ODOURLESS SHEA BASED ESTERS

Abstract

There are provided odorless shea based esters as an ingredient composition comprising: a) 81-97 wt % of at least one short chain alcohol alkyl ester, at least partially from a natural source, b) 3-19 wt % of triterpene esters where at least one is a cinnamic triterpene ester, and c) 1100 ppm or less of at least one short chain alcohol cinnamic ester. There is further provided a method of manufacturing the composition comprising a deodorization step. An advantage is that an odourless or an almost odourless composition can be provided.

Claims

1-21. (canceled)

22. An ingredient composition comprising: a) 81-97 wt % of at least one short chain alcohol alkyl ester, b) 3-19 wt % of triterpene esters, and c) 1100 ppm or less of at least one short chain alcohol cinnamic ester.

23. The ingredient composition of claim 22, wherein the at least one short chain alcohol alkyl ester is at least partially from a natural source.

24. The ingredient composition of claim 22, wherein at least one of the triterpene esters is a cinnamic triterpene ester.

25. The ingredient composition of claim 22, wherein the at least one short chain alcohol cinnamic ester is ethyl cinnamate, methyl cinnamate, propyl cinnamate or isopropyl cinnamate.

26. The ingredient composition of claim 22, wherein the at least one short chain alcohol cinnamic ester is ethyl cinnamate.

27. The ingredient composition of claim 22, wherein the ingredient composition comprises 800 ppm or less of the at least one short chain alcohol cinnamic ester.

28. The ingredient composition of claim 22, wherein the ingredient composition comprises 700 ppm or less of the at least one short chain alcohol cinnamic ester.

29. The ingredient composition of claim 22, wherein the ingredient composition comprises 600 ppm or less of the at least one short chain alcohol cinnamic ester.

30. The ingredient composition of claim 22, wherein the ingredient composition comprises 400 ppm or less of the at least one short chain alcohol cinnamic ester.

31. The ingredient composition of claim 22, wherein the ingredient composition comprises 200 ppm or less of the at least one short chain alcohol cinnamic ester.

32. A method of reducing an amount of ethyl cinnamate to 1100 ppm or less in a composition of ethyl esters of shea butter with a content of triterpene esters of 5-9 wt %, the method comprising deodorizing the composition, wherein at least 95 wt % of the composition is unmodified following deodorization.

33. The method of claim 32, wherein at least 98 wt % of the composition is unmodified following deodorization.

34. The method of claim 32, wherein at least 99 wt % of the composition is unmodified following deodorization.

35. The method of claim 32, comprising reducing the amount of ethyl cinnamate to 700 ppm or less.

36. The method of claim 32, wherein the composition comprises ethyl oleate, ethyl stearate, ethyl palmitate, and ethyl linolate.

37. The method of claim 36, wherein the content of ethyl oleate, ethyl stearate, ethyl palmitate, or ethyl linolate in the composition is not decreased by more than 2 wt % during deodorization.

38. The method of claim 36, wherein the content of ethyl oleate in the composition remains above 50 wt % during deodorization.

39. The method of claim 32, wherein the ethyl esters of shea butter are essentially odourless.

40. The method of claim 39, wherein the ethyl esters of shea butter comprise 400 ppm or less of a short chain alcohol cinnamic ester.

41. The method of claim 32, wherein a temperature ranges from 100-140 C. during deodorization.

42. The method of claim 32, wherein a pressure ranges from 1-5 mbar during deodorization.

43. The method of claim 32, wherein a steam flow ranges from 10-50 g/h during deodorization.

44. The method of claim 32, further comprising adding at least one bleaching earth.

45. A product obtained by the method of claim 32.

46. A personal care application comprising the ingredient composition of claim 22.

47. A cosmetic application comprising the ingredient composition of claim 22.

48. A skin care formulation comprising the ingredient composition of claim 22.

49. A hair color formulation comprising the ingredient composition of claim 22.

50. A lip care formulation comprising the ingredient composition of claim 22.

51. A colour cosmetic formulation comprising the ingredient composition of claim 22.

52. A sun care application comprising the ingredient composition of claim 22.

53. A lotion comprising the ingredient composition of claim 22.

54. An ointment comprising the ingredient composition of claim 22.

55. A cream comprising the ingredient composition of claim 22.

56. The ingredient composition of claim 22, wherein the ingredient composition functions as a constituent in soft-shelled capsules.

