WO1997046220A1

WO1997046220A1 - Vegetable oil compositions

Info

Publication number: WO1997046220A1
Application number: PCT/GB1997/001497
Authority: WO
Inventors: Keith Coupland; Julie Ann Nichols
Original assignee: Croda International Plc
Priority date: 1996-06-03
Filing date: 1997-06-03
Publication date: 1997-12-11
Also published as: CA2271166C; WO1997046649A1; DE69720737T2; EP0920300A1; CA2271162C; ES2203806T3; WO1997046219A1; DE69724629T2; CA2271166A1; EP0928185B1; EP0928185A1; AU2972697A; EP0920300B2; ES2196333T3; DE69724629D1; DE69720737T3; AU2972497A; ES2196333T5; EP0920300B1; CA2271162A1

Abstract

The use of an oil extracted from seeds of the borignaceae family in topical application to, or oral ingestion by, the human or animal body. This oil alone may be used for these purposes, or, preferably, it is used to form a part of a composition for topical application to, or oral ingestion by, the human or animal body.

Description

VEGETABLE OIL COMPOSITIONS

This invention relates to the use of oils containing glycerides of essential fatty acids, or of essential fatty acids formed from such oils, for topical and dietetic purposes. The invention also relates to compositions including such oils or essential fatty acids.

Fats and oils are triesters of glycerol; they are Icnown as triglycerides or triacylglycerols. If the triglyceride is solid at room temperature, then it is generally considered to be a fat, whereas if it is liquid at room temperature, then it is generally considered to be an oil. Most triglycerides in animals are fats, while most triglycerides in vegetables tend to be oils. Fatty acids can be obtained from fats or oils by hydrolysis.

Certain fatty acids, called essential fatty acids, must be present in the human diet and are used in the body to synthesise, for example, prostaglandins. There are two main series of essential fatty acids: one is called the n3 family (also Icnown as the ω-3 family); and the other is called the n6 family (also Icnown as the ω-6 family).

Stearidonic acid (SA) is a polyunsaturated fatty acid of the n3 family.

Chemically it can be described as 6c9cl2cl 5c-octadecatetraenoic acid or 18:4n3.

Other essential fatty acids are linoleic acid (LA), α-linolenic acid (ALA) and γ- linolenic acid (GLA) - these acids can be described as C18:2n6, C18:3n3 and

C 18:3n6 respectively.

It is Icnown that the oils of the pips of certain fruits contain triglycerides of a number of fatty acids. In GB-A-21 18567 it is disclosed that an oil -extracted from the pips of the fruit of blackcurrants, redcurrants and gooseberries contain triglycerides of fatty acids in the proportions shown in Table 1. Table 1

Fatty Acid Blackcurrants Red Currents Gooseberries

C 16:0 6-7 wt% 4-5 wt% 7-8 wt%

C 18:0 1 -2 wt% 1-2 wt% 1 -2 wt% C18: l cis 9-10 wt% 14- 15 wt% 15-16wt%

C 1 8: l trans 0.5 wt% 0.5- 1 wt% 1 -2 wt%

C 1 8:2n6 47-49 wt% 41 -42 wt% 29-41 wt%

C 18:3n6 15- 19 wt% 4-5 wt% 10-I2 wt%

C18:3n3 12- 14 wt% 29-31 wt% 19-20wt% C18:4n3 3-4 wt% 2.5-3.5 wt% 4-5 wt%

Stearidonic acid is found in marine oils, some plant oils and in lipids isolated from micro-organisms. It is produced in the human body by the biochemical transformation of linolenic acid. The metabolic transformation in the human body of n3 fatty adds by desaturation and elongation takes place as follows:

18:3 α-linolenic acid

Δ6 desaturase

18:4 stearidonic acid elongase I

20:4 eicosatetraenoic add

Δ5 desaturase

20:5 eicosapentaenoic add elongase

22:5 docosapentaenoic add

Δ4 desaturase

22:6 docosahexaenoic acid

The activity of the enzyme "Δ6 desaturase" is known to be of lower activity following certain illnesses, and in old age; its activity can also be lowered by poor diet and certain lifestyles. This is significant, because if the activity of Δ6 desaturase is lowered, then the body's capacity to make stearidonic acid (and the other compounds in the scheme shown above) is also lowered. One way to remedy this problem is to take a dietary supplement containing stearidonic acid.

