1,4:3,6-Dianhydro-D-glucitol

Loss of a second molecule of water occurs on heating (1) (106,107), (2), or (3) (108) with concentrated sulfuric or hydrochloric acid forming 1,4 3,6-dianhydro-D-glucitol (isosorbide) (5). Mannitol and iditol anhydrize under similar conditions to isomannide (6) and isoidide (7), respectively. In (6), both hydroxyl groups are oriented toward each other (endo) ia (7), both are oriented away from each other (exo) and ia isosorbide (5), one hydroxyl is endo and the other exo. XyUtol loses two moles of water to form l,3 2,5-dianhydrox5litol (109). 

Becker and coworkers 17" have shown that orally administered 1,4 3,6-dianhydro-D-glucitol, at doses of 1.5 to 2 g/kg, effectively lessens the intraocular pressure in patients having cataracts, and at doses of 0.5 to 2 g/kg for glaucoma. Only minimal side-effects were noted in two of nineteen patients. 

An analogous mechanism which affords the ion of m/e 86 occurs with 1,4 3,6-dianhydro-D-glucitol. ... 

Glucitol ("sorbitol") is converted at the initial rates of 0,135 x 10"4mol.min g cai.at 493 K and 8,8 x 10 mol.min g cat. at 533 K. The main path is its cyclization into, first, 1,4-anhydro-D-glucitol and then to 1,4-3,6-dianhydro-D-glucitol (isosorbide) (figure 1). Two secondary ways of conversion are observed leading to 2,5-anhydro-L-iditol and 2,5-anhydro-D-mannitol. 

The very interesting properties of 1,4 3,6-dianhydro-D-mannitol (LXIV), 1,4 3,6-dianhydro-D-glucitol (LXV), and 1,4 3,6-dianhydro-L-iditol (LXVI) have not yet been fully e.xplained, but an explanation of most... 

Dianhydro-D-glucitol dinitrate, see Isosorbide dinitrate, 2380 Dianilineoxodiperoxochromimn(Vl), 3523 Dianilinimn dichromate, 3537... 

An aqueous syrup of 1,4 3,6-dianhydro-D glucitol is slowly added to a cooled mixture of HNO3 and H2 4. After standing a few minutes the mixture is poured into cold water and the precipitated product is collected and recrystallized from ethanol. 

Dianhydro-D-glucitol Isosorbide dinitrate DiatrIzoic acid Metrizoic acid Diazomethane Diazepam Epirizoie Methoxsaien Pyrimethamine Dibenzo[a,e] cycioheptadiene Butriptyline... 

The di-O-alkylations of 1,4 3,6-dianhydro-D-glucitol, -mannitol and -iditol were reportedly facile under microwave irradiation in the presence of phase transfer catalysts. Yields in excess of 90% were routinely achieved after a reaction time of only a few minutes, and the method was found to be compatible with a wide range of alkylating agents. ... 

Okada, M., Tsunoda, K., Tachikawa, K. and Aoi, K. (2000) Biodegradable polymers based on renewable resources. IV. Enzymatic degradation of polyesters composed of 1,4 3,6-dianhydro-D-glucitol and aliphatic dicarboxylic acid moieties. Journal of Applied Polymer Science, T1 (2), 338-346. 

DIAN. See Bisphenol A Dianal. See Acrylic resin 1,4 3,6-Dianhydro-2,5-di-0-methyl-D-glucitol. See Dimethyl isosorbide 1,4 3,6-Dianhydro-D-glucitol monolaurate. See Isosorbide laurate (Z)-Dianhydro-D-mannitol, mono-9-octadecenoate Dianhydromannitol monooleate D-Dianhydromannitol monooleate. See Mannide monooleate 1,4 3,6-Dianhydrosorbitol 2,5-dinitrate. See Isosorbide dinitrate 1,2 3,4-Dianhydro-DL-threitol. See DL-Diepoxybutane p,p -Dianiline. See Benzidine 1,4-Dianilinobenzene. See N,N -Diphenyl-p-phenylenediamine... 

CAS 5306-85-4 EINECS/ELINCS 226-159-8 Synonyms 1,4 3,6-Dianhydro-2,5-di-0-methyl-D-glucitol 2,5-Di-o-methyl-1,4 3,6-dianhydro-D-glucitol DMI D-Glucitol, 1,4 3,6-dianhydro-2,5-di-o-methyl Isosorbide dimethyl ether Definition Dimethyl ether of an anhydride of an isomer of sorbitol Empincal C8H14O4... 

CAS 28454-97-9 EINECS/ELINCS 249-032-9 Synonyms 1,4 3,6-Dianhydro-D-glucitol monolaurate... 

With a cold mixture of nitric and sulfuric acids, styracitol gives a crystalline, explosive tetranitrate 99). With the same reagent, 1,4 3,6-dianhydro-D-glucitol and 1,4 3,6-dianhydro-D-mannitol give crystalline dinitrates, whereas 1,4-anhydro-D-glucitol and 1,4-anhydro-D-mannitol yield sirupy products. These anhydride nitrates show depressor action, similar to that of glycerol trinitrate and D-mannitol hexanitrate 100). 

The methyl, ethyl, and butyl ethers of the monoanhydro and dianhydro hexitols may be used as plasticizers 107). The diallyl and dimethallyl ethers of 1,4 3,6-dianhydro-D-glucitol slowly polymerize when in contact with oxygen 108). 

Acylation of 1,4 3,6-dianhydro-D-glucitol with acid anhydride in presence of lead oxide at room temperature gave mainly endo 0-5 ester, whereas using the anhydride alone at 120-140 c gave a mixture... 

Okada M, Tachikawa K, Aoi K (1999) Biodegradable polymers based on renewable resources. IIL copolyesters composed of 1,4 3,6-dianhydro-D-glucitol, l,l-bis(5-carboxy-2-furyl)ethaneand aliphatic dicarboxylic acid units. J Appl Polym Sci 74(14) 3342-3350 Okuda N, Soneura M, Ninomiya K, Katakura Y, Shioya S (2008) Biological detoxification of waste house wood hydrolysate using Ureibacillus thermosphaericus for bioethanol production. J Biosci Bioeng 106(2) 128-133... 

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