Shandong Huashang Chemical Co., Ltd. is a high-tech enterprise specializing in the research and development, manufacturing, and sales of fine chemicals. Headquartered in Jinan, Shandong, China, we are committed to delivering high-quality products to our global partners. Currently, over 90% of our products are exported to developed markets, including North America, Europe, Japan, South Korea, and the Middle East.
Product Description
Diacetone-D-glucose (CAS: 582-52-5), formally 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose, is a D-glucose derivative prepared by condensing D-glucose with acetone. It is a white to light yellow odorless crystalline powder, slightly soluble in water but soluble in most organic solvents. As a key chiral starting material, four of its five hydroxyl groups are protected by isopropylidene groups, leaving a free C-3 hydroxyl group for selective modifications, making it valuable in organic synthesis.
Uses
Organic & Chiral Synthesis: A versatile chiral synthon for enantioselective synthesis, with its free C-3 hydroxyl group enabling oxidation, reduction, alkylation and acylation. It is widely used in asymmetric synthesis of chiral sulfoxides and as a chiral auxiliary.
Pharmaceutical & Biopharmaceutical: An important pharmaceutical intermediate for antiviral, antibacterial and anti-inflammatory drugs, also used in drug modification and quality control reference standards.
Other Uses: A model compound for carbohydrate chemistry research, an analytical standard, and a building block for specialty chemicals, chiral ligands and new materials.
Molecular Formula & Structure
- Molecular Formula: C??H??O?
- Molecular Weight: 260.28 g/mol
- IUPAC Name: 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose
- Synonyms: Diacetone glucose; D-Glucose diisopropylidene acetal;
- EINECS Number: 209-486-0
- Chemical Structure: Furanose ring with two isopropylidene groups protecting 1,2- and 5,6-hydroxyl groups, free C-3 hydroxyl group (SMILES: CC(OC1C(C(C(O1)OC(C)(C)O)OC(C)(C)O)C)(C)).
Physical & Chemical Properties
- Appearance: White to light yellow crystalline powder, odorless, no visible impurities.
- Melting Point: 107–111 °C (lit.)
- Specific Rotation: -11° (c=5, EtOH)
- Solubility: Slightly soluble in water; soluble in ethanol, methanol, acetone; insoluble in non-polar solvents.
- Boiling Point: 362.8 °C (760 mmHg); Flash Point: 173.2 °C (closed cup)
- Stability: Stable under normal dry conditions; incompatible with strong oxidants; avoid light and moisture.
- Toxicity: Low toxicity (LD?? oral, mouse: 4000 mg/kg); irritant (Xi), causes eye/skin/respiratory irritation.
Synthesis & Storage
- Synthesis: Condensation of D-glucose with acetone (acid-catalyzed), purified by recrystallization (yield 70–80%).
- Storage: Sealed, inert atmosphere; -20 °C (long-term), room temperature (short-term); shelf life 2–3 years; avoid oxidants, light, moisture.
- Safety: Ventilated operation; wear protective gear; avoid contact/inhalation; rinse with water if contact occurs.
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