None of the materials in Table 1 is very useful as a source of stearidonic acid, because this acid is present in such a low concentration. In order to use these materials as a source of stearidonic acid it would be necessary either to use them in large quantities, or to carry out expensive chemical processing to concentrate the stearidonic add. Accordingly, there is a need for a material that is rich in stearidonic acid, and that does not contain any toxic compounds.

We have now found a rich natural, non-toxic, source of stearidonic acid, and this can be used to make a wide range of dietetic, cosmetic and health care products. In particular, we have found that the oil of seeds of the Borignaceae family are a rich source of stearidonic add. We have also found that the oil itself can be used in dietetic, cosmetic and health care products, without the need for additional treatment or purification.

In one aspect the invention provides the use of an oil extracted from seeds of the borignaceae family in topical application to, or oral ingestion by, the human or animal body. This oil alone may be used for these purposes, or, preferably, it is used to form a part of a composition for topical application to, or oral ingestion by, the human or animal body.

•In an espeάally advantageous embodiment the seeds are of the genus Echium, because this genus, has been found to be a particularly rich source of stearidonic acid. We have found that the seeds of Echium vulgaris and Echium plantagineum are very useful.

The oil extracted from the seeds of the Borignaceae family will contain the triglyceride of stearidonic add. In general, the oil will contain stearidonic add (in the form of the triglyceride) in an amount of greater than 5 wt%, preferably greater than 5.5 wt%, more preferably greater than 10 wt%, and most preferably greater than 15 wt%; the oil may contain as much as 20 wt% stearidonic acid, or more. We can obtain the oil at these concentrations without carrying out any purification process to increase the concentration of stearidonic acid in the oil. We have analysed the composition of three oils formed from the seeds of the Borignaceae family, and found that the fatty adds were present (in the form of triglycerides) in the amounts shown in Table 2.

Table 2 Fatty Acid E.vulgaris E. Plantagineum TrichodesmaZeylanicum

16:0 6.2 wt% 7.6 wt% 9.4 wt%

18:0 2.0 wt% 3.8 wt% 5.8 wt%

18: 1 8.0 wt% 16.7 wt% 26.8 wt%

18:2 (LA) 10.3 wt% 16 wt% 18.2 wt% 18:3 (GLA) 5.3 wt% 1 1.9 wt% 5.5 wt%

18:3 (ALA) 47.3 wt% 29.9 wt% 26.8 wt%

18:4 (SA) 19.8 wt% 12.3 wt% 5.7 wt%

Other 1.1 wt% 1.8 wt% 1.8 wt%

The oil extract can be used in a wide variety of topical applications, induding many cosmetic and dermatological applications. For example, the oil extract can be used in skin creams and emulsions, including cleansers, moisturising creams, and sun screens; shampoos; and bath oils. The oil also has a wide range of dietetic uses. For example, the oil can be provided as an additive to existing food products, for instance as an additive to milk or milk- based drinks; it may form be in the form of a dietary supplement, or part of a dietary supplement (eg a vitamin containing supplement), and may be provided in solid form, for example as a tablet or as a soft or hard gelatin capsule, or in liquid form.

The oil extract itself, or compositions formed from the oil extract, can be used to treat a wide variety of skin disorders such as dry skin, itchy skin, psoriasis, eczema and the like.

According to another aspect of the invention there is provided a composition for topical application to, or oral ingestion by, the human or animal body, comprising an oil extracted from the seeds of the Borignaceae family, or a physiologically acceptable derivative thereof, in combination with a physiologically acceptable carrier.

The precise nature of the carrier depends on the use desired for the composition. In addition, the carrier would usuallv contain other active ingredients, such as a moisturiser (eg for moisturising cream), a surfactant (eg for shampoo) or a

UV-blocking/absorbing compound (eg for a sun cream). Many specific examples of suitable carriers are disclosed in the Examples below.

The amount of the oil in the composition also depends upon the desired use. However, for most applications an amount of the oil from 1 wt% and 20 wt% is appropriate.

