18467-77-1

Basic information

• Product Name: DIKEGULAC DIHYDRAT
• Synonyms: DIKEGULAC DIHYDRAT;DIKEGULAC DIHYDRATE;2,3:4,6-bis-o-(1-methylethylidene)-alpha-l-xylo-2-hexulofuranosonicaci;diprogulic acid;L-Diacetoneketogulonic acid monohydrate (DAKS);DIKEGULAC MONOHYDRATE PESTANAL 250 MG;2,3:4,6-di-o-isopropyliden-2-oxo-l-gulonic acid;dikegulac hydrate
• CAS NO: 18467-77-1
• Molecular Formula: C₁₂H₁₈O₇
• Molecular Weight: 310.3
• EINECS: 242-348-8
• Mol File: 18467-77-1.mol

Chemical Properties

• Melting Point: 88-90 °C(lit.)
• Boiling Point: 375℃
• Flash Point: 140℃
• Appearance: /
• Density: 1.281
• Vapor Pressure: 1.16E-06mmHg at 25°C
• Refractive Index: 1.482
• Storage Temp.: 2-8°C
• CAS DataBase Reference: DIKEGULAC DIHYDRAT(CAS DataBase Reference)
• NIST Chemistry Reference: DIKEGULAC DIHYDRAT(18467-77-1)
• EPA Substance Registry System: DIKEGULAC DIHYDRAT(18467-77-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 18467-77-1(Hazardous Substances Data)

Usage

Purification Methods

Dissolve -DAG in Et2O, filter, dry (MgSO4) it, filter it again and evaporate to give a yellow oil. Addition of one drop of H2O induces crystallisation to the monohydrate, which also forms rhombic crystals on recrystallisation from 95% EtOH/H2O at room temperature. [Flatt et al. Synthesis 815 1979, Reichstein & Grussner Helv Chim Acta 17 311 1934, Takagi & Jeffrey Acta Crystallogr Sect B 34 2932 1978, cf Org Synth 55 80 1976, Beilstein 19/12 V 520.]

InChI:InChI=1/C12H18O7/c1-10(2)15-5-6-7(17-10)8-12(16-6,9(13)14)19-11(3,4)18-8/h6-8H,5H2,1-4H3,(H,13,14)

Upstream product

• 17682-70-1 2,3:4,6-bis-O-isopropylidene-L-sorbose 

Downstream Products

• 130059-79-9 (3aS,3bR,7aS,8aR)-2,2,5,5-Tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxine-8a-carboselenoic acid Se-phenyl ester 
• 50-81-7 ascorbic acid 
• 181481-54-9 (4S)-3,3-diethyl-4-{4-[(4-methylpiperazinyl)-carbonyl]phenoxy}azetidin-2-one 
• 52508-00-6 2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid potassium salt 
• 131156-47-3 (3aS,3bR,7aS,8aS)-2,2,5,5-tetramethyltetrahydro-3aH-[1,3]dioxolo[4',5':4,5]furo[3,2-d][1,3]dioxane 
• 528-81-4 6-deoxy-L-ascorbic acid 
• 62983-43-1 6-Desoxy-6-chlor-L-ascorbinsaeure 
• 62983-44-2 6-bromo-6-deoxy-(S)-ascorbic acid 
• 161687-28-1 (5S,9S)-N-((2'S,3'S)-3'-hydroxy-2'-methyl-3'-phenylpropionyl)-4-aza-5,9:6,10-di-O-isopropylidene-2,8-dioxabicyclo<4.3.0>nonan-3-one 

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CONVERSION OF 2,3:4,6-DI-O-ISOPROPYLIDENE-L-SORBOSE TO 2,3:4,6-DI-O-ISOPROPYLIDENE-2-KETO-L-GULONIC ACID BY CATALYTIC OXIDATION WITH OXYGEN ON PLATINUM

The kinetics of the oxidation of 2,3:4,6-di-O-isopropylidene-L-sorbose to 2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid by oxygen were determined in the aqueous alkaline medium and over platinum on carbon as the catalyst.The most adequate kinetic equation suggested on the basis of non-linear regression was that of the Langmuir-Hinshelwood type.The corresponding most probable reaction mechanism involved an equilibrium single-site adsorption of the substrate a dissociative dual-site adsorption of oxygen and a surface reaction between oxygen and the substrate to form aldehyde in the rate determining step; in the aqueous alkaline medium the aldehyde is oxidized in the next step to give the anion of 2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid.This mechanism appears to be generally applicable to the catalytic transformations of primary alcohols into carboxylic acids by oxygen or air under the above reaction conditions.A linear correlation of the relative reactivities of a series of water-soluble primary aliphatic alcohols with the Taft ?* constants shows the polar substituent effect to play the predominant role.However, ethanol is approximately twenty times as reactive as 2,3:4,6-di-O-isopropylidene-L-sorbose and this indicates that in the oxidation of the latter compound also strong steric effects should apply.