Deoxynojirimycin hydrochloride Chemical Properties

Melting point:

195-196°C

storage temp. 

Inert atmosphere,2-8°C

solubility 

Water (Slightly)

form 

Powder

color 

White

Water Solubility 

Soluble in water at 20mg/ml

BRN 

3563225

Stability:

Hygroscopic

InChI

InChI=1/C6H13NO4.ClH/c8-2-3-5(10)6(11)4(9)1-7-3;/h3-11H,1-2H2;1H/t3-,4+,5-,6-;/s3

InChIKey

ZJIHMALTJRDNQI-KOVNLEGCNA-N

SMILES

C([C@H]1NC[C@@H]([C@H]([C@@H]1O)O)O)O.Cl |&1:1,4,5,6,r|

CAS DataBase Reference

73285-50-4

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

26-36-24/25-22

WGK Germany 

3

F 

10

MSDS

• Language:English Provider:SigmaAldrich

Deoxynojirimycin hydrochloride Usage And Synthesis

Description

1-Deoxynojirimycin (1-DNJ) is an iminosugar that has been found in M. alba (mulberry) leaves and has diverse biological activities. It inhibits the activities of α- and β-glucosidase (IC₅₀s = 35 and 71 μM, respectively). 1-DNJ (5 mM) reduces the formation of N-linked complex oligosaccharides in IEC-6 cells. It inhibits HIV-1 envelope-mediated membrane fusion in CEM cells when used at a concentration of 2 mM. 1-DNJ (1-100 μg/ml) reduces the invasion and migration of B16/F10 mouse melanoma cells. It improves glucose and insulin tolerance in db/db mice when administered intravenously at doses ranging from 20 to 80 mg/kg per day for four weeks.

Chemical Properties

White Crystalline Solid

Uses

natural chitin synthase inhibitor

General Description

Specific glucosidase inhibitor, including trimming glucosidases I and II, that sequentially removes the three glucose residues from precursor Glc₃Man₉GlcNAc₂ in N-linked glycan biosynthesis.

Biochem/physiol Actions

Product does not compete with ATP.

References

[1] KUO GAO. 1-Deoxynojirimycin: Occurrence, Extraction, Chemistry, Oral Pharmacokinetics, Biological Activities and In Silico Target Fishing.[J]. Molecules, 2016, 21 1. DOI: 10.3390/molecules21111600
[2] ANA I AHUJA-CASARíN. Tuning the activity of iminosugars: novel N-alkylated deoxynojirimycin derivatives as strong BuChE inhibitors.[J]. Journal of Enzyme Inhibition and Medicinal Chemistry, 2021: 138-146. DOI: 10.1080/14756366.2020.1847101
[3] JULIAN A. CODELLI. Second-Generation Difluorinated Cyclooctynes for Copper-Free Click Chemistry[J]. Journal of the American Chemical Society, 2008, 130 34: 11486-11493. DOI: 10.1021/ja803086r
[4] MARIE-JEANNE PAPANDRéOU. The alpha-glucosidase inhibitor 1-deoxynojirimycin blocks human immunodeficiency virus envelope glycoprotein-mediated membrane fusion at the CXCR4 binding step.[J]. Molecular Pharmacology, 2002, 61 1 1: 186-193. DOI: 10.1124/mol.61.1.186
[5] RAN-JUH WANG  Miao L H  Chun Hung Yang. 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[J]. Journal of Agricultural and Food Chemistry, 2010, 58 16: 8988-8993. DOI: 10.1021/jf101401b
[6] QINGPU LIU. 1-Deoxynojirimycin Alleviates Insulin Resistance via Activation of Insulin Signaling PI3K/AKT Pathway in Skeletal Muscle of db/db Mice.[J]. Molecules, 2015, 20 1: 21700-21714. DOI: 10.3390/molecules201219794

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