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Name	Diacetone-D-glucose	EINECS	209-486-0
CAS No.	582-52-5	Density	1.214 g/cm³
PSA	66.38000	LogP	0.37520
Solubility	slightly soluble in water	Melting Point	110-111 °C(lit.)
Formula	C₁₂H₂₀O₆	Boiling Point	362.8 °C at 760 mmHg
Molecular Weight	260.287	Flash Point	173.2 °C
Transport Information	N/A	Appearance	white to light yellow crystal powder
Safety	24/25-36/37-26	Risk Codes	36/37/38
Molecular Structure		Hazard Symbols	Xi
Synonyms	Glucofuranose,1,2:5,6-di-O-isopropylidene-, a-D- (6CI,7CI,8CI);(-)-1,2:5,6-Di-O-isopropylidene-a-D-glucofuranose;1,2:5,6-Di-O-isopropylidene-D-glucofuranose;1,2:5,6-Di-O-isopropylidene-D-glucose;1,2:5,6-Di-O-isopropylidene-a-D-glucofuranose;1,2:5,6-Di-O-isopropylidene-a-D-glucose;1,2:5,6-Diisopropylidene-a-D-glucofuranose;D-Glucose diacetonide;Diacetone glucose;Diacetone-D-glucose;Glucosebisacetonide;Glucose diacetonide;NSC 1223;	Article Data	36

Diacetone-D-glucose Synthetic route

(3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole: (3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions

Conditions	Yield
With 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In methanol at 40℃;	100%
With tetrakis(triphenylphosphine) palladium(0); p-toluene sulfinic acid In dichloromethane for 0.416667h; Ambient temperature;	99%
With 1,3-dimethylbarbituric acid; Pd(PPh3) In tetrahydrofuran at 90℃; for 24h;	99%

: 153763-40-7
3-O-allyloxycarbonyl-1,2,5,6-di-O-isopropylidene-α-D-glucofuranose

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions

Conditions	Yield
With aminomethyl resin-supported N-propylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃;	100%
With palladium diacetate; sodium azide; trisodium tris(3-sulfophenyl)phosphine In water; acetonitrile at 25℃; for 1h;	71%

: 428500-97-4
3-O-(2-azidomethyl)phenylacetyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

A: 24331-94-0
1,4-dihydro-3(2H)-isoquinolinone

B: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions

Conditions	Yield
With hydrogen; Lindlar's catalyst In methanol at 20℃; for 3h;	A n/a B 100%

: 18685-18-2
3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water for 1h; Sealed tube; Irradiation;	98%
With hydrogen; palladium on activated charcoal In various solvent(s) at 20℃; under 760 Torr; for 10h;	90%
With 3,3-dimethyldioxirane In dichloromethane; acetone for 48h; Ambient temperature;	87.3%

: (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); p-toluene sulfinic acid In dichloromethane for 0.5h; Ambient temperature;	98%

: 16713-80-7
3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions

Conditions	Yield
With methanol; potassium permanganate; trimethylsulphonium iodide at 25℃; under 760.051 Torr; chemoselective reaction;	96%
acetylesterase from orange peel;	75%
With sodium methylate In tetrahydrofuran for 6h;

: 2280-44-6
D-Glucose

: 67-64-1
acetone

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions

Conditions	Yield
With iodine	96%
With phosphoric acid; zinc(II) chloride	93%
vanadyl triflate In acetonitrile at 20℃; for 10h;	89%

: 753488-63-0
1,2:5,6-di-O-isopropylidene-3-O-methylprenyl-α-D-glucofuranose

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions

Conditions	Yield
With (PhSO2)2; water In dichloromethane at 80℃;	96%

: 50-99-7
D-glucose

: 67-64-1
acetone

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions

Conditions	Yield
With phosphoric acid; zinc(II) chloride	95%
With phosphoric acid; zinc(II) chloride for 30h; Ambient temperature;	91%
With sulfuric acid Inert atmosphere;	85%

