DE2347454C2 - Process for the production of flavor compositions - Google Patents
Process for the production of flavor compositionsInfo
- Publication number
- DE2347454C2 DE2347454C2 DE2347454A DE2347454A DE2347454C2 DE 2347454 C2 DE2347454 C2 DE 2347454C2 DE 2347454 A DE2347454 A DE 2347454A DE 2347454 A DE2347454 A DE 2347454A DE 2347454 C2 DE2347454 C2 DE 2347454C2
- Authority
- DE
- Germany
- Prior art keywords
- photocitral
- flavor compositions
- acid
- production
- formula
- 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
Links
- 239000000796 flavoring agent Substances 0.000 title claims description 14
- 235000019634 flavors Nutrition 0.000 title claims description 14
- 239000000203 mixture Substances 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 9
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 claims description 4
- 229940043350 citral Drugs 0.000 claims description 4
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 claims description 4
- 239000008369 fruit flavor Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JCDLXWAYWSJVTP-UHFFFAOYSA-N Photocitral A Chemical compound CC1CCC(C(C)=C)C1C=O JCDLXWAYWSJVTP-UHFFFAOYSA-N 0.000 description 3
- -1 dimethylmethylene group Chemical group 0.000 description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- AGTSNXAZDKAPHU-UHFFFAOYSA-N 4,5,5-trimethylbicyclo[2.1.1]hexane-6-carbaldehyde Chemical compound C1CC2(C)C(C)(C)C1C2C=O AGTSNXAZDKAPHU-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 2
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 2
- 235000015122 lemonade Nutrition 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- UWKAYLJWKGQEPM-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl acetate Chemical compound CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
- 239000001629 3,7-dimethylocta-2,6-dienyl benzoate Substances 0.000 description 1
- JAABTUALKWMYLR-UHFFFAOYSA-N 4,5,5-trimethylbicyclo[2.1.1]hexane-3-carbaldehyde Chemical compound C1C2(C)C(C)(C)C1CC2C=O JAABTUALKWMYLR-UHFFFAOYSA-N 0.000 description 1
- IKOSQCITEZUTOE-UHFFFAOYSA-N 4-Hydroxypelargonic acid Chemical compound CCCCCC(O)CCC(O)=O IKOSQCITEZUTOE-UHFFFAOYSA-N 0.000 description 1
- SESFRYSPDFLNCH-UHFFFAOYSA-N Benzyl benzoate Natural products C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- YDVXYTIIPGKIJP-UHFFFAOYSA-N O-Benzoyl-geraniol Natural products CC(C)=CCCC(C)=CCOC(=O)C1=CC=CC=C1 YDVXYTIIPGKIJP-UHFFFAOYSA-N 0.000 description 1
- PFWYHTORQZAGCA-UHFFFAOYSA-N Piperonyl acetate Chemical compound CC(=O)OCC1=CC=C2OCOC2=C1 PFWYHTORQZAGCA-UHFFFAOYSA-N 0.000 description 1
- 235000007212 Verbena X moechina Moldenke Nutrition 0.000 description 1
- 235000018718 Verbena officinalis Nutrition 0.000 description 1
- 240000001519 Verbena officinalis Species 0.000 description 1
- 235000001594 Verbena polystachya Kunth Nutrition 0.000 description 1
- 235000007200 Verbena x perriana Moldenke Nutrition 0.000 description 1
- 235000002270 Verbena x stuprosa Moldenke Nutrition 0.000 description 1
- ZSBOMYJPSRFZAL-JLHYYAGUSA-N [(2e)-3,7-dimethylocta-2,6-dienyl] butanoate Chemical compound CCCC(=O)OC\C=C(/C)CCC=C(C)C ZSBOMYJPSRFZAL-JLHYYAGUSA-N 0.000 description 1
- OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 1
- UZFLPKAIBPNNCA-BQYQJAHWSA-N alpha-ionone Chemical compound CC(=O)\C=C\C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-BQYQJAHWSA-N 0.000 description 1
