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WO1993015612A1 - Matieres grasses pauvres en calories - Google Patents

Matieres grasses pauvres en calories Download PDF

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Publication number
WO1993015612A1
WO1993015612A1 PCT/EP1993/000222 EP9300222W WO9315612A1 WO 1993015612 A1 WO1993015612 A1 WO 1993015612A1 EP 9300222 W EP9300222 W EP 9300222W WO 9315612 A1 WO9315612 A1 WO 9315612A1
Authority
WO
WIPO (PCT)
Prior art keywords
fatty acid
fat
long chain
fatty acids
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1993/000222
Other languages
English (en)
Inventor
Frederick William Cain
Deryck Josef Cebula
Nanneke Joke De Fouw
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Unilever NV
Original Assignee
Unilever NV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Unilever NV filed Critical Unilever NV
Priority to CA002129631A priority Critical patent/CA2129631A1/fr
Priority to EP93917354A priority patent/EP0625009A1/fr
Publication of WO1993015612A1 publication Critical patent/WO1993015612A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/001—Spread compositions
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/346—Finished or semi-finished products in the form of powders, paste or liquids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G2200/00—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents
    • A23G2200/08—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents containing cocoa fat if specifically mentioned or containing products of cocoa fat or containing other fats, e.g. fatty acid, fatty alcohol, their esters, lecithin, paraffins

