DE1303074B - - Google Patents

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DE1303074B
DE1303074B DE19631303074D DE1303074DA DE1303074B DE 1303074 B DE1303074 B DE 1303074B DE 19631303074 D DE19631303074 D DE 19631303074D DE 1303074D A DE1303074D A DE 1303074DA DE 1303074 B DE1303074 B DE 1303074B
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margarine
protein
milk
flavoring
heptene
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DE19631303074D
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DE1303074C2 (en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/18—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon triple bonds as unsaturation
    • A—HUMAN NECESSITIES
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
    • A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
    • A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
    • A21D2/14—Organic oxygen compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A23D7/0056—Spread compositions
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/206—Dairy flavours
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
    • A23L27/215—Synthetic spices, flavouring agents or condiments containing amino acids heated in the presence of reducing sugars, e.g. Maillard's non-enzymatic browning
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    • C07C17/00—Preparation of halogenated hydrocarbons
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    • C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
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    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
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    • C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
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    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/296—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with lead derivatives
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    • C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
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Description

Aufgabe der Erfindung ist die Verwendung von Aromastoffen für Lebensmittel, die eine langandauernde Speicherung der Aromawirkung ermöglichen und bei deren Anwendung den Lebensmitteln ein sehr gutes butter- oder sahneartiges Aroma verliehen werden kann.The object of the invention is the use of flavorings for foods that have a long-lasting Enable storage of the flavor effect and, when used, the food a very good buttery or creamy flavor can be imparted.

Diese Aufgabe wird gelöst durch Verwendung von Umsetzungsprodukten von Hepten-(4)-al-(l) mit genießbarem Eiweiß oder Eiweiß enthaltenden, genießbaren Stoffen, wobei die Eiweißmoleküle SH-Gruppen und NH2- oder NH-Gruppen an benachbarten Kohlenstoffatomen enthalten, zur Aromatisierung von Lebensmitteln unter Erzeugung eines butter- oder sahneartigen Aromas, bzw. unter Verstärkung eines solchen.This object is achieved by using reaction products of heptene (4) -al- (l) with edible substances containing edible protein or protein-containing substances, the protein molecules containing SH groups and NH 2 or NH groups on adjacent carbon atoms for Flavoring foods to produce a buttery or creamy aroma or to enhance it.

Beispiele von für die Umsetzung mit Hepten-(4)-. al-(l) geeigneten Stoffen sind Milcheiweiß und beta-Lactoglobulin. Examples of implementation with Hepten- (4) -. Al- (l) suitable substances are milk protein and beta-lactoglobulin.

Lebensmittel, bei denen die erfindungsgemäß zu verwenden Aromastoffe angewendet werden können, sind z. B. Margarine, Butter, Käse, Back- und Bratfette, Speiseöle, Eiskrem, Kunstsahne, Gebäck, Kremsuppen, Saucen oder Süßwaren. Von besonderer Bedeutung ist die Erfindung bei der Herstellung vonFood in which the flavoring substances to be used according to the invention can be applied, are z. B. margarine, butter, cheese, baking and frying fats, edible oils, ice cream, synthetic cream, pastries, cream soups, Sauces or confectionery. The invention is of particular importance in the production of

to Margarine.to margarine.

Die Umsetzung zwischen dem Hepten-(4)-al-(l) und der in Betracht kommenden physiologisch verträglichen Substanz kann auf verschiedene Weise erfolgen. Die Komponenten können in einem inerten Lösungsmittel, z. B. in wäßrigem Alkohol oder Wasser, gelöst und in der Lösung zur Umsetzung gebracht werden. Der gegebenenfalls sich bildende Niederschlag kann abfiltriert, getrocknet und als trockenes Pulver aufbewahrt werden.The implementation between the heptene- (4) -al- (l) and the physiologically compatible one under consideration Substance can be done in several ways. The components can be in an inert Solvents, e.g. B. in aqueous alcohol or water, dissolved and reacted in the solution will. Any precipitate which may form can be filtered off, dried and as a dry one Powder to be stored.

Es ist auch möglich, die Umsetzung in einem entsprechenden Lebensmittel selbst oder in einer der Komponenten, aus denen das betreffende Lebensmittel zusammengesetzt wird, erfolgen zu lassen, d. h. die Bildung des Aromastoffes mit Speicherwirkung kann »in situ« bewirkt werden.It is also possible to implement it in a corresponding food itself or in one of the To allow components from which the food in question is put together, d. H. the formation of the aroma substance with storage effect can be brought about "in situ".