: 610-85-5, 7045-51-4, 19217-07-3, 30412-16-9, 34685-37-5, 36468-79-8, 36468-80-1, 36468-81-2, 36468-82-3, 36468-84-5, 36574-15-9, 36574-18-2, 36574-19-3, 36574-21-7, 36972-23-3, 36978-43-5, 37738-80-0, 40461-75-4, 40461-79-8, 40461-80-1, 40461-83-4, 40550-49-0, 41612-82-2, 41846-85-9, 41846-86-0, 41846-87-1, 41846-88-2, 41846-89-3, 41846-90-6, 41846-91-7, 41846-92-8, 41846-93-9, 41846-94-0, 41846-95-1, 41846-96-2, 41846-97-3, 41847-47-6, 41847-48-7, 41847-49-8, 41847-50-1, 41847-62-5, 41847-63-6, 41847-64-7, 41847-65-8, 41847-66-9, 41847-67-0, 41847-68-1, 51076-04-1, 89673-68-7, 131064-93-2, 131064-94-3, 131064-95-4, 131064-96-5, 131064-97-6, 131065-02-6, 131065-03-7, 131065-04-8, 131065-05-9, 131065-06-0
α-D-glucofuranose

: 67-64-1
acetone

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions

Conditions	Yield
With diphenylphosphinopolystyrene; iodine at 20℃; for 0.5h;	95%
With sulfuric acid; copper(II) sulfate at 20℃; for 18h;	90%
With sulfuric acid at 5 - 25℃; for 8h;	81.3%
With sulfuric acid at 0℃;
With sulfuric acid

Diacetone-D-glucose Chemical Properties

IUPAC Name: 5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
Following is the structure of Diacetone-D-glucose (CAS NO.582-52-5):

Empirical Formula: C₁₂H₂₀O₆
Molecular Weight: 260.2836
EINECS: 209-486-0
Index of Refraction: 1.483
Molar Refractivity: 61.24 cm³
Molar Volume: 214.3 cm³
Density: 1.214 g/cm³
Flash Point: 173.2 °C
Surface Tension: 43.6 dyne/cm
Enthalpy of Vaporization: 70.46 kJ/mol
Boiling Point: 362.8 °C at 760 mmHg
Water Solubility: slightly soluble
Storage temp.: −20 °C
Vapour Pressure: 9.94E-07 mmHg at 25 °C
Appearance of Diacetone-D-glucose (CAS NO.582-52-5): white to light yellow crystal powde
Product Categories of Diacetone-D-glucose (CAS NO.582-52-5): Pharmaceutical Intermediates; Sugars, Carbohydrates & Glucosides; chiral; Biochemistry; Glucose; O-Substituted Sugars; Sugars; Carbohydrates & Derivatives; Carbohydrates
Canonical SMILES: CC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)O)C
InChI: InChI=1S/C12H20O6/c1-11(2)14-5-6(16-11)8-7(13)9-10(15-8)18-12(3,4)17-9/h6-10,13H,5H2,1-4H3
InChIKey: KEJGAYKWRDILTF-UHFFFAOYSA-N

Diacetone-D-glucose Toxicity Data With Reference

orl-mus LD50:4 g/kg

ARZNAD Arzneimittel-Forschung. Drug Research. 29 (1979),986.

Diacetone-D-glucose (CAS NO.582-52-5) hasn't been listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65. And the toxicological properties have not been fully investigated. You can see actual entry in RTECS for complete information.

Diacetone-D-glucose Consensus Reports

Reported in EPA TSCA Inventory.

Diacetone-D-glucose Safety Profile

Mildly toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36/37-26
S24/25:Avoid contact with skin and eyes.
S36/37:Wear suitable protective clothing and gloves.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 2
RTECS: LZ4958000
F: 3-10
HS Code: 29329970

Diacetone-D-glucose Specification

Diacetone-D-glucose , its cas register number is 582-52-5. It also can be called 1,2:5,6-Diisopropylidene-D-glucose ; 1,2,5,6-Diisopropylidene-D-glucose ; D-Glucose diacetonide ; and Diacetone glucose . Its classification code is Drug / Therapeutic Agent.
Tri-p-tolyl phosphite (CAS NO.63845-31-8) could be stable under normal temperatures and pressures. It should avoid the condition like incompatible materials. It is not compatible with strong oxidizing agents. And also prevent it to broken down into hazardous decomposition products: carbon monoxide, carbon dioxide. However, its hazardous polymerization has not been reported.

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