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

Details

Stereochemistry RACEMIC
Molecular Formula C6H12O6
Molecular Weight 180.1561
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FRUCTOSE, DL-

SMILES

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

InChI

InChIKey=BJHIKXHVCXFQLS-UYFOZJQFSA-N
InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5-,6-/m1/s1

HIDE SMILES / InChI

Molecular Formula C6H12O6
Molecular Weight 180.1561
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Fructose, or fruit sugar, is a simple ketonic monosaccharide found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. In nature, fructose is produced as D-enantiomer. D-Fructose is one of the three dietary monosaccharides, along with glucose and galactose, that are absorbed directly into the bloodstream. L-fructose is an enantiomer of D-fructose. L-fructose does not occur naturally and can be produced synthetically from the racemic mixture of D- and L-fructose. L-fructose was investigated as a non-caloric sweetener; however it was detected that digestibility of L-fructose is 10% lower than D-fructose, and L-fructose did not found significant commercial application.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Inactive ingredient
SALLY HANSEN OUCH-RELIEF WAX KIT

Approved Use

For temporary relief of pain and itching associated with minor skin irritations due to hair removal

Launch Date

1.32537595E12
PubMed

PubMed

TitleDatePubMed
Fructose, weight gain, and the insulin resistance syndrome.
2002 Nov
Effects of fructose vs glucose on regional cerebral blood flow in brain regions involved with appetite and reward pathways.
2013 Jan 2
Challenging the fructose hypothesis: new perspectives on fructose consumption and metabolism.
2013 Mar 1
Uptake and metabolism of fructose by rat neocortical cells in vivo and by isolated nerve terminals in vitro.
2015 May
Health implications of high-fructose intake and current research.
2015 Nov
Effect of dietary fructose on portal and systemic serum fructose levels in rats and in KHK-/- and GLUT5-/- mice.
2015 Nov 1
Direct renal effects of a fructose-enriched diet: interaction with high salt intake.
2015 Nov 1
Role of Dietary Fructose and Hepatic De Novo Lipogenesis in Fatty Liver Disease.
2016 May
Patents

Sample Use Guides

Twenty healthy volunteers were randomized into two groups: group A received 300 mL of 22.5% glucose and group B received 300 mL of 22.5% fructose. The solution was consumed after 8 hours of overnight fasting, the repeated with the opposite solution after a 1 week washout period. At each intervention venous blood was collected at 0, 0.5, 1, 2 and 3 hours, ad blood-pressure was recorded at 0, 1, 2, and 3 hours.
Route of Administration: Oral
Nerve terminals were prepared from rat forebrains and purified synaptosomes were exposed to [U14C]fructose or [U14C]glucose for 10 minutes leading to the selective labeling of glutamate over aspartate and GABA, and Alanine. [U-14C]Fructose shoed a preference for labeling glutamate more strongly, and aspartate and GABA less strongly, than did [U-14C]glucose. Thus, the distribution of label between glutamate, aspartate, and GABA was significantly different in synaptosomes exposed to [U-14C]fructose or [U-14C]glucose, as reflected in an aspartate/glutamate labeling ratio of 0.07 and 0.53 and a GABA/glutamate labeling ratio of 0.03 and 0.36 for [U14C]fructose- and [U14C]glucose-exposed synaptosomes respectively. The increased labeling of glutamate indicates increased uptake of fructose into nerve terminals and oxidative fructose metabolism in these structures.
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:40:19 UTC 2021
Edited
by admin
on Sat Jun 26 15:40:19 UTC 2021
Record UNII
02T79V874P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FRUCTOSE, DL-
Systematic Name English
DL-FRUCTOSE [MI]
Common Name English
DL-FRUCTOSE
MI  
Systematic Name English
(+/-)-FRUCTOSE
Systematic Name English
.ALPHA.-ACROSE
Common Name English
METHOSE
Common Name English
ARABINO-2-HEXULOSE
Common Name English
FRUCTOSE, (+/-)-
Systematic Name English
Code System Code Type Description
RXCUI
2374739
Created by admin on Sat Jun 26 15:40:19 UTC 2021 , Edited by admin on Sat Jun 26 15:40:19 UTC 2021
PRIMARY
MERCK INDEX
M5573
Created by admin on Sat Jun 26 15:40:19 UTC 2021 , Edited by admin on Sat Jun 26 15:40:19 UTC 2021
PRIMARY Merck Index
CAS
30237-26-4
Created by admin on Sat Jun 26 15:40:19 UTC 2021 , Edited by admin on Sat Jun 26 15:40:19 UTC 2021
PRIMARY
CAS
6035-50-3
Created by admin on Sat Jun 26 15:40:19 UTC 2021 , Edited by admin on Sat Jun 26 15:40:19 UTC 2021
SUPERSEDED
FDA UNII
02T79V874P
Created by admin on Sat Jun 26 15:40:19 UTC 2021 , Edited by admin on Sat Jun 26 15:40:19 UTC 2021
PRIMARY