4,6-O-Ethylidene-a-D-glucose

Names

[ Name ]:
4,6-O-Ethylidene-a-D-glucose

[Synonym ]:
MFCD00210951
4,6-O-Ethylidene-α-D-glucopyranose
α-D-Glucopyranose, 4,6-O-ethylidene-
4,6-O-Ethylidene-a-D-glucose
4,6-O-Ethylidene-α-D-glucose
(4aR,7R,8R,8aS)-2-Methylhexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triol
(2R,4aR,6S,7R,8R,8aS)-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triol
EINECS 236-496-2

Biological Activity

[Description]:

4,6-O-ethylidene-α-D-glucose (Ethylidene-glucose), a glucose derivative, is a competitive exofacial binding-site inhibitor on glucose transporter 1 (GLUT1) with a Ki of 12 mM for wild-type 2-deoxy-D-glucose transport[1][2][3].

[Related Catalog]:

Research Areas >> Metabolic Disease

[Target]

Human Endogenous Metabolite

[In Vitro]

4,6-O-ethylidene-α-D-glucose (Ethylidene-glucose) shows poor affinity for malarial hexose transporter (PfHT1; Ki>50 mM). 4,6-O-ethylidene-α-D-glucose inhibits wild-type transport with a Ki of approximately 12 mM, but this is increased to greater than 120 mM in the Gln282-Leu mutant[1]. 4,6-O-ethylidene-α-D-glucose inhibits glucose exit competitively but its penetration into human red cells is unaffected by glucose in the medium. The potentiation of the development of FDNB inhibition by sugars in the incubating medium is absent when 4,6-O-ethylidene-α-D-glucose is used and there was a slight protective action. 4,6-O-ethylidene-α-D-glucose penetrates human red cells by simple diffusion supported by its penetration of guinea-pig red cells at similar rates, by the occurrence of osmotic haemolysis in isosmotic solutions which is unaffected by copper ions and by the relatively high ether/water partition of the compound<[3].

[References]

[1]. M Hashiramoto, et al. Site-directed Mutagenesis of GLUT1 in Helix 7 Residue 282 Results in Perturbation of Exofacial Ligand Binding. J Biol Chem. 1992 Sep 5;267(25):17502-7.

[2]. Malay Patra, et al. A Potent Glucose-Platinum Conjugate Exploits Glucose Transporters and Preferentially Accumulates in Cancer Cells. Angew Chem Int Ed Engl. 2016 Feb 12;55(7):2550-4.

[3]. G F Baker, et al. The Permeation of Human Red Cells by 4,6-O-ethylidene- -D-glucopyranose (Ethylidene Glucose). J Physiol. 1973 May;231(1):129-42.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
386.6±42.0 °C at 760 mmHg

[ Melting Point ]:
168-170ºC

[ Molecular Formula ]:
C₈H₁₄O₆

[ Molecular Weight ]:
206.193

[ Flash Point ]:
187.6±27.9 °C

[ Exact Mass ]:
206.079041

[ PSA ]:
88.38000

[ LogP ]:
0.54

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.539

MSDS

Click to get detail MSDS

Safety Information

[ WGK Germany ]:
3

[ HS Code ]:
2932999099

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%