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1-deoxynojirimycin
(2R,3R,4R,5S)-2-hydroxymethyl-piperidine-3,4,5-triol

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CAS Number: 19130-96-2Picture of molecule3D/inchi
Other(deleted CASRN):70956-02-4
FDA UNII: FZ56898FLE
Nikkaji Web:J261.805B
Beilstein Number:3588039
MDL:MFCD00063474
XlogP3-AA:-2.30 (est)
Molecular Weight:163.17341000
Formula:C6 H13 N O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
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Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 361.12 °C. @ 760.00 mm Hg (est)
Flash Point: 387.00 °F. TCC ( 197.30 °C. ) (est)
logP (o/w): -1.177 (est)
Soluble in:
 water, 1e+006 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
1-Deoxynojirimycin 98%
BOC Sciences
For experimental / research use only.
1-Deoxynojirimycin
Carbosynth
For experimental / research use only.
1-Deoxynojirimycin
Changsha Organic Herb
Mulberry Leaves Extract 1-DNJ
Glentham Life Sciences
1-Deoxynojirimycin
Santa Cruz Biotechnology
For experimental / research use only.
Deoxynojirimycin
Shaanxi Haokang Bio-technology
1-Deoxynojirimycin (Folium Mori Extract)
Sigma-Aldrich
For experimental / research use only.
1-Deoxynojirimycin analytical standard
 
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:
oral-rat LD50 > 5000 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED
International Journal of Toxicology. Vol. 16(Suppl

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for 1-deoxynojirimycin usage levels up to:
 not for fragrance use.
 
Recommendation for 1-deoxynojirimycin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :29435
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
(2R,3R,4R,5S)-2-(hydroxymethyl)piperidine-3,4,5-triol
Chemidplus:0019130962
RTECS:TN4350300 for cas# 19130-96-2
 
References:
 (2R,3R,4R,5S)-2-(hydroxymethyl)piperidine-3,4,5-triol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):29435
Pubchem (sid):134993236
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (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):C16843
HMDB (The Human Metabolome Database):HMDB35359
FooDB:FDB014031
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
D-5-amino-1,5-dideoxyglucopyranose
1,5-deoxy-1,5-imino-D-mannitol
1-deoxy-nojirimycin
1-deoxymannojirimycin
1,5-dideoxy-1,5-imino-D-glucitol
 duvoglustat
(2R,3R,4R,5S)-2-hydroxymethyl-3,4,5-trihydroxypiperidine
(2R,3R,4R,5S)-2-hydroxymethyl-piperidine-3,4,5-triol
[2R-(2a,3b,4a,5b)]-2-(hydroxymethyl)-3,4,5-piperidinetriol
(2R,3R,4R,5S)-2-(hydroxymethyl)piperidine-3,4,5-triol
 moranoline
3,4,5-piperidinetriol, 2-(hydroxymethyl)-, (2R,3R,4R,5S)-
 

Articles:

PubMed:Central Administration of 1-Deoxynojirimycin Attenuates Hypothalamic Endoplasmic Reticulum Stress and Regulates Food Intake and Body Weight in Mice with High-Fat Diet-Induced Obesity.
PubMed:Intake of mulberry 1-deoxynojirimycin prevents colorectal cancer in mice.
PubMed:Metabolic Effect of 1-Deoxynojirimycin from Mulberry Leaves on db/db Diabetic Mice Using Liquid Chromatography-Mass Spectrometry Based Metabolomics.
PubMed:Fate of d-Fagomine after Oral Administration to Rats.
PubMed:Decreased formation of branched-chain short fatty acids in Bacillus amyloliquefaciens by metabolic engineering.
PubMed:Use of Bacillus amyloliquefaciens HZ-12 for High-Level Production of the Blood Glucose Lowering Compound, 1-Deoxynojirimycin (DNJ), and Nutraceutical Enriched Soybeans via Fermentation.
PubMed:Supplementation of a Fermented Soybean Extract Reduces Body Mass and Prevents Obesity in High Fat Diet-Induced C57BL/6J Obese Mice.
PubMed:A 28-Day Repeated Dose Toxicological Study of an Aqueous Extract of Morus Alba L.
PubMed:Effects of Applied Nitrogen Amounts on the Functional Components of Mulberry (Morus alba L.) Leaves.
PubMed:Concurrent Therapy with a Low-carbohydrate Diet and Miglitol Remarkably Improved the Postprandial Blood Glucose and Insulin Levels in a Patient with Reactive Hypoglycemia due to Late Dumping Syndrome.
PubMed:Prevention Effects and Possible Molecular Mechanism of Mulberry Leaf Extract and its Formulation on Rats with Insulin-Insensitivity.
PubMed:Pressurized liquid extraction of Aglaonema sp. iminosugars: Chemical composition, bioactivity, cell viability and thermal stability.
PubMed:Identification and Determination of the Polyhydroxylated Alkaloids Compounds with α-Glucosidase Inhibitor Activity in Mulberry Leaves of Different Origins.
PubMed:Effect of solar radiation on the functional components of mulberry (Morus alba L.) leaves.
PubMed:Chronic adjunction of 1-deoxynojirimycin protects from age-related behavioral and biochemical changes in the SAMP8 mice.
PubMed:Multiple Comparisons of Glucokinase Activation Mechanisms of Five Mulberry Bioactive Ingredients in Hepatocyte.
PubMed:Mulberry 1-Deoxynojirimycin Inhibits Adipogenesis by Repression of the ERK/PPARγ Signaling Pathway in Porcine Intramuscular Adipocytes.
PubMed:Inhibition of α-glucosidase activity by N-deoxynojirimycin analogs in several insect phloem sap feeders.
PubMed:Miglitol protects against age-dependent weight gain in mice: A potential role of increased UCP1 content in brown adipose tissue.
PubMed:1-deoxynojirimycin isolated from Bacillus subtilis improves hepatic lipid metabolism and mitochondrial function in high-fat-fed mice.
PubMed:Mulberry leaf extract improves postprandial glucose response in prediabetic subjects: a randomized, double-blind placebo-controlled trial.
PubMed:A Comparison of Food-grade Folium mori ( Sāng Yè) Extract and 1-Deoxynojirimycin for Glycemic Control and Renal Function in Streptozotocin-induced Diabetic Rats.
PubMed:Comparative evaluation of polysaccharides isolated from Astragalus, oyster mushroom, and yacon as inhibitors of α-glucosidase.
PubMed:1-Deoxynojirimycin attenuates high glucose-accelerated senescence in human umbilical vein endothelial cells.
PubMed:Evaluation of general toxicity and genotoxicity of the silkworm extract powder.
PubMed:Cotreatment with the α-glucosidase inhibitor miglitol and DPP-4 inhibitor sitagliptin improves glycemic control and reduces the expressions of CVD risk factors in type 2 diabetic Japanese patients.
PubMed:Mulberry 1-deoxynojirimycin pleiotropically inhibits glucose-stimulated vascular smooth muscle cell migration by activation of AMPK/RhoB and down-regulation of FAK.
PubMed:Miglitol prevents diet-induced obesity by stimulating brown adipose tissue and energy expenditure independent of preventing the digestion of carbohydrates.
PubMed:Comparison of inhibitory activities and mechanisms of five mulberry plant bioactive components against α-glucosidase.
PubMed:Studies targeting α-glucosidase inhibition, antiangiogenic effects, and lipid modification regulation: background, evaluation, and challenges in the development of food ingredients for therapeutic purposes.