Beispielsweise enthält Sauermilch (und also auch mit Sauermilch hergestellte Margarine) /?-Lactoglobulin und beim Säuerungsvorgang freigesetztes Cystein und freigesetzte Milcheiweißabbauprodukte, die an benachbarten Kohlenstoffatomen des Moleküls eine Mercapto- und eine Amino- oder Iminogruppe aufweisen. Die Reaktion findet leicht statt, wobei sich das GleichgewichtFor example, sour milk (and therefore also margarine made with sour milk) contains /? - lactoglobulin and cysteine and milk protein breakdown products released during the acidification process, those on adjacent carbon atoms of the molecule have a mercapto and an amino or imino group exhibit. The reaction takes place easily, with the equilibrium

CH2- CH — CO — + C6H11CHO =^ CH2- CH — CO— + H2O SH NH- SN-CH 2 - CH - CO - + C 6 H 11 CHO = ^ CH 2 - CH - CO— + H 2 O SH NH- SN-

einstellt.adjusts.

Die erste Formel gibt die in den Eiweißsubstanzen oder Eiweißabbauprodukten enthaltene Cysteineinheit wieder, wobei die freien Valenzen an andere Aminosäuren gebunden sind. Wenn das Cystein nur mit seiner Carboxylgruppe gebunden ist, enthält das Molekül eine NH2-=Gmp.pe. C8H11CHO ist die Formel des Hepten-(4)-als-(l); C0H11 ist der Hexen-(3)-yl-rest. The first formula represents the cysteine unit contained in the protein substances or protein breakdown products, whereby the free valences are bound to other amino acids. If the cysteine is only bound with its carboxyl group, the molecule contains an NH 2 - = Gmp.pe. C 8 H 11 CHO is the formula of heptene- (4) -al- (l); C 0 H 11 is the hexen- (3) -yl radical.

Die erfindungsgemäß zu verwendenden Arotnatisierungsmittei vermögen insbesondere ihre Aromawirkung unter den Umständen und Bedingungen zu entfalten, denen die Lebensmittel, welche mit den betreffenden Aromalisierungsmitteln versetzt sind, bei ihrer Benutzung unterliegen. Es kann hierbei insbesondere Erhitzung und/oder Enzymeinwirkung eine Rolle spielen.The aromatizing agents to be used according to the invention in particular are able to increase their aromatic effect under the circumstances and conditions unfold, which the food, which are mixed with the flavoring agents in question subject to their use. In particular, heating and / or the action of enzymes can be involved Role-play.

Die Speicherwirkung ist z. B. von besonderer Bedeutung beim Ausbraten von Margarine. Das gebundene Hepten-(4)-al-(l) wird dann allmählich wieder freigesetzt. bsThe storage effect is z. B. of particular importance when frying margarine. The bound heptene- (4) -al- (l) then gradually becomes again released. bs

Es wurde festgestellt, daß das cis-lsomere und das trans-Isomere des Hepten-(4)-als-(l) benutzt werden können. Das erstgenannte hat eine erheblich größere Aromatisierungswirkung als das letztgenannte. Hinsichtlich der Größenordnung der Aromatisierungsintensität kann etwa gesagt werden, daß man von dem trans-Isomeren. die zehnfache Menge im Vergleich mit dem cis-Isomeren braucht. Auch haben die beiden Isomeren ein etwas verschiedenes Arona, so daß in gewissen Fällen auch ein Gemisch vorteilhaft sein kann. Im allgemeinen wird aber das cislsomere bevorzugt.It was found that the cis-isomer and the trans isomers of heptene (4) as (l) can be used. The former has a considerably larger one Flavoring effect than the latter. With regard to the magnitude of the flavor intensity can roughly be said that one of the trans isomer. ten times the amount in comparison with the cis isomer needs. The two isomers also have a slightly different Arona, so that in certain cases a mixture can also be advantageous. In general, however, the cis isomeric preferred.

