COMPOSITION COMPRISING ONE OR MORE ESTERIFIED PHYTOSTEROLS AND/OR PHYTOSTANOLS INTO WHICH ARE SOLUBILIZED ONE OR MORE UNESTERIFIED PHYTOSTEROLS AND/OR PHYTOSTANOLS, IN ORDER TO ACHIEVE THERAPEUTIC AND FORMULATION BENEFITS

Abstract

A composition comprises one or more free (unesterified) phytosterols and/or phytostanols which are substantially completely dissolved in one or more esterified phytosterols and/or phytostanols. The present invention further provides a composition comprising one or more esterified phytosterols and/or phytostanols which are substantially completely dissolved in an edible oil.

Description

EXAMPLES

The present invention is described by the following non-limiting examples:

Example 1

Formulation and Processing for Fat Spreads Containing Stanol—Sterol Ester Mixture

Plain Fat Spread
% Sterols as stanols          20.00
Total sterols and stanols (%) 7.38
Serving size (g)              10
Servings per day              3
Sterol intake g/day           2.22

Formulation

Fat Phase
Canola Oil (Clear Valley 65, Cargill) 28.227%
Sterol Ester (Phytosource)       11.11%
Solid Fat (Magfat CAF 50, Premium Vegetable Oils) 2.000%
Flavour (BuFlaCon 15X fat, DairyChem) 0.020%
Mono- and Di-glycerides (MONO-DI HV 60, Danisco) 0.300%
Lecithin (Leciprime 1800 IPM, Cargill) 0.080%
Stanol (Phytosource)             0.74%
Beta Carotene (22% HS HP, BASF)  0.002%

Water Phase
Water                            52.081%
Buttermilk Powder                1.000%
Pectin (Grindsted Pectin RS 400, Danisco)I 0.500%
Starch (EmTex 12688, Cerestar)   2.400%
Flavour DairyChem (BuFlaCon #200 NND) 0.040%
Citric acid (to pH 4.8) (ADM)    0.006%
Salt (Morton)                    1.500%

Procedure

• • 1. Weigh buttermilk powder, starch, citric acid and salt, to create a homogenous powder pre-mix
  • 2. Heat the water to 85° C. and slowly add pectin, stirring with a high shear mixer until solution is clear. Allow to hydrate for 5 minutes
  • 3. Slowly, add powder pre-mix to the pectin solution, and stir well until uniform, using a high shear mixer (make sure there are no clumps left in suspension)
  • 4. Add the water soluble flavour
  • 5. Pasteurize at 60° C. for 15 minutes (or a different combination of time and temperature)
  • 6. Weigh canola oil and add it in a swept surface emulsion tank. Heat the oil to 85° C.
  • 7. Add solid fat and keep mixing until it is completely melted
  • 8. Add stanol an keep mixing until it is completely dissolved
  • 9. Add sterol esters, while mixing continuously
  • 10. After the oil phase becomes clear, add mono & di-glycerides, lecithin, fat soluble flavour and colour, while mixing until homogenous
  • 11. Start adding the water phase into the fat phase, while maintaining the temperature at 65-70° C. and mixing continuously until the emulsion is uniform
  • 12. Pump the emulsified mixture into the swept surface heat exchanger and pinworker
  • 13. Package

Example 2

Fat Spread Containing Omega-3-Fatty Acids
% Sterols as stanols          20.00
Total sterols and stanols (%) 7.38
Serving size (g)              10
Servings per day              3
Sterol intake g/day           2.22
% Omega fatty acids           1.68
Omegas intake g/day           0.66

Formulation

Fat Phase
Canola Oil (Clear Valley 65, Cargill) 25.427%
Flaxseed oil (>60% omega-3-fatty acids) (Omegaflo, Omega 2.800%
Nutrition)
Sterol Ester (Phytosource)       11.11%
Solid Fat (Magfat CAF 50, Premium Vegetable Oils) 2.000%
Flavour (BuFlaCon 15X fat, DairyChem) 0.020%
Mono- and Di-glycerides (MONO-DI HV 60, Danisco) 0.300%
Lecithin (Leciprime 1800 IPM, Cargill) 0.080%
Stanol (Phytosource)             0.74%
Beta Carotene (22% HS HP, BASF)  0.002%

