D-1,5-anhydrofructose
1,5-anhydro-D-fructose
Identification
| Name | D-1,5-anhydrofructose |
| CAS Number | 75414-43-6 |
| FDA UNII | Search |
| Molecular Formula | C6 H10 O5 |
| Molecular Weight | 162.14170000 |
| Nikkaji Number | J398.667E |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 1.185e+005 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for D-1,5-anhydrofructose usage levels up to | not for fragrance use. |
| Recommendation for D-1,5-anhydrofructose flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
1,5-
anhydro-D-fructose
(4S,5S,6R)-4,5-
dihydroxy-6-(hydroxymethyl)oxan-3-one
D-
fructose, 1:5-anhydro-
PubMed:
Production of 1,5-anhydro-d-fructose by an α-glucosidase belonging to glycoside hydrolase family 31.
PubMed:
The structure of substrate-free 1,5-anhydro-D-fructose reductase from Sinorhizobium meliloti 1021 reveals an open enzyme conformation.
PubMed:
Crystal structure of α-1,4-glucan lyase, a unique glycoside hydrolase family member with a novel catalytic mechanism.
PubMed:
Effect of 1,5-anhydro-D-fructose on the inhibition of adipogenesis in 3T3-L1 adipocytes.
PubMed:
Two structures of a thiazolinyl imine reductase from Yersinia enterocolitica provide insight into catalysis and binding to the nonribosomal peptide synthetase module of HMWP1.
PubMed:
Lyase activity of glycogen synthase: Is an elimination/addition mechanism a possible reaction pathway for retaining glycosyltransferases?
PubMed:
1,5-Anhydro-D-fructose: A natural antibiotic that inhibits the growth of gram-positive bacteria and microbial biofilm formation to prevent nosocomial infection.
PubMed:
Study on administration of 1,5-anhydro-D-fructose in C57BL/6J mice challenged with high-fat diet.
PubMed:
1,5-anhydro-D-fructose and its derivatives: biosynthesis, preparation and potential medical applications.
PubMed:
1,5-Anhydro-D-fructose: biocatalytic and chemical synthetic methods for the preparation, transformation and derivatization.
PubMed:
Attenuation of LPS-induced iNOS expression by 1,5-anhydro-d-fructose.
PubMed:
Synthesis of 4-O-glycosylated 1,5-anhydro-D-fructose and of 1,5-anhydro-D-tagatose from a common intermediate 2,3-O-isopropylidene-D-fructose.
PubMed:
Inhibition spectrum studies of microthecin and other anhydrofructose derivatives using selected strains of Gram-positive and -negative bacteria, yeasts and moulds, and investigation of the cytotoxicity of microthecin to malignant blood cell lines.
PubMed:
1,5-Anhydro-D-fructose attenuates lipopolysaccharide-induced cytokine release via suppression of NF-kappaB p65 phosphorylation.
PubMed:
The anhydrofructose pathway of glycogen catabolism.
PubMed:
Structure of monkey dimeric dihydrodiol dehydrogenase in complex with isoascorbic acid.
PubMed:
Mouse AKR1E1 is an ortholog of pig liver NADPH dependent 1,5-anhydro-D-fructose reductase.
PubMed:
1,5-anhydro-D-fructose from D-fructose.
PubMed:
Crystal structure of NADP(H)-dependent 1,5-anhydro-D-fructose reductase from Sinorhizobium morelense at 2.2 A resolution: construction of a NADH-accepting mutant and its application in rare sugar synthesis.
PubMed:
A cold active (2R,3R)-(-)-di-O-benzoyl-tartrate hydrolyzing esterase from Rhodotorula mucilaginosa.
PubMed:
A new chemical synthesis of Ascopyrone P from 1,5-anhydro-D-fructose.
PubMed:
Synthesis of 1,4-anhydro-D-fructose and 1,4-anhydro-D-tagatose.
PubMed:
Catabolism of 1,5-anhydro-D-fructose in Sinorhizobium morelense S-30.7.5: discovery, characterization, and overexpression of a new 1,5-anhydro-D-fructose reductase and its application in sugar analysis and rare sugar synthesis.
PubMed:
Examination of 1,5-anhydro-D-fructose and the enolone ascopyrone P, metabolites of the anhydrofructose pathway of glycogen and starch degradation, for their possible application in fruits, vegetables, and beverages as antibrowning agents.
PubMed:
A 90-day toxicological evaluation of 1,5-anhydro-d-fructose in Sprague-Dawley rats.
PubMed:
Enzymatic description of the anhydrofructose pathway of glycogen degradation II. Gene identification and characterization of the reactions catalyzed by aldos-2-ulose dehydratase that converts 1,5-anhydro-D-fructose to microthecin with ascopyrone M as the intermediate.
PubMed:
A novel family of glucosyl 1,5-anhydro-d-fructose derivatives synthesised by transglucosylation with dextransucrase from Leuconostoc mesenteroides NRRL B-512F.
PubMed:
Basic toxicology and metabolism studies of 1,5-anhydro-D-fructose using bacteria, cultured mammalian cells, and rodents.
PubMed:
Synthesis and co-polymerization of an unsaturated 1,5-anhydro-D-fructose derivative.
PubMed:
Enzymatic description of the anhydrofructose pathway of glycogen degradation; I. Identification and purification of anhydrofructose dehydratase, ascopyrone tautomerase and alpha-1,4-glucan lyase in the fungus Anthracobia melaloma.
PubMed:
Preparation and reactivity of a novel disaccharide, glucosyl 1,5-anhydro-D-fructose (1,5-anhydro-3-O-alpha-glucopyranosyl-D-fructose).
PubMed:
1,5-Anhydro-D-fructose; a versatile chiral building block: biochemistry and chemistry.
PubMed:
Antioxidant effects of 1,5-anhydro-D-fructose, a new natural sugar, in vitro.
PubMed:
1,5-Anhydro-D-fructose increases glucose tolerance by increasing glucagon-like peptide-1 and insulin in mice.
PubMed:
alpha-1,4-glucan lyases producing 1,5-anhydro-D-fructose from starch and glycogen have sequence similarity to alpha-glucosidases.
PubMed:
A group of alpha-1,4-glucan lyase genes from the fungi Morchella costata, M. vulgaris and Peziza ostracoderma. Cloning, complete sequencing and heterologous expression.
PubMed:
A group of alpha-1,4-glucan lyases and their genes from the red alga Gracilariopsis lemaneiformis: purification, cloning, and heterologous expression.
PubMed:
Analysis of 1,5-anhydro-D-fructose, microthecin, and 4-deoxy-glycero-hexo-2,3-diulose in algae using gas chromatography-mass spectrometry in selected ion monitoring mode.
PubMed:
Purification and some properties of a hepatic NADPH-dependent reductase that specifically acts on 1,5-anhydro-D-fructose.
PubMed:
Efficient purification, characterization and partial amino acid sequencing of two alpha-1,4-glucan lyases from fungi.
PubMed:
NMR of all-carbon-13 sugars: an application in development of an analytical method for a novel natural sugar, 1,5-anhydrofructose.
PubMed:
alpha-1,4-Glucan lyase, a new class of starch/glycogen degrading enzyme. III. Substrate specificity, mode of action, and cleavage mechanism.
PubMed:
Effects of 1,5-anhydro-D-fructose on selected glucose-metabolizing enzymes.
PubMed:
Oxidation of 1,5-anhydro-D-glucitol to 1,5-anhydro-D-fructose catalyzed by an enzyme from bacterial membranes.