D-Fructose

HCID 2723872CAS 30237-26-4

Grundinformationen

Standard-SMILES
OCC1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O
InChIKey
LKDRXBCSQODPBY-VRPWFDPXSA-N
Summenformel
C6H12O6
Durchschnittliche Molmasse
180,16 g/mol
Monoisotopische Masse
180,0633881

Überblick

D-fructopyranose is a fructopyranose having D-configuration. It has a role as a sweetening agent. It is a D-fructose, a fructopyranose and a cyclic hemiketal.

Namen und Bezeichner

Bevorzugter Name
D-Fructose
IUPAC
(3S,4R,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol

Namen und Synonyme

D-fructopyranosefructopyranosed-fructopyranosidefructopyranosideD-FrulevugenD-arabino-Hex-2-ulopyranose(3S,4R,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrolD-Arabino-Hex-2-ulo-PyranoseAdvantose FS 95fructosterillaevosan
Weitere Namen anzeigen
FuructonLevulosaLevulosa IbysLevulosa MeinLevulosa GrifolsLevulosado BraunKrystar 300Levulosa, Apir

Datenbank-Bezeichner

CAS
30237-26-4、57-48-7、6347-01-9、7660-25-5
PubChem CID
2723872
DTXSID
DTXSID201371662
ChEMBL
CHEMBL1232863、CHEMBL2325229
ChEBI
CHEBI:37714
EC Number
200-333-3
Nikkaji
J1.167.127F

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

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Monosaccharides and Derivatives
Cosmetics · 2 Einträge

Cosmetic ingredients (Fructose) -> CIR (Cosmetic Ingredient Review)

Humectant

Pesticides · 2 Einträge

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Approved

OdorODORLESS
TasteSWEET
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT, FORMULATION AID, NUTRITIVE SWEETENER, PROCESSING AID, SOLVENT OR VEHICLE, STABILIZER OR THICKENER, TEXTURIZER -> FDA Substance added to food

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 3 Einträge

This chemical does not meet GHS hazard criteria for 100% (172 of 172) of all reports.

Not Classified

Aggregated GHS information provided per 172 reports by companies from 2 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: D-Fructose

D-Fructose is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of D-Fructose are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Reg. (EU) 2015/1392, Reg. (EU) No 540/2011

Fructose: 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.

D-Fructose: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - D-Fructose: Environment tier I assessment
Fire HazardsCombustible. Finely dispersed particles form explosive mixtures in air.
Hazards SummaryMay cause mechanical irritation; [ICSC] May cause irritation; [Sigma-Aldrich MSDS]
Chemical DangersReacts with strong oxidants. This generates fire and explosion hazard.
Physical DangersDust explosion possible if in powder or granular form, mixed with air.

Sicherheit und Schutzausrüstung

Fire FightingUse water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures · 4 Einträge

Fresh air, rest.

Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth.

Safe StorageSeparated from strong oxidants.
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.

Spillage DisposalPersonal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting.
Eye PreventionWear safety goggles.

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.

Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Signs and Symptoms · 2 Einträge

Cough.

Redness. Pain.

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).

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.

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

V - Various

QV - Various

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.

MeSH Pharmacological ClassificationSubstances that sweeten food, beverages, medications, etc., such as sugar, saccharine or other low-calorie synthetic products. (From Random House Unabridged Dictionary, 2d ed)
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 · 6 Einträge

CIR ingredient: Fructose

Sweetest of the sugars found in fruits and honey; Added to ice cream to prevent sandiness; [Merck Index] Used as a preservative and as an intravenous infusion in parenteral feeding; [ChemIDplus] Used as an additive to food/foodstuffs and in pharmaceuticals; [IUCLID] Used as flavoring agent or adjuvant, formulation aid, nutritive sweetener, processing aid, solvent, stabilizer or thickener, and texturizer for foods; [FDA]

MEDICATION (VET)

MEDICATION

To prevent sandiness in ice cream /D-Fructose/

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

U.S. Imports(1985) 1.95X10+9 g /levulose/
U.S. Production · 5 Einträge

2023: 50,000,000 - <100,000,000 lb

(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/

Consumer UsesSoil amendments (fertilizers)
Industry UsesSoil amendments (fertilizers)
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/

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