Definitions

  • the present invention relates to reduced calorie fats, in particular triglyceride materials containing long chain fatty acids, preferably in combination with medium chain fatty acids.
  • the present invention relates to the use of triglyceride materials containing long chain fatty acids in food-products, especially confectionery products.
  • Triglyceride fats made with long chain fatty acids are reduced in calories, because the long chain fatty acids are poorly digested by the body.
  • WO 91/09537 relates to fat and sugar containing food products, wherein the sugar contains a 5-C-hydroxymethyl hexose or derivative thereof and the fat contains a triglyceride with medium long fatty acid chains and long fatty acid chains.
  • Preferred exemplified medium chain fatty acids are mixtures of C 8 and C 10 fatty acids, the preferred exemplified long chain fatty acid is Behenic acid.
  • WO 91/09099 describes a process for selectively making triglycerides comprising two medium chain fatty acids and one long chain fatty acid, wherein a monoglyceride of a C 18 _ 2 fatty acid is reacted with a C 8 _ 10 fatty acid at a temperature of 140 to 250°C in the absence of a catalyst under the continuous removal of water.
  • the preferred exemplified long chain fatty acid is Behenic acid
  • preferred medium chain fatty acids are mixtures of C 8 and C - ⁇ ⁇ o-
  • WO 91/09098 describes a process for selectively making triglycerides comprising two medium chain fatty acids and one long chain fatty acid, wherein a monoglyceride of a C 18 _ 2 fatty acid is reacted with a C 8 _ 10 anhydride at a temperature of 90 to 190°C in the absence of a catalyst.
  • the preferred exemplified long chain fatty acid is Behenic acid
  • preferred medium chain fatty acids are mixtures of C 8 and C 10 .
  • US 5,023,106 describes a flavoured confectionery product comprising triglycerides with medium and long chain saturated fatty acids, wherein the medium chain fatty acid material is a mixture of Caprylic and Capric acid in a ratio of 4 to 1 to 1 to 4 and the long chain saturated fatty acid is behenic acid. Also described is a process for preparing a flavoured confectionery product containing these materials. Similar confectionery products and processes for producing these are describes in US 4,888,196 (P&G) and EP 390 408.
  • US 4,863,753 discloses a reduced calorie peanut butter comprising a dispersion of finely divided peanut particles in a continuous oil phase, wherein the oil phase comprises medium chain triglycerides.
  • Preferred medium chain fatty acids are C 6 to C 10 saturated fatty acids which are used in combination with C 17 to C 26 unsaturated fatty acids.
  • US 3,595,673 relates to high melting hard butter materials consisting essentially of randomly esterified triglycerides with high levels of C 12 saturated fatty acids in combination with C 16 _ 18 saturated fatty acids and no or low levels of C Q _ 10 , C 14 and C 20 and higher fatty acids.
  • US 3,353,964 (P&G) relates to corandomized triglycerides containing saturated C 6 _ 14 fatty acids and from 0.3 to 5% of 20 _ 22 fatty acids, wherein the ratio between short chain fatty acids and long chain fatty acids is from 100 to 1 to 1 to 1 .
  • EP 422 490 (P&G) relates to unit dosage amounts of triglycerides for absorption of cholesterol containing from 1-10 grams of a triglyceride fat containing high levels of c 20 - 24 saturated fatty acids.
  • Exemplified preferred reduced calorie triglycerides comprise Behenic acid as the long chain fatty acid and C 8 and C 10 mixtures as the remaining fatty acids.
  • EP 322,027 relates to reduced calorie fats made from triglycerides containing medium and long chain saturated fatty acids.
  • the exemplified preferred long chain saturated fatty acid is behenic acid.
  • Preferred exemplified medium chain saturated acids are mixtures of caprylic and capric acid. This document also provides a listing of theoretically possible triglycerides containing mixtures of medium and long chain saturated fatty acids.
  • EP 311 167 (P&G) relates to reduced calorie fats with improved auto-ignition properties, said fats comprising medium and long chain saturated fatty acids in combination with long chain unsaturated fatty acids.
  • the exemplified preferred long chain saturated fatty acid is stearic acid, preferred long chain unsaturated fatty acid are linoleic acid, oleic acid and linolenic acid.
  • the preferred exemplified medium chain saturated fatty acid is caprylic acid.
  • EP 216 419 (P&G) relates to nutritional fats consisting essentially of triglycerides comprising at the 2-position a fatty acid which is either a saturated fatty acid group, or oleoyl or linolenoyl and at the 1- and 3-positions a group selected from n-heptonoyl, n-octanoyl, N-nonanoyl, n- decanonyl and n-undecanoyl.
  • the overall picture emerging from the above mentioned prior art is therefore a preference for combinations of behenic acid and mixtures of C 8 and C 10 fatty acids.
  • the present invention aims at providing novel triglyceride materials comprising a mixture of long chain fatty acids in combination with shorter fatty acids. It is believed that fat compositions of the present invention are advantageous for one or more of the following reasons:
  • the fat compositions of the invention contain fatty acid chains which are favourable as far as their effect on heart health is concerned;
  • fat compositions of the invention are easy to manufacture and to process and are stable upon storage;
  • the present invention relates to a fatty composition
  • a fatty composition comprising 5-100% of a triglyceride material of the formula:
  • R 1 is a C 20 _ 24 fatty acid and R 2 is a C 12 fatty acid; preferably R 1 and R 2 are saturated fatty acid materials. Also preferable R 1 is a C 20 fatty acid.
  • Fat compositions of the invention consist of at least 5% by weight of long chain fatty acid triglycerides, the balance of the fat composition being made up of other fatty materials.
  • fat-compositions of the invention may comprise in addition to the long chain fatty acid triglyceride, optionally up to 95 wt% of further fat components such as other triglyceride materials and lipid fat replacers such as polyol fatty acid esters and jojoba oil, it is preferred that for use in e.g. chocolate products the weight ratio of these fat-components to the long chain fatty acid triglyceride is less than 2 : 1, more preferred less than 1 : 1 or even less than 0.5: 1.