We have described above the use of oil extracted from the seeds of the Borignaceae family, and compositions including such oils. This oil contains glycerides of a number of fatty acids including stearidonic acid. However, it is possible to process the oil extracted from the seeds to convert it at least partially to the corresponding fatty acids of the triglycerides in the oil. This processing would typically a saponification step to hydrolyse the triglycerides, an acidification step, and at least one separation step to recover the stearidonic acid and other fatty adds. There may also be a purification step to purify the stearidonic acid.

The present invention also includes the use of stearidonic acid formed from an oil extracted from seeds of the borignaceae family in topical application to, or oral ingestion by, the human or animal body. The stearidonic acid so formed may be used alone for these purposes, or, preferably, it is used to form a part of a composition for topical application to, or oral ingestion by, the human or animal body. The stearidonic acid may be part of a mixture of essential fatty adds formed from an oil extracted from the seed of the borignaceae family.

The following examples illustrate the invention.

Example 1

10 kg of the seeds of echium plantagineum were crushed and the oil was extracted with 15 litres of petroleum ether (BP 40-60 °C). The petroleum ether extract was evaporated to yield 1 741 g of a golden yellow oil. The oil was converted to the corresponding fatty acid methyl esters and was analysed by gas chromatography. The lipid profile was as follows:

Fatty Acid Fatty Acid Content

16:0 7.2 wt%

18:0 4.0 wt%

18: 1 18.2 wt%

18:2 (LA) 16.5 wt%

18:3 (GLA) 1 1.8 wt%

18:3 (ALA) 28.9 wt%

18:4 (SA) 12.2 wt%

Other 1.2 wt%

The values in obtained in this example are slightly different from those in Table 2 due to insignificant experimental errors.

Example 2

20 g of the seeds of trichodesma zeylanicum seeds were crushed and placed in a Soxhlet extraction thimble. An oil was isolated by refluxing n-hexane around the crushed seed to produce a solution of the oil in n-hexane. The oil was separated from the n-hexane by rotoevaporation; 5 g of a green oil was recovered. An aliquot of the oil was converted to the corresponding fatty acid methyl esters and was analysed by gas chromatography. The lipid profile was as follows:

Fatty Acid Fatty Acid Content 16:0 9.4 wt%

18:0 5.7 wt%

18: 1 25.5 wt%

18:2 (LA) 19.0 wt%

18:3 (GLA) 5.5 wt% 18:3 (ALA) 26.5 wt%

18:4 (SA) 5.9 wt%

Other 2.5 wt%

Example 3

A sun screen oil was prepared from the following ingredients:

Butyl methoxydibenzoylmethane (Parsol 1789)( 1 ) 2.0 wt%

Octyl methoxycinnamate (Parsol MCX)( 1 ) 7.5 wt%

Benzophenone-3 (Uvinul M40)(2) 4.5 wt%-

PPG-2 myristyl ether proprionate(Promyristyl PM3)(3) 10.0 wt% Oil from Example 1 2.0- 10.0 wt%

Caprylic/capric triglycerides (Crodamol GTCC) to 100 wt%

Perfume, preservatives, colour qs

( 1 ) From Givaudan

(2) From BASF (3) From Croda

The sun screen oil was formed bv blending the ingredients, heating gently. The resultant blend was stirred to cool.

5

Example 4

A physical block sun screen cream was prepared from the following ingredients:

I O

Oil Phase:

Myristyl myristate (Crodamol MM)( 1 ) 1.5 wt%

Dimethicone (silicone 200/200cs)(2) 7.0 wt%

Glyceryl stearate (GMS N/E) ( 1 ) 2.5 wt% 5 Stearic acid (Crosterene) ( 1 ) 3.0 wt%

