Isosorbide

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Isosorbide
Isosorbide.svg
Identifiers
CAS number 652-67-5 N
PubChem 12597
ChemSpider 12077 YesY
KEGG D00347 YesY
ChEMBL CHEMBL1200660 N
Jmol-3D images Image 1
Properties
Molecular formula C6H10O4
Molar mass 146.14 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
Solubility in water in water (>850 g/L), alcohols and ketones
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Isosorbide is a heterocyclic compound that is derived from glucose. Isosorbide and its two isomers, namely isoidide and isomannide, are 1,4:3,6-dianhydrohexitols. It is a white solid that is prepared from the double dehydration of sorbitol. Isosorbide is a non-toxic diol produced from biobased feedstocks, that is biodegradable and thermally stable. It is used in medicine and has been touted as a potential biofeedstock.

Production[edit]

Hydrogenation of glucose gives sorbitol. Isosorbide is obtained by double dehydration of sorbitol:

(CHOH)4(CH2OH)2 → C6H10O2(OH)2 + 2 H2O

An intermediate in the dehydration is the monocycle sorbitan.[1]

Application[edit]

Isosorbide is used as a diuretic used mainly to treat hydrocephalus and is also used to treat glaucoma.[2] Other medications are derived from isosorbide, including isosorbide dinitrate and isosorbide mononitrate, are used to treat angina pectoris. Other isosorbide-based medicines are used as osmotic diuretics and for treatment of esophageal varices. Like other nitric oxide donors (see biological functions of nitric oxide), these drugs lower portal pressure by vasodilation and decreasing cardiac output. Isosorbide dinitrate and hydralazine are the two components of the anti-hypertensive drug isosorbide dinitrate/hydralazine (Bidil).

Isosorbide is also used as a building block for polymers such as polycarbonates or polyesters.[3]

References[edit]

  1. ^ M. Rose, R. Palkovits (2012). "Isosorbide as a Renewable Platform chemical for Versatile Applications—Quo Vadis?". ChemSusChem 5 (1): 167–176. doi:10.1002/cssc.201100580. PMID 22213713. 
  2. ^ PubChem 12597
  3. ^ Bersot J.C. (2011). "Efficiency Increase of Poly (ethylene terephthalate‐co‐isosorbide terephthalate) Synthesis using Bimetallic Catalytic Systems". Macromol. Chem. Phys. 212 (19): 2114–2120. doi:10.1002/macp.201100146.