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247898

Sigma-Aldrich

Isosorbide dimethyl ether

98%

Synonym(s):

DMI, Dimethyl isosorbide, 1,4:3,6-Dianhydro-2,5-di-O-methyl-D-glucitol, 1,4:3,6-Dianhydrosorbitol 2,5-dimethyl ether, 2,5-Di-O-methyl-1,4:3,6-dianhydro-D-glucitol

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About This Item

Empirical Formula (Hill Notation):
C8H14O4
CAS Number:
Molecular Weight:
174.19
Beilstein/REAXYS Number:
80854
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

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assay

98%

form

liquid

optical activity

[α]21/D +96.1°, c = 2 in chloroform

refractive index

n20/D 1.461 (lit.)

bp

93-95 °C/0.1 mmHg (lit.)

density

1.15 g/mL at 25 °C (lit.)

SMILES string

CO[C@H]1COC2[C@@H](COC12)OC

InChI

1S/C8H14O4/c1-9-5-3-11-8-6(10-2)4-12-7(5)8/h5-8H,3-4H2,1-2H3/t5-,6+,7-,8-/m1/s1

InChI key

MEJYDZQQVZJMPP-ULAWRXDQSA-N

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Application

Isosorbide dimethyl ether (DMI), a sustainable solvent, is widely used in various cosmetic and pharmaceutical formulations.[1]
General applications:
  • DMI can be used as an alternative green solvent for epoxidation of cyclooctene[2], Baylis–Hillman reaction of isomaltulose-derived aldehydes with α,β-unsaturated ketones[3] and also in solid-phase synthesis.[4]
  • It can be used as a coalescent for water-borne paints, where it acts as a co-solvent during the water loss phase and as a coalescing agent during the film formation.[5]

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

240.8 °F - closed cup

flash_point_c

116 °C - closed cup

ppe

Eyeshields, Gloves


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Adrian P Funke et al.
Pharmaceutical research, 19(5), 661-668 (2002-06-19)
Highly lipophilic basic drugs, the antiestrogens AE 1 (log P = 5.82) and AE 2 (log P = 7.8) shall be delivered transdermally. Transdermal permeation of drugs, enhancers, and solvents from various fluid formulations were characterized by in-vitro permeation studies
Solubilizing and hydrotropic properties of isosorbide monoalkyl-and dimethyl-ethers.
Durand M, et al.
Journal of Surfactants and Detergents, 12(4), 371-378 (2009)
Greener solvents for solid-phase synthesis.
Lawrenson S, et al.
Green Chemistry, 19(4), 952-962 (2017)
Isosorbide mono-and di-alkyl ethers, a new class of sustainable coalescents for water-borne paints.
Durand M, et al.
Progress in Organic Coatings, 69(4), 344-351 (2010)
B W Barry et al.
The Journal of investigative dermatology, 82(1), 49-52 (1984-01-01)
The occluded vasoconstrictor assay was used to assess the effect of penetration enhancers on the topical bioavailability of a representative steroid, betamethasone 17-benzoate, with dimethylisosorbide (DMI) as a reference solvent. In the initial test, only N-methyl-2-pyrrolidone (NMP) increased the steroid

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