PVP/eicosene copolymer (Antaron V220)(3) 0.5 wt%

Nonionic emulsifying blend (Polawax GP200)( 1 ) 2.0 wt%

Octyl hydroxystearate (Crodamol OHS)( 1 ) 5.0 wt%

Oil from Example 1 2.0- 10.0 wt% 0 Super refined shea butter( 1 ) 5.0 wt%

Caprylic/capric triglycerides (Crodamol GTCC)( 1 ) 9.0 wt%

Titanium dioxide 5.0 wt%

Water Phase: 5 Deionised water to l00 wt%

Flobeads (CL-2080)(5) 5.0 wt%

Glycerine 3.0 wt%

Triethanolamine 0.9 wt%

Perfume, preservatives, colour qs ( 1 ) From Croda

(2) From Dow Corning

(3) From GAF

(4) From K&K Greef (5) From Landsdowne Chemicals

The sun screen cream was made by heating the oil phase (including titanium dioxide) and water phase separately to 80-85 °C, then adding the water phase to the oil phase with vigorous agitation. The triethanolamine was then added. At 45 °C the Flobeads were added. The stirring was continued until the temperature reached about 55°C, and then the composition was passed through suitable homogenising equipment, such as a triple roll mill).

Example 5 A shampoo was prepared from the following ingredients:

Sodium laureth sulphate (Empicol ESB3)( 1 ) 50.0 wt%

Cocamidopropyl betaine (Incronam 30)(2) 5.0 wt%

Oil from Example 1 1 -5 wt% Polysorbate-20 (Crillet 1 )(2) 3.0 wt%

PPG-5-ceteth- 10-ρhosρhate (Crodafos SG) (2) 3.0 wt%

Triethanolamine to pH 6.5-7.0

Butylated hydroxytoluene 0.01 wt%

Deionised water to 100 wt% Perfume, preservatives, colour qs

( 1 ) From Albright <SL Wilson

(2) From Croda The shampoo was prepared by first forming a premix by solubilising the essential fatty acid containing oil from Example 1 in the surfactant mixture

(polysorbate-20 and PPG-5-ceteth- 10-phosphate). The other ingredients were combined and, when homogeneous, they were added to the premix. The resultant mixture was stirred until clear.

Example 6

A cleanser was prepared from the following ingredients:

Oil Phase:

Nonionic emulsifying wax (Polawax GP200)( 1 ) 2.0 wt%

Cetearyl alcohol (Crodacol CS90EP)( 1 ) 1.0 wt%

Glyceryl stearate (Cithrol GMS N/E DP2186) ( 1 ) 1.0 wt%

Caprylic/capric triglycerides (Crodamol GTCC)( 1 ) 8.0 wt% Rosehip oil (2) 1.0 wt%

Oil from Example 1 1- 10 wt%

Water Phase:

Glycerin 2.0 wt% Carbomer 981 (carbopol 981 - 2% aqueous solution)(3) 5.0 wt%

Triethanolamine to pH 6.5

Deionised water to 100 wt%

Perfume, preservative, colour qs

( 1 ) From Croda

(2) From Novarom

(3) From B F Goodrich

The deanser was prepared by heating the water and oil phase separately to 65-70°C, then adding the water phase to the oil phase with stirring. The pH was then adjusted to pH 6.5 with the triethanolamine. The resultant mixture was stirred to cool.

Example 7

A moisturising facial oil was prepared from the following ingredients:

Oil from Example 1 5.0- 1 5.0 wt%

Tocopheryl acetate(2) 5.0 wt% butylated hydroxytoluene 0.05 wt%

Caprylic/capric triglycerides (Crodamol GTCC) ( 1 ) to 100 wt%

Perfume, preservatives, colour qs

( 1 ) From Croda (2) From Roche

The facial oil was prepared by incorporating the butylated hydroxytoluene in the caprylic/capric triglyceride with gentle warming and stirring. The resultant mixture was stirred to cool, then the remaining ingredients were added, whilst stirring.

Example 8

A moisturising body cocktail was prepared from - the following ingredients:

Oil from Example 1 5.0 to 20.0 wt%

Super refined grapeseed oil( 1 ) 20.0 wt%

Tocopheryl acetate(2) 2.0 wt%

Caprylic/capric triglycerides (Crodamol GTCC)(1 ) to 100 wt% Perfume, preservatives, colour qs

( 1 ) From Croda

(2) From Roche

The body cocktail was prepared by combining the preservatives and the caprylic/capric triglycerides with gentle warming and stirring. The resultant mixture was stirred to cool. The remaining ingredients were added, whilst stirring.

