Technical Data

B8996-57
CAS Number
141206-42-0
Grade
Highly Purified
Molecular Formula
C₁₀H₂₁NO₄
Molecular Weight
219.28
EU Commodity Code
38220090
Shipping Temp
RT
Storage Temp
-20°C
N-(n-Butyl)deoxygalactonojirimycin
(2R,3S,4R,5S)-1-Butyl-2-(hydroxymethyl)-3,4,5-piperidinetriol; NBDGJ

An extremely potent and selective a-D-galactosidase inhibitor. A selective inhibitior of GlcCer synthesis.

Synonyms
(2R,3S,4R,5S)-1-Butyl-2-(hydroxymethyl)-3,4,5-piperidinetriol; NBDGJ
CAS No
141206-42-0
Molecular Formula
C₁₀H₂₁NO₄
Molecular Weight
219.28
Appearance
White to off-white solid
Purity (HPLC)
≥98%
Proton NMR
Conforms to Structure
Elemental Analysis
%C: 54.08, %H: 9.41, %N: 6.26 Conforms
MS
Conforms to Structure
Specific Rotation
-21.2° (c = 0.2, Water; 4hr)
TLC Conditions
SiO2; Dichloromethane: Methane: Ammonium Hydroxide (20:10:1). Visualized with ninhydrin; single spot (Rf= 0.5).
Melting Point
123-124°C
Solubility
Methanol (Slightly), Water (Slightly)
Storage and Stability
Store at -20°C. Hygroscopic. Under Inert Atmosphere. For maximum recovery of product, centrifuge the original vial prior to removing the cap.

Intended for research use only. Not for use in human, therapeutic, or diagnostic applications.

References
1. Platt, F.M., Neises, G.R., Karlsson, G.B., et al. N-Butyldeoxygalactonojirimycin inhibits glycolipid biosynthesis but does not affect N-linked oligosaccharide processing. J. Biol. Chem 269(43), 27108-27114 (1994).|2. Walden, C.M., Sandhoff, R., Chuang, C.C., et al. Accumulation of glucosylceramide in murine testis, caused by inhibition of β-glucosidase 2: implications for spermatogenesis. J. Biol. Chem. 282(45), 32655-32664 (2007).|3. Ridley, C.M., Thur, K.E., Shanahan, J., et al. β-Glucosidase 2 (GBA2) activity and imino sugar pharmacology. J. Biol. Chem. 288(36), 26052-26066 (2013).|4. Wennekes, T., Meijer, A.J., Groen, A.K., et al. Dual-action lipophilic iminosugar improves glycemic control in obese rodents by reduction of visceral glycosphingolipids and buffering of carbohydrate assimilation. J. Med. Chem. 53(2), 689-698 (2010).|5. Gupta, V., Hild, S.A., Jakkaraj, S.R., et al. N-Butyldeoxygalactonojirimycin induces reversible infertility in male CD rats. Int. J. Mol. Sci. 21(1), (2020).|6. Kasperzyk, J.L., El-Abbadi, M.M., Hauser, E.C., et al. N-butyldeoxygalactonojirimycin reduces neonatal brain ganglioside content in a mouse model of GM1 gangliosidosis. J. Neurochem. 89(3), 645-653 (2004).|7. Andersson et al., 2004. Improved outcome of N-butyldeoxygalactonojirimycin-mediated substrate reduction therapy in a mouse model of Sandhoff disease. Neurobiology of Disease 16(3):506-515.; Kasperzyk et al., 2004. N‐butyldeoxygalactonojirimycin reduces neonatal brain ganglioside content in a mouse model of GM1 gangliosidosis. J Neurochem 89(3):645-53|8. Paulsen, H., et al.: Chem. Ber., 113, 2601 (1980)|9. Daniel, P.F., et al.: Proc. Int. Carbo. Symp., 13th, Ithaca, NY, Abstr. C43 (1986)
USBio References
No references available
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