27299-12-3

Basic information

• Product Name: 1,4-ANHYDRO-D-GLUCITOL
• Synonyms: 1,4-ANHYDRO-D-GLUCITOL;1,4-ANHYDRO-D-SORBITOL;Arlitan;1,4-Sorbitan (300 mg);1,4-Anhydroglucitol
• CAS NO: 27299-12-3
• Molecular Formula: C₆H₁₂O₅
• Molecular Weight: 164.16
• EINECS: 248-391-9
• Product Categories: Carbohydrates & Derivatives
• Mol File: 27299-12-3.mol
• Article Data: 63

Chemical Properties

• Melting Point: 112-113°C
• Boiling Point: 442.547 °C at 760 mmHg
• Flash Point: 221.445 °C
• Appearance: /
• Density: 1.573 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.597
• Storage Temp.: Refrigerator
• PKA: 13.69±0.60(Predicted)
• CAS DataBase Reference: 1,4-ANHYDRO-D-GLUCITOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-ANHYDRO-D-GLUCITOL(27299-12-3)
• EPA Substance Registry System: 1,4-ANHYDRO-D-GLUCITOL(27299-12-3)

Safety Data

• RIDADR: UN 2811 6.1 / PGIII
• Hazardous Substances Data: 27299-12-3(Hazardous Substances Data)

Usage

Description

1,4-Anhydro-D-glucitol, also known as 1,4-dideoxy-1,4-imino-D-arabinitol, is a naturally occurring sugar alcohol derived from D-glucitol. It is a white solid with unique chemical properties that make it a valuable compound in various industries.

Uses

1. Used in Pharmaceutical Industry:
1,4-Anhydro-D-glucitol is used as an intermediate in the synthesis of Prostaglandins, which are a group of naturally occurring lipid compounds that have various important physiological effects, including the regulation of blood flow and inflammation.
2. Used in Chemical Synthesis:
Due to its unique chemical structure, 1,4-Anhydro-D-glucitol can be utilized as a building block in the synthesis of various complex organic compounds, contributing to the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
3. Used in Research and Development:
As a versatile compound with distinct chemical properties, 1,4-Anhydro-D-glucitol can be employed in research and development for the study of carbohydrate chemistry, enzymatic reactions, and the development of new methodologies in organic synthesis.

InChI:InChI=1/C6H12O5/c7-1-3(8)6-5(10)4(9)2-11-6/h3-10H,1-2H2/t3-,4+,5-,6-/m1/s1

Upstream product

• 69-65-8 mannitol 
• 6706-59-8 L-Sorbitol 
• 2296-40-4 1-O-methyl-2,3,4,6-tetra-O-trimethylsilyl-β-D-glucopyranoside 
• 2641-79-4 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 67-56-1 methanol 
• 3615-56-3 D-Sorbose 
• 488-43-7 1-Amino-1-deoxy-D-glucitol 
• 50-70-4 D-sorbitol 
• 4137-33-1 ethyl 1-thio-α-D-glucofuranoside 
• 79875-96-0 (R)-2-(benzyloxy)-1-((2R,3R,4S)-3,4-bis(benzyloxy)tetrahydrofuran-2-yl)ethanol 
• 79875-95-9 2,3,6-tri-O-benzyl-5-O-toluene-p-sulphonyl-1,4-anhydro-D-glucitol 
• 535-94-4 β-D-Glcp-(1->4)-D-glucitol 
• 7664-93-9 sulfuric acid 