  • the fat- compositions contain long chain fatty acid triglycerides substantially in the absence of other fat components.
  • the ratio of long chain fatty acid triglycerides to other fat components is between 1:19 and 1:1, more 0 preferred 1:12 and 1:3.
  • mixtures of triglyceride materials are present these can generally be detected as such by techniques like GC , HPLC, DSC etc.
  • the present invention is not specific to edible fat- 0 containing compositions in any particular food area. It may be suitably be applied to food products such as spreads, margarines, creams, shortenings, bakery products such as doughs, cakes and biscuits, fried and snack products, fresh, hard and processed cheeses, meat emulsions, 5 mayonnaise and dressings, confectionery products, such as desserts, fillings, chocolates, candies, chews, and ice ⁇ creams.
  • the long chain fatty acid triglycerides of the invention are used in confectionery products, especially in chocolate type confectionary products.
  • the food-product is a spread.
  • Fat compositions for use in chocolate confectionery products preferably comprise in addition to the long chain fatty acid triglyceride material as defined above 0-50% by weight of cocoa butterfat, more preferably 5-40%.
  • Especially preferred fat compositions for use in chocolate confectionary products are solid at ambient temperature
  • the chocolate confectionary product of the invention comprises a fat composition substances having an N-value at 20°C of at least 60, more preferred 70-100, most preferred 80-95 and an N-value at 35 °C of less than 15, more preferred from 0-8 , most preferred from 0-3.
  • the N-value is conveniently measured by nuclear magnetic relaxation technique and is a direct measure of the level of solid fat content at the relevant temperature. This method is suitable described in Fette, Seifen,
  • Preferred spread products of the invention are oil and water emulsions which comprise from 5-95% more preferred 10-90, most preferred 60-90% by weight of the fat composition, the balance of the composition being water and optionally other ingredients like emulsifiers, gelling agents, flavouring, colouring materials, preservatives, etc.
  • Long chain fatty acid triglycerides of the invention may be prepared by any suitable technique for preparing triglyceride materials.
  • a suitable technique may for example include the random esterification of a 1:2 molar mixture of long chain fatty acids and medium chain fatty acids.
  • Food products of the invention can be prepared by any suitable technique.
  • Chocolate confectionery products may for example be made as described in US 4,810,516. preferably the cooling regime applied to the chocolate is such that the product can be demoulded within 30 minutes after moulding.
  • a chocolate product was prepared with the following formulation:
  • A 100% of a triglyceride with 2 C 12 fatty acids and 1 C 20 fatty acid.
  • B 85 wt% of a triglyceride with 2 C 12 fatty acids and 1 C 20 fatty acid and 15 wt% of cocoa butter (added in addition to the cocoa butter which was inherently present in the cocoa powder) .
  • Example A and B are in accordance to the present invention, while examples C and D are included for reference purposes. Products A and B are generally of better quality than products C and D (melting behaviour, crystallisation behaviour etc) .
  • a fat composition A was made of 87 wt% non hydrogenated sunflower oil and 13 wt% of a long chain fatty acid triglyceride with 1 C 20 and two C 12 saturated fatty acids.
  • a third fat composition C was made of the same composition as A, except that there was included 13% of a triglyceride prepared by random esterification of a 2:1 molar mixture of C 12 and C 20 saturated fatty acids.
  • compositions A-C can be used as frying compositions. Compositions A and C are preferred over composition B (reference) .
  • fat composition 80 water 20 monoglyceride (from Palm oil 58°C) 0.1 colouring/flavouring/ preservatives 0.1
  • Standard votator line processing may be used to prepare this product.
  • products with fat compositions A and C are preferred for their oral melting properties to products with fat composition B.
  • a fat composition B is made of 40 wt% of a non hydrogenated soybean oil, 30 wt% of palm oil hardened to a slip melting point of about 43 °C and 30 wt% a long chain triglyceride with one C 20 and two C 12 saturated fatty acids.
  • a fat composition C is made of 40 wt% of a non hydrogenated soybean oil and 60 wt% of a long chain triglyceride with one C 20 and two C 12 saturated fatty acids.
  • a fat composition D is made of 40 wt% of a non hydrogenated soybean oil, 30 wt% of Palm oil hardened to a slip melting point of about 43 °C and 30 wt% of a triglyceride obtained by the random esterification of a 2:1 molar mixture of C 12 and C 20 saturated fatty acids.
  • Fat compositions A-D are used for preparing a bakery margarine of 82 wt% of the fat composition, 1% NaCl, 0.15% monoglyceride (from Palm oil 58°C) , the balance water.
  • Vol-au-vents are prepared from a dough of 1000 wt parts flour (Banket extra ex Meneba) , 800 weight parts of bakery margarine and 560 weight parts water by preparing a predough of water and flour and folding in the bakery margarine at 20°C (6 half turns in three) .
  • the fat compositions B-D are preferred over fat composition A, because of handleability of the fat composition (especially for D) and quality of the final product.
  • Fat A was a C 12 /C 10 /C 22 triglyceride
  • fat B was a randomized C 20 (C 12 ) 2 triglyceride.
  • the fats had the following carbon number profile:
  • the chocolates (1) were manufactured by mixing all dry ingredients with the fat and the lecithin in a ball mill at 60°C for 5.5. hours.
  • the other chocolates (2) were made by adding extra cocoa butter to the chocolates 1.
  • the chocolates were formed into bars by melting the solid chocolate at 52°C in a batch tempering kettle followed by depositing 50 g portions into polycarbonate chocolate moulds (4x3 squares) .
  • the mould temperature was 20°C.
  • the moulds were placed at the centre section of a cooling tunnel, the temperature of the tunnel was set at 15°C, 10°C and 15°C. the moulds were removed from the cooling tunnel and turned upside down.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Confectionery (AREA)
  • Edible Oils And Fats (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Fats And Perfumes (AREA)

