Isosorbide

Isosorbide
Names
Preferred IUPAC name
(3R,3aR,6S,6aR)-Hexahydrofuro[3,2-b]furan-3,6-diol
Other names
D-Isosorbide; 1,4:3,6-Dianhydro-D-sorbitol; 1,4-Dianhydrosorbitol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.010.449
KEGG
UNII
  • InChI=1S/C6H10O4/c7-3-1-9-6-4(8)2-10-5(3)6/h3-8H,1-2H2/t3-,4+,5-,6-/m1/s1 Y
    Key: KLDXJTOLSGUMSJ-JGWLITMVSA-N Y
  • InChI=1/C6H10O4/c7-3-1-9-6-4(8)2-10-5(3)6/h3-8H,1-2H2/t3-,4+,5-,6-/m1/s1
    Key: KLDXJTOLSGUMSJ-JGWLITMVBP
  • O[C@@H]1[C@H]2OC[C@@H](O)[C@H]2OC1
Properties
C6H10O4
Molar mass 146.142 g·mol−1
Appearance Highly hygroscopic white flakes
Density 1.30 at 25 °C
Melting point 62.5 to 63 °C (144.5 to 145.4 °F; 335.6 to 336.1 K)
Boiling point 160 °C (320 °F; 433 K) at 10 mmHg
in water (>850 g/L), alcohols and ketones
Pharmacology
None
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references
Isosorbide
Clinical data
Trade namesIsmotic, Isobide, others
License data
Identifiers
CompTox Dashboard (EPA)
ECHA InfoCard100.010.449

Isosorbide is a bicyclic chemical compound from the group of diols and the oxygen-containing heterocycles, containing two fused furan rings. The starting material for isosorbide is D-sorbitol, which is obtained by catalytic hydrogenation of D-glucose, which is in turn produced by hydrolysis of starch. Isosorbide is discussed as a plant-based platform chemical from which biodegradable derivatives of various functionality can be obtained.

In 2021, it was the 111th most commonly prescribed medication in the United States, with more than 5 million prescriptions.

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