Water Phase
Water                            52.081%
Buttermilk Powder                1.000%
Pectin (Grindsted Pectin RS 400, Danisco)l 0.500%
Starch (EmTex 12688, Cerestar)   2.400%
Flavour DairyChem (BuFlaCon #200 NND) 0.040%
Citric acid (to pH 4.8) (ADM)    0.006%
Salt (Morton)                    1.500%

Procedure

• • 1. Weigh buttermilk powder, starch, citric acid and salt, to create a homogenous powder pre-mix
  • 2. Heat the water to 85° C. and slowly add pectin, stirring with a high shear mixer until solution is clear. Allow to hydrate for 5 minutes
  • 3. Slowly, add powder pre-mix to the pectin solution, and stir well until uniform, using a high shear mixer (make sure there are no clumps left in suspension)
  • 4. Add the water soluble flavour
  • 5. Pasteurize at 60° C. for 15 minutes (or a different combination of time and temperature)
  • 6. Weigh canola and fish oil and add them in a swept surface emulsion tank. Heat the oil to 85° C.
  • 7. Add solid fat and keep mixing until it is completely melted
  • 8. Add stanol an keep mixing until it is completely dissolved
  • 9. Add sterol esters, while mixing continuously
  • 10. After the oil phase becomes clear, add mono & di-glycerides, lecithin, fat soluble flavour and colour, while mixing until homogenous
  • 11. Start adding the water phase into the fat phase, while maintaining the temperature at 65-70° C. and mixing continuously until the emulsion is uniform
  • 12. Pump the emulsified mixture into the swept surface heat exchanger and pinworker
  • 13. Package

Example 3

Plain VIVOLA ™ Oil (an oil useful for cooking and dressings etc . . . )
% Sterols as stanols          20.00
Total sterols and stanols (%) 5.12
Serving size (g)              12
Servings per day              3
Sterol intake g/day           1.84

Ingredients
MCT Oil (NEOBEE 1053, Stepan)    63.361%
Canola Oil (Safeway)             13.270%
Olive Oil (Bertolli Extra Light) 11.880%
Coconut Oil (Omegaflo, Omega Nutrition) 6.050%
Tall Oil Sterol Esters (Phytosource) 5.10%
Tall Oil Stanols (Phytosource)   0.34%

Procedure

• • 1. Weigh MCT oil and stanol and blend together in a stainless steel vessel. Stir well using a Caframo mixer.
  • 2. Heat the MCT oil with stanol at 70° C. with continuous stirring for 10 minutes until all stanol powder is fully dissolved.
  • 3. Add sterol esters and continue mixing until they are fully dissolved
  • 4. Cool down to 50° C. leaving the mix at room temperature and then add coconut oil, olive oil, canola oil and flaxseed oil in this particular order.
  • 5. Leave the oil blend to cool down at room temperature.
  • 6. Fill the oil into bottles and then seal with caps.
  • 7. Store VIVOLA™ oil at room temperature.

Example 4

VIVOLA ™ Oil Containing Omega-3-Fatty Acids
% Sterols as stanols            20.00
Total sterols and stanols (%)   5.12
Serving size (g)                12
Servings per day                3
Sterol intake g/day             1.84
% Omega fatty acids             3.86
Omegas fatty acids intake g/day 1.39

Ingredients
MCT Oil (NEOBEE 1053, Stepan)    63.361%
Olive Oil (Bertolli Extra Light) 11.880%
Canola Oil (Safeway)             6.830%
Flaxseed Oil (Omegaflo, Omega Nutrition) 6.440%
Coconut Oil (Omegaflo, Omega Nutrition) 6.050%
Tall Oil Sterol Esters (Phytosource) 5.10%
Tall Oil Stanols (Phytosource)   0.34%

Procedure

• • 1. Weigh MCT oil and stanol and blend together in a stainless steel vessel. Stir well using a Caframo mixer.
  • 2. Heat the MCT oil with stanol at 70° C. with continuous stirring for 10 minutes until all stanol powder is fully dissolved.
  • 3. Add sterol esters and continue mixing until they are fully dissolved
  • 4. Cool down to 50° C. leaving the mix at room temperature and then add coconut oil, olive oil, canola oil and flaxseed oil in this particular order.
  • 5. Leave the oil blend to cool down at room temperature.
  • 6. Fill the oil into bottles and then seal with caps.
  • 7. Store VIVOLA™ oil at room temperature.
  • 8. Attention! This oil may show some precipitation if it will be stored at temperatures below 8° C.

