dextro-fagomine

1,2,5-trideoxy-1,5-imino-D-arabino-hexitol

CAS: 53185-12-9 C6 H13 N O3 MW: 147.17421000 sweet

Identification

Namedextro-fagomine
IUPAC(2R,3R,4R)-2-(hydroxymethyl)piperidine-3,4-diol
CAS Number53185-12-9
FDA UNII1M10C1P4SM
Molecular FormulaC6 H13 N O3
Molecular Weight147.17421000
Nikkaji NumberJ265.072J

Regulatory

Physical Properties

Appearance white crystalline powder (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 315.00 to 316.00 °C. @ 760.00 mm Hg (est)
Flash Point 339.00 °F. TCC ( 170.50 °C. ) (est)
logP (o/w) -0.880 (est)
Soluble in water, 1e+006 mg/L @ 25 °C (est)

Organoleptic Properties

Taste Description slightly sweet

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

Categoryfood additive, dietary supplements
Recommendation for dextro-fagomine usage levels up tonot for fragrance use.
Recommendation for dextro-fagomine flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

buckwheat buckwheat seed mulberry fruit

Synonyms

D- fagomine (2R,3R,4R)-2-( hydroxymethyl)piperidine-3,4-diol 1,2,5- trideoxy-1,5-imino-D-arabino-hexitol 1,2,5- trideoxy-1,5-imino-dextro-arabino-hexitol PubMed: A concise synthesis of N-substituted fagomine derivatives and the systematic exploration of their α-glycosidase inhibition. PubMed: Metabolic effects of mulberry leaves: exploring potential benefits in type 2 diabetes and hyperuricemia. PubMed: Effect of (D)-fagomine on excreted enterobacteria and weight gain in rats fed a high-fat high-sucrose diet. PubMed: Applications and limitations of the I2-mediated carbamate annulation for the synthesis of piperidines: five- versus six-membered ring formation. PubMed: Divergent synthesis of 4-epi-fagomine, 3,4-dihydroxypipecolic acid, and a dihydroxyindolizidine and their β-galactosidase inhibitory and immunomodulatory activities. PubMed: [Synthetic medicinal chemistry of the biomolecular components mimics]. PubMed: The presence of D-fagomine in the human diet from buckwheat-based foodstuffs. PubMed: Synthesis of carbohydrates in a continuous flow reactor by immobilized phosphatase and aldolase. PubMed: Stereoselective synthesis and biological evaluation of D-fagomine, D-3-epi-fagomine and D-3,4-epi-fagomine analogs from D-glyceraldehyde acetonide as a common building block. PubMed: [Study on chemical constituents of Peganum multisectum]. PubMed: Determination of D-fagomine in buckwheat and mulberry by cation exchange HPLC/ESI-Q-MS. PubMed: D-Fagomine lowers postprandial blood glucose and modulates bacterial adhesion. PubMed: Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors. PubMed: [Chemical constituents from root barks of Morus atropurpurea]. PubMed: Synthesis and inhibitory activities of novel C-3 substituted azafagomines: a new type of selective inhibitors of α-L-fucosidases. PubMed: Determination of iminosugars in mulberry leaves and silkworms using hydrophilic interaction chromatography-tandem mass spectrometry. PubMed: Cytotoxicity and enzymatic activity inhibition in cell lines treated with novel iminosugar derivatives. PubMed: Microarray expression profiling of Arabidopsis thaliana L. in response to allelochemicals identified in buckwheat. PubMed: [Alkaloid constituents from silkworm dropping of Bombyx mori]. PubMed: [Chemical constituents from leaves of Morus multicaulis]. PubMed: Fructose-6-phosphate aldolase in organic synthesis: preparation of D-fagomine, N-alkylated derivatives, and preliminary biological assays. PubMed: General synthesis and biological evaluation of alpha-1-C-substituted derivatives of fagomine (2-deoxynojirimycin-alpha-C-glycosides). PubMed: The first synthesis of substituted azepanes mimicking monosaccharides: a new class of potent glycosidase inhibitors. PubMed: Asymmetric synthesis of the four possible fagomine isomers. PubMed: Detection of polyhydroxyalkaloids in Lonchocarpus extracts by GC-MS of acetylated derivatives. PubMed: Iminosugars: potential inhibitors of liver glycogen phosphorylase. PubMed: Processing glucosidase inhibition by 1-azafagomine. PubMed: Polyhydroxylated pyrrolidine and piperidine alkaloids from Adenophora triphylla var. japonica (Campanulaceae). PubMed: Potentiation of glucose-induced insulin secretion by fagomine, a pseudo-sugar isolated from mulberry leaves. PubMed: Antihyperglycemic effects of N-containing sugars from Xanthocercis zambesiaca, Morus bombycis, Aglaonema treubii, and Castanospermum australe in streptozotocin-diabetic mice. PubMed: Specific alpha-galactosidase inhibitors, N-methylcalystegines--structure/activity relationships of calystegines from Lycium chinense. PubMed: Fagomine isomers and glycosides from Xanthocercis zambesiaca. PubMed: Two subsites on the active center of pig kidney trehalase. PubMed: Potentiating effects on pilocarpine-induced saliva secretion, by extracts and N-containing sugars derived from mulberry leaves, in streptozocin-diabetic mice. PubMed: Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases. PubMed: N-containing sugars from Morus alba and their glycosidase inhibitory activities. PubMed: Sugars with nitrogen in the ring isolated from the leaves of Morus bombycis. PubMed: 2-Hydroxymethyl-3,4-dihydroxy-6-methyl-pyrrolidine (6-deoxy-DMDP), an alkaloid beta-mannosidase inhibitor from seeds of Angylocalyx pynaertii. PubMed: Behavioral and electrophysiological study of antifeedant mechanisms associated with polyhydroxy alkaloids. PubMed: Thermospray liquid chromatographic-mass spectrometric analysis of castanospermine-related alkaloids in Castanospermum australe.