- 229940011037 anethole Drugs 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 239000001111 citrus aurantium l. leaf oil Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- GVYLWCPUAAZCES-UHFFFAOYSA-N ethanol;octanoic acid Chemical compound CCO.CCCCCCCC(O)=O GVYLWCPUAAZCES-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- YDVXYTIIPGKIJP-QINSGFPZSA-N geranyl benzoate Chemical compound CC(C)=CCC\C(C)=C/COC(=O)C1=CC=CC=C1 YDVXYTIIPGKIJP-QINSGFPZSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- LVECZGHBXXYWBO-UHFFFAOYSA-N pentadecanolide Natural products CC1CCCCCCCCCCCCC(=O)O1 LVECZGHBXXYWBO-UHFFFAOYSA-N 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 125000001443 terpenyl group Chemical group 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
-
- 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
- A23L27/203—Alicyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Nutrition Science (AREA)
- Health & Medical Sciences (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Seasonings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Confectionery (AREA)
Description
Die Verbindungen der Formel
CH,The compounds of the formula
CH,
CHOCHO
worin R1 Wasserstoff, R2 die Isopropyliden- oder die Isopropenylgruppe oder Ri zusammen mit R2 eine Dimethylmethylengruppe darstellen,where R 1 is hydrogen, R 2 is the isopropylidene or isopropenyl group or Ri together with R 2 is a dimethylmethylene group,
also das 2-Formyl-l-isopropenyl-3-methyl-cyclopentan (Substanz A) das i-Forrnyl-l-isopropylidenO-methyl-cyclopentan (Substanz B) und der 1,6,6-Trimethyl-bicyclo[2.1.l]hexan-2-aldehyd (Substanz C) sind bekannte Aldehyde (Tetrahedron 19 (1963), 1995-2007, J. Qrg, Chem. 23, (1958), 153-157). Keiner dieser Verbindungen wurde aber bisher irgendwelche parfümistische Bedeutung oder Bedeutung als Aromastoff zugeschrieben. so the 2-formyl-1-isopropenyl-3-methyl-cyclopentane (substance A) the i-formyl-1-isopropylidene-O-methyl-cyclopentane (Substance B) and the 1,6,6-trimethyl-bicyclo [2.1.l] hexane-2-aldehyde (Substance C) are known aldehydes (Tetrahedron 19 (1963), 1995-2007, J. Qrg, Chem. 23, 153-157 (1958)). However, none of these compounds has so far been perfumed at all Assigned importance or importance as a flavoring substance.
Es wurde nun überraschenderweise festgestellt, daß diese Aldehyde und Gemische dieser Aldehyde über sehr wertvolle Geschmackstoffqualitäten verfügen, aufgrund derer sich diese Verbindungen hervorragend zur Verbesserung von Geschmackstoffkompositionen vom Hesperiden (Agrumen)-Typ, wie vom Typ »Verveine« (Verbena) eignen.It has now surprisingly been found that these aldehydes and mixtures of these aldehydes over have very valuable flavor qualities, due to which these compounds are excellent to improve flavor compositions of the hesperides (citrus) type, such as the »verveine« type (Verbena) are suitable.
Gegenstand der Erfindung ist demgemäß das in den vorstehenden Patentansprüchen aufgezeigte Verfahren zur Herstellung von Geschmackstoffkompositionen.The invention accordingly relates to the method indicated in the preceding claims for the production of flavor compositions.
Die Formel I soll, wie im Anspruch 1 aufgezeigt, sämtliche auf Grund der asymmetrischen Kohlenstoffatome möglichen Stereoisomeren umfassen.As indicated in claim 1, the formula I should all be based on the asymmetric carbon atoms possible stereoisomers include.