Die Mengen des erfindungsgemäß zu verwendet; Aromatisierungsmittel mit Speicherwirkung, die zweckmäßig bei Lebensmitteln angewendet werden, hängen von vielen Faktoren ab, wie z. B. der Beschaffenheit und der Zusammensetzung des Lebensmittels, den Umständen unter denen es hergestellt, aufbewahrt oder/und verwendet wird, der Art und Menge gegebenenfalls vorgesehener zusätzlicher Aromastoffe oder der Geschmacksrichtung der Verbraucher. The amounts of the to be used according to the invention; Storage flavoring agents that Appropriately used in food, depend on many factors, such as: B. the nature and the composition of the food, the circumstances under which it was produced, is kept and / or used, the type and amount of any additional Flavorings or the taste of the consumer.

Im allgemeinen kommen Mengen in Betracht, die, auf eis- bzw. trans-Hepten-(4)-al-(l) berechnet, zwischen 5 Gewichtsteilen auf 10" bzw. 1010 und 5 Gewichtsleilen auf 10" bzw. 10° Gewichtsteile des Lebensmittels liegen, und zwar vorzugsweise für dasIn general, amounts which, calculated on cis- or trans-hepten- (4) -al- (l), are between 5 parts by weight to 10 "or 10 10 and 5 parts by weight to 10" or 10 ° parts by weight of the food, preferably for the

cis-Isomere 5 Gewichtsteile je ΙΟ10 bis 5 Gewichtsteile je 108, und insbesondere 1 Gewichtsteil je 109 bis 3 Gewichtsteile je 109 Gewichtsteilen des Lebensmittels. Das letztere trifft z. B. für Margarine zu.cis-isomer 5 parts by weight per ΙΟ 10 to 5 weight parts per 10 8, and particularly 1 part by weight per 10 9 to 3 parts by weight per 10 9 parts by weight of the foodstuff. The latter applies e.g. B. for margarine too.

Die nach dem Verfahren gemäß der Erfindung zuverwenden Aromatisierungsmittel können gegebenenfalls in Kombination mit bekannten Aromatisierungsmitteln oder Mitteln, die gleichzeitig eine Aromatisierung und eine Haltbarmachung des Lebensmittels herbeiführen, zur Anwendung gelangen. Man kann dadurch bei den betreffenden Lebensmitteln gewünscht abgerundete Aromawirkungen oder bestimmte Aromanuancen erzielen und gegebenenfalls eine stufenweise erfolgende Aromawirkung herbeiführen. The flavoring agents to be used by the process according to the invention can optionally in combination with known flavoring agents or agents that simultaneously aromatize and bring about a preservation of the food, are used. One can thereby desired rounded flavor effects for the food concerned or achieve certain aroma nuances and, if necessary, bring about a gradual aroma effect.

Aromastoffe, die zusammen mit den gemäß der Erfindung herstellbaren Aromatisierungsmitteln verwendet werden können, sind z. B. Diacetyl, niedrige Fettsäuren, wie Buttersäure, sowie Stoffe, die gleichzeitig eine Aromatisierungs- und eine Haltbarmachungswirkung in fetthaltigen Lebensmitteln hervorrufen können, wie bestimmte Lactone.Flavoring substances used together with the flavoring agents which can be prepared according to the invention can be, are z. B. diacetyl, lower fatty acids such as butyric acid, and substances at the same time cause a flavoring and a preservation effect in fatty foods can like certain lactones.

Margarine, hergestellt aus handelsüblicher Fettphase und einer Wasserphase, die aus gleichen Teilen entrahmter Milch und Wasser zusammengesetzt war und deren pH-Wert durch Ansäuren mit Salzsäure auf 4,7 gebracht worden war, wurde mit einem handelsüblichen Gemisch von niedrigen Fettsäuren, Lactonen und Diacetyl und 1,8 mg/kg (bezogen auf das Fett) des Aromatisierungsmittels, hergestellt aus cis-Hepten-(4)-al-(l) und /J-Lactoglobulin) aromatisiert und von einer Prüfergruppe, bestehend aus neun Personen, beurteilt.Margarine, made from a commercially available fat phase and a water phase, which are made up of equal parts Skimmed milk and water was composed and their pH value by acidifying with hydrochloric acid had been brought to 4.7, was with a commercial mixture of lower fatty acids, Lactones and diacetyl and 1.8 mg / kg (based on fat) of the flavoring agent made from cis-heptene- (4) -al- (l) and / J-lactoglobulin) and assessed by a group of nine people.

