloxy-2-hydroxy-4,4-dimethyloxolane 

Relevant articles and documents

Industrial kinetic resolution ofd,l-pantolactone by an immobilized whole-cell biocatalyst

Immobilized whole-cells ofPichia pastorisharboring recombinantd-lactonase were entrapped in calcium alginate gels and used as an efficient biocatalyst for catalytic kinetic resolution ofd,l-pantolactone. The immobilized whole-cell biocatalyst exhibited good catalytic stability, which was applied for stereospecific hydrolysis ofd-pantolactone for up to 56 repeated batch reactions without obvious loss in the catalytic activity and enantioselectivity.

Synthesis method of chiral 2-hydroxy-1, 4-dicarbonyl compound and pantoic acid lactone

The invention discloses a chiral 2-hydroxy-1, 4-dicarbonyl compound synthesized by catalyzing asymmetric Aldol reaction of fatty aldehyde and glyoxylate or fatty aldehyde and acylformaldehyde monohydrate by taking tetrapeptide TP or an enantiomer ent-TP thereof as a chiral catalyst, and application of a synthetic product. The method for synthesizing the chiral 2-hydroxy-1, 4-dicarbonyl compound through the asymmetric Aldol reaction is shown as a formula 1 and a formula 2. The asymmetric Aldol reaction of fatty aldehyde and glyoxylate or fatty aldehyde and acylformaldehyde monohydrate is catalyzed to synthesize the optically active 2-hydroxy-1, 4-dicarbonyl compound, then the optically active pantoic acid lactone can be further synthesized, and the method has advantages of mild reaction conditions, easy operation, low catalyst consumption, high yield and the like, and can synthesize the 2-hydroxy-1, 4-dicarbonyl compounds with two configurations by using tetrapeptide and the enantiomerthereof.

STEREOSELECTIVE SYNTHESIS OF ENANTIOMERICALLY-ENRICHED PANTOLACTONE

The present invention relates stereoselective synthesis of enantiomerically enriched pantolactone.