Isosorbide

Isosorbide

Names
Other names D-Isosorbide; 1,4:3,6-Dianhydro-D-sorbitol; 1,4-Dianhydrosorbitol
Identifiers
CAS Number	652-67-5
ChEMBL	ChEMBL1200660
ChemSpider	12077
Jmol 3D model	Interactive image
KEGG	D00347
PubChem	12597
UNII	WXR179L51S
InChI 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 Key: KLDXJTOLSGUMSJ-JGWLITMVSA-N 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
SMILES O[C@@H]1[C@H]2OC[C@@H](O)[C@H]2OC1
Properties
Chemical 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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

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

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 bio based polymers such as polyesters.^[3]

References

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. CID 12597 from PubChem
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.