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

Modify Date: 2024-01-05 19:24:44

4,6-O-Ethylidene-a-D-glucose Structure
4,6-O-Ethylidene-a-D-glucose structure
Common Name 4,6-O-Ethylidene-a-D-glucose
CAS Number 13224-99-2 Molecular Weight 206.193
Density 1.4±0.1 g/cm3 Boiling Point 386.6±42.0 °C at 760 mmHg
Molecular Formula C8H14O6 Melting Point 168-170ºC
MSDS N/A Flash Point 187.6±27.9 °C

 Use of 4,6-O-Ethylidene-a-D-glucose


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].

 Names

Name 4,6-O-Ethylidene-α-D-glucose
Synonym More Synonyms

 4,6-O-Ethylidene-a-D-glucose 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
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

 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%

 Synonyms

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