Example 5

Chewable Candies
% Sterols as stanols          20.00
Total sterols and stanols (%) 5.12
Serving size (g)              12
Servings per day              3
Sterol intake g/day           1.84

Ingredients
Corn syrup (White, Crown Lily)   38.880%
Sugar (Golden Yellow, Rogers)    34.990%
Water                            10.144%
Tall Oil Sterol Esters (Phytosource) 7.69%
Corn starch (Safeway)            4.670%
Skim milk powder (Safeway)       3.110%
Tall Oil Stanols                 0.51%

Procedure

• • 1. Weigh corn syrup and sugar into a saucepan. Warm up and mix until all sugar is melted.
  • 2. Add the sterol esters into the syrup mixture, and keep mixing until they are fully dissolved.
  • 3. Weigh milk powder, corn starch and stanol, and add them into the water. Blend them homogenously.
  • 4. Heat the water mixture to 70-80 C.
  • 5. Transfer the water mixture into the syrup mixture.
  • 6. Heat the mixture and keep stirring up until the temperature reaches 121 C.
  • 7. Pour the mixture into a Pyrex baking tray. Cool it down to ˜35 C.
  • 8. Cut into squares and wrap in waxed paper.

Example 6

Processed Cheddar Cheese
% Sterols as stanols          20.00
Total sterols and stanols (%) 5.98
Serving size (g)              30
Servings per day              1
Sterol intake g/day           1.80

Ingredients
Cheddar Cheese Curd (Laack Cheese, WI) 88.15%
Tall Oil Sterol Esters (Phytosource) 9.00%
Disodium Phosphate (DSP, Rhodia Foods) 1.5%
Trisodium Phosphate (TSP, Rhodia Foods) 0.75%
Tall Oil Stanols (Phytosource)   0.60%

Procedure

• • 1. Add Cheddar curd, stanol powder, sterol esters and stabilizers (i.e. DSP and TSP) to the cheese cooker (all at once) and start heating directly to ˜76° C. (169° F.), while mixing continuously. Equipment: Custom Stainless Equipment Co. Santa Rosa, Calif. 95401, Model No: CDB-0718 FVX, Serial No: 82079
  • 2. Mold/Package in 5 lb loaf boxes with liners
  • 3. Store in cooler

Example 7

Chocolate
% Sterols as stanols          20.00
Total sterols and stanols (%) 5.21
Serving size (g)              12
Servings per day              3
Sterol intake g/day           1.87

Ingredients
Regular/Sugar Free Dark Chocolate (Schokinag) 86.440%
Tall Oil Sterol Esters (Phytosource) 7.83%
Liquid Coconut Oil (Kokoheart-23, Bunge 3.095%
Foods/Solae)
Butter Oil (Lactantia, Parmalat) 1.895%
Tall Oil Stanols (Phytosource)   0.52%
Lecithin (Canasperse U.B. F. -K, Bunge Foods/ 0.220%
Solae)

Procedure

1. Filling Mixture:

• • a. Weigh 25,000 g chocolate and mix it at 28 C with stanols, coconut oil, lecithin, and half of sterol esters. Continue mixing until homogenous.

2. Chocolate Shells:

• • a. Melt the rest of the chocolate in designated melter, then add the butter oil and the rest of sterol esters. Mix well until uniform.
  • b. Pump melted chocolate to the designated tempering unit.
  • c. Pump tempered chocolate to the depositing stations of the moulding machines

3. Add the filling mixture into the temperate chocolate moulds

4. Cool down the mould through a cooling tunnel

5. Package the chocolate

Example 8

Mayonnaise
% Sterols as stanols          20.00
Total sterols and stanols (%) 3.99
Serving size (g)              15
Servings per day              3
Sterol intake g/day           1.79

Ingredients
Tall Oil Stanols (Phytosource)   0.40%
Tall Oil Sterol Esters (Phytosource) 6.00%
Canola oil (Safeway)             43.721%
Fresh Egg Yolk (Safeway)         21.930%
Water                            15.020%
Modified Starch (‘Textra’ - NACAN) 3.880%
Vinegar (Safeway)                3.680%
Mustard (Safeway)                2.520%
Lemon Juice (Safeway)            2.100%
Salt (Morton)                    0.750%

