Isosorbide

Base Information

• Chemical Name: Isosorbide
• CAS No.: 652-67-5
• Deprecated CAS: 151380-60-8,152881-21-5,42750-75-4,49871-92-3,50974-60-2,7241-88-5,2088100-88-1,152881-21-5,42750-75-4,49871-92-3,50974-60-2,7241-88-5
• Molecular Formula: C6H10O4
• Molecular Weight: 146.143
• Hs Code.: 2932.99
• European Community (EC) Number: 211-492-3
• NSC Number: 40725
• UNII: WXR179L51S
• DSSTox Substance ID: DTXSID5046196
• Nikkaji Number: J7.077G
• Wikipedia: Isosorbide
• Wikidata: Q1243800
• NCI Thesaurus Code: C60773
• RXCUI: 6057
• Metabolomics Workbench ID: 152377
• ChEMBL ID: CHEMBL1200660
• Mol file: 652-67-5.mol

Synonyms:Dianhydrosorbitol;Isosorbide

Chemical Property of Isosorbide

Chemical Property:

• Appearance/Colour: off-white to light yellow or beige crystal
• Vapor Pressure: 4.71E-07mmHg at 25°C
• Melting Point: 60-63 °C(lit.)
• Refractive Index: 45 ° (C=5, H2O)
• Boiling Point: 372.1 °C at 760 mmHg
• PKA: 13.17±0.40(Predicted)
• Flash Point: 178.8 °C
• PSA: 58.92000
• Density: 1.475 g/cm³
• LogP: -1.49420
• Storage Temp.: Refrigerator
• Sensitive.: Hygroscopic
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Water Solubility.: Soluble in alcohols, water and ketones.
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 146.05790880
• Heavy Atom Count: 10
• Complexity: 122

Purity/Quality:

98% ^*data from raw suppliers

AT 101 ^*data from reagent suppliers

Safty Information:

• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C2C(O1)C(CO2)O)O
• Isomeric SMILES: C1[C@H]([C@@H]2[C@H](O1)[C@H](CO2)O)O
• Recent ClinicalTrials: Chemotherapy AND Bcl-xL Inhibitor (AT-101) For Organ Preservation In Adults With Advanced Laryngeal Cancer
• Recent EU Clinical Trials: Phase I/II Study of Combined Treatment with
• Recent NIPH Clinical Trials: The clinical evaluation of the Kampo therapy for Meniere disease.
• Uses: Isosorbide is a reagent widely used to prepare detergents, cleansers, cosmetics, agrochemicals and vasodilators. pharmaceutical intermediate for dimethyl ether and mono- and dinitrate derivatives; the nitrate esters find use as vasodilators and coronary disease therapeutics. D-Isosorbide is used as a reagent in the preparation of detergents, agrochemicals, cleansers, cosmetics and vasodilators. It is also employed as a pharmaceutical intermediate for dimethyl ether and mono- and dinitrate derivatives, which is used as vasodilators and coronary disease therapeutics. It is used in the treatment of hydrocephalus and glaucoma. It finds application as a building block for polymers like polycarbonates and polyesters.
• Biological Functions: emergency treatment of acute angle-closure glaucoma. It should not be confused with isosorbide dinitrate, an antianginal drug.
• Clinical Use: Isosorbide is basically a bicyclic form of sorbitol that is used orally to cause a reduction in intraocular pressure in glaucoma cases. Although a diuretic effect is noted, its ophthalmologic properties are its primary value.

Technology Process of Isosorbide

There total 104 articles about Isosorbide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

(3S,3aR,6S,6aR)-6-(benzoyloxy)hexahydrofuro[3,2-b]furan-3-yl benzoate (3014-56-0,24332-64-7) → 1,4:3,6-dianhydro-L-iditol (641-74-7,652-67-5,5627-19-0,24332-71-6,28218-68-0,28948-16-5,28980-83-8,89825-36-5,124508-14-1,151380-60-8)

Guidance literature:

With potassium cyanide; sodium methylate; In methanol; at 25 ℃; for 2h;

DOI:10.1016/S0957-4166(02)00411-1

Reference yield: 75.0%

D-sorbitol (50-70-4) → 2,5-anhydro-d-sorbitol (51607-79-5) + Isosorbide (652-67-5) + 1,4-anhydro-D-glucitol (7726-97-8,10334-28-8,20662-31-1,22554-76-3,22554-77-4,22554-79-6,27299-12-3,28218-56-6,32742-35-1,40026-08-2,51196-40-8,51607-77-3,53648-56-9,96243-58-2,124379-08-4,124379-13-1) + 3,6-anhydro-D-glucitol (53648-56-9) + 2,5-anhydro-D-mannitol (41107-82-8)

Guidance literature:

sulfuric acid; In water; at 125 - 145 ℃; under 18 - 20 Torr; Industry scale;

Reference yield: 60.0%

D-sorbitol (50-70-4) + carbonic acid dimethyl ester (616-38-6) → 1,4:3,6-dianhydro-D-mannitol (641-74-7) + 1,4:3,6-dianhydro-L-iditol (641-74-7,652-67-5,5627-19-0,24332-71-6,28218-68-0,28948-16-5,28980-83-8,89825-36-5,124508-14-1,151380-60-8) + isosorbide dimethyl ether (5306-85-4)

Guidance literature:

With triethylamine; In biphenyl; at 90 - 200 ℃; for 48h; under 63756.4 Torr; Reagent/catalyst; Autoclave; Inert atmosphere;

DOI:10.1002/cssc.201601382

upstream raw materials:

D-sorbitol

tetrachloromethane

toluene-4-sulfonic acid

3,6-anhydro-D-glucitol

Downstream raw materials:

di-O-lauroyl-1,4;3,6-dianhydro-D-glucitol

[(3S,3aR,6R,6aR)-6-acetoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] acetate

di-O-trityl-1,4;3,6-dianhydro-D-glucitol

1,4:3,6-dianhydro-2,5-di-O-benzyl-D-glucitol

Refernces

• 1、 Li, Ning,Huber, George W.. "Aqueous-phase hydrodeoxygenation of sorbitol with Pt/SiO2-Al2O3: Identification of reaction intermediates". . p. 48 - 59. Retrieved 2010.
• 2、 Guo, Jiaxing,Huang, Long,Li, Cuiqing,Liu, Shanshan,Song, Yongji,Wang, Xincheng. "Sequential dehydration of sorbitol to isosorbide over acidified niobium oxides". . p. 4226 - 4234. Retrieved 2021/06/30.
• 3、 Cheng, Yu,Fan, Chao,Guo, Lina,Huang, Benhua,Li, Xiaoyong,Luque, Rafael,Ma, Xiaomo,Meng, Xu,Pan, Cheng,Sun, Yang,Yang, Juncheng,Zhang, Junjie,Zhang, Weining,Zheng, Aqun. "Efficient and selective aqueous photocatalytic mono-dehydration of sugar alcohols using functionalized yttrium oxide nanocatalysts". . p. 5333 - 5344. Retrieved 2020/09/17.