57. A food application comprising the ingredient composition of claim 22.

58. The ingredient composition of claim 22, wherein the ingredient composition functions as a release agent in a food application.

Description

EXAMPLES

Example 1

Production of Shea Butter Oil Ethylate

[0087] The raw material used was:

[0088] Shea butter oil characterized by being liquid and with a triterpene ester content of 10 wt %.

[0089] Ethanol containing 99.5 wt % ethanol originating from sugar cane.

[0090] The catalyst was NaOEt (NaOCH2CH3).

[0091] Citric Acid:

[0092] 5000 g of the shea butter oil, refined, bleached and deodorized according to standard procedure, was blended with ethanol (1250 g). 50 gram of the catalyst was added and the mixture blended and heated at 1 atm by vigorous stirring. When the temperature reached 75 C. the temperature was kept at 75 C. for 30 minutes in order for the reaction to reach steady state. After the 30 minutes reaction time the stirring was stopped to allow the glycerol to sediment at the bottom. After 30 minutes of separation two phases were seen. The upper phase (the ester phase) and a lower phase (glycerol phase) were seen. The glycerol phase was removed and weighed (435 g). Another 12.5 grams of catalyst were added to the remaining phase under stirring and the temperature increased to 75 C. and then kept at 75 C. for 30 minutes, 1 atm and vigorous stirring to once again reach steady state and a low mono glyceride content (below 1 wt %). The stirring was turned off to allow a glycerol phase to appear. The glycerol phase was once again removed (35 g). The ester was washed with water to stop reaction and remove traces of soap and then dried. The excess of ethanol was removed during the drying process. The theoretical yield would be 4675 gram, and 4200 grams were collected. The final product was characterized by comprising three classes of molecules; monoglycerides, fatty acid ethyl esters and triterpene (TTP) esters.

[0093] The mono glyceride content was less than 1 wt %, the TTP ester content was approximately 10 wt % and the ethyl ester content was approximately 89 wt %.

[0094] Three classes of triterpene esters were identified/detected; triterpene acetate, triterpene cinnamate and triterpene oleate (and other long chain fatty acids). About 3 wt. % triterpene acetates, about 5 wt. % of triterpene cinnamates and less than 2% of triterpene esters of long chain fatty acids. So most original triterpene cinnamates remain hut some reacts with the ethanol and creates ethyl cinnamate.

[0095] The ethyl long chain fatty acid content contained a number of esters.

TABLE-US-00005 Ethyl oleate 52.4% Ethyl stearate 24.3% Ethyl palmitate 5.2% Ethyl linoleate 6.2% unsaponifiable 9.7% Other 2.2% Ethyl cinnamate 2000 ppm

[0096] The ethyl cinnamate level was determined to 2000 ppm.

Experiment 2: Bleaching

[0097] The standard procedure of bleaching. 3500 grams from experiment 1 was heated to 95 C. (10 mbar). The vacuum was released and 7 grams of bleaching earth was added (Tonsil). During the bleaching (20 minutes) the temperature was kept at 95 C., (10 mbar) and with stirring. The vacuum was released and then the product was filtered via a 5 micron filter.

TABLE-US-00006 Ethyl oleate 52.6% Ethyl stearate 24.4% Ethyl palmitate 5.2% Ethyl linoleate 6.3% Unsaponifiable 9.4% Other 2.1% Ethyl 1600 Ppm cinnamate

[0098] The ethyl cinnamate was determined to 1600 ppm

Experiment 3: Deodorisation 100 C.

[0099] 350 gram of the ester in experiment 1 was deodorized (100 C., 2 mbar, 20 g/h steam) for 30 minutes.

[0100] The remaining contained 9 wt. % of unsaponifiable in form of Triterpene esters. The ethyl ester content was 90%.

TABLE-US-00007 Ethyl oleate 52.5% Ethyl stearate 24.5% Ethyl 5.3% palmitate Ethyl linoleate 6.2% unsaponifiable 9.4% Other 2.1% Ethyl 370 Ppm cinnamate Yield 99%

Experiment 4: Deodorisation 110 C.

[0101] 350 gram of the ester in experiment 1 was deodorized (110 C. 2 mbar, 20 g/h steam) for 30 minutes.