Procedure

• • 1. Weigh canola oil and stanol and blend together in a stainless steel vessel. Stir well using a Caframo mixer.
  • 2. Heat the canola oil with stanol at 70° C. with continuous stirring for 10 minutes until all stanol powder is fully dissolved.
  • 3. Add sterol esters and continue mixing until they are fully dissolved
  • 4. Mix starch with cold water to create a thick slurry (20.54%). Heat the slurry at high temperature until it starts boiling and becomes a transparent paste
  • 5. Separately, mix the egg yolks slowly, for 1-2 minutes
  • 6. Slowly, start adding the oil, while also adding the starch paste, little by little. Continue to alternate mixing in the oil and the starch paste until they are both uniformly incorporated into the mayonnaise
  • 7. Add the vinegar, mustard, lemon juice and salt, one by one, and mix well until uniform

Example 9

Ranch Dressing
% Sterols as stanols          20.00
Total sterols and stanols (%) 2.00
Serving size (g)              30
Servings per day              3
Sterol intake g/day           1.80

Ingredients
Butter Milk             46.93%
Canola oil              20.70%
Vinegar                 7.75%
Skim milk powder        7.49%
Buttermilk Powder       3.14%
Tall Oil Sterol Ester   3.01%
Fresh Egg Yolk          2.33%
Parmesan                2.01%
Whey protein            1.66%
Lemon juice             1.24%
Salt                    0.99%
Butter Buds - High      0.93%
Concentrate
Sugar                   0.59%
TIC Gum - Saladizer 250 0.20%
Onion powder            0.19%
Garlic powder           0.19%
Sodium Benzoate         0.15%
Tall Oil Stanol         0.20%
Parsley                 0.09%
Chives                  0.09%
Oregano                 0.09%
White pepper            0.04%

Procedure

• • 1. Weigh canola oil and stanol and blend together in a stainless steel vessel.
  • 2. Stir well using a Caframo mixer.
  • 3. Heat the canola oil with stanol at 70° C. with continuous stirring for 10 minutes until all stanol powder is fully dissolved.
  • 4. Add sterol esters and continue mixing until they are fully dissolved
  • 5. Mix slowly egg yolk with gum, then start adding canola oil (prepared above) little by little
  • 6. Slowly, start adding the buttermilk, and continue mixing until homogenous Separately, mix all dry ingredients, then slowly start adding the powder mix into the liquid mix above
  • 7. Add vinegar and lemon juice

Example 10

Granola Bar
% Sterols as stanols          20.00
Total sterols and stanols (%) 7.18
Serving size (g)              25
Servings per day              1
Sterol intake g/day           1.80

Ingredients           %
Cereals
Quick Oats            30.970
Crisp Rice            10.700
Coconut               6.280
Binder
Tall Oil Stanol       0.72
Tall Oil Sterol Ester 10.80
Canola Oil            3.330
White Sugar           7.500
Molasses              3.000
Corn Syrup            25.500
Salt                  0.200
Vanilla Flavour       0.800
SSL                   0.200

Procedure

• • 1. Mix cereals and coconut
  • 2. Melt stanol in oil bringing to a boil. Take pot from heat source, add sterol esters, honey, molasses and sugar and
  • 3. Mix well, while binder is cooling down and becomes thicker
  • 4. Add flavour to the binder and mix well.
  • 5. Add binder to cereal mixture while hot (60-70 C), otherwise it will be too tough and will not allow mixing
  • 6. Mix well and roll in a mold.
  • 7. Cut the bars, then cool them down and pack

Examples 11—describes the use of liquid “premixes” of the composition of the present invention, in the preparation of various foods and nutraceuticals:

Example 11

Foods Formulated With Pre-Mixes

TABLE 1
Examples Of 100 kg of Pre-Mixes For Foods
	PREMIX
	A	B	C	D
Free Stanols	1.77	1.39	4.22	4.22
Sterol Esters	97.73	76.68	61.63	61.63
Omega fatty acids	0.00	21.93	0.00	34.15
Canola Oil	0.50	0.00	34.15	0.00
Total (kg)	100	100	100	100
Percent of total sterols as	97.21	97.21	90.23	90.23
esters
Percent of total sterols as	14.00	14.00	20.00	20.00
stanols

All pre-mixes are prepared under conditions that exclude oxygen; usually with a nitrogen blanket. All omega fatty acids have been deodourized prior to use. The omega fatty acids can be either purified omega fatty acid from fish oil (>60% omegas) or flax seed oil (>60% alpha-linoleic acid). The sterol esters have a sterol content of >60%.