Beispiele solcher Isomeren sind insbesondere:Examples of such isomers are in particular:
CHOCHO
worin R1 Wasserstoff, R2 die Isopropyliden- oder die Isopropenylgruppe. oder R1 zusammen mit R2 eine Dimethylmethylengruppe darstellen, und wobei die Formel I sämtliche möglichen Stereoisomeren umfassen soll,wherein R 1 is hydrogen, R 2 is the isopropylidene or isopropenyl group. or R 1 together with R 2 represent a dimethylmethylene group, and where the formula I is intended to include all possible stereoisomers,
zusetzt.clogs.
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man als Verbindung der Formel I 2-Formyl-l-isopropenyl-3-methylcyc!opentan zusetzt. 2. The method according to claim 1, characterized in that the compound of formula I 2-Formyl-1-isopropenyl-3-methylcyc! Opentane is added.
3. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man als Verbindung der Formel I 2-Formyi-l-isppropyliden-3-methylcyclopentan zusetzt. 3. The method according to claim 1, characterized in that the compound of formula I 2-Formyi-l-isppropylidene-3-methylcyclopentane is added.
4. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man als Verbindung der Formel I den 1,6,6-Trimethylbicyclo[2.1.1 ]hexan-2-aldehyd zuseizt. 4. The method according to claim 1, characterized in that that the 1,6,6-trimethylbicyclo [2.1.1] hexane-2-aldehyde is added as a compound of the formula I.
-CHO-CHO
trans/trans-Photocitra! Atrans / trans-Photocitra! A.
CHOCHO
epi-Photocitral Aepi-Photocitral A
-CHO-CHO
CHOCHO
cis/cis-Photocitral Λcis / cis photocitral Λ
-CHO-CHO
Photocitral BPhotocitral B
Der erfindungsgemäße Zusatz der Substanz A, B oder C oder eines Gemisches von mehreren dieser Substanzen, in sterisch einheitlicher Form oder in Form von Stereoisomeren-Gemischen kann innerhalb weiter Grenzen variieren.The addition according to the invention of substance A, B or C or a mixture of several of these Substances in sterically uniform form or in the form of stereoisomer mixtures can continue within Limits vary.
Bei der Herstellung von Geschmackstoffkompositionen können einem 0,1 —10 Gew,-°/o Citral enthaltendem Fruchtaroma eine oder mehrere Verbindungen der Formel I in Mengen von wenigen Promille zugegeben werden, um Geschmackstoffkompositionen mit einer sogenannten grünen Hesperidennote zu erzeugen. Die erhaltenen Aromen können z. B. zu Flüssigkeiten, Pasten oder Pulvern formuliert werden. Die Produkte können z. B. sprühgetrocknet, vakuumgetrocknet oder lyophilisiert werden. Die Formulierung solcher Aromen sowie die Aromatisierung von Nahrungs- oder Genußmitteln und Getränken kann auf an sich bekannte Art und Weise (vgl. z.B. J. Merory, Food flavourings, composition, manufacture and use; Avi Publ. Co. Inc Westport 1968) vorgenommen werden.In the production of flavor compositions, a 0.1-10% by weight of citral can be used Fruit flavor one or more compounds of the formula I are added in amounts of a few parts per thousand to create flavor compositions with a so-called green hesperid note. the obtained flavors can, for. B. be formulated into liquids, pastes or powders. The products can e.g. B. spray-dried, vacuum-dried or lyophilized. The formulation of such flavors as well as the flavoring of foodstuffs or luxury foods and beverages can be carried out in a manner known per se und Weise (see e.g. J. Merory, Food flavors, composition, manufacture and use; Avi Publ. Co. Inc Westport 1968).
Die Verbindungen der Formel I können verwendet werden zur Erzeugung von Geschmackstoffkompositionen in Nahrungsmitteln (z. B. Yoghurt, Puddings) in Genußmitteln (z. E. Konditorerzeugnissen wie Bonbons, sog. Soft Ice) und in Getränken (z. B. Mineralwässern, Sirups).The compounds of the formula I can be used to produce flavor compositions in foods (e.g. yoghurt, puddings) in luxury foods (e.g. confectionery products such as sweets, so-called soft ice) and in beverages (e.g. mineral waters, syrups).
