Method of producing an oil extract from seeds of plants via a binary azeotropic solvent mixture

• US 7,615,657 B2
• Filed: 01/28/2003
• Issued: 11/10/2009
• Est. Priority Date: 01/28/2002
• Status: Active Grant

• Current Assignee: New Zealand Botanical Oils Ltd.
• Original Assignee: New Zealand Botanical Oils Ltd.
• Inventors: Kennett, Graham, Stephenson, Lawrence, Colin Tutty, Geoffrey, Bathurst, Christopher Francis
• Primary Examiner(s): Carr; Deborah D
• Application Number:
  US10/502,566
• Publication Number:
  US 20050042347A1
• Time in Patent Office: 2,478 Days
• Field of Search: 554/12
• US Class Current: 554/12
• CPC Class Codes: A61K 2300/00 Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
• CPC Class Codes: A61K 36/185 Magnoliopsida (dicotyledons)
• CPC Class Codes: A61K 36/31 Brassicaceae or Cruciferae (Mustard family), e.g. broccoli, cabbage or kohlrabi
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: A61P 17/06 Antipsoriatics
• CPC Class Codes: A61P 17/10 Anti-acne agents
• CPC Class Codes: C11B 1/10 by extracting
• CPC Class Codes: C11B 3/12 by distillation

Abstract

The invention describes a method of producing extracts from the seeds of meadowfoam, brassicas and crambe plants. A number of subsidiary processes and steps are shown in order to extract differing fractions of oil. Products produced from the above method are also described including uses and methods of these products which include a variety of skin conditions including eczema, facial eczema, dermatitis, external ulcers, welts, rashes, insect bites, allergic reactions and other irritations, burns, wounds, psoriasis, acneiform eruptions, dryness, dry skin, irritation, skin atrophy, secondary infections and the like. The extracts are also described as being a useful compound for treatment of the symptoms of such skin conditions as described above. In particular the use and extraction of glucosinolate (GSL), thiocyanates (TCL) and isothiocyanates (ITCL) is described.

Claims

1. A method of producing an oil extract from seeds of plants selected from the group including:

meadowfoam;

brassicas;

crambe;

said method including the steps of;

(a) washing the seed with a solvent, whereby oil from the seed is dissolved in the solvent;

(b) separating a spent seed solvent solution, wherein the spent seed solvent solution is a binary azeotropic mixture of aliphatic solvents and alcohols;

(c) distilling the spent seed solvent solution at a temperature of equal to or less than 120°

C., and a pressure equal to or less than 50 kPa to obtain an oil extract from the spent seed solvent solution; and

(d) deodorising the oil extract to remove any adverse odours in the oil extract,

wherein the oil extract produced contains a glucosinolates (GSL).

2. The method as claimed in claim 1, wherein the oil extract also contains isothiocyanate (ITCL) and thiocyanate (TCL).

3. The method as claimed in claim 1, wherein the oil extract also contains nitrile thiones and phenolic compounds.

4. The method as claimed in claim 1 wherein the solvent is a binary azeotropic mixture of hexane and ethanol.

5. The method as claimed in claim 4, wherein the azeotropic mixture is approximately 79% hexane and 21% ethanol.

6. The method as claimed in claim 1, wherein solvent distilled from the oil extract in step (c) is recycled into the washing step (a).

7. The method as claimed in claim 1, wherein the seeds are dressed and dried before step (a).

8. The method as claimed in claim 1, wherein the seeds are crushed before step (a).

9. The method as claimed in claim 1, wherein the seeds are crushed to a flaked condition before step (a).

10. The method as claimed in claim 1, further comprising, after step (b), storing the oil extract and allowing seek husk residue to settle and be filtered from the oil.

11. The method as claimed in claim 1, wherein said deodorising comprises adding water to the oil extract and subsequently boiling off the water and residual solvent, leaving a deodorised oil extract.

12. The method as claimed in claim 11, wherein the boiling occurs in an oven heated to a temperature less than 120°

C.

13. The method as claimed in claim 11, wherein the boiling occurs in an oven heated to a temperature less than 80°

C.

14. The method as claimed in claim 1, wherein said deodorising comprises adding a masking substance to the oil extract.

15. The method as claimed in claim 1, further comprising, after step (b), drying the spent seeds to separate remaining solvent as a condensate.

