alpha-D-Glucose pentaacetate Chemical Properties

Melting point:

110°C

Boiling point:

435.58°C (rough estimate)

Density 

1.3984 (rough estimate)

refractive index 

1.5376 (estimate)

FEMA 

2524 | GLUCOSE PENTAACETATE

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

Appearance

White to off-white Solid

Odor Type

odorless

Water Solubility 

1.5g/L(18 ºC)

InChI

InChI=1S/C16H22O11/c1-8(18)23-7-14(25-10(3)20)16(27-12(5)22)15(26-11(4)21)13(6-17)24-9(2)19/h6,13-16H,7H2,1-5H3/t13-,14+,15+,16+/m0/s1

InChIKey

UAOKXEHOENRFMP-ZJIFWQFVSA-N

SMILES

O=C[C@H](OC(=O)C)[C@@H](OC(=O)C)[C@H](OC(=O)C)[C@H](OC(=O)C)COC(=O)C

LogP

1.27

CAS DataBase Reference

3891-59-6(CAS DataBase Reference)

NIST Chemistry Reference

D-Glucose, 2,3,4,5,6-pentaacetate(3891-59-6)

EPA Substance Registry System

Glucose 2,3,4,5,6-pentaacetate (3891-59-6)

Safety Information

HS Code 

29400090

alpha-D-Glucose pentaacetate Usage And Synthesis

Chemical Properties

White solid

Chemical Properties

Glucose pentaacetate is odorless, but has a bitter favor.

Preparation

By acetylation of glucose using any number of techniques, including ZnCl2 and pyridine, sodium acetate, and acetic anhydride and pyridine.

Taste threshold values

Taste characteristics at 100 ppm: bitter-like with a citrus tonic favor.

Synthesis

General procedure for the synthesis of 2,3,4,5,6-D-glucose pentaacetate from D-anhydrous glucose and acetic anhydride: D-glucose (0.36 g; 2 mmol) was dissolved in N,N'-dimethylimidazolium or N,N'-butylmethyl H-phosphonate methyl ester (1 g) at room temperature, followed by slow addition of acetic anhydride (1.02 g; 10 mmol). Continuous stirring is required during the reaction, noting that the reaction is exothermic and the mixture will gradually become homogeneous. The reaction can be continued at room temperature for 15 hours or accelerated at 50 °C to completion in 5 hours. At the end of the reaction, the target product 2,3,4,5,6-D-glucose pentaacetate is precipitated by the addition of water (0.72 g) to give a final yield of 92%.

References

[1] Patent: US2010/121075, 2010, A1. Location in patent: Page/Page column 8
[2] Heterocycles, 1987, vol. 26, # 6, p. 1549 - 1556
[3] Bulletin of the Chemical Society of Japan, 2010, vol. 83, # 7, p. 799 - 801
[4] Journal of Natural Products, 2011, vol. 74, # 8, p. 1812 - 1816

alpha-D-Glucose pentaacetate(3891-59-6)Related Product Information

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