Method of Preparation No. 1:

• 1. Heat the sterol esters to 90 degrees, with mixing add vegetable oil and or omega fatty acids and stanols.
• 2. Fill mixtures into food grade steel drums under a nitrogen blanket.
• 3. Store mixtures at refrigerator temperature.

Method of Preparation No. 2

• 1. The esters at the end of the manufacturing process are at temperatures above 100 degrees. The esters are then passed through a deodourizing process.
• 2. The exit stream is blended with stanols that have been dissolved at 90 degrees in vegetable oil and or omega fatty acids.
• 3. Fill mixtures into food grade steel drums under a nitrogen blanket.
• 4. Store mixtures at refrigerator temperature.

Margarines - Dosages, Stanols And Omega Fatty Acids Content
	PREMIX
	A	B	C	D
	Servings per day	3	3	3	3
	Serving Size (g)	10.0	10.0	10.0	10.0
	% Total Sterols in food	6.00	6.00	6.00	6.00
	Gm Sterols per day	1.80	1.80	1.80	1.80
	Gm Omega-FA per day	0.00	0.50	0.00	0.90

TABLE 3
Formulations of Margarines
Fat Phase (Total 42.5 kg)	A	B	C	D
Kg of pre-mix/100 kg	9.9	12.7	14.6	14.6
Canola oil	18.3	15.6	13.6	13.6

Solid fat, 2.0 kg; Flavour, 0.02 kg; mono- and diglycerides, 0.30 kg; lecithin, 0.08 kg, beta-carotene 0.002 kg.

Water Phase: (Total 57.5 kg) water, 52.1 kg; Buttermilk powder, 1.0 kg; Pectin, 0.5 kg; Starch, 2.4 kg; Flavour, 0.04 kg; citric acid, 0.006 kg, salt, 1.5 kg

Method of Preparation (as Described above in Previous Examples with Premix Added at Steps 8/9)

TABLE 4
Mayonaises And Salad Dressings, Dosages, Stanols And Omega Fatty
Acids Content
	PREMIX
	A	B	C	D
Servings per day	3.00	3.00	3.00	3.00
Serving Size (g)	15.00	15.00	15.00	15.00
% Total Sterols in food	4.00	4.00	4.00	4.00
% total sterols as stanols	14.00	14.00	20.00	20.00
Gm Sterols per day	1.80	1.80	1.80	1.80
Gm Omega-FA per day	0.00	0.50	0.00	0.50
Kg of pre-mix/100 kg of food	6.60	8.42	15.31	15.31

TABLE 5
Mayonaises And Salad Dressings Formulations
	PREMIX
	A	B	C	D
Kg of pre-mix/100 kg of food	6.60	8.42	15.31	15.31

TABLE 6
Processed Cheese, Dosages, Stanols And Omega Fatty Acids
	A	B	C	D
Servings per day	3.00	3.00	3.00	3.00
Serving Size (g)	30.00	30.00	30.00	30.00
% Total Sterols in food	2.00	2.00	2.00	2.00
% total sterols as stanols	14.00	14.00	20.00	20.00
Gm Sterols per day	1.80	1.80	1.80	1.80
Gm Omega-FA per day	0.00	0.50	0.00	0.50
Kg of pre-mix/100 kg of	3.30	4.21	7.66	7.66
cheese

TABLE 7
Processed Cheese formulation
	A	B	C	D
	Kg of pre-mix/100 kg of	3.30	4.21	7.66	7.66
	cheese

TABLE 8
Chocolates pre-mixes for formulations - 100 kg
E
Stanols       3.00
Sterol Esters 70.89
Coconut oil   14.59
Butter Oil    10.83
Lecithin      0.69

TABLE 9
Chocolates, dosages, and stanols using pre-mixes
                               E
Servings per day               3
Serving Size (g)               10.0
% Total Sterols in food        6.00
% total sterols as stanols     17.00
% Total phytosterols as esters 93.72
Gm Sterols per day             1.80
Gm Omega-FA per day            0.00
Kg of pre-mix/100 kg of        13.2
Chocolate

TABLE 10
Chocolate Filling Formulation
E
Kg of pre-mix/100 kg of Chocolate 13.2

TABLE 11
Examples of softgels with sterols esters and free tall oil stanols,
dosages and stanols content
	Formulation
	E	F	G	H
Capsules per day	4	4	4	6
Gm sterols per day	1.8	1.8	1.8	1.8
Gm sterols per capsule	0.450	0.450	0.450	0.300
% Total sterols as esters	97.21	94.88	92.56	90.23
% Total sterols as	14.00	16.00	18.00	20.00
stanols

