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15760

Sigma-Aldrich

D-(−)-Fructose

meets analytical specification of Ph. Eur., BP

Synonym(s):

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/REAXYS Number:
1239004
EC Number:
200-333-3
MDL number:
MFCD00148910
UNSPSC Code:
12352201
PubChem Substance ID:
57647520

form

solid

optical activity

[α]20/D −93.5 to −91.0°, c = 10% in H2O

quality

meets analytical specification of Ph. Eur., BP

impurities

5-hydroxymethylfurfurol and related substances, complies
 acidity or alcalinity, complies
 foreign sugar, complies
 residual solvents, complies
≤0.5% water (Karl Fischer)

ign. residue

≤0.1% (as SO4)

mp

119-122 °C (dec.) (lit.)

cation traces

Ba:, in accordance
Pb: ≤0.5 mg/kg

suitability

in accordance for appearance of solution

application(s)

pharmaceutical (small molecule)

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 was used as a test compound in NMR study for examining the mechanism of dehydration of D-fructose to 5-hydroxymethylfurfural in DMSO at 150°C.[1]

Biochem/physiol Actions

D-(-)-Fructose enhances mood and causes gastrointestinal disturbances in fructose malabsorbers.[2]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SZBB2770V
SZBB0410
SZBA3060
SZBB1680
SZBC0160V

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Ananda S Amarasekara et al.
Carbohydrate research, 343(18), 3021-3024 (2008-10-03)
The anomeric composition of d-fructose in dimethyl sulfoxide changes when the solution is heated from room temperature to 150 degrees C, with a small increase in the alpha-furanose form at the expense of the beta-pyranose tautomer. Additionally, a small amount
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
B P Chumpitazi et al.
Alimentary pharmacology & therapeutics, 42(4), 418-427 (2015-06-25)
A low fermentable oligosaccharides, disaccharides, monosaccharides and polyols (FODMAP) diet can ameliorate symptoms in adult irritable bowel syndrome (IBS) within 48 h. To determine the efficacy of a low FODMAP diet in childhood IBS and whether gut microbial composition and/or metabolic
Souhir Marsit et al.
Molecular biology and evolution, 32(7), 1695-1707 (2015-03-10)
Although an increasing number of horizontal gene transfers have been reported in eukaryotes, experimental evidence for their adaptive value is lacking. Here, we report the recent transfer of a 158-kb genomic region between Torulaspora microellipsoides and Saccharomyces cerevisiae wine yeasts
K Shiraga et al.
Carbohydrate research, 406, 46-54 (2015-02-07)
Terahertz time-domain attenuated total reflection measurements of monosaccharide (glucose and fructose) and disaccharide (sucrose and trehalose) solutions from 0.146 M to 1.462 M were performed to evaluate (1) the hydration state and (2) the destructuring effect of saccharide solutes on
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