Example 9

A dispersible bath oil was made from the following ingredients:

Oil from Example 1 1.0 to 5.0 wt% Tocopheryl acetate (2) 3.0-5.0 wt%

Laureth-3 ( Volpo L3 Special) ( 1 ) 12.5 wt%

Isopropyl myristate (Crodamol IPM) ( 1 ) 20.0 wt%

Caprylic/capric triglycerides (Crodamol GTCC)( 1 ) to 100 wt%

Perfume, preservatives, colour qs

( 1 ) From Croda

(2) From Roche

The bath oil was prepared by adding the preservatives to the caprylic/capric triglycerides with gentle warming and stirring. The remaining ingredients were added, and the resultant mixture was stirred to cool.

Example 10

A skin lotion was prepared from the following ingredients: Oil Phase:

Oil from Example 2 5.0- 10.0 wt%

C₁₀-C₃₀ cholesterol/lanosterol esters (Super Sterol ester) ( 1 ) 1 .0 wt%

Stearic acid (Crosterene SA4130) ( 1 ) 2.0 wt% Glyceryl stearate S/E (GMS S/E GE0802)( 1 ) 2.0 wt%

Nonionic emulsifying wax (Polawax GP200)( 1 ) 0.75 wt%

Water Phase:

Glycerin 6.0 \vt% Triethanolamine 0.9 wt%

Deionised water to 100 wt%

Perfume, preservatives, colour qs

( 1 ) From Croda

The slcin lotion was prepared by heating the oil and water phases separately to 65-70°C, then adding the water phase to the oil phase while stirring. The resultant mixture was stirred to cool, and the perfume was added at 45 °C.

Example 1 1

An emollient slcin cream was prepared from the following ingredients:

Oil Phase:

Oil from Example 2 10 wt% Nonionic emulsifying wax (Polawax GP200)( 1 ) 4.0 wt%

Synthetic beeswax (Syncrowax BB4)( 1 ) 2.0 wt%

Myristyl myristate (Crodamol MM)( 1 ) 1.0 wt%

Butylated hydroxytoluene 0.05 wt% Water Phase:

Carbomer 941 (Carbopol 941 )(2) 0.2 wt%

Triethanolamine 0.2 wt%

Deionised water to 100 wt% Perfume, preservatives colour qs

( 1 ) From Croda

(2) From B F Goodrich

The slcin cream was prepared by hydrating the Carbopol 941 in water at 60-70°C, then adding the rest of the aqueous phase components at a similar temperature while stirring. The oil phase components were heated to 65-70°C, then the water phase components were added to the oil phase components at 65 °C whilst stirring. The perfume was added when the cream had cooled to below 45 °C.

Example 12

An emollient slcin cream was prepared from the following ingredients:

Oil Phase: Oil from Example 2 20 wt%

Nonionic emulsifying wax (Polawax GP200) ( 1 ) 5.0 wt%

Synthetic beeswax (Syncrowax BB4)( 1 ) 2.0 wt%

Cetostearyl stearate (Crodamol CSS( l) 5.0 wt%

Butylated hydroxytoluene 0.05 wt%

Water Phase:

Carbomer 941 (Carbopol 941 )(2) 0.2 wt%

Triethanolamine 0.2 wt%

Glycerin 3.0 wt% Deionised water to 100 wt%

Perfume, preservatives colour qs

( 1 ) From Croda (2) From B F Goodrich

The skin cream was prepared by hydrating the Carbopol 941 in water at 60-70°C, then adding the rest of the aqueous phase components at a similar temperature while stirring. The oil phase components were heated to 65-70°C, then the water phase components were added to the oil phase components at 65 °C whilst stirring. The perfume was added when the cream had cooled to below 45 °C.