TABLE 12
100 kg batches of fill material
	Formulation
	E	F	G	H
	Free Stanols (kg)	1.76	3.10	3.64	4.00
	Sterol Esters (kg)	97.24	90.90	71.56	58.48
	Vegetable oil (kg)	1.00	6.00	24.80	37.52
	Total Weight (kg)	100	100	100	100

TABLE 13
Soft gelatin capsules fill weights
	Formulation
	E	F	G	H
	Gm free stanols per	0.013	0.024	0.035	0.031
	capsule
	Gm sterol esters per	0.729	0.712	0.694	0.451
	capsule
	Gm vegetable oil per	0.007	0.047	0.241	0.290
	capsule
	Fill weight of capsule	0.750	0.783	0.970	0.772
	(gm)

The fill material with formulation E was somewhat viscous and recoveries of capsules were relatively low. The higher proportions of vegetable oil as shown in formulations F, G, and H will result in a more liquid fill and higher recoveries. The solubility of the stanols was about 3% in the esters, but was over 4% in corn oil used in this example.

Procedure: The stanols component was blended with the vegetable oil in a cobalt mill and then mixed with esters which had been warmed to 40 degrees.

Capsule material contained beef gelatin (BSE free), glycerin, water, titanium oxide masking agent, and light yellow colouring agent.

Although beef gelatin was used in formulation E, other gelatins such as, pork, fish or non-animal (plant) gelatins may also easily be used.

Example 12 (Dissolution of Stanols in Esters)

Composition of:

0.344% stanol

11.5% sterol esters

Stanols

Code: FCP-3P2

BRI ID: FM-P2-83

Manuf.lot# 5QC27H-2

Description (Dry Form, Room Temp):

• • white powder composed of longitudinally shaped granules/crystals. White flour-like feel.

Sterol Esters

Description:

Temp (−) 18 C—solid

Temp 13-15 C—sticky texture, viscosity less than that of, for example, honey at room temperature, therefore has a semi-high viscosity. Able to be pumped?—no

Temp 35 C-viscosity—slightly more viscous than regular canola oil at room temp

• • appearance—resembles canola oil (clear, golden color)

Temp 60 C viscosity—that of canola oil at room temp, however more sticky to touch than normal oil

Stanols with Sterol Esters Description

• • 1. 0.344 g stanol added to 11.5 g sterol esters. Sterol ester increased to temp 90° C.

Stanols dissolved fully

• • 2. Stanol/sterol esters, fully dissolved, cooled to 35 C

No apparent recrystallization of stanols into its original crystals. Sterol esters appear smooth, no appearance of crystals within

• • 3. Stanol/sterol esters, same sample as above, cooled to 25 C

Stanols dissolved fully, Good appearance and handling.

End Composition: 97% esters and 3% stanols

REFERENCES

• 1. Law M. R., Wald N. J., Wu., Hacksaw Z A., Bailey A.; Systemic underestimation of association between serum cholesterol concentration and ischemic heart disease in observational studies: Data from BUPA Study; Br. Med. J. 1994; 308:363-366
• 2. Law M. R., Wald N. J., Thompson S. G.; By how much and how quickly does reduction in serum cholesterol concentration lower risk of ischemic heart disease? Br. Med. J. 1994; 308:367-373
• 3. Kannel W B, Castelli W P, Gordon T et al. Lipoprotein cholesterol in the prediction of atherosclerotic disease: new perspectives based on the Framingham Heart Study. Ann Intern Med. 1995; 90:85-91
• 4. Singh B K, Mehta J L. Management of dyslipidemia in the primary prevention of coronary heart disease. Curr Opin Cardiol. 2002; 17:503-11
• 5. La Rosa J. C., Hunninghake D. Bush D. et al.; The cholesterol facts: A summary of the evidence relating to dietary fats, serum cholesterol and coronary heart disease: A joint statement by the American Heart Association and the National Heart, Lung and Blood Institute. Circulation 1990; 81:1721-1733
• 6. Havel R. J., Rapaport E. Drug Therapy: Management of Primary Hyperlipidemia. New England Journal of Medicine, 1995; 332:1491-1498
• 7. Kuccodkar et al.; Effects of plant sterols on cholesterol metabolism. Atherosclerosis, 1976; 23:239-248
• 8. Lees R. S., Lees A. M. Effects of sitosterol therapy on plasma lipid and lipoprotein concentrations. In: Greten H (Ed) Lipoprotein Metabolism. Springer-Verlag, Berlin, Heidelberg, New York, 1976:119-124
• 9. Lees A. M., Mok H. Y. I., Lees R. S., McCluskey M. A., Grundy S. M. Plant sterols as cholesterol-lowering agents: clinical trials in patients with hypercholesterolemia and studies of sterol balance. Atherosclerosis 1977; 28: 325-338

