GB797134A - Improvements in or relating to oleaginous foodstuffs - Google Patents

Improvements in or relating to oleaginous foodstuffs

Info

Publication number
GB797134A
GB797134A GB360755A GB360755A GB797134A GB 797134 A GB797134 A GB 797134A GB 360755 A GB360755 A GB 360755A GB 360755 A GB360755 A GB 360755A GB 797134 A GB797134 A GB 797134A
Authority
GB
United Kingdom
Prior art keywords
acid
delta
hydroxy
keto
epsilon
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.)
Expired
Application number
GB360755A
Inventor
Reginald James Taylor
Dennis Chapman
Jan Boldingh
Pauline Haverkamp Begemann
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 PLC
Original Assignee
Unilever PLC
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 PLC filed Critical Unilever PLC
Priority to GB360755A priority Critical patent/GB797134A/en
Publication of GB797134A publication Critical patent/GB797134A/en
Expired legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A23D9/013Other fatty acid esters, e.g. phosphatides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Edible Oils And Fats (AREA)

Abstract

Esters of aliphatic gamma-, delta- and epsilon-hydroxy C8-C14 carboxylic acids, for use as food additives (see Groups I and VI) are prepared by methods illustrated in the following examples. The esters are preferably derived from low molecular weight mono- or polyhydric alcohols, e.g. methanol, ethanol, propylene glycol and glycerol, and may be partial esters. Thus: (1) glycerol is heated under carbon dioxide with the lactone of delta-hydroxy decanoic acid in the presence of sulphuric acid and the product, mainly a monoglyceride, is recovered by neutralization and extraction with ethyl acetate; (2) tri-delta keto-decanoyl glyceride is converted into the corresponding tri-hydroxyglyceride by catalytic hydrogenation in ethyl acetate; (3) excess glycerol and the lactone of (1) are heated together in methanolic sodium methylate and the resulting glyceride is isolated by extraction with ether; (4) the same lactone is reacted with a mixture of glycerol and potassium glycerate yielding a mixture of glycerides; (5) the methyl ester of delta-keto decanoic acid containing a little of the free acid is reacted at 180-190 DEG C. with 1:2-isopropylidine-glycerol in the presence of lead oxide yielding the isopropylidene glyceride of the keto acid which is isolated and treated with aqueous HCl at - 18 DEG C. to form the a -monoglyceride of the keto acid, which is isolated and reduced by means of hydrogen in the presence of nickel on kieselguhr and the resulting a -mono glyceride of delta-hydroxy decanoic acid is recovered by solvent extraction; (7) the propylene glycol di-ester of epsilon-hydroxy tetradecanoic acid is prepared by heating propylene glycol with epsilon-keto tetradecanoic acid in the presence of zinc dust to yield the corresponding glycol diester which is isolated and then catalytically hydrogenated to form the desired hydroxy acid di-ester. The keto acid used in (7) may be prepared by oxidizing 2-octyl-cyclohexanone-1 with chromic oxide in sulphuric acid. Specifications 743,845, 748,645 and 748,764, [all in Group I], are referred to.ALSO:Butter-like flavour is imparted to oleaginous foods, e.g., margarine and shortening, by incorporation of a small quantity of an ester of an aliphatic gamma-, delta- or epsilon-hydroxy C8-C14 carboxylic acid. The ester may be of a low molecular weight monohydric, a dihydric, or a trihydric, alcohol. The foods may contain other flavouring substances, e.g., diacetyl, acetyl-methyl carbinol, a lower fatty acid, sweet or sour milk. Examples are concerned with (i) the addition to a blend of fats for margarine of mixed mono-, di- and tri-glycerides (60 per cent monoglyceride) of delta-hydroxy nonanoic, decanoic and dodecanoic acids, the concentrations of the glycerides of the respective acids being 1, 20 and 10 parts per million, (ii) the addition to margarine containing 6 per cent of soured milk of a preparation of the propylene glycol diester of epsilon-hydroxy tetradecanoic acid in the concentration 12 parts per million. Specifications 743,845, 748,645 and 748,764 are referred to.ALSO:Butter-like flavour is imparted to oleaginous foods, e.g artificial cream, cooking and salad oils, margarine and shortening, by incorporation of a small quantity of an ester of an aliphatic gamma-, delta- or epsilon-hydroxy C8-C14 carboxylic acid. The ester may be of a low molecular weight monohydric, a dihydric or a trihydric, alcohol. The foods may contain other flavouring substances, e.g. diacetyl, acetyl-methyl carbinol, a lower fatty acid, sweet or sour milk. Examples are concerned with (i) preparing a viscous oil of monoglyceride content 72 pe cent by reacting the lactone of delta-hydroxy decanoic acid and glycerol in the presence of concentrated sulphuric acid; (ii) preparing a trihydroxy glyceride of m. pt. 39-44 DEG C. by reduction of tri-delta-keto-decanoyl glyceride; (iii) reacting the lactone of delta-hydroxy decanoic acid and dry glycerol in the presence of sodium methylate in methanol; (iv) preparing a mixed glyceride product of monoglyceride content 35.5 per cent by reaction of the lactone of delta-hydroxy decanoic acid and glycerol in the presence of potassium glycerate; (v) preparing the alpha-monoglyceride of delta-hydroxydecanoic acid, of m.pt. 6 DEG C., by reacting the methyl ester of delta-keto-decanoic acid, delta-keto-decanoic acid and 1,2-isopropylidene glycerol, isolating, and then reducing, the alpha-monoglyceride of delta-keto-decanoic acid so produced; (vi) the incorporation in margarine fats of a mixture of mono-, di- and tri-glycerides of delta-hydroxy nonanoic, decanoic and dodecanoic acids, the concentrations of the glycerides of the respective acids being 1, 20 and 10 parts per million; (vii) preparing the propylene glycol diester of epsilon-hydroxy tetradecanoic acid, of m.pt. 55.5 DEG C., by oxidizing 2-octyl-cyclohexanone-1 with chromic oxide in sulphuric acid to epsilon-keto-tetradecanoic acid, reacting this acid with propylene glycol, and reducing the propylene glycol diester so formed; incorporating 12 parts per million of such propylene glycol diester of epsilon-hydroxy tetradecanoic acid in a margarine containing 6 per cent of soured milk. Specifications 743,845, 748,645 and 748,764 are referred to.
GB360755A 1955-02-07 1955-02-07 Improvements in or relating to oleaginous foodstuffs Expired GB797134A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB360755A GB797134A (en) 1955-02-07 1955-02-07 Improvements in or relating to oleaginous foodstuffs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB360755A GB797134A (en) 1955-02-07 1955-02-07 Improvements in or relating to oleaginous foodstuffs

