L-Gulonolactone

Base Information

• Chemical Name: L-Gulonolactone
• CAS No.: 1128-23-0
• Molecular Formula: C6H10O6
• Molecular Weight: 178.142
• Hs Code.: 29400090
• UNII: 56830VTX9G
• DSSTox Substance ID: DTXSID00331407
• Nikkaji Number: J208.558E
• Wikidata: Q27102468
• Metabolomics Workbench ID: 38342
• Mol file: 1128-23-0.mol

Synonyms:L-Gulonolactone;1128-23-0;L-Gulono-1,4-lactone;(3S,4R,5R)-5-((S)-1,2-Dihydroxyethyl)-3,4-dihydroxydihydrofuran-2(3H)-one;gamma-Gulonolactone;L-Gulono-gamma-lactone;L-Gulonic gamma-lactone;L-Gulonic acid gamma-lactone;L(+)-Gulonic acid gaMMa-lactone;L-(+)-Gulonic Acid gamma-Lactone;L-(+)-Gulono-1,4-lactone;(3S,4R,5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one;56830VTX9G;l-Gulonic acid, gamma-lactone;UNII-56830VTX9G;l-Gulonic acid, .gamma.-lactone;L-GULONIC-gamma-LACTONE;L-Gulonic acid g-lactone;Gulonic acid-1,4-lactone;MFCD00064331;Reduced ascorbate;Reduced ascorbic acid;bmse000235;L-Gulonic acid, g-lactone;L-Gulonic acid |A-lactone;.GAMMA.-GULONOLACTONE;SCHEMBL418680;CHEBI:17587;DTXSID00331407;L-GULONO-.GAMMA.-LACTONE;L-Gulonic acid gamma-lactone, 95%;s6182;AKOS015901191;CS-W017344;DS-3671;HY-W016628;L-(+)-GLUTONIC ACID GAMMA-LACTONE;G0235;L-(+)-GULONIC ACID .GAMMA.-LACTONE;C01040;GULONIC ACID [L-(+)], .GAMMA.-LACTONE;A894520;Q27102468;10CD678E-3FFC-46B6-8CF7-9AC5D196AE46;WURCS=2.0/1,1,0/[A1121h_1-4]/1/;(3S,4R,5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxydihydrofuran-2(3H)-one

Chemical Property of L-Gulonolactone

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 1.01E-10mmHg at 25°C
• Melting Point: 187-190 °C(lit.)
• Refractive Index: 56 ° (C=2, H2O)
• Boiling Point: 467.939 °C at 760 mmHg
• PKA: 12.06±0.60(Predicted)
• Flash Point: 201.545 °C
• PSA: 107.22000
• Density: 1.766 g/cm³
• LogP: -3.01320
• Storage Temp.: 0-6°C
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Sparingly)
• Water Solubility.: Soluble in water
• XLogP3: -2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 178.04773803
• Heavy Atom Count: 12
• Complexity: 181

Purity/Quality:

98%, ^*data from raw suppliers

L-Gulonic acid-1,4-lactone ^*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: C(C(C1C(C(C(=O)O1)O)O)O)O
• Isomeric SMILES: C([C@@H]([C@@H]1[C@@H]([C@@H](C(=O)O1)O)O)O)O
• Uses: L-Gulono-1,4-lactone is a precursor in the biosynthesis of ascorbic acid, one of the many forms of Vitamin C.

Technology Process of L-Gulonolactone

There total 17 articles about L-Gulonolactone 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: 99.0%

ascorbic acid (50-81-7,98966-42-8) → L-gulono-1,4-lactone (1128-23-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In water; at 50 ℃; for 24h; under 2585.7 Torr;

DOI:10.1021/jo00327a029

Reference yield: 90.0%

mannitol (69-65-8) → γ lactone of dl-mannonic acid (1128-23-0,1128-24-1,1198-69-2,1668-08-2,2426-46-2,2782-07-2,3158-30-3,3327-64-8,6322-07-2,10238-03-6,10366-82-2,18404-70-1,22430-23-5,23666-11-7,26301-79-1,29474-78-0,74464-44-1,78184-43-7,83602-36-2,119008-75-2,127997-10-8)

Guidance literature:

With 1-Phenylbut-1-en-3-one; rhodium hydrido (PEt₃)3 complex; In N,N-dimethyl-formamide; at 60 - 80 ℃;

DOI:10.1055/s-1998-1705

Reference yield: 90.0%

→ L-gulono-1,4-lactone (1128-23-0)

Guidance literature:

upstream raw materials:

L-gluconic acid

D-Glucaro-1,4-lacton

ascorbic acid

5-O-methanesulfonyl-2,3,4,6-tetra-O-pyvaloyl-D-mannonitrile

Downstream raw materials:

L-gulose

2,3-dioxo-propionic acid

acetaldehyde

D-gluconic acid

Refernces

• 1、 Soriano,Meserole,Mulcahy. "Catalytic hydrogenation of L-ascorbic acid (vitamin C): A stereoselective process for the production of L-gulono-1,4-lactone". . p. 3263 - 3265. Retrieved 1995.
• 2、 Sutter,Reichstein. "-". . p. 1210,1216. Retrieved 1938.
• 3、 Kutus, Bence,Peintler, Gábor,Buckó, ákos,Balla, Zsolt,Lupan, Alexandru,Attia, Amr A.A.,Pálinkó, István,Sipos, Pál. "The acidity and self-catalyzed lactonization of L-gulonic acid: Thermodynamic, kinetic and computational study". . p. 14 - 22. Retrieved 2018/07/29.
• 4、 Archer, Robert M.,Royer, Sylvain F.,Mahy, William,Winn, Caroline L.,Danson, Michael J.,Bull, Steven D.. "Syntheses of 2-keto-3-deoxy-D-xylonate and 2-keto-3-deoxy-L-arabinonate as stereochemical probes for demonstrating the metabolic promiscuity of sulfolobus solfataricus towards D-xylose and L-arabinose". supporting information. p. 2895 - 2902. Retrieved 2013/03/28.