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- Isosaccharinic_acid abstract "Isosaccharinic acid (ISA) is a six-carbon sugar acid which is formed by the action of calcium hydroxide on lactose and other carbohydrates. It is of interest because it may form in intermediate-level nuclear waste stores when cellulose is degraded by the calcium hydroxide in cements such as Portland cement. The calcium salt of the alpha form of ISA is very crystalline and quite insoluble in cold water, but in hot water it is soluble. ISA is thought to form by means of a series of reactions in which calcium ions acting as lewis acids catalyze two of the three steps. The first step is likely to be a rearrangement of the reducing sugar end of the cellulose (or lactose) into a keto sugar, the second step is likely to be a reaction similar to the base catylised dehydration which oftein occurs after an aldol reaction. In this second step an alkoxide (derived from a sugar) takes the role of the hydroxide leaving group, this second step is not likely to require the lewis acidity of the calcium. The final step is a benzilic acid rearrangement from a 1,2-diketone (1,5,6-trihydroxyhexane-2,3-dione) which is formed from the carbohydrate.4Under acidic conditions sugars tend to form furans such as furfural and 5-hydroxymethylfurfural by a series of dehydrations of the carbohydrate.In acidic solutions the acid tends to form a 5-membered ring (lactone) by forming an ester between the carboxylic acid group and one of the alcohols. When treated with under anhydrous conditions with acetone, an acid and a dehydration agent two of the alcohol groups can be protected as a cyclic acetone acetal thus leaving behind only one alcohol,2 prolonged treatment with 2,2-dimethoxypropane forms a protected form of ISA where all four of the alcohol groups are protected as acetone acetals and the carboxylic acid is in the form of the methyl ester.3 These protected forms of ISA have been used as a starting material for chiral organic compounds anthracyclines.2".
- Isosaccharinic_acid iupacName "(2S,4S)-2,4,5-Trihydroxy-2-(hydroxymethyl)pentanoic acid".
- Isosaccharinic_acid thumbnail Isosaccharinic_acid.png?width=300.
- Isosaccharinic_acid wikiPageExternalLink WR2006-06web.pdf.
- Isosaccharinic_acid wikiPageID "24389962".
- Isosaccharinic_acid wikiPageLength "4540".
- Isosaccharinic_acid wikiPageOutDegree "29".
- Isosaccharinic_acid wikiPageRevisionID "636302771".
- Isosaccharinic_acid wikiPageWikiLink 2,2-Dimethoxypropane.
- Isosaccharinic_acid wikiPageWikiLink 2,2-dimethoxypropane.
- Isosaccharinic_acid wikiPageWikiLink Acetone.
- Isosaccharinic_acid wikiPageWikiLink Acetone_acetal.
- Isosaccharinic_acid wikiPageWikiLink Acid.
- Isosaccharinic_acid wikiPageWikiLink Aldol.
- Isosaccharinic_acid wikiPageWikiLink Anthracycline.
- Isosaccharinic_acid wikiPageWikiLink Anthracyclines.
- Isosaccharinic_acid wikiPageWikiLink Benzilic_acid_rearrangement.
- Isosaccharinic_acid wikiPageWikiLink Calcium.
- Isosaccharinic_acid wikiPageWikiLink Calcium_hydroxide.
- Isosaccharinic_acid wikiPageWikiLink Carbohydrate.
- Isosaccharinic_acid wikiPageWikiLink Carboxylic_acid.
- Isosaccharinic_acid wikiPageWikiLink Category:Sugar_acids.
- Isosaccharinic_acid wikiPageWikiLink Cellulose.
- Isosaccharinic_acid wikiPageWikiLink Cement.
- Isosaccharinic_acid wikiPageWikiLink Dehydration.
- Isosaccharinic_acid wikiPageWikiLink Diketone.
- Isosaccharinic_acid wikiPageWikiLink Ester.
- Isosaccharinic_acid wikiPageWikiLink Furan.
- Isosaccharinic_acid wikiPageWikiLink Furans.
- Isosaccharinic_acid wikiPageWikiLink Furfural.
- Isosaccharinic_acid wikiPageWikiLink Hydroxide.
- Isosaccharinic_acid wikiPageWikiLink Lactone.
- Isosaccharinic_acid wikiPageWikiLink Lactose.
- Isosaccharinic_acid wikiPageWikiLink Leaving_group.
- Isosaccharinic_acid wikiPageWikiLink Lewis_acid.
- Isosaccharinic_acid wikiPageWikiLink Lewis_acids_and_bases.
- Isosaccharinic_acid wikiPageWikiLink Nuclear_waste.
- Isosaccharinic_acid wikiPageWikiLink Portland_cement.
- Isosaccharinic_acid wikiPageWikiLink Radioactive_waste.
- Isosaccharinic_acid wikiPageWikiLink Salt_(chemistry).
- Isosaccharinic_acid wikiPageWikiLink Sugar_acid.
- Isosaccharinic_acid wikiPageWikiLinkText "Isosaccharinic acid".
- Isosaccharinic_acid hasPhotoCollection Isosaccharinic_acid.
- Isosaccharinic_acid imagefile "Isosaccharinic acid.png".
- Isosaccharinic_acid iupacname "-245".
- Isosaccharinic_acid othernames "3".
- Isosaccharinic_acid verifiedfields "changed".
- Isosaccharinic_acid verifiedrevid "419309036".
- Isosaccharinic_acid watchedfields "changed".
- Isosaccharinic_acid wikiPageUsesTemplate Template:Chembox.
- Isosaccharinic_acid wikiPageUsesTemplate Template:Reflist.
- Isosaccharinic_acid subject Category:Sugar_acids.
- Isosaccharinic_acid hypernym Acid.
- Isosaccharinic_acid type Article.
- Isosaccharinic_acid type ChemicalCompound.
- Isosaccharinic_acid type ChemicalSubstance.
- Isosaccharinic_acid type Article.
- Isosaccharinic_acid type Carbohydrate.
- Isosaccharinic_acid type Chemical.
- Isosaccharinic_acid type ChemicalObject.
- Isosaccharinic_acid type Thing.
- Isosaccharinic_acid type Q11173.
- Isosaccharinic_acid comment "Isosaccharinic acid (ISA) is a six-carbon sugar acid which is formed by the action of calcium hydroxide on lactose and other carbohydrates. It is of interest because it may form in intermediate-level nuclear waste stores when cellulose is degraded by the calcium hydroxide in cements such as Portland cement. The calcium salt of the alpha form of ISA is very crystalline and quite insoluble in cold water, but in hot water it is soluble.".
- Isosaccharinic_acid label "Isosaccharinic acid".
- Isosaccharinic_acid sameAs m.07s3_q5.
- Isosaccharinic_acid sameAs Izosaharinska_kiselina.
- Isosaccharinic_acid sameAs Izosaharinska_kiselina.
- Isosaccharinic_acid sameAs Q6086309.
- Isosaccharinic_acid sameAs Q6086309.
- Isosaccharinic_acid wasDerivedFrom Isosaccharinic_acid?oldid=636302771.
- Isosaccharinic_acid depiction Isosaccharinic_acid.png.
- Isosaccharinic_acid isPrimaryTopicOf Isosaccharinic_acid.