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47748

Sigma-Aldrich

D-(−)-Fructose

tested according to Ph. Eur.

Synonym(s):

Laevulosum (Fructosum), D-Levulose, Fruit sugar

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About This Item

Empirical Formula (Hill Notation):
C6H12O6
CAS Number:
57-48-7
Molecular Weight:
180.16
Beilstein:
1239004
EC Number:
200-333-3
MDL number:
MFCD00148910
UNSPSC Code:
12352201
PubChem Substance ID:
329757342
NACRES:
NA.21

Agency

USP/NF
tested according to Ph. Eur.

Quality Level

100

form

solid

impurities

≤0.5% water

color

colorless

useful pH range

5.0-7.0 (25 °C, 18 g/L)

mp

119-122 °C (dec.) (lit.)

solubility

alcohol: soluble 1 gm in 15 ml
methanol: soluble 1 gm in 14 ml
H2O: freely soluble
acetone: freely soluble (Hot)
acetone: slightly soluble
pyridine: soluble

SMILES string

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

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

InChI key

BJHIKXHVCXFQLS-UYFOZJQFSA-N

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Application

D-(−)-Fructose has been used as a test compound for investigating the enzyme that catalyzes the synthesis of activator for phosphofructokinase termed “activation factor” by utilizing ATP and D-fructose-6-P.

Biochem/physiol Actions

D-(−)-Fructose can enhance mood and gastrointestinal disturbances in fructose malabsorbers. It also possess metabolic and endocrine impact that shows that increased consumption of fructose is a contributing factor in the development of obesity and the accompanying metabolic abnormalities observed in the insulin resistance syndrome.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL2196
BCCK0725
BCCJ5434
BCCH6535
BCCH6536

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Sharon S Elliott et al.
The American journal of clinical nutrition, 76(5), 911-922 (2002-10-26)
This review explores whether fructose consumption might be a contributing factor to the development of obesity and the accompanying metabolic abnormalities observed in the insulin resistance syndrome. The per capita disappearance data for fructose from the combined consumption of sucrose
E Furuya et al.
The Journal of biological chemistry, 256(14), 7109-7112 (1981-07-25)
We have recently discovered an activator for phosphofructokinase termed "activation factor" (Furuya, E., and Uyeda, K. (1980) Proc. Natl. Acad. Sci. U. S. A. 77, 5861-5864). In this paper, we investigated the enzyme responsible for its synthesis. We have found
M Ledochowski et al.
Scandinavian journal of gastroenterology, 35(10), 1048-1052 (2000-12-01)
Fructose malabsorption is characterized by the inability to absorb fructose efficiently. As a consequence fructose reaches the colon where it is broken down by bacteria to short fatty acids, CO2 and H2. Bloating, cramps, osmotic diarrhea and other symptoms of
Jérémy Lothier et al.
Planta, 240(3), 629-643 (2014-07-16)
The first 6-fructan exohydrolase (6-FEH) cDNA from Lolium perenne was cloned and characterized. Following defoliation, Lp6 - FEHa transcript level unexpectedly decreased together with an increase in total FEH activity. Lolium perenne is a major forage grass species that accumulates
Carlos A Roncal Jimenez et al.
Kidney international, 86(2), 294-302 (2013-12-18)
The epidemic of chronic kidney disease in Nicaragua (Mesoamerican nephropathy) has been linked with recurrent dehydration. Here we tested whether recurrent dehydration may cause renal injury by activation of the polyol pathway, resulting in the generation of endogenous fructose in
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