PubMed:1-Deoxynojirimycin isolated from a Bacillus subtilis stimulates adiponectin and GLUT4 expressions in 3T3-L1 adipocytes.
PubMed:Intake of mulberry 1-deoxynojirimycin prevents diet-induced obesity through increases in adiponectin in mice.
PubMed:Kinetic and thermodynamic analysis of the inhibitory effects of maltose, glucose, and related carbohydrates on wheat β-amylase.
PubMed:A novel gelatin crosslinking method retards release of mulberry 1-deoxynojirimycin providing a prolonged hypoglycaemic effect.
PubMed:Isolation of the putative biosynthetic gene cluster of 1-deoxynojirimycin by Bacillus amyloliquefaciens 140N, its production and application to the fermentation of soybean paste.
PubMed:Production of the α-glycosidase inhibitor 1-deoxynojirimycin from Bacillus species.
PubMed:Dysphagia as a risk factor for mortality in Niemann-Pick disease type C: systematic literature review and evidence from studies with miglustat.
PubMed:Anti-diabetic effect of a traditional Chinese medicine formula.
PubMed:Traditional medicinal herbs and food plants have the potential to inhibit key carbohydrate hydrolyzing enzymes in vitro and reduce postprandial blood glucose peaks in vivo.
PubMed:Effect of environmental conditions on the α-glucosidase inhibitory activity of mulberry leaves.
PubMed:[Report of attendance at the Parseghian Scientific Conference for Niemann-Pick Type C (NP-C) Research, South Bend, Indiana: in search of new therapeutic possibilities for a very rare illness].
PubMed:Miglitol administered before breakfast increased plasma active glucagon-like peptide-1 (GLP-1) levels after lunch in patients with type 2 diabetes treated with sitagliptin.
PubMed:Treatment of genetically obese mice with the iminosugar N-(5-adamantane-1-yl-methoxy-pentyl)-deoxynojirimycin reduces body weight by decreasing food intake and increasing fat oxidation.
PubMed:Effect of mulberry leaf extract with enriched 1-deoxynojirimycin content on postprandial glycemic control in subjects with impaired glucose metabolism.
PubMed:Identification of the genes involved in 1-deoxynojirimycin synthesis in Bacillus subtilis MORI 3K-85.
PubMed:Comparison of 1-deoxynojirimycin and aqueous mulberry leaf extract with emphasis on postprandial hypoglycemic effects: in vivo and in vitro studies.
PubMed:1-Deoxynojirimycin inhibits metastasis of B16F10 melanoma cells by attenuating the activity and expression of matrix metalloproteinases-2 and -9 and altering cell surface glycosylation.
PubMed:Effects of pre-meal versus post-meal administration of miglitol on plasma glucagon-like peptide-1 and glucosedependent insulinotropic polypeptide levels in healthy men.
PubMed:Effects of miglitol, sitagliptin or their combination on plasma glucose, insulin and incretin levels in non-diabetic men.
PubMed:Simple, selective, and rapid quantification of 1-deoxynojirimycin in mulberry leaf products by high-performance anion-exchange chromatography with pulsed amperometric detection.
PubMed:Determination of iminosugars in mulberry leaves and silkworms using hydrophilic interaction chromatography-tandem mass spectrometry.
PubMed:Comparison of absorption of 1-deoxynojirimycin from mulberry water extract in rats.
PubMed:Purification and identification of 1-deoxynojirimycin (DNJ) in okara fermented by Bacillus subtilis B2 from Chinese traditional food (Meitaoza).
PubMed:Optimization of 1-deoxynojirimycin extraction from mulberry leaves by using response surface methodology.
PubMed:Intake of 1-deoxynojirimycin suppresses lipid accumulation through activation of the beta-oxidation system in rat liver.
PubMed:Phytochemical profiles of different mulberry (Morus sp.) species from China.
PubMed:Validation of an ion trap tandem mass spectrometric analysis of mulberry 1-deoxynojirimycin in human plasma: application to pharmacokinetic studies.
PubMed:Antioxidant constituents in the dayflower (Commelina communis L.) and their alpha-glucosidase-inhibitory activity.
PubMed:Antiobesity effects and improvement of insulin sensitivity by 1-deoxynojirimycin in animal models.