Publications (1)

Publication Number Publication Date
GB797134A true GB797134A (en) 1958-06-25

Family

ID=9761526

Family Applications (1)

Application Number Title Priority Date Filing Date
GB360755A Expired GB797134A (en) 1955-02-07 1955-02-07 Improvements in or relating to oleaginous foodstuffs

Country Status (1)

Country Link
GB (1) GB797134A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2142339A (en) * 1983-06-20 1985-01-16 Cumberland Packing Corp Margarine and the like spread with natural butter flavour
WO2010143097A1 (en) * 2009-06-09 2010-12-16 Firmenich Sa Lactone flavour precursor
CN110672580A (en) * 2019-09-28 2020-01-10 上海如海光电科技有限公司 Raman rapid detection method for tetrahydrocannabinol in food beverage and vegetable oil

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2142339A (en) * 1983-06-20 1985-01-16 Cumberland Packing Corp Margarine and the like spread with natural butter flavour
WO2010143097A1 (en) * 2009-06-09 2010-12-16 Firmenich Sa Lactone flavour precursor
CN110672580A (en) * 2019-09-28 2020-01-10 上海如海光电科技有限公司 Raman rapid detection method for tetrahydrocannabinol in food beverage and vegetable oil
CN110672580B (en) * 2019-09-28 2023-05-30 上海如海光电科技有限公司 Raman rapid detection method for tetrahydrocannabinol in food and beverage and vegetable oil

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