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Beta-D-Fructopyranose

HCID 24310
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Grundinformationen

CAS
7660-25-5
Standard-SMILES
OC[C@@]1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O
InChIKey
LKDRXBCSQODPBY-ARQDHWQXSA-N
Summenformel
C6H12O6
Durchschnittliche Molmasse
180,16 g/mol
Monoisotopische Masse
180,0633881

Überblick

Beta-D-fructopyranose is a D-fructopyranose in which the anomeric centre has beta-configuration. It is an enantiomer of a beta-L-fructopyranose.

Namen und Bezeichner

Bevorzugter Name
Beta-D-Fructopyranose
IUPAC
(2R,3S,4R,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol
Englischer Name
beta-D-Fructopyranose
Summenformel
C6H12O6
Molmasse
180.16

Namen und Synonyme

beta-D-Fructopyranose7660-25-5(2R,3S,4R,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrolCHEBI:41005DTXSID0023082RefChem:937010GlyTouCan:G31484IMDTXCID503082G31484IM(2R,3S,4R,5R)-2-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol3oaybeta-fructopyranose
Weitere Namen anzeigen
Fructopyranoseβ-D-FructopyranoseS(-)-FRUCTOSEFrutabsLevungenLaevoralFructosterilFRUCTOSE HPLCFructose powderFructose,HPLC≥96%
MFCD00065409BETA-D-FRUCTOPYRANOSE [HSDB]F0060D85171Fructopyranose, beta-D-BDF|A-D-fructopyranoseHSDB 526

Datenbank-Bezeichner

CAS
7660-25-5
PubChem CID
24310
DTXSID
DTXSID0023082
ChEBI

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-2,8
Polarare Oberfläche (TPSA)
110 Ų
H-Brücken-Donoren
5
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
1
Schwere Atome
12
Formalladung
0
Komplexität
162

Experimentelle und physikochemische Eigenschaften

OdorODORLESS
TasteSWEET
Color/Form · 3 Einträge

CLEAR COLORLESS LIQUID IN WATER

COLORLESS CRYSTALS OR AS A WHITE, CRYSTALLINE OR GRANULAR POWDER

White crystals

Other Experimental Properties · 2 Einträge

Orthorhombic, bisphenodial prisms from alc, dec 103-105 °C. Sweetest of the sugars. Shows mutarotation. Specific optical rotation: -132 deg to -92 deg (c=2) @ 20 °C/D. Rapid and anomalous mutarotation involve pyranose-furanose interconversion. The final mutarotation value is obtained instantly in the presence of hydroxyl ions. pKa= 12.06 @ 18 °C. Freely sol in water. One gram dissolves in 15 ml alc, in 14 ml methanol. Slightly sol in cold, freely in hot acetone; sol in pyridine, ethylamine, methylamine. /D-Fructose/

MP: 103 °C (dec); density: 1.60 @ 20 °C/4 °C /beta-levulose/

Physikochemische Eigenschaften

Schmelzpunkt
103 °C · 103°C
Siedepunkt
232.96 °C · 232.96°C (rough estimate)
Dichte
1.6 · 1.6000

Sicherheit und Regulatorisches

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

Gefahrenhinweise

Regulatory Information · 2 Einträge

Chemical: .beta.-D-Fructopyranose

.beta.-D-Fructopyranose: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationIMAP assessments - .beta.-D-Fructopyranose: Human health tier I assessment

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxikologische Informationen

Interactions · 2 Einträge

IN CONTROLLED STUDY OF PATIENTS WITH ACUTE ALCOHOLIC INTOXICATION, IV INFUSION OF LARGE DOSE...CAUSED SMALL BUT STATISTICALLY SIGNIFICANT INCR IN RATE OF FALL OF BLOOD ETHANOL LEVELS. ... USUAL EXPLANATION FOR THIS EFFECT OF FRUCTOSE... IS ENHANCEMENT OF ACTION OF ALC DEHYDROGENASE BY SUGAR ITSELF OR BY ONE OF ITS METABOLITES.

