D-1,5-anhydrofructose

1,5-anhydro-D-fructose

CAS: 75414-43-6 C6 H10 O5 MW: 162.14170000

Identification

NameD-1,5-anhydrofructose
CAS Number75414-43-6
FDA UNIISearch
Molecular FormulaC6 H10 O5
Molecular Weight162.14170000
Nikkaji NumberJ398.667E

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 ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for D-1,5-anhydrofructose usage levels up tonot for fragrance use.
Recommendation for D-1,5-anhydrofructose flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

morchella vulgaris fruit PMC

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.