16. The method as claimed in claim 15, wherein the drying is by a combination of steam treatment, under a vacuum, and the application of heat.

17. The method as claimed in claim 15, wherein said condensate is added to the solvent solution during step (b).

18. A method of producing a light oil fraction from seeds of plants selected from the group consisting of:

meadowfoam, brassicas, and crambe;

the method comprising the steps of;

(i) forming a mixture from the oil extract, said oil extract comprising glucosinolates (GSL), isothiocyanate (ITCL) and thiocyanate (TCL) wherein the extract is derived from meadowfoam, with a solvent selected from the group consisting of;

alcohol;

water; and

a combination thereof; and

(ii) separating the mixture of step (i) into a solvent solution and oil;

(iii) drying the solvent solution from step (ii) to remove solvent; and

(iv) collecting the light oil fraction.

19. The method as claimed in claim 18, wherein approximately equal volumes of the solvent and the oil extract are mixed.

20. The method as claimed in claim 18, wherein the alcohol is selected from the group consisting of:

methanol;

ethanol;

other lower alcohols; and

any combination thereof.

21. A method as claimed in claim 18, wherein steps (i) to (iv) are repeated one or more times.

25. The method as claimed in claim 18, wherein the light oil fraction contains glucosinolates (GSL).

26. The method as claimed in claim 25, wherein the light oil fraction also contains isothiocyanate (ITCL) and thiocyanate (TCL).

27. The method as claimed in claim 25, wherein the light oil fraction contains nitrile thiones and phenolic compounds.

22. A method of producing a light oil fraction from seeds of plants selected from the group consisting of:

meadowfoam, brassicas, and crambe, the method comprising the steps of;

(i) mixing the oil extract, said oil extract comprising glucosinolates (GSL), isothiocyanate (ITCL) and thiocyanate (TCL) wherein the extract is derived from meadowfoam, with at least one alcohol to make a first alcohol solution;

(ii) separating the first alcohol solution from the oil;

(iii) mixing the oil from step (ii) with at least one other alcohol to that used in step (i) to make a second alcohol solution;

(iv) separating the alcohol solution from the oil; and

(v) drying the alcohol solution and the second alcohol solution either separately or together to remove alcohol solvent and collecting a light oil fraction.

23. The method as claimed in claim 22, wherein approximately equal volumes of alcohol and oil extract are mixed in steps (i) and (iii).

24. The method as claimed in claim 22, wherein the alcohol in step (i) is methanol and the alcohol in step (iii) is ethanol.

33. The method as claimed in claim 22, wherein the light oil fraction contains glucosinolates (GSL).

28. A method of producing an aqueous solution from the seeds of plants selected from the group consisting of:

meadowfoam, brassicas, and crambe;

the method comprising the step of;

mixing the oil extract, said oil extract comprising glucosinolates (GSL), isothiocyanate (ITCL) and thiocyanate (TCL) wherein the extract is derived from meadowfoam, with a base aqueous solution.

29. The method as claimed in claim 28, wherein a light oil fraction is further mixed into the base aqueous solution, the light oil fraction being produced from seeds of plants selected from the group consisting of:

meadowfoam, brassicas, and crambe; and

said light oil fraction being produced by a method comprising the steps of;

(a) washing the seeds with a solvent, whereby oil from the seeds is dissolved in the solvent;

(b) separating spent seed and solvent solution;

(c) distilling the solvent solution at a temperature of equal to or less than 120°

C., and a pressure equal to or less than 50 kPa to obtain an oil extract from the solvent solution, wherein the oil extract produced contains glucosinolates (GSL);

(d) forming a mixture from the oil extract with a solvent selected from the group consisting of;

alcohol, water, and combinations thereof;

(e) separating the mixture of step (d) into a solvent solution and oil; and

(f) drying the solvent solution of step (e) to remove solvent and collecting the light oil fraction.

30. The method as claimed in claim 28, wherein the oil extract, and light oil fraction, forms 1 to 50% wt of the combined mixture.

31. The method as claimed in claim 28, wherein the base aqueous solution has a water component.

32. The method as claimed in claim 28, wherein the base aqueous solution is a cream or ointment.

34. A filtered oil extract comprising an extract of meadowfoam, said filtered oil extract containing glucosinolates (GSL), isothiocyanate (ITCL) and thiocyanate (TCL) compounds in therapeutically effective amounts.