REDUCTION IN MUTAGENICITY OF CIGARETTE SMOKE BY INTERACTION OF SMOKE CONDENSATES WITH ADDED FRUCTOSE.

Natural Pollution SourcesOccurs in a large number of fruits, honey and as the sole sugar in bull and human semen... /D-Fructose/
Human Toxicity Excerpts · 2 Einträge

INFUSION OF FRUCTOSE HAS BEEN ASSOCIATED WITH INCREASED URIC ACID PRODUCTION & HYPERURICEMIA. IN PATIENTS WITH HEREDITARY FRUCTOSE INTOLERANCE (ALDOLASE DEFICIENCY), FRUCTOSE CAN CAUSE SEVERE REACTIONS (HYPOGLYCEMIA, NAUSEA, VOMITING, TREMORS, COMA, CONVULSIONS).

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 3 Einträge

IN ABSENCE OF GLUCOSE, FRUCTOSE IS PHOSPHORYLATED PERIPHERALLY BY HEXOKINASE TO FRUCTOSE-6-PHOSPHATE, &, ON ACCOUNT OF HIGH KM VALUE FOR FRUCTOSE & LOW KM VALUE FOR GLUCOSE, LATTER IS PREFERENTIALLY PHOSPHORYLATED BY THIS ENZYME IN PERIPHERAL TISSUES.

ORAL FRUCTOSE IS OFTEN CONVERTED TO GLUCOSE IN INTESTINAL MUCOSA OF A NUMBER OF SPECIES, SUCH AS GUINEA PIG, HAMSTER, & DOG. NEWBORN PIGS & YOUNG CALVES UP TO 1 MO OF AGE CANNOT UTILIZE IT. SPECIES...WITH LOW GLUCOSE-6-PHOSPHATE DEHYDROGENASE & RELATED ENZYME DEFICIENCIES MAY HAVE DIFFICULTY IN METABOLIZING IT.

FRUCTOSE IS MORE RAPIDLY METABOLIZED & MORE QUICKLY CONVERTED TO GLYCOGEN THAN IS DEXTROSE, & PRESENCE OF INSULIN IS NOT NECESSARY FOR THIS REACTION TO TAKE PLACE. WHEN...INJECTED LOWER LEVELS OF BLOOD SUGAR & LESS SPILLAGE RESULT THAN WHEN SIMILAR AMT OF DEXTROSE ARE GIVEN @ SAME RATE.

Absorption, Distribution and Excretion · 2 Einträge

TWICE THE CONCN OF FRUCTOSE CAN BE INFUSED AT THE SAME RATE AS DEXTROSE WITH BETTER RETENTION AND LESS DISTURBANCE OF FLUID BALANCE.

...ADVANTAGES OF FRUCTOSE IS ITS RAPID REMOVAL FROM EXTRACELLULAR SPACE, & THEREFORE, URINARY EXCRETION IS MINIMIZED.

Verwendung und Herstellung

Uses · 5 Einträge

MEDICATION (VET)

MEDICATION

To prevent sandiness in ice cream /D-Fructose/

Therap cat: Fluid and nutrient replenisher, and ferric form as hematinic. /D-Fructose/

For more Uses (Complete) data for FRUCTOSE (9 total), please visit the HSDB record page.

U.S. Imports(1985) 1.95X10+9 g /levulose/
U.S. Production · 4 Einträge

(1976) 9X10+11 G (HIGH FRUCTOSE CORN SYRUP-EST

(1980) 2.66X10+12 g /total indust distribution of high-fructose corn syrup/

(1980) 3.20X10+9 g /consumption of crystalline fructose/

World output of fructose syrup (fructose content of total solids >95%) is estimated at 25,000 t/a and of the crystalline product at 35,000 t/a. The market for crystalline fructose is predicted to be 100,000 t/a in the 1990s. /D-Fructose/