Example 13

An emollient dispersible bath oil was prepared from the following ingredients:

PEG-20 Evening Primrose glycerides (Crovol EP40) ( 1 ) 15.0 wt%

Oleyl alcohol (Novol) ( 1 ) 17.5 wt%

Octyl palmitate (Crodamol OP)( 1 ) 8.0 wt% Oil from Example 2 1.0 to 20.0 wt%

Light mineral oil (25cS/25 °C) to 100 wt%

Perfume, preservatives, colour qs

( 1 ) from Croda

The bath oil was prepared by blending all the ingredients together at ambient temperature. Example 14

A lipid emulsion for dietetic use was prepared from the following ingredients:

Oil from Example 1 10.0 wt%

Lecithin (Centomix E)( 1 ) 2.0 wt%

Sorbitan monolaureate (Crill 1 )(2) 1 .66 wt%

Polysorbate-20 (Crillet 1 )(2) 0.34 wt%

Distilled water 86 wt%

( 1 ) From Stem

(2) From Croda

The emulsion was prepared by adding the emulsifiers to the oil, then adding the water while homogenising the mixture in a suitable mixer, such as a homogeniser. The mixture was homogenised for 5 minutes. The resultant emulsion can be used for human ingestion as a dietary supplement. It can be used as an additive for milk or milk drinks.

Example 15

A lipid emulsion for dietetic use was prepared from the following ingredients:

Oil from Example 2 10.0 wt% Sorbitan monolaureate (Crill 1 )( 1 ) 1.66 wt%

Polysorbate-20 (Crillet 1 ) ( 1 ) 0.34 wt%

Distilled water 88 wt%

( 1 ) From Croda The emulsion was prepared by adding the emulsifiers to the oil, then adding the water while homogenising the mixture in a suitable mixer, such as a homogeniser. The mixture was homogenised for 5 minutes. The resultant emulsion can be used for human ingestion as a dietary supplement. It can be used as an additive for milk or milk drinks.

Whilst certain embodiments of the invention have been described above, it will be appreciated that modifications can be made.

Claims

1 . A composition for topical application to, or oral ingestion by, the human or animal body, comprising an oil extracted from the seeds of the Borignaceae family, or a physiologically acceptable derivative thereof, in combination with a physiologically acceptable carrier.

2. A composition according to claim 1 , wherein the carrier includes a moisturiser.

3. A composition according to claim 1 or 2, wherein the carrier includes a surfactant.

4. A composition according to claim 1 , 2 or 3, wherein the carrier includes a UV blocker/absorber.

5. A composition according to any preceding daim, containing from 1 wt% to 20 wt% of said oil.

6. A composition according to any preceding claim, containing fatty acids corresponding to the triglycerides of said oil.

7. A composition according to any preceding claim, wherein the seeds are of the genus Echium.

8. A composition according to any preceding claim, wherein the seeds are of the genus Echium Vulgaris, Echium Plantagineum or Trichodesma Zeylanicum.

9. A composition according to any preceding daim, wherein the oil contains at least 5 wt% of the triglyceride of stearidonic acid.

10. A composition according to any preceding claim, wherein the oil contains at least 10 wt% of the triglyceride of stearidonic acid.

1 1 . A composition according to any one of claims 1 to 8, wherein the derivative is a fatty acid derivative containing at least 5 wt% stearidonic acid.

12. A composition according to any one of claims 1 to 8, wherein the derivative is a fatty acid derivative containing at least 10 wt% stearidonic acid.

13. The use of an oil extracted from seeds of the borignaceae family, or a derivative thereof, in topical application to, or oral ingestion by, the human or animal body.

14. The use of an oil extracted from seeds of genus Echium of the borignaceae family, or a derivative thereof, in topical application to, or oral ingestion by, the human or animal body.

15. The use of an oil extracted from seeds of the genus Echium Vulgaris or Echium Plantagineum of the borignaceae family, or a derivative thereof, in topical application to, or oral ingestion by, the human or animal bodv.

16. The use according to daim 13, 14 or 15, wherein the oil, or derivative thereof, is provided in combination with a physiologically acceptable carrier.

17. The use according to claim 13, 14, 15 or 16, wherein the oil contains at least 5% of the triglyceride of stearidonic acid.

18. The use according to daim 13, 14, 15 or 16, wherein the oil contains at least 10% of the trigylceride of stearidonic acid.

19. A composition containing stearidonic acid or the triglyceride of stearidonic acid, comprising an oil extracted from the Echium genus of the seeds of the Borignaceae.

20. A composition according to claim 19, wherein the oil is extracted from the genus Echium Vulgaris or Echium Plantagineum.

2 1 . A composition according to claim 19 or 20, comprising at least 10 wt% stearidonic acid or the triglyceride of stearidonic acid.