1,3-fatty diol compounds and derivatives thereof

Patent metadata

Field	Value
Publication number	US-12304883-B2
Application number	US-202117494303-A
Country	US
Kind code	B2
Filing date	Oct 5, 2021
Priority date	Sep 14, 2016
Publication date	May 20, 2025
Grant date	May 20, 2025

Abstract

The disclosure relates to the field of specialty chemicals. In particular, the disclosure provides novel 1,3-fatty-diol compounds and derivatives thereof which are useful e.g., in the production of personal care products, surfactants, detergents, polymers, paints, coatings, and as emulsifiers, emollients, and thickeners in cosmetics and foods, as industrial solvents and plasticizers, etc.

First claim

We claim:

1. A compound having a structure according to Formula VI

a stereoisomer thereof, or a pharmaceutical salt thereof, wherein
R 3 and R 4 are independently selected from the group consisting of H, a monosaccharide,
a disaccharide, a trisaccharide, and a polysaccharide, wherein each of the monosaccharide, disaccharide, trisaccharide or polysaccharide is bound via an anomeric carbon to the oxygen at C-1 and/or C-3 in Formula VI;
m is zero, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18;
a chiral center exists at C-3; and
the chiral center at C-3 has an R configuration or an S configuration; and
R 3 and R 4 are not both H.

2. The compound of claim 1 , wherein neither R 3 nor R 4 are H.

3. The compound of claim 1 , wherein the disaccharide, trisaccharide, or polysaccharide comprises a pentose sugar, a hexose sugar, or a mixture thereof.

4. The compound of claim 3 , wherein the disaccharide, trisaccharide, or polysaccharide comprises a hexose sugar selected from allose, altrose, glucose, mannose, gulose, iodose, galactose, talose, and a mixture of any two or more thereof.

5. The compound of claim 1 , wherein the disaccharide, trisaccharide, or polysaccharide comprises a furanose sugar, a pyranose sugar, or a mixture of any two or more thereof.

6. The compound of claim 1 , wherein R 3 and R 4 are different monosaccharides.

7. The compound of claim 1 , wherein R 3 and R 4 are the same monosaccharide.

8. A composition comprising the compound of claim 1 , wherein the composition is a personal care product, a pharmaceutical, a food product, or an agricultural formulation.

9. The composition of claim 8 , further comprising:
a compound according to Formula V

wherein
n is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14;
R 1 and R 2 are independently selected from H, a monosaccharide, a disaccharide, a trisaccharide, and a polysaccharide, wherein each of the monosaccharide, disaccharide, trisaccharide, or polysaccharide is bound at an anomeric carbon;
the double bond is in a (Z) or an (E) configuration;
a chiral center exists at C-3; and
the chiral center at C-3 has an R configuration or an S configuration.

10. The composition of claim 9 , wherein:
one or both of R 1 and R 2 is not H; and
one or both of R 3 and R 4 is not H.

11. The composition of claim 10 , wherein the compound according to Formula V is an alkyl polyglycoside and the compound according to Formula VI is an alkyl polyglycoside.

12. The compound of claim 1 , wherein m is 3, 5, 7, or 9.

13. The compound of claim 1 , wherein the monosaccharide, disaccharide, trisaccharide, or polysaccharide is bound at the anomeric carbon via an α-glycosidic bond or a β-glycosidic bond.

14. The compound of claim 1 , wherein the monosaccharide is a pentose sugar, a hexose sugar, a furanose sugar, or a pyranose sugar.

15. The compound of claim 14 , wherein the monosaccharide is a hexose sugar selected from allose, altrose, glucose, mannose, gulose, iodose, galactose, and talose.

16. The compound of claim 1 , wherein the chiral center at C-3 has an R configuration.

17. The compound of claim 1 , wherein R 3 is glucose.

18. The compound of claim 1 , wherein the compound is an alkyl polyglycoside.

19. The compound of claim 1 , wherein:
the disaccharide, trisaccharide, or polysaccharide comprises an α-glycosidic linkage or a β-glycosidic linkage; or
the trisaccharide or polysaccharide comprises an α-glycosidic linkage, a β-glycosidic linkage, or mixtures thereof.

20. The composition of claim 9 , wherein:
the monosaccharide, disaccharide, trisaccharide, or polysaccharide comprises a pentose sugar or a hexose sugar, or a mixture thereof;
the monosaccharide, disaccharide, trisaccharide, or polysaccharide comprises furanose sugars, pyranose sugars, or a mixture of any two or more thereof;
the monosaccharide, disaccharide, trisaccharide, or polysaccharide comprises allose, altrose, glucose, mannose, gulose, iodose, galactose, talose, furanose, pyranose, or xylose, or a mixture of any two or more thereof; or
R 1 is glucose and R 3 is glucose.

Assignees

• Genomatica Inc

Inventors

• Wang Haibo
• Bond Risha Lindig

Classifications

• C07H15/10

  containing unsaturated carbon-to-carbon bonds · CPC title

• A61Q19/00

  Preparations for care of the skin · CPC title

• A61K8/604

  Alkylpolyglycosides; Derivatives thereof, e.g. esters · CPC title

• A61K8/062

  Oil-in-water emulsions · CPC title

• A61K8/345

  containing more than one hydroxy group · CPC title