FComEx: 1,5-Anhydrosorbitol (PC000750)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:29 UTC

Update date

2017-01-19 02:36:35 UTC

FoodComEx ID

PC000750

FoodDB Record

FDB023050

Chemical Information

Name

1,5-Anhydrosorbitol

Description

1,5-Anhydrosorbitol or 1,5-anhydroglucitol (1,5-AG) is a validated marker of short-term glycemic control. This substance is derived mainly from food, is well absorbed in the intestine, and is distributed to all organs and tissues. It is metabolically stable, being excreted in the urine when its level exceeds the renal threshold. It is reabsorbed in the renal tubules, and is competitively inhibited by glucosuria, which leads to a reduction in its level in serum. The correlation between this reduction and the amount of glucose present in urine is so close that 1,5 AG can be used as a sensitive, day-to-day, real-time marker of glycemic control. It provides useful information on current glycemic control and is superior to both hemoglobin A1C and fructosamine in detecting near-normoglycemia. 1,5-AG in human plasma has been proposed for several years as a short-term, retrospective marker of glycaemic control and seems to be the most suitable parameter for monitoring glucose excursions. The decrease in serum 1,5-AG is very sensitive to urinary glucose excretion. It is a metabolically inert polyol that competes with glucose for reabsorption in the kidneys. Otherwise stable levels of 1,5-AG are rapidly depleted as blood glucose levels exceed the renal threshold for glucosuria. 1,5-AG is also more tightly associated with glucose fluctuations and postprandial glucose. (PMID: 18088226, 12166605, 7783360, 8940824) [HMDB]

CAS Number

154-58-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,5-AG	hmdb
1,5-anhydro-D-glucitol	hmdb
1,5-Anhydro-D-sorbitol	hmdb
1,5-Anhydroglucitol	hmdb

Chemical Formula

C6H12O5

IUPAC name

(2R,3S,4R,5S)-2-(hydroxymethyl)oxane-3,4,5-triol

InChI Identifier

InChI=1S/C6H12O5/c7-1-4-6(10)5(9)3(8)2-11-4/h3-10H,1-2H2/t3-,4+,5+,6+/m0/s1

InChI Key

MPCAJMNYNOGXPB-SLPGGIOYSA-N

Isomeric SMILES

OC[C@H]1OC[C@H](O)[C@@H](O)[C@@H]1O

Average Molecular Weight

164.1565

Monoisotopic Molecular Weight

164.068473494

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharides

Alternative Parents