Sugar-derived gelator

Patent metadata

Field	Value
Publication number	US-9278989-B2
Application number	US-201314383654-A
Country	US
Kind code	B2
Filing date	Mar 8, 2013
Priority date	Mar 8, 2012
Publication date	Mar 8, 2016
Grant date	Mar 8, 2016

Abstract

There is provided a novel gelator containing a sugar derivative. A gelator including a compound of Formula (1) or Formula (2):

wherein each of R 1 and R 3 is independently a linear or branched alkyl group having a carbon atom number of 1 to 20, a cyclic C 3-20 alkyl group, or a linear or branched alkenyl group having a carbon atom number of 2 to 20, n is 0 or an integer of 1 to 4, R 2 is a hydrogen atom, a linear or branched alkyl group having a carbon atom number of 1 to 10, or an aryl group optionally having a substituent, and R 4 and R 5 are each a hydroxy group.

First claim

The invention claimed is:

1. A gelator comprising:
a compound of Formula (1) or Formula (2):

(where
each of R 1 and R 3 is independently a linear or branched alkyl group having a carbon atom number of 1 to 20, a cyclic C 3-20 alkyl group, or a linear or branched alkenyl group having a carbon atom number of 2 to 20; n is 0 or an integer of 1 to 4;
R 2 is a hydrogen atom, a linear or branched alkyl group having a carbon atom number of 1 to 10, or an aryl group optionally having a substituent; and
R 4 and R 5 are each a hydroxy group).

2. The gelator according to claim 1 , wherein
the compound of Formula (1) is a compound of Formula (3):

[where R 1 , R 2 , R 3 , and n are the same as the respective definitions described in Formula (1)].

3. The gelator according to claim 1 , wherein
the compound of Formula (1) is a compound of Formula (4):

[where R 1 , R 2 , R 3 , and n are the same as the respective definitions described in Formula (1)].

4. A gel comprising:
the gelator as claimed in claim 1 ; and
a hydrophobic organic solvent, a hydrophilic organic solvent, water, a hydrophilic organic solution, a hydrophobic organic solution, or an aqueous solution.

5. The gel according to claim 4 , wherein
the hydrophobic organic solvent is at least one selected from the group consisting of plant oils, esters, silicone oils, and hydrocarbons.

6. The gel according to claim 4 , wherein
the hydrophilic organic solvent is at least one selected from the group consisting of methanol, ethanol, 2-propanol, i-butanol, pentanol, hexanol, 1-octanol, isooctanol, acetone, cyclohexanone, acetonitrile, dioxane, glycerol, propylene glycol, ethylene glycol, and dimethyl sulfoxide.

7. The gel according to claim 4 , wherein
the hydrophilic organic solution is a mixed solvent of the hydrophilic organic solvent selected from the group consisting of methanol, ethanol, 2-propanol, i-butanol, pentanol, hexanol, 1-octanol, isooctanol, acetone, cyclohexanone, acetonitrile, dioxane, glycerol, propylene glycol, ethylene glycol, and dimethyl sulfoxide and water.

8. The gel according to claim 4 , wherein
the hydrophobic organic solution is a mixed solvent of the hydrophobic organic solvent selected from the group consisting of plant oils, esters, silicone oils, and hydrocarbons and water.

9. The gel according to claim 4 , wherein
the aqueous solution is an aqueous solution containing an organic acid, an inorganic acid, at least one inorganic salt selected from the group consisting of inorganic carbonates, inorganic sulfates, inorganic phosphates, and inorganic hydrogen phosphates, or at least one organic salt selected from the group consisting of acetates, lactates, citrates, organic amine hydrochlorides, and organic amine acetates.

10. The gel according to claim 9 , wherein
the organic acid is at least one selected from the group consisting of acetic acid, citric acid, succinic acid, lactic acid, malic acid, maleic acid, fumaric acid, and trifluoroacetic acid, the inorganic acid is at least one selected from the group consisting of hydrochloric acid, phosphoric acid, carbonic acid, sulfuric acid, nitric acid, and boric acid, the inorganic salt is at least one selected from the group consisting of calcium carbonate, sodium carbonate, potassium carbonate, sodium sulfate, potassium sulfate, magnesium sulfate, potassium phosphate, sodium phosphate, disodium hydrogen phosphate, and sodium dihydrogen phosphate, and the organic salt is at least one selected from the group consisting of sodium acetate, potassium acetate, sodium lactate, potassium lactate, sodium citrate, potassium citrate, ethylenediamine hydrochloride, ethylenediaminetetraacetate, and trishydroxymethylaminomethane hydrochloride.

11. A base material for cosmetics or a base material for medical use, the base material comprising:
the gelator as claimed in claim 1 .

12. A base material for cosmetics or a base material for medical use, the base material comprising:
the gelator as claimed in claim 1 ; and
at least one polymer compound.

13. A gel electrolyte comprising:
the gelator as claimed in claim 1 .

14. A cell culture base material comprising:
the gelator as claimed in claim 1 .

15. A base material for preserving biomolecules, the base material comprising:
the gelator as claimed in claim 1 .

16. A base material for external use, the base material comprising:
the gelator as claimed in claim 1 .

17. A base material for biochemistry, the base material comprising:
the gelator as claimed in claim 1 .

18. A base material for food, the base material comprising:
the gelator as claimed in claim 1 .

19. A base material for dryland farming, the base material comprising:
the gelator as claimed in claim 1 .

20. A method for producing the compound of Formula (1) or Formula (2) as claimed in claim 1 , the method comprising:
reacting a compound of Formula [A]:

(where each of R 1 and R 3 is independently a linear or branched alkyl group having a carbon atom number of 1 to 20, a cyclic C 3-20 alkyl group, or a linear or branched alkenyl group having a carbon atom number of 2 to 20; and n is 0 or an integer of 1 to 4) with an acetalizing agent, and subsequently subjecting the obtained acetal derivative to annulation reaction with glucose, mannose, a derivative of glucose, or a derivative of mannose, thus producing the compound of Formula (1) or Formula (2), wherein
the reactions are carried out in a one-pot system in the presence of ethanol and p-toluenesulfonic acid.

Assignees

• Univ Kyushu
• Inst Of Systems Information Technologies And Nanotechnologies
• Nissan Chemical Ind Ltd

Inventors

• Ono Fumiyasu
• Shinkai Seiji
• Hirata Osamu

Classifications

• A61Q19/00

  Preparations for care of the skin · CPC title

• C09K3/00

  Materials not provided for elsewhere · CPC title

• H01B1/12

  organic substances {(organic macromolecular compounds or compositions C08)} · CPC title

• A61K8/042

  Gels · CPC title

• A61K2800/10

  General cosmetic use · CPC title