Gegenübergestellt wurde eine auf dieselbe Weise hergestellte Margarine, die jedoch das erfindungsgemäße Aromatisierungsmittel nicht enthielt. Es wurde gefragt, welche Probe die butterähnlichste sei. Sieben Personen bezeichneten die Margarine, die das erfindungsgemäße Aromatisierungsmittel enthielt, als die butterähnlichste. Der statistische Zuverlässigkeitsprozentsatz ist 8O°/o. Die organoleptische Prüfung zeigte, daß die Anwendung des erfindungsgemäßen Aromatisierungsmittels eine deutliche Verbesserung gegenüber handelsüblicher aromatisierter Margarine ergibt.A margarine produced in the same way was compared, but the one according to the invention Flavoring agent not included. It was asked which sample was the most butter-like. Seven people identified the margarine containing the flavoring agent of the present invention as the most butter-like. The statistical percentage of confidence is 80 ° / o. The organoleptic examination showed that the use of the flavoring agent according to the invention was a significant improvement compared to commercially available flavored margarine.

Beispiel 1
(a) Herstellung des Aromatisierungsmittelsexample 1
(a) Preparation of the flavoring agent

500 mg /i-Lactoglobulin und 20 mg cis-Hepten-(4)-al-(l) wurden in 20 ml Wasser gelöst. Die Lösung wurde im Kühlschrank über Nacht stehengelassen, wonach sich ein Niederschlag gebildet hatte. Der Niederschlag wurde abgesaugt und getrocknet. Die Ausbeute betrag 272mg (52%>). Das Aromatisierungsmittel ist im trockenen Zustand haltbar. Wurde der nasse Niederschlag einem hohen Vakuum (< 10~5 Torr) ausgesetzt, konnte in den abgesaugten Dämpfen kein Hepten-(4)-al-(l) nachgewiesen werden. Nach Erhitzung des Reaktionsproduktes mit Wasser konnte durch Extraktion mit optisch leerem Petroläther Hepten-(4)-al-(l) durch Überführung in das 2,4-Dinitrophenylhydiazon nachgewiesen werden.500 mg / i-lactoglobulin and 20 mg cis-heptene- (4) -al- (l) were dissolved in 20 ml of water. The solution was left to stand in the refrigerator overnight, after which a precipitate had formed. The precipitate was filtered off with suction and dried. The yield is 272 mg (52%>). The flavoring agent is stable when dry. If the wet precipitate was exposed to a high vacuum (<10 ~ 5 Torr), no heptene- (4) -al- (l) could be detected in the extracted vapors. After the reaction product had been heated with water, extraction with optically empty petroleum ether could detect hepten- (4) -al- (l) by converting it into 2,4-dinitrophenylhydiazone.

Das Ultraviolettspektrum des Aromatisierungsmittels, bestimmt in einer Lösung eines Phosphatpuffers, pH = 6,8, hat ein Maximum bei 279 bis 280 nm, dessen Extinktion E=1,l3cm2/mg ist (/i-Lactoglobulin zeigt bei derselben Wellenlänge eine Extinktion von E = 0,91 cmä/mg).The ultraviolet spectrum of the flavoring agent, determined in a solution of a phosphate buffer, pH = 6.8, has a maximum at 279 to 280 nm, the extinction of which is E = 1.13 cm 2 / mg (/ i-lactoglobulin shows an absorbance of e = 0.91 cm ä / mg).

Es wurde ferner der Zirkulardichroismus bei zwei Wellenlängen, d. h. der Unterschied der Absorption S bei links- bzw. rechtszirkular polarisierter Strahlung bei Wellenlängen in der Nähe des Absorptionsmaximums bestimmt. Bei einer Lösung des Aromatisierungsmittels in einem Phosphatpuffer (pH = 6,8, c = 0,225 %) wurde ein Unterschied in der MoIekularextinktion bei 291 nm von Δε = —0,017 und bei 215 nm von Δε = —2,19 gefunden (/i-Lactoglobulin zeigte bei denselben Wellenlängen einen Wert von Δε = —0,021 bzw. —1,78).The circular dichroism at two wavelengths, ie the difference in absorption S for left-hand and right-hand circularly polarized radiation at wavelengths in the vicinity of the absorption maximum, was also determined. In a solution of the flavoring agent in a phosphate buffer (pH = 6.8, c = 0.225%), a difference in MoIekularextinktion at 291 nm was of Δε = -0.017 and at 215 nm of Δε = -2.19 found (/ i Lactoglobulin showed a value of Δε = −0.021 and −1.78 at the same wavelengths.

