a-Homonojirimycin

Names

[ CAS No. ]:
119557-99-2

[ Name ]:
a-Homonojirimycin

[Synonym ]:
Hnj cpd
3,4,5-Piperidinetriol, 2,6-bis(hydroxymethyl)-, (2α,3α,4β,5α,6β)-
(2r,3r,5s,6r)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol
(2R,3S,4R,5R,6R)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol
MFCD06797112
Homonojirimycin
(2R,3R,4R,5S,6R)-2,6-Bis(hydroxymethyl)piperidine-3,4,5-triol
2,6-Dideoxy-2,6-imino-D-glycero-L-gulo-heptitol
a-Homonojirimycin
α-Homonojirimycin
(2R,3R,4R,5S,6R)-2,6-Bis(hydroxymethyl)-3,4,5-piperidinetriol

Biological Activity

[Description]:

α-Homonojirimycin is a potent α-glucosidase inhibitor[1].

[Related Catalog]:

Research Areas >> Metabolic Disease

[References]

[1]. Geoffrey C. et al. α-Homonojirimycin [2,6-dideoxy-2,6-imino-d-glycero-l-gulo-heptitol] from omphalea diandra L.: isolation and glucosidase inhibtion. 1988, 29(49), 6483-6485.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
432.0±45.0 °C at 760 mmHg

[ Melting Point ]:
207ºC

[ Molecular Formula ]:
C₇H₁₅NO₅

[ Molecular Weight ]:
193.198

[ Flash Point ]:
224.7±19.3 °C

[ Exact Mass ]:
193.095016

[ PSA ]:
113.18000

[ LogP ]:
-2.62

[ Vapour Pressure ]:
0.0±2.3 mmHg at 25°C

[ Index of Refraction ]:
1.583

[ Storage condition ]:
-20°C

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures

Bioorg. Chem. 16 , 7330-7336, (2008)

An amyio-1, 6-glucosidase inhibitor enhanced inhibition of hepatic glucose production in combination with glycogen phosphorylase inhibitor. The inhibitory activity of 1-deoxynojirimycin ( 1) toward hu...

Homonojirimycin analogues and their glucosides from Lobelia sessilifolia and Adenophora spp. (Campanulaceae).

Carbohydr. Res. 323(1-4) , 73-80, (2000)

2,6-Dideoxy-7-O-(beta-D-glucopyranosyl) 2,6-imino-D-glycero-L-gulo- heptitol (7-O-beta-D-glucopyranosyl-alpha-homonojirimycin, 1) was isolated from the 50% methanol extract of the whole plant of Lobel...

Eight stereoisomers of homonojirimycin from D-mannose.

Org. Lett. 14(8) , 2050-3, (2012)

Although there are 32 6-azidoheptitols, there are only 16 homonojirimycin (HNJ) stereoisomers. Two epimeric azidoalditols derived from d-mannose allow the synthesis in water of eight stereoisomers of ...