dextro-fagomine
1,2,5-trideoxy-1,5-imino-D-arabino-hexitol
 
Notes:
Alkaloid from buckwheat seeds (Fagopyrum esculentum)
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(2R,3R,4R)-2-(hydroxymethyl)piperidine-3,4-diol (Click)
CAS Number: 53185-12-9Picture of molecule
FDA UNII: 1M10C1P4SM
Nikkaji Web: J265.072J
XlogP3-AA: -1.40 (est)
Molecular Weight: 147.17421000
Formula: C6 H13 N O3
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: food additive, dietary supplements
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist: Search
Google Patents: Search
US Patents: Search
EU Patents: Search
IBM Patents: Obtain
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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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)
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Organoleptic Properties:
 sweet  
Taste Description:
slightly sweet
  
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Cosmetic Information:
None found
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Suppliers:
Carbosynth
For experimental / research use only.
Fagomine
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: food additive, dietary supplements
Recommendation for dextro-fagomine usage levels up to:
 not for fragrance use.
 
Recommendation for dextro-fagomine flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
ClinicalTrials.gov: search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 72259
National Institute of Allergy and Infectious Diseases: Data
 (2R,3R,4R)-2-(hydroxymethyl)piperidine-3,4-diol
Chemidplus: 0053185129
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References:
 (2R,3R,4R)-2-(hydroxymethyl)piperidine-3,4-diol
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 72259
Pubchem (sid): 135030130
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C10144
HMDB (The Human Metabolome Database): Search
FooDB: FDB011491
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 buckwheat
Search Trop  Picture
 buckwheat seed
Search Trop  Picture
 mulberry fruit
Search Trop  Picture
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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
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Articles:
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.
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