CAS 582-52-5 Diacetone-D-glucose (HCID 7067560)

Substructure search Find similar structures

Basic information

CAS: 582-52-5
Standard SMILES: CC1(C)O[C@H]2O[C@H]([C@H]3COC(C)(C)O3)[C@H](O)[C@H]2O1
InChIKey: KEJGAYKWRDILTF-JDDHQFAOSA-N
Molecular formula: C12H20O6
Average molar mass: 260.28 g/mol

Overview

See other relationships...

Names & identifiers

Preferred name: Diacetone-D-glucose
IUPAC: (3aR,5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
English name: Diacetone-D-glucose
Molecular formula: C12H20O6
Molecular weight: 260.28

Names & synonyms

Diacetone-D-glucoseDiacetoneglucose1,2:5,6-Di-O-isopropylidene-alpha-D-glucofuranoseD-Glucose diacetonideDiacetone glucose(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol1,2:5,6-Di-O-isopropylidene-a-D-glucofuranoseGlucose diacetonideGlucose Bisacetonide(3aR,5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol1,2:5,6-Diisopropylidene-D-glucose1,2:5,6-Bis-O-(1-methylethylidene)-a-D-Glucofuranose

Show more names

GLUCOFURANOSE1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose1,2:5,6-DIISOPROPYLENE-ALPHA-D-GLUCOFURANOSE1,2:5,6-O-DI-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSIDE(3aR,3aα,6aα)-5α-[(4R)-2,2-Dimethyl-1,3-dioxolane-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d]-1,3-dioxole-6α-ol

R3P8TN410C14686-89-61:2,5:6-Di-O-isopropylidene-alpha-D-glucofuranose(3aR,5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-6-olMFCD00005544UNII-R3P8TN410CDiacetonglucoseNSC-1223

Properties

Computed structural properties

XLogP: 0
Topological polar surface area: 66.4 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 6
Rotatable bonds: 1
Heavy atoms: 18
Formal charge: 0
Complexity: 341

Physicochemical properties

Melting point: 110 · 110-111 °C(lit.)
alpha: -11 · -11 º (c=5, EtOH)
Boiling point: 323.54 °C · 323.54°C (rough estimate)
Density: 1.1432 · 1.1432 (rough estimate)
refractive index: -18.5 ° · -18.5 ° (C=5, H2O)
storage temp.: -20 °C · Inert atmosphere,Store in freezer, under -20°C
solubility: Chloroform (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)
form: Powder
pka: 13.15 · 13.15±0.60(Predicted)
color: White to yellow
optical activity: 20 · [α]20/D 18°, c = 1% in H2O
Water Solubility: slightly soluble
Merck: 14 · 14,2965
BRN: 84386 · 84386
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/t6-,7+,8-,9-,10-/m1/s1

Safety & regulation

Safety data

F: 3-10
PPE: Eyeshields, Gloves, type N95 (US)
wgk: 2
tsca: TSCA listed
rtecs: LZ4958000
hs_code: 29329970
Toxicity: LD50 oral in mouse: 4gm/kg
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 24/25-36/37-26
Storage Class: 11 - Combustible Solids
Hazard statements: H302
REACH Registrations: Active
Precautionary statements: P280-P305+P351+P338

Chemistry & industry

Applications · 2 items

UsesIt is mainly used in biochemical reaction and used as medicine intermediate. It is used in synthesize for below products: L-gulose;1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose; Alllose; ;1,2:5,6-Double-O-Isopropylidene-3-C-(1-Methoxycarbonyl)Ethide-alfa-D-Furanose) ;1,2:5,6-Di-O-isopropylidene-a-D-ribo-hexofuranose-3-ulose;6-deoxy idose.

Uses1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose is a compound useful in organic synthesis.