U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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

PubMed

TitleDatePubMed
The riddle of L-glucose pentaacetate insulinotropic action (review).
1998 Oct
An open-label trial of L-glucose as a colon-cleansing agent before colonoscopy.
2003 Jul
Effects of biopretreatment on pyrolysis behaviors of corn stalk by methanogen.
2014 Jul
Pyrolytic characteristics of sweet potato vine.
2015 Sep

Sample Use Guides

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
Name Type Language
LEVOGLUCOSE
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
L-GLUCOSE
Systematic Name English
FM-602
Code English
Levoglucose [WHO-DD]
Common Name English
GLUCOSE, L-
Systematic Name English
(2S,3R,4S,5S)-2,3,4,5,6-PENTAHYDROXYHEXANAL
Systematic Name English
L(-)-GLUCOSE
Common Name English
LEVOGLUCOSE [USAN]
Common Name English
levoglucose [INN]
Common Name English
(3S,4R,5R,6S)-6-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-2,3,4,5-TETRAOL
Systematic Name English
Code System Code Type Description
INN
9353
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
PRIMARY
CHEBI
37626
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
PRIMARY
EVMPD
SUB126925
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
PRIMARY
NCI_THESAURUS
C175113
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
PRIMARY
CAS
41846-87-1
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
ALTERNATIVE
DRUG BANK
DB12970
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
PRIMARY
PUBCHEM
10954115
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
PRIMARY
USAN
XX-45
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
PRIMARY
ECHA (EC/EINECS)
213-068-3
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
PRIMARY
FDA UNII
02833ISA66
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
PRIMARY
CAS
19982-85-5
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
ALTERNATIVE
SMS_ID
300000039636
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
PRIMARY
CAS
921-60-8
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
PRIMARY
WIKIPEDIA
L-GLUCOSE
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID101015237
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
PRIMARY
ChEMBL
CHEMBL1873035
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
PRIMARY
CHEBI
37624
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
PRIMARY
RXCUI
1788981
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
PRIMARY
DAILYMED
02833ISA66
Created by admin on Fri Dec 15 19:47:03 GMT 2023 , Edited by admin on Fri Dec 15 19:47:03 GMT 2023
PRIMARY