(b) Verwendung des Aromatisierungsmittels(b) Use of the flavoring agent

Eine Margarine wurde durch Emulgieren von 10 kg handelsüblichen Margarinefetten und 2 kg Wasserphase hergestellt, wobei ein gebräuchliches Emulgiermittel angewendet wurde. Die Wasserphase bestand auf 1 kg entrahmter Milch und 1 kg Wasser; der pH-Wert der Wasserphase wurde durch Zugabe von Salzsäure auf 4,7 eingestellt. In diese Mischung wurden ungefähr 225 mg eines Aromagemisches eingearbeitet, das durch Mischen von 200 mg Dodecanolid-(5,l) 40 g Butanolid-(4,1), 100 g Octanolid-(4,1), 40 g Buttersäure, 20 g Hexansäure, 20 g Octansäure, 20 g Decansäure und 10 g Diacetyl erhalten worden war; außerdem wurde eine Suspension von 18 mg des nach (a) hergestellten trockenen Aromatisierungsmittels in 10 ml kaltes Wasser eingearbeitet. Die gesamte Mischung wurde in bekannter Weise durch Emulgieren, Homogenisieren und Bearbeiten in einer Votatorvorlage zu Margarine verarbeitet.A margarine was made by emulsifying 10 kg of commercially available margarine fats and 2 kg Water phase produced using a common emulsifier. The water phase insisted on 1 kg of skimmed milk and 1 kg of water; the pH of the water phase was increased by adding adjusted to 4.7 by hydrochloric acid. Approximately 225 mg of a flavor mixture were incorporated into this mixture, by mixing 200 mg dodecanolide (5, l) 40 g butanolide (4.1), 100 g octanolide (4.1), 40 g of butyric acid, 20 g of hexanoic acid, 20 g of octanoic acid, 20 g of decanoic acid and 10 g of diacetyl were obtained had been; a suspension of 18 mg of the dry flavoring agent prepared according to (a) was also used incorporated into 10 ml of cold water. The entire mixture was made in a known manner processed into margarine by emulsifying, homogenizing and processing in a voter template.

Die erhaltene Margarine hatte ein sehr butterähnliches Aroma und wurde besser beurteilt als eine auf dieselbe Weise mit denselben Bestandteilen, aber ohne das erfindungsgemäße Aromatisierungsmittel hergestellte Margarine.The margarine obtained had a very butter-like aroma and was rated better than one the same way with the same ingredients but without the flavoring agent according to the invention manufactured margarine.

Statt des trockenen Aromatisierungsmittels kann man auch den nassen Niederschlag, nachdem man den Wassergehalt bestimmt hat, um die gewünschte Menge zu ermitteln, sofort nach der Isolierung der Margarinemischung zusetzen.Instead of the dry flavoring agent, one can also use the wet precipitate after one determined the water content to determine the desired amount immediately after isolating the Add margarine mixture.

Die folgenden Beispiele zeigen, daß der erfindungsgemäß zu verwendende Aromastoff nicht nur aus Heptenal und einem /Ϊ-Lactoglobulin, sondern auch aus Heptenal und Gemischen, welche /?-Lactoglobu-Hn oder Milcheiweißabbauprodukte mit einer Mercapto- und einer Amino- bzw. einer Iminogruppe an benachbarten Kohlenstoffatomen des Moleküls enthalten, hergestellt werden kann. Solche Gemische sind z. B. Sauermilch oder Sauermilch enthaltende Zubereitungen, wie Milchmargarine.The following examples show that the flavoring substance to be used according to the invention not only consists of Heptenal and a / Ϊ-lactoglobulin, but also from Heptenal and mixtures, which /? - Lactoglobu-Hn or milk protein degradation products with a Mercapto and an amino or an imino group on adjacent carbon atoms of the molecule contain, can be produced. Such mixtures are e.g. B. containing sour milk or sour milk Preparations such as milk margarine.

