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beta-D-fructose

HCID 439709
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Grundinformationen

CAS
470-23-5
Standard-SMILES
OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O
InChIKey
RFSUNEUAIZKAJO-ARQDHWQXSA-N
Summenformel
C6H12O6
Durchschnittliche Molmasse
180,16 g/mol
Monoisotopische Masse
180,0633881

Überblick

Beta-D-fructofuranose is a D-fructofuranose. It has a role as a mouse metabolite. It is an enantiomer of a beta-L-fructofuranose.

Namen und Bezeichner

Bevorzugter Name
beta-D-fructose
IUPAC
(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol
Englischer Name
(2R,3S,4S,5R)-2,5-Bis(hydroxymethyl)-oxolane-2,3,4-triol
Summenformel
C6H12O6
Molmasse
180.16

Namen und Synonyme

beta-D-fructofuranosebeta-Levulosebeta-D-Fructosebeta-Fruit sugar53188-23-1beta-D-Arabino-hexuloseB986VTP17JCHEBI:28645DTXSID60859011RefChem:937011GlyTouCan:G23778LQBETA-D.-FRUCTOFURANOSE
Weitere Namen anzeigen
Lactulose Impurity 31Lactulose Impurity 11Cyanocobalamin Impurity 13 Acetate
DTXCID103081DTXSID20273991G23778LQ470-23-5Fructooligosaccharides(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)tetrahydrofuran-2,3,4-triolb-D-Fructofuranose308066-66-2

Datenbank-Bezeichner

CAS
470-23-5、53188-23-1、57-48-7
PubChem CID
439709
DTXSID
DTXSID60859011
ChEMBL
CHEMBL604608
ChEBI
CHEBI:28645
UNII
B986VTP17J
Nikkaji
J450.088A

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
-2,3
Polarare Oberfläche (TPSA)
110 Ų
H-Brücken-Donoren
5
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
2
Schwere Atome
12
Formalladung
0
Komplexität
162

Experimentelle und physikochemische Eigenschaften

Solubility778 mg/mL at 20 °C
Melting Point119 - 122 °C
Physical DescriptionSolid

Physikochemische Eigenschaften

Siedepunkt
440.1 · 440.1±45.0 °C(Predicted)
Dichte
1.694 · 1.694±0.06 g/cm3(Predicted)
pka
11.42 · 11.42±0.70(Predicted)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Toxikologische Informationen

Health Effects · 1 Eintrag

Acute consumption of fructose or high fructose corn syrup is essentially non-toxic. Chronic, excess fructose consumption has been shown to be a cause (or indirect cause) of gout, insulin resistance, hypertension, obesity, fatty liver disease, elevated LDL cholesterol and elevated triglycerides, leading to metabolic syndrome. In Wistar rats, a laboratory model of diabetes, 10% fructose feeding as opposed to 10% glucose feeding was found to increase blood triglyceride levels by 86%, whereas the same amount of glucose had no effect on triglycerides. A 2008 study found a substantial risk of incident gout associated with the consumption of fructose or fructose-rich foods. It is suspected that the fructose found in soft drinks (e.g., carbonated beverages) and other sweetened drinks is the primary reason for this increased incidence.

Exposure RoutesIngestion
Toxicity Summary · 1 Eintrag

Fructose is distinct from other sugars in its ability to cause intracellular ATP depletion, nucleotide turnover, and the generation of uric acid. Uric acid is generated via fructose due to its rapid phosphorylation (to fructose-1-phosphate) in the liver, leading to a rapid drop in free phosphate and ATP. This drop in ATP leads to the stimulation of adenosine monophosphate (AMP) deaminase which deaminates AMP to produce IMP, which is subsequently converted to uric acid (A15346). Uric acid is normally an anti-oxidant but without sufficient amounts of ascorbic acid (vitamin C) present in the plasma, it functions as a pro-oxidant. Because many soft drinks and foods that are sweetened with high fructose corn syrup do not contain vitamin C, the resulting uric acid can lead to a number of harmful effects, including gout, chronic inflammation, hypertension, increased adiposity, fatty liver disease and obesity (A15346). Many studies have shown that elevated uric acid levels are associated with several metabolic and cardiovascular conditions, including diabetes and coronary artery disease (A15346). Elevated serum uric acid has also been shown to be the most reliable predictor for the development of hypertension and incident renal disease (A15347) as well as fatty liver disease (A15348). Fructose-induced uric acid generation also causes mitochondrial oxidative stress that stimulates fat accumulation independent of excessive caloric intake (A15349). Several studies have demonstrated that oxidative stress is one of the earliest phenomena observed in vascular, renal, liver cells and adipocytes exposed to uric acid (A15347). High fructose consumption is also associated with more severe depletion of liver ATP, which may impair liver "energy balance”. High-fructose beverages have also been shown to lead to lower circulating insulin and leptin levels, and higher ghrelin levels. Since leptin and insulin decrease appetite and ghrelin increases appetite, some researchers suspect that eating large amounts of fructose increases the likelihood of weight gain.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Free fructose is absorbed directly by the intestine. When fructose is consumed in the form of sucrose, it is digested (broken down) and then absorbed as free fructose. Fructose absorption occurs on the mucosal membrane via facilitated transport involving GLUT5 and GLUT2 transport proteins. Fructose is phosphorylated in the liver by fructokinase (Km= 0.5 mM). Fructokinase initially produces fructose 1-phosphate, which is split by aldolase B to produce the trioses dihydroxyacetone phosphate (DHAP) and glyceraldehyde. DHAP is then converted to glycerol-3-phophate which stimulates production of triglycerides. Nearly half (45%) of all pure fructose consumed is used up within 3-6 hours by the body for energy. If fructose is consumed with glucose (as it typically is in nature), up to 66% of it is used for energy within the same time frame. Roughly a third (29%) to a half (54%) of all fructose consumed is converted to glucose. Less than 1% of fructose appears to be directly converted to triglycerides.

Tissue LocationsLiver
Cellular LocationsExtracellular
Metabolite PathwaysAmino Sugar Metabolism

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

Methyl-4-oxovalerat5-(Ethoxymethyl)-2-furaldehyde1,2:4,5-Di-O-isopropylidene-beta-D-fructopyranose5-(Hydroxymethyl)-2-furaldehyd

Zugehörige Reaktionen

3
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 267173
HRID 267173als Produktuspto-grants-1976_03
Reaktionsgleichung von HRID 267174
HRID 267174als Produktuspto-grants-1976_03
Reaktionsgleichung von HRID 444590
HRID 444590als Produktuspto-grants-1981_04

Notizen zur Verbindung

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Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity Data · 1 Eintrag

Consuming more than 100 g a day of pure fructose may lead to a modest but statistically significant rise in body weight of 0.44 kg a week. Consuming 100 g or more of fructose a day also significantly increases fasting levels of serum triglycerides. LD50: 15000 mg/kg (intravenous, rabbit)

Sicherheitsdaten

Alarmwort
Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302