Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C6H12O6 |
Molecular Weight | 180.1559 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO
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
DescriptionSources: http://onlinelibrary.wiley.com/doi/10.1002/14356007.a12_047.pub2/abstract | https://www.ncbi.nlm.nih.gov/pubmed/12399260 | https://www.ncbi.nlm.nih.gov/pubmed/26567197 | https://www.ncbi.nlm.nih.gov/pubmed/26316589 | https://www.ncbi.nlm.nih.gov/pubmed/26856717 | https://www.ncbi.nlm.nih.gov/pubmed/23493541https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.200600356 |
http://onlinelibrary.wiley.com/doi/10.1002/14356007.a12_047.pub2/abstract |
https://www.ncbi.nlm.nih.gov/pubmed/26594441 |
https://books.google.ru/books?id=nZrwBwAAQBAJ&pg=PA59&lpg=PA59&dq=%22l-fructose%22&source=bl&ots=kAl43H3Ini&sig=ACfU3U3RmEF0Y1D8WrnNoe6kJdICbTywoQ&hl=en&sa=X&ved=2ahUKEwih49yMzL7hAhUlyaYKHa2JBNkQ6AEwEXoECDQQAQ#v=onepage&q=%22l-fructose%22%20sweetener&f=false
Sources: http://onlinelibrary.wiley.com/doi/10.1002/14356007.a12_047.pub2/abstract | https://www.ncbi.nlm.nih.gov/pubmed/12399260 | https://www.ncbi.nlm.nih.gov/pubmed/26567197 | https://www.ncbi.nlm.nih.gov/pubmed/26316589 | https://www.ncbi.nlm.nih.gov/pubmed/26856717 | https://www.ncbi.nlm.nih.gov/pubmed/23493541https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.200600356 |
http://onlinelibrary.wiley.com/doi/10.1002/14356007.a12_047.pub2/abstract |
https://www.ncbi.nlm.nih.gov/pubmed/26594441 |
https://books.google.ru/books?id=nZrwBwAAQBAJ&pg=PA59&lpg=PA59&dq=%22l-fructose%22&source=bl&ots=kAl43H3Ini&sig=ACfU3U3RmEF0Y1D8WrnNoe6kJdICbTywoQ&hl=en&sa=X&ved=2ahUKEwih49yMzL7hAhUlyaYKHa2JBNkQ6AEwEXoECDQQAQ#v=onepage&q=%22l-fructose%22%20sweetener&f=false
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.
CNS Activity
Approval Year
PubMed
Title | Date | PubMed |
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Fructose, weight gain, and the insulin resistance syndrome. | 2002 Nov |
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Effects of fructose vs glucose on regional cerebral blood flow in brain regions involved with appetite and reward pathways. | 2013 Jan 2 |
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Challenging the fructose hypothesis: new perspectives on fructose consumption and metabolism. | 2013 Mar 1 |
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Uptake and metabolism of fructose by rat neocortical cells in vivo and by isolated nerve terminals in vitro. | 2015 May |
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Health implications of high-fructose intake and current research. | 2015 Nov |
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Effect of dietary fructose on portal and systemic serum fructose levels in rats and in KHK-/- and GLUT5-/- mice. | 2015 Nov 1 |
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Direct renal effects of a fructose-enriched diet: interaction with high salt intake. | 2015 Nov 1 |
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Role of Dietary Fructose and Hepatic De Novo Lipogenesis in Fatty Liver Disease. | 2016 May |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02590913
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25708447
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.
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