Downstream Products

• 53905-78-5 [(2R)-2-acetoxy-2-[(2R,3R,4S)-3,4-diacetoxytetrahydrofuran-2-yl]ethyl] acetate 
• 86319-38-2 O³,O⁵-((Ξ)-benzyliden)-1,4-anhydro-D-glucitol 
• 42776-66-9 O⁶-(toluene-4-sulfonyl)-1,4-anhydro-D-glucitol 
• 39798-50-0 O²,O³,O⁵-tribenzoyl-O⁶-(toluene-4-sulfonyl)-1,4-anhydro-D-glucitol 
• 89064-67-5 tetra-O-methyl-1,4-anhydro-D-glucitol 
• 31880-44-1 2,3,5,6-tetra-O-acetyl-1,4-anhydro-D-glucitol 
• 144522-54-3 1,4-anhydro-2,3,5,6-tetra-O-toluene-p-sulphonyl-D-glucitol 
• 652-67-5 Isosorbide 
• 55730-74-0 1,4-anhydro-5,6-O-isopropylidene-2-O-methanesulfonyl-D-glucitol 
• 55730-75-1 Methanesulfonic acid (2R,3S,4S)-2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methanesulfonyloxy-tetrahydro-furan-3-yl ester 
• 101069-26-5 1,4-anhydro-2-O-tert-butyldiphenylsilyl-5,6-O-isopropylidene-D-glucitol 
• 101069-38-9 [(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-formyl-tetrahydro-furan-3-yl]-acetic acid ethyl ester 
• 101125-99-9 1,4-anhydro-2-O-tert-butyldiphenylsilyl-5,6-O-isopropylidene-D-ribo-3-hexulose 
• 101069-37-8 [(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(1,2-dihydroxy-ethyl)-tetrahydro-furan-3-yl]-acetic acid ethyl ester 

Relevant articles and documents

Sequential dehydration of sorbitol to isosorbide over acidified niobium oxides

Isosorbide is a bio-based functional diol, which is prepared by sequential dehydration of sorbitol and widely used in plasticizers, monomers, solvents or pharmaceuticals. In this study, a variety of acidified Nb2O5catalysts were prepared and used for the sequential dehydration of sorbitol to isosorbide. Acidification can effectively regulate the surface acidity of catalysts, which was measured by pyridine infrared spectroscopy and NH3-TPD analysis. The catalytic performance was related to the surface acidity, including the reaction temperature and the amount of catalysts. After optimization of reaction conditions, the yield of isosorbide reached 84.1% with complete sorbitol conversion during reaction at 150 °C for 3 h over 2 M sulfuric acid modified Nb2O5. Finally, the reaction mechanism regarding the role of Lewis acid sites was discussed. This study is of great significance for further development of an efficient catalytic system for the dehydration of carbohydrates to isosorbide.

Efficient and selective aqueous photocatalytic mono-dehydration of sugar alcohols using functionalized yttrium oxide nanocatalysts

The mono-dehydration of sugar alcohols such as d-sorbitol and d-mannitol generates 1,4-sorbitan and 1,4-mannitan, respectively, which are relevant platform molecules for the synthesis of detergents and pharmaceuticals. Most reported catalytic systems provided access to di-dehydrated products, while mono-dehydration required special efforts, particularly regarding selectivity and reaction temperature. A series of functionalized yttrium oxides were prepared via sol-gel synthesis in this work, which not only showed an interesting micropipe-like morphology, but also contained functional components. These materials were investigated as photocatalysts in the dehydration of d-sorbitol and d-mannitol, exhibiting high selectivity to mono-dehydration. The effects of solvent, temperature and catalyst were fully discussed. A catalytic mechanism was proposed based on the experimental results and calculations.

Direct conversion of cellulose into isosorbide over Ni doped NbOPO4catalysts in water

Isosorbide is a versatile chemical intermediate for the production of a variety of drugs, chemicals, and polymers, and its efficient production from natural cellulose is of great significance. In this study, bifunctional catalysts based on niobium phosphates were prepared by a facile hydrothermal method and used for the direct conversion of cellulose to isosorbide under aqueous conditions. NH3-TPD analysis showed that a high acid content existed on the catalyst surface, and pyridine infrared spectroscopic analysis confirmed the presence of both Lewis acid and Br?nsted acid sites, both of which played an important role in the process of carbohydrate conversion. XRD and H2-TPR characterization determined the composition and the hydrogenation centers of the catalyst. An isosorbide yield of 47% could be obtained at 200 °C for 24 h under 3 MPa H2 pressure. The Ni/NbOPO4 bifunctional catalyst retains most of its activity after five consecutive runs with slightly decreased isosorbide yield of 44%. In addition, a possible reaction mechanism was proposed that the synergistic effect of surface acid sites and hydrogenation sites was favorable to enhancing the cascade dehydration and hydrogenation reactions during the conversion of cellulose to isosorbide. This study provides as an efficient strategy for the development of novel multifunctional heterogeneous catalysts for the one-pot valorisation of cellulose. This journal is