[0102] The remaining contained 9 wt. % of unsaponifiable in form of Triterpene esters. The ethyl ester content was 90%.

TABLE-US-00008 Ethyl 10 ppm cinnamate Yield 99%

Experiment 5: Deodorisation 120 C.

[0103] 350 gram of the ester in experiment 1 was deodorized (120 C., 2 mbar, 20 g/h steam) for 30 minutes.

[0104] The remaining contained 9 wt. % of unsaponifiable in form of Triterpene esters. The ethyl ester content was 90%.

TABLE-US-00009 Ethyl 12 Ppm cinnamate Yield 98%

Experiment 6: Deodorisation 130 C.

[0105] 350 gram of the ester in experiment 1 was deodorized (130 C., 2 mbar, 20 g/h steam) for 30 minutes.

[0106] The remaining contained 9 wt. % of unsaponifiable in form of Triterpene esters. The ethyl ester content was 90%.

TABLE-US-00010 Ethyl <10 Ppm cinnamate yield 96%

Experiment 7: Deodorisation 140 C.

[0107] 350 gram of the ester in experiment 1 was deodorized (140 C., 2 mbar, 20 g/h steam) for 30 minutes.

[0108] The remaining contained 10 wt. % of unsaponifiable in form of Triterpene esters. The ethyl ester content was 90%.

TABLE-US-00011 Ethyl oleate 52.1% Ethyl stearate 24.1% Ethyl 5.2% palmitate Ethyl linoleate 6.1% unsaponifiable 10.3% Other 2.1% Ethyl <10 Ppm cinnamate Yield 90%

Experiment 8: Deodorisation 150 C.

[0109] 350 gram of the ester in experiment 1 was deodorized (150 C., 2 mbar, 20 g/h steam) for 30 minutes.

[0110] The remaining contained 15 wt. % of unsaponifiable in form of Triterpene esters. The ethyl ester content was 84%.

TABLE-US-00012 Ethyl oleate 49.0% Ethyl stearate 22.6% Ethyl 4.9% paimitate Ethyl linoleate 6.0% unsaponifiable 15.6% Other 1.9% Ethyl <10 Ppm cinnamate Yield 55%

Table 1

[0111] Summary of Yield from the deodorisation step.

TABLE-US-00013 Ethyl cinnamate Yield Experiment 1 2000 ppm % Experiment 2 1600 ppm % Experiment 3 370 ppm 99 wt. % Experiment 4 10 ppm 99 wt. % Experiment 5 12 ppm 98 wt % Experiment 6 <10 ppm 96 wt % Experiment 7 <10 ppm 90 wt % Experiment 8 <10 ppm 55 wt %

Experiment 9

[0112] Bleaching: 6 Mt of Lipex SheaLight with an ethyl cinnamate level of 2200 ppm was added to a 10 M3 reactor. The product was 1 was heated to 95 C. (10 mbar), The vacuum was released and 120 kg of bleaching earth was added (Tonsil). During the bleaching (60 minutes) the temperature was kept at 95 C., (10 mbar) and with stirring, The vacuum was released and then the product was filtered via a 5 micron filter, to remove bleaching earth. The product were then recirculated into the reactor and underwent a steam deodorisation, 2 hours at 120 C., 1 mbar pressure. The level of Ethyl Cinnamate was 400 ppm. The yield for (including bleaching and steam deodorisation) was 97%.

Experiment 10 Evaluation of Odor Threshold Value

[0113] Nine persons were testing in a blind test five samples containing different levels (400, 600, 800, 1600 and 2000 ppm) of ethyl cinnamate.

[0114] The panelists were first allowed to smell 100 wt. % of ethyl cinnamate to learn which odor to identify. Then the panelist did receive 5 bottles containing different levels of ethyl cinnamate. The panelists were allowed to add sample on the skin to identify the odor.

[0115] Three panelists claimed to smell the ethyl cinnamate in all samples while one did not smell in any sample.

TABLE-US-00014 persons claimed they persons claimed smell could not smell ethyl PPM ethyl cinnamate cinnamate 400 0 9 600 3 6 800 6 3 1600 8 1 2000 8 1

[0116] The odour threshold for ethyl cinnamate in a matrix comprising long chain alkyl esters is thus estimated to be 700 ppm, defined as the level where 50% of the testers do not smell the test substance.