(S)-gamma-valerolactone

Base Information

• Chemical Name: (S)-gamma-valerolactone
• CAS No.: 19041-15-7
• Molecular Formula: C5H8 O2
• Molecular Weight: 100.117
• Hs Code.: 2932209090
• European Community (EC) Number: 803-193-7
• Nikkaji Number: J82.827K
• Wikidata: Q27121270
• Metabolomics Workbench ID: 57048
• Mol file: 19041-15-7.mol

Synonyms:(5S)-5-methyloxolan-2-one;19041-15-7;(S)-gamma-valerolactone;(S)-GAMMA-METHYL-GAMMA-BUTYROLACTONE;(-)-gamma-valerolactone;(-)-(S)-gamma-valerolactone;(S)-(-)-gamma-valerolactone;(5S)-5-methyldihydrofuran-2(3H)-one;(-)-(S)-5-methyl-2-oxotetrahydrofuran;2(3H)-Furanone, dihydro-5-methyl-, (5S)-;(S)-5-methyldihydrofuran-2(3H)-one;SCHEMBL265331;CHEBI:48571;(s)-5-methyl-dihydro-furan-2-one;AKOS006279066;(S)-gamma-Valerolactone, >=97.5% (GC);CS-0233222;EN300-131841;Q27121270

Chemical Property of (S)-gamma-valerolactone

Chemical Property:

• PSA: 26.30000
• LogP: 0.71190
• Storage Temp.: 2-8°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 88.1

Purity/Quality:

97% ^*data from raw suppliers

(S)-γ-Valerolactone ≥97.5% (GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(=O)O1
• Isomeric SMILES: C[C@H]1CCC(=O)O1
• General Description: (S)-Gamma-methyl-gamma-butyrolactone, also known as (S)-gamma-valerolactone, is an optically active chiral platform molecule derived from biomass-based levulinic acid. It can be synthesized via asymmetric hydrogenation using ruthenium or nickel-based catalysts, achieving high chemoselectivity and moderate to good enantioselectivity (up to 82% ee). (S)-GAMMA-METHYL-GAMMA-BUTYROLACTONE serves as a valuable intermediate in sustainable chemistry, with potential applications in industrial-scale production due to its efficient synthesis from renewable feedstocks. Additionally, its enantiomeric form has been studied in allergenic contexts, though stereospecific effects vary depending on the biological system.

Technology Process of (S)-gamma-valerolactone

There total 85 articles about (S)-gamma-valerolactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

4-benzoyloxy-5(S)-methyl-2(5H)-furanone (118574-86-0) → benzoic acid (65-85-0,8013-63-6) + (S)-γ-valerolactone (19041-15-7)

Guidance literature:

With hydrogen; platinum(IV) oxide; In tetrahydrofuran; for 1.5h;

Reference yield:

levulinic acid (123-76-2) → (R)-5-methyl-2-oxotetrahydrofuran (58917-25-2) + (S)-γ-valerolactone (19041-15-7)

Guidance literature:

With C₁₇H₃₃ClIrNP₂; hydrogen; potassium hydroxide; In methanol; at 100 ℃; for 24h; under 38002.6 Torr; Optical yield = 14 %ee; enantioselective reaction; Autoclave; Glovebox;

DOI:10.1016/j.jorganchem.2015.05.002

Reference yield:

levulinic acid methyl ester (624-45-3) → (+/-)-γ-hydroxy-γ-methylbutyric acid methylester (126252-14-0) + (R)-5-methyl-2-oxotetrahydrofuran (58917-25-2) + (S)-γ-valerolactone (19041-15-7)

Guidance literature:

With L-Tartaric acid; hydrogen; acetic acid; sodium bromide; In tetrahydrofuran; water; at 99.84 ℃; for 20h; under 67506.8 Torr; Reagent/catalyst; enantioselective reaction; Autoclave;

DOI:10.1007/s10562-017-1968-x

upstream raw materials:

5-methylenedihydrofuran-2-one

(5R)-(iodomethyl)-γ-butyrolactone

γ-hydroxyvaleric acid

(+/-)-γ-hydroxy-γ-methylbutyric acid methylester

Downstream raw materials:

(3RS,5S)-3-phenylseleno-5-methyldihydro-2(3H)-furanone

S-(-)-γ-methyl-(R/S)-γ-butyrolactol

(S)-6-(triisopropylsiloxy)hept-2-en-1-yl para-toluenesulfonate

(S)-(-)-α-(2-chlorobenzylidene)-γ-methyl-γ-butyrolactone