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08012

Supelco

1-Deoxynojirimycin

analytical standard

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C6H13NO4
CAS Number:
19130-96-2
Molecular Weight:
163.17
Beilstein:
3588039
MDL number:
MFCD00063474
UNSPSC Code:
85151701
PubChem Substance ID:
329748539
NACRES:
NA.24

grade

analytical standard

Quality Level

100

Assay

≥95.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

format

neat

SMILES string

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

InChI

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

InChI key

LXBIFEVIBLOUGU-JGWLITMVSA-N

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General description

1-Deoxynojirimycin is a polyhydroxypiperidine alkaloid and glucose analog, that has an -NH group substituting the O atom in the pyranose ring. It shows a significant α-glucosidase inhibitory effect in addition to antioxidant, antimicrobial, antidiabetic, antitumor, and anti-inflammatory behavior. It is commonly found in the roots of mulberry trees.

Application

DNJ may be used as a reference standard for the determination of DNJ in:
  • Mulberry leaves by high-performance liquid chromatography (HPLC) equipped with evaporative light scattering detector (ELSD) as well as direct analysis in real-time (DART) ionization source coupled with triple quadrupole tandem mass spectrometry (MS/MS).
  • Silkworms by hydrophilic interaction chromatography (HILIC) with MS/MS operating on multiple reaction monitoring (MRM) mode.
  • Mulberry leaves of 132 varieties belonging to nine Morus species following its derivatization with fluorenylmethyl chloroformate (FMOC-Cl) by high-performance liquid chromatography (HPLC) combined with photodiode array (PDA) detector
  • Development of an analytical method based on hydrophilic interaction chromatography (HILIC) coupled with tandem mass spectrometry (MS/MS) in positive ion electrospray ionization mode in the leaves of 32 cultivars of different Morus species
  • HPLC method-based separation and quantification in the ethanol extracts of the leaves of Morus alba L. and Morus nigra with fluorimetric detection following pre-column derivatization with 9-fluorenylmethyl chloroformate
  • 146 varieties of mulberry fruits from nine genera by HPLC in combination with UV-Vis dual-wavelength detection
  • Human plasma by hybrid quadrupole/linear ion trap tandem mass spectrometry (QTRAP MS/MS).

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM6090
BCCL9843
BCCJ9283
BCCF9487
BCCD8547

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You-Gui Li et al.
PloS one, 8(6), e65892-e65892 (2013-06-12)
We had previously shown that deoxynojirimycin-polysaccharide mixture (DPM) not only decreased blood glucose but also reversed the damage to pancreatic β-cells in diabetic mice, and that the anti-hyperglycemic efficacy of this combination was better than that of 1-deoxynojirimycin (DNJ) or
Validation of an ion trap tandem mass spectrometric analysis of mulberry 1-deoxynojirimycin in human plasma: application to pharmacokinetic studies
Nakagawa K, et al.
Bioscience, Biotechnology, and Biochemistry, 72(8), 2210-2213 (2008)
Bi-Qing Li et al.
PloS one, 8(6), e65207-e65207 (2013-06-14)
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Alex de la Fuente et al.
Organic letters, 15(14), 3638-3641 (2013-06-27)
A practical synthesis of the previously unreported N-acetyl-D-allosamine glycomimetic DAJNAc is described. The reaction sequence involves Pd-catalyzed allylic substitution by phthalimide in an azaheterobicyclic scaffold as the key step. The new iminosugar resulted in being a stronger β-N-acetylglucosaminidase (human placenta)
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