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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H12O6
Molecular Weight 180.1559
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOGLUCOSE

SMILES

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

InChI

InChIKey=GZCGUPFRVQAUEE-VANKVMQKSA-N
InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4+,5+,6+/m1/s1

HIDE SMILES / InChI

Molecular Formula C6H12O6
Molecular Weight 180.1559
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Levoglucose (L-glucose) is the stereoisomer of D-glucose. L-Glucose does not occur naturally in higher living organisms, but can be synthesized in the laboratory. L-Glucose is indistinguishable in taste from D-glucose, but cannot be used by living organisms as source of energy because it cannot be phosphorylated by hexokinase, the first enzyme in the glycolysis pathway. Levoglucose may be used as diagnostic aid. It has been investigated as a non-nutritive food sweetener. However, L-glucose produced significant laxation, with an average of 4 to 5 loose watery stools in a 24-hour period. This laxative property clearly reduced the use of L-glucose as a food additive. The mechanism of laxation after L-glucose ingestion is unknown, but malabsorption of the compound with secondary osmotic diarrhea is likely. L-glucose is a well-tolerated, safe, and efficacious means of cleansing the colon for colonoscopy. The L-glucose pentaacetate anomers could be used as novel insulinotropic tools in the treatment of non-insulin-dependent diabetes mellitus.

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
The 24-g packet of L-glucose was dissolved in 8 ounces (240 mL) of water and consumed over 10 minutes or less.
Route of Administration: Oral
Substance Class Chemical
Record UNII
02833ISA66
Record Status Validated (UNII)
Record Version