Summary
In previous work 3-stearoyl-d-glucose was found to have superior bread softening action. This paper describes its synthesis by reaction of stearoyl chloride with 1,2∶5,6-diisopropylidene-d-glucose and subsequent deacetonation of the intermediate stearoyl diisopropylidene-d-glucose. Acetonation of the product, followed by saponification of the acyl group, produced 1,2∶5,6-diisopropylidene-d-glucose and indicated that the substance is 3-stearoyl-d-glucose.
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References
Baer, E., and Fischer, H. O. L., J. Biol. Chem.,128, 475–489. (1939).
Bates, F. J., “Polarimetry, Saccharimetry, and the Suggars,” Cire. C440, Natl. Bur. Standards, p. 174, Washington, D. C., U. S. Government Printing Office 1942.
Doerschuk, A. P., J. Am. Chem. Soc.,74, 4202–4203 (1952).
Kent-Jones, D. W., and Amos, A. J., “Modern Cereal Chemistry,” 5th ed., p. 301, Liverpool, England, The Northern Publishing Company, 1957.
Mehltretter, C. L., Alexander, B. H., Mellies, R. L., and Rist, C. E., J. Am. Chem. Soc.,73, 2424–2427 (1951).
Ofelt, C. W., Mehltretter, C. L., MacMasters, M. M., Otey, F. H., and Senti, F. R., Cereal Chem.,35(2), 142–145 (1958).
Ralston, A. W., and Selby, W. M., J. Am. Chem. Soc.,61, 1019–1020 (1939).
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Otey, F.H., Mehltretter, C.L. Preparation of 3-stearoyl-D-glucose—A bread-softening agent. J Am Oil Chem Soc 35, 455–457 (1958). https://doi.org/10.1007/BF02539913
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DOI: https://doi.org/10.1007/BF02539913