Patent GB-797134-A (GB)
Title: Improvements in or relating to oleaginous foodstuffs
Inventor: TAYLOR REGINALD JAMES
IPC: A23D9/013
Filed: 1955-02-07
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.