Abstract

Une composition de matière grasse comprend 5 à 100 % en poids d'une matière à triglycérides à acide gras à chaîne longue de formule: (I) ou (II), dans lesquelles R1 représente un acide gras C¿20-24 et R?2 représente un acide gras C¿12?. De préférence, les compositions de matière grasse sont utilisées dans des produits alimentaires, notamment dans des produits de confiserie au chocolat.
PCT/EP1993/000222 1992-02-07 1993-02-01 Matieres grasses pauvres en calories Ceased WO1993015612A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CA002129631A CA2129631A1 (fr) 1992-02-07 1993-02-01 Matieres grasses a teneurs en calorie reduites
EP93917354A EP0625009A1 (fr) 1992-02-07 1993-02-01 Matieres grasses pauvres en calories

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9202665.7 1992-02-07
GB929202665A GB9202665D0 (en) 1992-02-07 1992-02-07 Reduced calorie fats

Publications (1)

Publication Number Publication Date
WO1993015612A1 true WO1993015612A1 (fr) 1993-08-19

Family

ID=10710029

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1993/000222 Ceased WO1993015612A1 (fr) 1992-02-07 1993-02-01 Matieres grasses pauvres en calories

Country Status (6)

Country Link
EP (1) EP0625009A1 (fr)
AU (1) AU3452493A (fr)
CA (1) CA2129631A1 (fr)
GB (1) GB9202665D0 (fr)
WO (1) WO1993015612A1 (fr)
ZA (1) ZA93809B (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5492714A (en) * 1994-11-08 1996-02-20 The Procter & Gamble Company Reduced calorie fats which comprise reduced calorie triglycerides containing medium and long chain fatty acids and which exhibit rapid crystallization to beta phase
US5589216A (en) * 1994-11-08 1996-12-31 The Procter And Gamble Company Reduced calorie confectionery compositions which contain reduced calorie fats which exhibit rapid transformation to beta phase
WO1998019554A1 (fr) * 1996-11-06 1998-05-14 Unilever N.V. Cristallisation de graisse de triglyceride
US12439933B2 (en) 2022-06-16 2025-10-14 Savor Foods Limited Fat formulations

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU31173A1 (fr) *
GB874182A (en) * 1957-02-11 1961-08-02 Unilever Ltd Improvements in or relating to shortenings
BE653320A (fr) * 1963-09-23 1965-03-22
FR1459649A (fr) * 1964-12-28 1966-04-29 Nat Biscuit Co Nouvelles compositions de revêtement de confiserie à base de beurre dur et de chocolat
EP0115655A1 (fr) * 1982-12-30 1984-08-15 Unilever N.V. Emulsions eau-dans-huile

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU31173A1 (fr) *
GB874182A (en) * 1957-02-11 1961-08-02 Unilever Ltd Improvements in or relating to shortenings
BE653320A (fr) * 1963-09-23 1965-03-22
FR1459649A (fr) * 1964-12-28 1966-04-29 Nat Biscuit Co Nouvelles compositions de revêtement de confiserie à base de beurre dur et de chocolat
EP0115655A1 (fr) * 1982-12-30 1984-08-15 Unilever N.V. Emulsions eau-dans-huile

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5492714A (en) * 1994-11-08 1996-02-20 The Procter & Gamble Company Reduced calorie fats which comprise reduced calorie triglycerides containing medium and long chain fatty acids and which exhibit rapid crystallization to beta phase
US5589216A (en) * 1994-11-08 1996-12-31 The Procter And Gamble Company Reduced calorie confectionery compositions which contain reduced calorie fats which exhibit rapid transformation to beta phase
WO1998019554A1 (fr) * 1996-11-06 1998-05-14 Unilever N.V. Cristallisation de graisse de triglyceride
EP0846421A1 (fr) * 1996-11-06 1998-06-10 Unilever N.V. Cristallisation de graisse triglycéridique
US5888575A (en) * 1996-11-06 1999-03-30 Lipton, Division Of Conopco, Inc. Triglyceride fat crystallization
US12439933B2 (en) 2022-06-16 2025-10-14 Savor Foods Limited Fat formulations

Also Published As

Publication number Publication date
ZA93809B (en) 1994-08-05
EP0625009A1 (fr) 1994-11-23
CA2129631A1 (fr) 1993-08-19
AU3452493A (en) 1993-09-03
GB9202665D0 (en) 1992-03-25

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