Pantolactone

Base Information

• Chemical Name: Pantolactone
• CAS No.: 599-04-2
• Deprecated CAS: 16562-48-4,631-68-5
• Molecular Formula: C6H10O3
• Molecular Weight: 130.144
• Hs Code.: 29322090
• European Community (EC) Number: 209-963-3
• UNII: J288D7O0JS
• DSSTox Substance ID: DTXSID90881249
• Nikkaji Number: J13.798G
• Wikidata: Q27102042
• RXCUI: 1427236
• Metabolomics Workbench ID: 49904
• ChEMBL ID: CHEMBL4587869
• Mol file: 599-04-2.mol

Synonyms:2,4-dihydroxy-3,3-dimethylbutyric acid gamma-lactone;pantolactone;pantolactone, (R)-isomer;pantolactone, (S)-isomer;pantolactone, 2-(14)C-labeled cpd, (+,-)-isomer;pantoyl lactone

Chemical Property of Pantolactone

Chemical Property:

• Appearance/Colour: White crystalline powder or crystals
• Vapor Pressure: 0.0181mmHg at 25°C
• Melting Point: 91 °C(lit.)
• Refractive Index: -50.8 ° (C=2, H2O)
• Boiling Point: 224.6 °C at 760 mmHg
• PKA: 13.12±0.40(Predicted)
• Flash Point: 99 °C
• PSA: 46.53000
• Density: 1.165 g/cm³
• LogP: -0.06970
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Sparingly), Water (S
• Water Solubility.: almost transparency
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 130.062994177
• Heavy Atom Count: 9
• Complexity: 139

Purity/Quality:

99.9% ^*data from raw suppliers

D-Pantolactone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(COC(=O)C1O)C
• Isomeric SMILES: CC1(COC(=O)[C@@H]1O)C
• Uses: D-(-)-PANTOLACTONE is an important intermediate in the synthesis of pantothenic acid as well as a degradation product of pantothneic acid in the liver. Causes disorientation and hypothermia, and prevents phenamine-induced hyperthermia. D-(-)-Pantolactone is a chiral auxiliary used in many asymmetric synthesis reactions.It can be used as a chiral starting material to synthesize:An insect sex pheromone named 1S,2S,3R-1-acetoxymethyl-2,3,4,4-tetrameth-ylcyclopentane.(-)-Enantiomer of (R)-8-hydroxy-4,7,7-trimethyl-7,8-dihydrocyclopenta[e]isoindole-1,3(2H,6H)-dione, a norsesquiterpene alkaloid.A bicyclic diterpene named isofregenedadiol.

Technology Process of Pantolactone

There total 171 articles about Pantolactone 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: 95.0%

ketopantolactone (13031-04-4) → (S)-pantolactone (79-50-5,599-04-2,5405-40-3,52126-90-6) + (R)-Pantolacton (599-04-2)

Guidance literature:

With hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (2S,4S)-N-butoxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine; In toluene; at 50 ℃; for 45h; under 37503 Torr; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1007/BF00816861

Reference yield: 95.0%

ketopantolactone (13031-04-4) → (S)-pantolactone (79-50-5,599-04-2,5405-40-3,52126-90-6) + (R)-Pantolacton (599-04-2)

Guidance literature:

With hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (2S,4S)-N-butoxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine; In toluene; at 50 ℃; for 45h; under 37503 Torr; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1007/BF00816861

Reference yield: 91.0%

(S)-3-(benzyloxy)-4,4-dimethyldihydrofuran-2(3H)-one (20374-33-8,97024-23-2,117895-47-3,96089-96-2) → (S)-pantolactone (79-50-5,599-04-2,5405-40-3,52126-90-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; for 24h;

DOI:10.1055/s-0031-1290489

upstream raw materials:

pantolactone

ketopantolactone

(RS)-2-acetoxy-3,3-dimethyl-γ-butyrolactone

DL-sodium pantoate

Downstream raw materials:

O-(4-nitro-benzoyl)-L-pantolactone

N-phenethyl-L-pantamide

O-(toluene-4-sulfonyl)-L-pantolactone

pantetheine

Refernces

• 1、 Zhou, Xue-Ming,Zheng, Cai-Juan,Song, Xiao-Ping,Chen, Guang-Ying,Cao, Yu-Hua,Huang, A-Qian,Su, Shao-Hui,Chen, Wen-Xing,Yang, Hui. "A new phenolic glycoside from Saprosma merrillii". . p. 2429 - 2433. Retrieved 2016.
• 2、 Aberhart. "-". . p. 1354. Retrieved 1979.
• 3、 Beutel,Tishler. "-". . p. 1463. Retrieved 1946.
• 4、 Ojima,I. et al.. "-". . p. 3444 - 3446. Retrieved 1978.
• 5、 Hapiot, Frederic,Agbossou, Francine,Mortreux, Andre. "Synthesis of New Chiral Arene Ruthenium(II) Aminophosphinephosphinite Complexes and Use in Asymmetric Hydrogenation of an Activated Keto Compound". . p. 515 - 518. Retrieved 1994.
• 6、 -. "NEW TRANSITION METAL CATALYST". Page/Page column 10-11. . Retrieved 2021/05/15.
• 7、 -. "Preparation method of hydroxyaldehyde and method for resolving optical isomer by using electrodialysis technology". Paragraph 0270-0285. . Retrieved 2020/12/15.