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
CHEBI:41005
UNII
R73GS1TJE0
Nikkaji
J53.982A
Brechungsindex
1.617 · 1.6170 (estimate)
storage temp.
2 · Storage temp. 2-8°C
pka
11.52 · 11.52±0.70(Predicted)
Aggregatzustand
Solid
Farbe
White to off-white
InChI
InChI=1/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4-,5+,6-/s3
InChIKey
LKDRXBCSQODPBY-ZSYVZJKANA-N
SMILES
C([C@]1(OC[C@@H](O)[C@@H](O)[C@@H]1O)O)O |&1:1,4,6,8,r|
CAS Datenbank
7660 · 7660-25-5
NIST chemische Informationen
Fructose(7660-25-5)
CAS Number Unlabeled
57 · 57-48-7

IV INFUSION OF FRUCTOSE DEPLETED HEPATIC ATP & TOTAL ADENOSINE PHOSPHATES IN HUMANS, THEREBY INTERFERING WITH VARIOUS ENERGY-DEPENDENT REACTIONS.

Non-Human Toxicity ExcerptsIV INFUSION OF D-FRUCTOSE DEPLETED HEPATIC ATP & TOTAL ADENOSINE PHOSPHATES IN RATS, THEREBY INTERFERING WITH VARIOUS ENERGY-DEPENDENT REACTIONS.

Sicherheitsdaten

Giftige Stoffe Daten
7660-25-5(Hazardous Substances Data)
Methods of Manufacturing · 5 Einträge

ACTION OF IMMOBILIZED GLUCOSE ISOMERASE (DERIVED PRINCPLY FROM STREPTOMYCES SPECIES) ON DEXTROSE (FRUCTOSE AND HIGH FRUCTOSE (42%) CORN SYRUP); HYDROLYSIS OF INULIN (FRUCTOSE); HYDROLYSIS OF BEET SUGAR FOLLOWED BY LIME SEPARATION (FRUCTOSE)

Prepared by adding absolute alc to the syrup obtained from acid hydrolysis of inulin: Bates et al, Natl Bur Std (US), Circ C440, 399 (1942). Prepn from dextrose: Cantor, Hobbs, US patent 2,354,664 (1944 to Corn Prod Refining). From sucrose by enzymatic conversion: Koepsell et al, US patent 2,729,587 (1956 to USA). /D-Fructose/

Hydrolysis of inulin; hydrolysis of beet sugar followed by lime separation; from cornstarch by enzymic or microbial action.

Hydrolysis of sucrose produces a mixture of glucose and fructose, from which fructose can be separated by chromatography. /D-Fructose/

The saccharification of starch produces glucose, which can be isomerized with the aid of the enzyme glucose isomerase ... to "high-fructose corn syrup" HFCS ... . /D-Fructose/

Formulations/Preparations · 5 Einträge

FRUCTOSE INJECTION, NF, IS STERILE SOLN OF FRUCTOSE IN WATER...10% SOLN, PH 3.0-6.0.

DOSAGE FORMS- INJECTION NF: 100 G/1000 ML; FRUCTOSE & SODIUM CHLORIDE INJECTION NF: 100 G (FRUCTOSE) & 9 G (SODIUM CHLORIDE)/1000 ML.

High-fructose corn syrups ... contain 42, 55 or 90% fructose on a dry weight basis

Crystalline fructose is essentially pure

For more Formulations/Preparations (Complete) data for FRUCTOSE (6 total), please visit the HSDB record page.

General Manufacturing Information · 3 Einträge

HOMOGENEITY DETERMINED BY PAPER...& GAS-LIQUID CHROMOTOGRAPHY SYSTEMS...

Fructose is crystallized on a large scale in either of two ways: by cooling an aqueous solution or by inducing precipitation from such a solution by adding organic solvents such as methanol or ethanol. /D-Fructose/

...CAN BE INFUSED IV IN HIGHER (TWICE) CONCN THAN DEXTROSE WITHOUT AS MUCH... PLASMA HYPERTONICITY; ALSO...SMALLER VOL OF WATER INFUSED, WHEN FRUCTOSE IS CONVERTED FROM BLOOD THERE IS LESS RESIDUAL HYDREMIA.

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

6-O-α-D-Glucopyranosyl-D-fructoseSpinosyn ALactuloseFructoseSpinosad D1,2:4,5-DI-O-ISOPROPYLIDENE-BETA-D-FRUCTOPYRANOSE

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