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D9305

Sigma-Aldrich

1-Deoxynojirimycin hydrochloride

Synonym(s):

1,5-Dideoxy-1,5-imino-D-sorbitol hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C6H13NO4 · HCl
CAS Number:
73285-50-4
Molecular Weight:
199.63
Beilstein:
3563225
MDL number:
MFCD00133247
UNSPSC Code:
12352201
PubChem Substance ID:
24278397
NACRES:
NA.32

Assay

≥98% (TLC)

Quality Level

200

form

powder

solubility

water: 19.60-20.40 mg/mL, clear, colorless

antibiotic activity spectrum

viruses

Mode of action

enzyme | inhibits

storage temp.

2-8°C

SMILES string

Cl[H].OC[C@H]1NC[C@H](O)[C@@H](O)[C@@H]1O

InChI

1S/C6H13NO4.ClH/c8-2-3-5(10)6(11)4(9)1-7-3;/h3-11H,1-2H2;1H/t3-,4+,5-,6-;/m1./s1

InChI key

ZJIHMALTJRDNQI-VFQQELCFSA-N

Gene Information

human ... GAA(2548)

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General description

Chemical structure: glucosamine

Application

1-Deoxynojirimycin hydrochloride has been used
  • to study its effects on the loss-of-function of N-glycosylation pathway on hair cell regeneration
  • as an endoplasmic reticulum (ER) α-glucosidase I and II inhibitor to study its effects on TMED3-cystic fibrosis transmembrane conductance regulator (CFTR) interaction
  • as an insect trehalase inhibitor in TREH inhibition bioassay

Biochem/physiol Actions

1-Deoxynojirimycin (DNJ) is a naturally occurring alkaloid azasugar or iminosugar. It is observed in mulberry leaves, Commelina communis, and bacterial strains including Bacillus and Streptomyces species. DNJ acts as an α-glucosidase inhibitor and exhibits anti-viral anti-diabetic, anti-inflammatory, anti-obesity, and antioxidant properties.
α-Glucosidase inhibitor

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Stephen G Davies et al.
Organic letters, 15(8), 2042-2045 (2013-04-11)
The asymmetric syntheses of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin are described herein. The ring-closing iodoamination of two epimeric bishomoallylic amines to give the corresponding 5-iodomethylpyrrolidines was followed by in situ ring-expansion to give two diastereoisomerically pure (>99:1 dr) cyclic carbonates. Subsequent deprotection
Chaluntorn Vichasilp et al.
Food chemistry, 134(4), 1823-1830 (2013-02-28)
Mulberry 1-deoxynojirimycin (DNJ), a potent α-glycosidase inhibitor, has therapeutic potency in the suppression of postprandial blood glucose levels thereby possibly preventing diabetes mellitus. However, DNJ has a relatively short half-life in vivo (about 2 h). Therefore, several doses of mulberry
Mark Walterfang et al.
Orphanet journal of rare diseases, 7, 76-76 (2012-10-09)
Niemann-Pick disease type C (NP-C) is a rare neurovisceral disease characterised by progressive neurological deterioration and premature death, and has an estimated birth incidence of 1:120,000. Mutations in the NPC1 gene (in 95% of cases) and the NPC2 gene (in
I Neverova et al.
Analytical biochemistry, 222(1), 190-195 (1994-10-01)
A spectrophotometric assay for glucosidase I using the synthetic trisaccharide alpha-D-Glc 1-->2 alpha-D-Glc 1-->3 alpha-D-Glc-O(CH2)8COOCH3 is reported. The terminal glucose is released from the substrate by the enzyme and quantitated using glucose oxidase, peroxidase, and o-dianisidine. The trisaccharide is specific
Hee-Woong Kim et al.
Microorganisms, 11(6) (2023-06-28)
This study examines the possibility of directly producing and utilizing useful substances in the intestines of animals using anaerobic bacteria that can grow in the intestines of animals. A facultative anaerobe producing a large amount of α-glucosidase inhibitor was isolated
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