Beispiel 2Example 2

22 mg cis-Hepten-(4)-al-(l) (etwa 0,2 mMol) wurden mit 1 Liter Sauermilch innig gemischt, wobei sich der Aldehyd mit dem in der Sauermilch enthaltenden /i-Lactoglobulin oder mit den während der Säuerung entstehenden Milcheiweißabbauprodukten, die an benachbarten Kohlenstoffatomen des Moleküls eine Mercapto- und eine Amino- bzw. eine Iminogruppe aufweisen, umsetzt. Von diesem Präparat wurden 100 ml mit 50 Liter Sauermilch verdünnt und 1000 kg Margarine einverleibt. Die so hergestellte Margarine hatte ein sehr butterähnliches Aroma.22 mg of cis-heptene- (4) -al- (l) (about 0.2 mmol) were intimately mixed with 1 liter of sour milk, whereby the aldehyde with the i-lactoglobulin contained in the sour milk or with the during acidification resulting milk protein breakdown products that are attached to neighboring carbon atoms of the molecule Have mercapto and an amino or an imino group. From this preparation were 100 ml diluted with 50 liters of sour milk and incorporated 1000 kg margarine. The margarine made in this way had a very buttery aroma.

Man kann das mit dem AMehyd behandelte Milcheiweiß auch abfiltrieren und trocken aufbewahren, um Suppen oder Gebäck zu aromatisieren.The milk protein treated with the AMehyd can also be filtered off and stored in a dry place, to flavor soups or pastries.

Beispiel 3Example 3

500 g eines Konzentrats, das durch innige Mischung von 200 g Dodecanolid-(5,1), 40 g Butanolid-(4,1), 100 g Octanolid-(4,1), 40 g Buttersäure, 20 g Capronsäure, 20 g Caprylsäure, 20 g Caprinsäure, 10 g Diacetyl und 0,08 g cis-Hepten-(4)-al-(l) mit 10 kg raffiniertem Speiseöl (Erdnußöl) hergestellt worden war, wurden 1000 kg Milchmargarine während ihrer Herstellung einverleibt, wobei der Aldehyd mit dem in der Milch enthaltenen /J-Lactog'obulin oder den Milcheiweißabbauprodukten mit benachbarten SH- und NH-Gruppen unter Bildung des Aromastoffes mit Speicherwirkung reagierte. Das Aroma der so hergestellten Margarine war sehr butterähnlich.500 g of a concentrate obtained by intimately mixing 200 g of dodecanolide (5.1), 40 g of butanolide (4.1), 100 g octanolide (4.1), 40 g butyric acid, 20 g caproic acid, 20 g caprylic acid, 20 g capric acid, 10 g diacetyl and 0.08 g of cis-heptene- (4) -al- (l) had been made with 10 kg of refined edible oil (peanut oil), 1000 kg of milk margarine were incorporated during their production, whereby the aldehyde with the in the milk contained / J-Lactog'obulin or the Milk protein breakdown products with neighboring SH and NH groups with formation of the flavoring substance responded with memory effect. The aroma of the margarine produced in this way was very similar to butter.

Beispiel 4Example 4

500 g einer Emulsion, die durch innige Mischung von 200 g Dodecanolid-f5,l), 40 g Butanolid-(4,1), WO g Octanolid-(4,1), 40 g Buttersaure, 20 g Capronsäure 20 g Caprylsäure, 20 g Capnnsaure 10 g Diacety und 0,08 gcis-Hepten-(4)-al-(l) mit 8 kg raffinierten? Speiseöl (Erdnußöl) und Emulgierung nut 2 kg Sauermilch erhalten worden war, wobei das Heptanal mit dem in der Sauermüch enthaltenen y-Lactoglobulin oder den Milcheiweißabbauprodukfen mit benachbarten SH- und NH-Gnippen, wie sie bei der Säuerung entstehen, unter Bildung des Somastoffes reagiert, wurde 1000 kg Marganne während ihrer Herstellung aus Fettphase und entweder Sauermilch- oder Wasserphase einverleibt Die Γο erhaltene Margarine hatte ein sehr butterahnhches Aroma.500 g of an emulsion obtained by intimately mixing 200 g of dodecanolide-f5, l), 40 g of butanolide- (4.1), WO g octanolide (4.1), 40 g butyric acid, 20 g caproic acid 20 g caprylic acid, 20 g capric acid 10 g diacety and 0.08 gcis-heptene- (4) -al- (l) with 8 kg refined? Edible oil (peanut oil) and emulsification only 2 kg sour milk had been obtained, the Heptanal with the y-lactoglobulin contained in the Sauermüch or the milk protein degradation products with neighboring SH and NH gi ribs like them arise during the acidification, reacting with the formation of the soma substance, was 1000 kg Marganne during their preparation from fat phase and either The sour milk or water phase incorporated Γο preserved margarine had a very buttery cream Aroma.

