2,3,4-triacylhexoses and mixtures thereof

Details 2,3,4-triacylhexoses and mixtures thereof 2,3,4-triacylhexoses and mixtures thereof

C - Chemistry, Metallurgy

07

H

99/156, 167/310,

C07H 13/06 (2006.01) A21D 2/08 (2006.01) A21D 10/04 (2006.01) A23D 7/015 (2006.01) A23L 1/24 (2006.01) A23L 1/305 (2006.01) A61K 8/60 (2006.01) A61K 8/97 (2006.01) A61Q 1/06 (2006.01) A61Q 3/02 (2006.01) A61Q 5/06 (2006.01) A61Q 9/02 (2006.01) A61Q 15/00 (2006.01) A61Q 17/04 (2006.01) A61Q 19/00 (2006.01) A61Q 19/10 (2006.01)

Patent

CA 1288770

2,3,4-TRIACYLHEXOSES AND MIXTURES THEREOF ABSTRACT The present invention comprises a new class of 2,3,4-tri-0-acylhexoses and mixtures thereof. Members of the new class of compounds are comprised of a hexose sugar having fatty acids attached at the 2, 3 and 4 positions of the hexose moiety. The fatty acids can be saturated or unsaturated, and can have a relative molecular size of up to C30. When at least one of the acylating fatty acid groups on the hexose molecule contains more than 7 carbons, the resulting 2,3,,4-tri-0-acylhexoses (or mixtures thereof) have a non-bitter taste. On the other hand, when none of the acylating fatty acids have more than 7 carbons, the resulting 2,3,4-tri-0-acylhexoses (and mixtures that contain them) are bitter when tasted. The new 2,3,4-tri-0-acylhexoses can be synthesized using known chemical methods. Alternatively, the new compounds, and especially mixtures thereof, are obtained as the result of selective extraction and purification of the epicuticular exudate from Lycoperstcon pennellii plant parts. Mixtures of 2,3,4-tri-0-acylhexoses, especially as found in the Lycopersicon pennellii natural plant extract, or the glucolipid fraction thereof, are useful as evaporation suppressants, antitranspirants and antidesiccants. The Lycoperstcon pennellii natural plant extract is also useful as an ingredient in cosmetic and toiletry formulations, while the non-bitter glucolipid subfraction is especially useful as a "low calorie" substitute for fats in foods.

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