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329207

Sigma-Aldrich

Dianhydro-D-glucitol

98%

Sinónimos:

1,4:3,6-Dianhydro-D-sorbitol, D-Isosorbide

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About This Item

Fórmula empírica (notación de Hill):
C6H10O4
Número de CAS:
652-67-5
Peso molecular:
146.14
Beilstein/REAXYS Number:
80510
EC Number:
211-492-3
MDL number:
MFCD00064827
UNSPSC Code:
12352201
PubChem Substance ID:
24859776
NACRES:
NA.22

assay

98%

form

solid

optical activity

[α]20/D +45.2°, c = 3 in H2O

mp

60-63 °C (lit.)

SMILES string

O[C@H]1CO[C@@H]2[C@H](O)CO[C@H]12

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

InChI key

KLDXJTOLSGUMSJ-JGWLITMVSA-N

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Application

Dianhydro-D-glucitol is a greener ingredient widely used as a monomer and building block for a variety of polymers and functional materials, for medical and pharmaceutical applications. It is also used as a fuel or fuel additive.
Applications include:
  • Preparation of renewable polyesters for coating applications.
  • Synthesis of isosorbide esters such as oligo(isosorbide adipate) (OSA), oligo(isosorbide suberate) (OSS), and isosorbide dihexanoate (SDH) as renewable alternatives to phthalate plasticizers.
  • Synthesis of biodegradable porous polyurethane scaffolds for tissue repair and regeneration.
  • Synthesis of the aspirin prodrug, isosorbide-2,5-diaspirinate (ISDA).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Jonathan Lai et al.
ChemSusChem, 4(8), 1104-1111 (2011-07-19)
The telomerisation of 1,3-butadiene with a Pd/TPPTS catalytic system in water or an organic solvent was used for the synthesis of C8 ethers from isosorbide, an agro-based diol. The use of water/oil biphasic reaction conditions allowed the selective synthesis of
Bleeding from ruptured oesophageal varices: propranolol for primary prevention.
Prescrire international, 21(125), 73-77 (2012-03-21)
Neal T Wasserman et al.
Veterinary ophthalmology, 16(1), 20-24 (2012-04-20)
To evaluate and compare the effects of oral isosorbide and glycerol on intraocular pressure (IOP), serum osmolality (SOSM), and blood glucose (BG) in normal dogs. Ten normal dogs were administered an oral dose of either isosorbide (1.5 g/kg), glycerol (1.5g/kg)
Discovery of a ?true? aspirin prodrug.
Moriarty LM, et al.
Journal of Medicinal Chemistry, 51(24), 7991-7999 (2008)
Xiaoli Wang et al.
Journal of medicinal chemistry, 56(7), 3078-3089 (2013-03-21)
In search of novel anti-ischemic stroke agents with higher potency than a known drug 3-n-butylphthalide (NBP), a series of hybrids ((S)- and (R)-5a-f) from optically active ring-opened NBP derivative and isosorbide were synthesized for evaluating their anti-ischemic stroke activity. Compound
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