Claims (2)

Patentansprüche:Patent claims: 1. Verwendung von Umsetzungsprodukten von Hepten-(4)-ai-(l) mit genießbarem Eiweiß oder Eiweiß enthaltenden genießbaren Stoffen, wobei die Eiweißmoleküle SH-Gruppen und NH.,- oder NH-Gruppen an benachbarten Kohlenstoffatomen enthalten, zur Aromatisierung von Lebensmitteln unter Erzeugung eines butter- oder sahneartigen Aromas bzw. unter Verstärkung eines solchen.1. Use of reaction products of Hepten- (4) -ai- (l) with edible protein or Edible substances containing protein, with the protein molecules SH groups and NH., - or Contain NH groups on neighboring carbon atoms, for flavoring food to produce a buttery or buttery flavor creamy aroma or with enhancement of such. 2. Verwendung des Umsetzungsprodukts von Hepten-(4)-al-(l) mit Milcheiweiß oder /3-Lactoglobulin gemäß Anspruch 1.2. Use of the reaction product of heptene- (4) -al- (l) with milk protein or / 3-lactoglobulin according to claim 1.
DE19631303074D 1962-07-24 1963-07-24 FLAVORING FOOD Expired DE1303074C2 (en)

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DE1517128A Expired DE1517128C3 (en) 1962-07-24 1963-07-24 Process for producing or enhancing a creamy or buttery flavor in fatty foods
DE19631493297 Granted DE1493297B2 (en) 1962-07-24 1963-07-24 ORGANIC COMPOUNDS OF THE GENERAL FORMULA CH LOW 3-CH LOW 2-CH = CH- (CH LOW 2) LOW M-CH = CH- (CH LOW 2) LOW N-X AND THE METHOD FOR THEIR PRODUCTION
DE19631303074D Expired DE1303074C2 (en) 1962-07-24 1963-07-24 FLAVORING FOOD
DEU9992A Pending DE1277836B (en) 1962-07-24 1963-07-24 cis- and trans-Hepten- (4) -al- (1), as well as processes for the production of cis- or trans-Hepten- (4) -al- (1) suitable for flavoring foods

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DE19631493297 Granted DE1493297B2 (en) 1962-07-24 1963-07-24 ORGANIC COMPOUNDS OF THE GENERAL FORMULA CH LOW 3-CH LOW 2-CH = CH- (CH LOW 2) LOW M-CH = CH- (CH LOW 2) LOW N-X AND THE METHOD FOR THEIR PRODUCTION

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DE3062001D1 (en) * 1979-06-12 1983-03-24 Procter & Gamble Flavor composition and use thereof in foods
US4338472A (en) * 1981-01-21 1982-07-06 Hydrocarbon Research, Inc. Catalytic hydrogenolysis of alditols to produce polyols
US5204023A (en) * 1989-04-12 1993-04-20 Unilever Patent Holdings B.V. Malodors reduction
GB8908199D0 (en) * 1989-04-12 1989-05-24 Unilever Plc Malodors reduction
EP0729931B1 (en) * 1995-03-03 1998-08-19 Dow Corning Corporation Process for the preparation of 1,5-hexadiene
US6790815B1 (en) 1998-07-10 2004-09-14 Procter & Gamble Company Amine reaction compounds comprising one or more active ingredient

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DE1038549B (en) * 1952-08-08 1958-09-11 Unilever Nv Process for the production of ª € -oxydekaneeurelactone serving as a flavoring agent
DE1030328B (en) * 1952-08-08 1958-05-22 Unilever Nv Process for the production of the ªŠ-oxycarboxylic acids serving as flavoring agents with 9 to lactones saturated straight-chain carbon atoms
DE1030327B (en) * 1952-08-08 1958-05-22 Unilever Nv Process for the production of the ª € -oxycaprinsaeurelactons serving as a flavoring agent
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AT262733B (en) 1968-06-25
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CH470848A (en) 1969-04-15
DE1493297B2 (en) 1973-01-25
DE1517128B2 (en) 1973-04-26
DE1517128A1 (en) 1969-04-03
DE1277836B (en) 1968-09-19
GB1068712A (en) 1967-05-10
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DE1795617B2 (en) 1976-11-04
DE1493297A1 (en) 1972-04-20

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E77 Valid patent as to the heymanns-index 1977