FURTHER REFERENCES

• Amundsen A L, Ntanios F, Put N, Ose L.Long-term compliance and changes in plasma lipids, plant sterols and carotenoids in children and parents with FH consuming plant sterol ester-enriched spread. Eur J Clin Nutr. 2004 December; 58(12):1612-20.
• Assmann G, Cullen P, Erbey J, Ramey D R, Kannenberg F, Schulte H. Plasma sitosterol elevations are associated with an increased incidence of coronary events in men: results of a nested case-control analysis of the Prospective Cardiovascular Munster (PROCAM) study. Nutr Metab Cardiovasc Dis. 2006 January; 16(1):13-21.
• Berges R R, Kassen A, Senge T. Treatment of symptomatic benign prostatic hyperplasia with beta-sitosterol: an 18-month follow-up. BJU Int. 2000 May; 85(7):842-6.
• Coleman C I, Hebert J H, Reddy P. The effect of phytosterols on quality of life in the treatment of benign prostatic hyperplasia. Pharmacotherapy. 2002 November; 22(11):1426-32
• Glueck C J, Speirs J, Tracy T, Streicher P, Illig E, Vandegrift J.Relationships of serum plant sterols (phytosterols) and cholesterol in 595 hypercholesterolemic subjects, and familial aggregation of phytosterols, cholesterol, and premature coronary heart disease in hyperphytosterolemic probands and their first-degree relatives. Metabolism. 1991 August; 40(8):842-8.
• Gylling H, Siimes M A, Miettinen T A. Sitostanol ester margarine in dietary treatment of children with familial hypercholesterolemia. J Lipid Res. 1995 August; 36(8):1807-12.
• Hallikainen M A, Sarkkinen E S, Uusitupa M I. Plant stanol esters affect serum cholesterol concentrations of hypercholesterolemic men and women in a dose-dependent manner. J Nutr. 2000 April; 130(4):767-76.
• Hendriks H F, Weststrate J A, van Vliet T, Meijer G W. Spreads enriched with three different levels of vegetable oil sterols and the degree of cholesterol lowering in normocholesterolaemic and mildly hypercholesterolaemic subjects.

Eur J Clin Nutr. 1999 April; 53(4):319-27.

• Jones P J, Ntanios F Y, Raeini-Sarjaz M, Vanstone C A.

Cholesterol-lowering efficacy of a sitostanol-containing phytosterol mixture with a prudent diet in hyperlipidemic men.

Am J Clin Nutr. 1999 June; 69(6):1144-50.

• Ketomaki A M, Gylling H, Antikainen M, Siimes M A, Miettinen T A.

Red cell and plasma plant sterols are related during consumption of plant stanol and sterol ester spreads in children with hypercholesterolemia.

J. Pediatr. 2003 May; 142(5):524-31.

• O'Neill F H, Sanders T A, Thompson G R. Comparison of efficacy of plant stanol ester and sterol ester: short-term and longer-term studies. Am J Cardiol. 2005 Jul. 4; 96(1A):29D-36D.
• Scientific Committee on Food Report: General view of the Scientific Committee on Food on the long-term effects of the intake of elevated levels of phytosterols from multiple dietary sources, with particular attention to the effects on β-carotene. SCF/CS/NF/20 ADD 1 Final 3 Oct. 2002.
• Sudhop T, Gottwald B M, von Bergmann K. Serum plant sterols as a potential risk factor for coronary heart disease. Metabolism. 2002 December; 51 (12):1519-21.
• Vanstone C A, Raeini-Sarjaz M, Parsons W E, Jones P J. Unesterified plant sterols and stanols lower LDL-cholesterol concentrations equivalently in hypercholesterolemic persons. Am J Clin Nutr. 2002 December; 76(6):1272-8.
• Weststrate J A, Meijer G W. Plant sterol-enriched margarines and reduction of plasma total- and LDL-cholesterol concentrations in normocholesterolaemic and mildly hypercholesterolaemic subjects. Eur J Clin Nutr. 1998 May; 52(5):334-43.