PubMed:N-butyldeoxynojirimycin causes weight loss as a result of appetite suppression in lean and obese mice.
PubMed:[In-vitro study of the drug interactions between Miglitol, an alpha-glucosidase inhibitor, and adsorbents].
PubMed:Occurrence of orally administered mulberry 1-deoxynojirimycin in rat plasma.
PubMed:Influence of food intake on the pharmacokinetics of miglustat, an inhibitor of glucosylceramide synthase.
PubMed:Food-grade mulberry powder enriched with 1-deoxynojirimycin suppresses the elevation of postprandial blood glucose in humans.
PubMed:Effects of miglitol, an alpha-glucosidase inhibitor, on glycaemic status and histopathological changes in islets in non-obese, non-insulin-dependent diabetic Goto-Kakizaki rats.
PubMed:The sensitivity of murine spermiogenesis to miglustat is a quantitative trait: a pharmacogenetic study.
PubMed:Binding residues and catalytic domain of soluble Saccharomyces cerevisiae processing alpha-glucosidase I.
PubMed:Inhibitory effects of mulberry leaf extract on postprandial hyperglycemia in normal rats.
PubMed:Determination of 1-deoxynojirimycin in mulberry leaves using hydrophilic interaction chromatography with evaporative light scattering detection.
PubMed:An improved purification procedure for soluble processing alpha-glucosidase I from Saccharomyces cerevisiae overexpressing CWH41.
PubMed:Detailed kinetic analysis of a family 52 glycoside hydrolase: a beta-xylosidase from Geobacillus stearothermophilus.
PubMed:Purification and characterization of vanilla bean (Vanilla planifolia Andrews) beta-D-glucosidase.
PubMed:A novel method for the assay of alpha-glucosidase inhibitory activity using a multi-channel oxygen sensor.
PubMed:The effects of miglitol on glucagon-like peptide-1 secretion and appetite sensations in obese type 2 diabetics.
PubMed:Dose-dependent efficacy of miglitol, an alpha-glucosidase inhibitor, in type 2 diabetic patients on diet alone: results of a 24-week double-blind placebo-controlled study.
PubMed:Alpha-retaining glucosyl transfer catalysed by trehalose phosphorylase from Schizophyllum commune: mechanistic evidence obtained from steady-state kinetic studies with substrate analogues and inhibitors.
PubMed:Polyhydroxylated alkaloids isolated from mulberry trees (Morusalba L.) and silkworms (Bombyx mori L.).
PubMed:Glucosidase inhibitor from Umbilicaria esculenta.
PubMed:Glucose tolerance and insulin resistance in the JCR:LA-corpulent rat: effect of miglitol (Bay m1099).
PubMed:Miglitol (BAY m 1099) treatment of diabetic hypothalamic-dietary obese rats improves islet response to glucose.
PubMed:Advantages of alpha-glucosidase inhibition as monotherapy in elderly type 2 diabetic patients.
PubMed:Effect of miglitol administration to non-insulin-dependent diabetic rats.
PubMed:Differential scanning calorimetric studies on the domain structure of Aspergillus glucoamylase.
PubMed:Effects of Bay m 1099, an α-Glucosidase Inhibitor, on Starch Metabolism in Germinating Wheat Seeds.
PubMed:The effects of the intestinal glucosidase inhibitory BAY M 1099 (miglitol) on glycemic status of obese-diabetic rats.
PubMed:alpha-Glucosidase inhibition by miglitol in NIDDM patients.
PubMed:The effects of low-dose Bay-m-1099 (Miglitol) on serum lipids and liver enzyme activity of obese and obese-diabetic corpulent rats.
PubMed:Inhibition of intestinal alpha-glucosidase and postprandial hyperglycemia by N-substituted moranoline derivatives.
PubMed:The effect of two new alpha-glucosidase inhibitors on metabolic responses to a mixed meal in normal volunteers.
PubMed:Chronic effects of an alpha-glucosidase inhibitor (Bay o 1248) on intestinal disaccharidase activity in normal and diabetic mice.
PubMed:Influence of an absorbable alpha-glucosidase inhibitor (Bay o 1248) on the endocrine and exocrine pancreas of the rat.
PubMed:Effect of the alpha-glucosidase inhibitor Bay-O-1248 on the metabolic response of nondiabetic and diabetic rats to a high-carbohydrate diet.
 
Notes:
an alpha-glucosidase inhibitor with antiviral action. derivatives of deoxynojirimycin may have anti-hiv activity. Alkaloid from Morus spp.
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