52079-23-9

Basic information

• Product Name: (S)-(-)-alpha-Hydroxy-gamma-butyrolactone
• Synonyms: (3S)-3-HYDROXYDIHYDROFURAN-2(3H)-ONE;2,4-DIHYDROXYBUTYRIC ACID LACTONE;(S)-2-HYDROXYBUTYROLACTONE;(S)-(-)-DIHYDRO-3-HYDROXY-2(3H)-FURANONE;(S)-(-)-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE;(S)-2-Hydroxy-gamma-butyrolactone;2,4-Dihydroxybutyric acid lactone (S)-2-Hydroxybutyrolactone;(S)-(-)-ALPHA-HYDROXY--BUTYROLACTONE
• CAS NO: 52079-23-9
• Molecular Formula: C₄H₆O₃
• Molecular Weight: 102.09
• EINECS: 434-990-4
• Product Categories: Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Chiral Reagents;Chiral Building Blocks;Lactones;Organic Building Blocks
• Mol File: 52079-23-9.mol
• Article Data: 43

Chemical Properties

• Boiling Point: 133 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: colourless liquid
• Density: 1.309 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00371mmHg at 25°C
• Refractive Index: n20/D 1.467(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.07±0.20(Predicted)
• CAS DataBase Reference: (S)-(-)-alpha-Hydroxy-gamma-butyrolactone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-alpha-Hydroxy-gamma-butyrolactone(52079-23-9)
• EPA Substance Registry System: (S)-(-)-alpha-Hydroxy-gamma-butyrolactone(52079-23-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 52079-23-9(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Liquid

Uses

Different sources of media describe the Uses of 52079-23-9 differently. You can refer to the following data:
1. (3S)-3-Hydroxydihydrofuran-2(3H)-one (cas# 52079-23-9) is a compound useful in organic synthesis.
2. Used to prepare the polyether antibiotic monensin, functionalized D-ring side chains of vitamin D analogs, and pesticides.

InChI:InChI=1/C4H6O3/c5-3-1-2-7-4(3)6/h3,5H,1-2H2/t3-/m0/s1

Upstream product

• 117-34-0 2,2-diphenylacetic acid 
• 19444-84-9 3-hydroxyoxolan-2-one 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 97-67-6 (S)-Malic acid 
• 153011-57-5 (5S)-(2,2-Cyclohexylidene-4-oxo-1,3-dioxolan-5-yl)acetic acid 
• 617-55-0 dimethyl (S)-malate 
• 76-86-8 Triphenylsilyl chloride 
• 617-48-1 malic acid 
• 196512-77-3 (2RS,5S)-5-carboxymethyl-2-trichloromethyl-4-oxo-1,3-dioxolane 
• 76224-59-4 (2S)-2-Acetoxy-4-hydroxybuttersaeure-ethylester 
• 672-15-1 L-homoserine 
• 73991-95-4 2-[(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid 
• 174563-88-3 (5R)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-one 
• 135247-43-7 methyl 2,4-dihydroxybutanoate 

Downstream Products

• 130626-32-3 (S)-(-)-3-<(2-Methoxyethoxy)methoxy>-2-oxolanone 
• 159216-42-9 (S)-α-methoxy-γ-butyrolactone 
• 172603-73-5 (S)-2,4-Dihydroxy-N-((2R,3S,4S,5S,6S)-4-hydroxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl)-butyramide 
• 83680-34-6 (3S)-3-(Tetrahydroxy-2H-2-pyranyloxy)tetrahydro-2-furanone 
• 317855-21-3 (3S)-3-(methoxymethoxy)dihydro-2(3H)-furanone 
• 586976-83-2 (R)-3-Methoxymethoxy-dihydro-furan-2-one 
• 666706-29-2 (R)-α-N,N-diboc-aminoxy-γ-butyrolactone 
• 857904-22-4 1-[({[(3R)-2-oxotetrahydro-3-furanyl]oxy}carbonyl)oxy]-2,5-pyrrolidinedione 
• 883998-42-3 (S)-2-hydroxy-4-(naphthalen-2-ylthio)butanoic acid 
• 1055325-40-0 n-butyl (S)-2-hydroxy-4-iodobutanoate 
• 883998-35-4 (R)-2-hydroxy-4-(naphthalen-2-ylthio)butanoic acid 
• 220352-11-4 (R)-dihydro-3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2(3H)-furanone 
• 943654-12-4 (S)-3-(4-chloro-5-fluoroindolin-1-yl)-dihydrofuran-2(3H)-one 
• 1190832-67-7 (R)-α-benzyloxy-γ-butyrolactone 

Relevant articles and documents

Preparation method of alpha-hydroxyl-gamma-butyrolactone

The invention belongs to the field of preparation of organic compounds, and provides a preparation method of alpha-hydroxyl-gamma-butyrolactone. The method is characterized in that malic acid is used as a raw material, and alpha-hydroxyl-gamma-butyrolactone is synthesized with high yield through four steps of reactions, namely, carboxyl and alpha-hydroxyl protection, beta-carboxyl reduction, protecting group removal and internal esterification. The method has the advantages of easily available raw materials, mild reaction conditions and low cost, and is suitable for large-scale preparation of alpha-hydroxy-gamma-butyrolactone.

SYNTHETIC PRECURSOR OF EPOTHILONE FOR IMPROVING PRODUCTION OF EPOTHILONE AND METHOD FOR PREPARING EPOTHILONE USING THE SAME

The present invention relates to a compound for increasing production of epothilone in actinomyces, and to a method for producing epothilone with increased yield. The method for producing epothilone of the present invention includes a step of culturing actinomyces in which epothilone-biosynthesizing genes in Sorangium cellulosum including epoD, epoE, epoF, orf6, orf3, and orf14 are introduced in a culture medium. According to the present invention, it is possible to increase the production yield of epothilone in actinomyces, even in actinomyces in which epoA, epoP, epoB, and epoC are not introduced therein.COPYRIGHT KIPO 2016

Kinetic resolution of racemic 2-hydroxy-γ-butyrolactones by asymmetric esterification using diphenylacetic acid with pivalic anhydride and a chiral acyl-transfer catalyst

Various optically active 2-hydroxy-γ-butyrolactone derivatives are produced via the kinetic resolution of racemic 2-hydroxy-γ-butyrolactones with diphenylacetic acid using pivalic anhydride and (R)-benzotetramisole ((R)-BTM), a chiral acyl-transfer catalyst. Importantly, the substrate scope of this novel protocol is fairly broad (12 examples, s-value; up to over 1000). In addition, we succeeded in disclosing the reaction mechanism to afford high enantioselectivity using theoretical calculations and expounded on the substituent effects at the C-3 positions in 2-hydroxylactones.