Claims

1. A composition comprising one or more free (unesterified) phytosterols and/or phytostanols which are substantially completely dissolved in one or more esterified phytosterols and/or phytostanols.

2. The composition of claim 1 comprising free (unesterified) phytostanol which is substantially completely dissolved in one or more esterified phytosterols and/or phytostanols.

3. The composition of claim 1 comprising from 1-15% by weight unesterified phytosterol and/or phytostanol substantially completely dissolved in 85-99% by weight of one or more esterified phytosterols and/or phytostanols.

4. The composition of claim 1 comprising from 1-10% by weight unesterified phytosterol and/or phytostanol substantially completely dissolved in 90-99% by weight of one or more esterified phytosterols and/or phytostanols.

5. The composition of claim 1 comprising from 4-8% by weight unesterified phytosterol and/or phytostanol substantially completely dissolved in 92-96% by weight of one or more esterified phytosterols and/or phytostanols.

6. The composition of claim 1 wherein the composition additionally comprises an edible oil to which the free (unesterifed) phytosterols and/or phytostanols are added prior to the substantially complete dissolution in the esterified phytosterols and/or phytostanols.

7. The composition of claim 6 wherein the edible oil is selected from the group consisting of olive, rapeseed, canola, sunflower, safflower, sesame, soyabean, corn, coconut, peanut, cottonseed, hemp, flaxseed, and pumpkinseed.

8. The composition of claim 1 incorporated into foods, beverages and nutraceuticals.

9. The composition of claim 1 wherein the edible oil is high in one or more of omega 3 polyunsaturated fatty acids, omega 6 polyunsaturated fatty acids and omega 9 polyunsaturated fatty acids.

10. The composition of claim 1 wherein the edible oil is of marine or fish origin.

11. The composition of claim 1 supplemented with omega fatty acids derived from microalgae.

12. The composition of claim 1 wherein the phytosterols and phytostanols are derived from either tall oil or vegetable oil sources.

13. A method of stabilizing from oxidation a composition of one or more esterified phytosterols and phytostanols which comprises solubilizing therein one or more free (unesterified) phytosterols or phytostanols.

14. The method of claim 13 wherein one or more free phytostanols are solubilised therein.

15. The method of claim 13 wherein from 1-15% by weight unesterified phytosterol and/or phytostanol is solubilised in 85-99% by weight of one or more esterified phytosterols and/or phytostanols.

16. A method of maintaining a composition of one or more esterified phytosterols and phytostanols liquid and readily pourable at room temperature which comprises solubilizing therein one or more free (unesterified) phytosterols or phytostanols.

17. The method of claim 16 wherein the free (unesterified) phytosterols or phytostanols are provided for solubilization in a small amount of an edible oil carrier.

18. The composition of claim 1 wherein the phytosterol is selected from the group consisting of sitosterol, campesterol, stigmasterol, brassicasterol (including dihydrobrassicasterol), desmosterol, chalinosterol, poriferasterol, clionasterol, ergosterol, coprosterol, codisterol, isofucosterol, fucosterol, clerosterol, nervisterol, lathosterol, stellasterol, spinasterol, chondrillasterol, peposterol, avenasterol, isoavenasterol, fecosterol, pollinastasterol and all natural or synthesized forms and derivatives thereof, including isomers.

19. The composition of claim 1 wherein the phytostanol is selected from the group consisting of all saturated or hydrogenated phytosterols and all natural or synthesized forms and derivatives thereof, including isomers.

20. The composition claim 1 wherein the esters of phytosterols and/or phytostanols are in form selected from the group consisting of: aliphatic acid esters, aromatic acid esters, phenolic acid esters, cinnamate esters, ferulate esters, phytosterol/phytostanol glycosides, and phytosterol/phytostanol acylglycosides.

21. The composition of claim 8 wherein the phytosterol and/or phytostanol (in free and ester form) is added to in an amount totalling from between 0.05% to 10% by weight of the food or beverage product.

22. The composition of claim 8 wherein the food product is fat-based.

23. The composition of claim 8 wherein the food is selected from the group consisting of dairy products, margarine, spreads, peanut and other butters, shortening, meats, poultry, seafood, sauces, fruits, vegetables, grains, grain-derived products, baked goods, fried snack products, confections and chocolate.