Geschmacksprüfungen mit handelsüblichen Zitronenaromen mit und ohne Zusatz von Photocitral in Limonade eingearbeitet, zu 10 g Aroma/100 1 Limonade haben ergeben, daß ein Panel die mit Photocitral angereicherten Proben eindeutig erkannte und klar bevorzugte: Das Photocitral enthaltende Aroma wirkte echter, natürlicher. Der Citral-Gehalt im Aroma war dabei 9 Gew.-%, der Photocitralgehalt 0,4 Promille im Aroma.Taste tests with commercially available lemon flavors with and without the addition of Photocitral in Lemonade incorporated, to 10 g flavor / 100 l lemonade showed that a panel clearly recognized the samples enriched with Photocitral preferred: The aroma containing photocitral appeared truer, more natural. The citral content in the flavor was 9% by weight, the photocitral content 0.4 parts per thousand in the aroma.
Fruchtaromen-Bouqu -:
(Typ Tutti-Frutti, auf Ester-Basis)Fruit flavor bouquet -:
(Type Tutti-Frutti, based on ester)
Capronaldehyd
Caprinsäure 10% in Aethanol
Caprylsäure 10% in Aethanol
Capronsäure 10% in Aethanol
Sandeihoizöi
Rosenöl bulgarisch
Jasmin Absolu
Anethol natürlich
Petitgrainöl
PhenylethylalkoholCapronaldehyde
Capric acid 10% in ethanol
Caprylic acid 10% in ethanol
Caproic acid 10% in ethanol
Sandeihoizöi
Bulgarian rose oil
Jasmine Absolu
Anethole, of course
Petitgrain oil
Phenylethyl alcohol
Gewichtsteile Parts by weight
1
1 Buuersäurebutylester1
1 butyl acid ester
BenzaldehydBenzaldehyde
PentadecanolidPentadecanolide
Phenylessigsäurelinalyleste:Phenylacetic acid linalyl esters:
Buttersäureterpenylester EssigsäurelinalylesterButyric acid terpenyl ester acetic acid linalyl ester
EssigsäcreäthylesterEthyl acetate
Essigsäurepiperonylester ButtersäuregeranylesterPiperonyl acetate, butyric acid geranyl ester
Benzoesäuregeranylester BenzoesäurebenzylesterGeranyl benzoate Benzoic acid benzyl ester
CaprylsäurelinalylesterElinalyl caprylate
Aldehyde 18Aldehydes 18
(y-Nonalacton,(y-nonalactone,
4-Hydroxynonansäurelactan, y-n-Amylbutyrolacton)4-hydroxynonanoic acid lactane, y-n-amylbutyrolactone)
LinaloolLinalool
Pclargonsäureäthy !esterPclargonic acid ethyester
CitronellolCitronellol
VanillinVanillin
AldehydCHAldehyde CH
(y-Undecslacton,(y-undecslactone,
4-Hydroxyundecensäurelacton, y-n-Heptylbutyrolacton,4-hydroxyundecenoic acid lactone, y-n-heptylbutyrolactone,
Undecanolid-1,4)Undecanolide-1,4)
CapronsäureäthyiisterCaproic acid ether
a-Ionona-ionone
ButtersäureamylfsterButyric acid amyl window
CitralCitral
Acetaldehydacetaldehyde
ButtersäureäthylesterButyric acid ethyl ester
LaurylalkoholLauryl alcohol
d-Limonend-limes
10 10 10 12 1210 10 10 12 12
1212th
2020th
2020th
2020th
5050
5050
200200
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Der Zusatz von 5%o Photocitral-Gemisch (58% Photocitral, 16% Photocitral B, 6% epi-Photocitral A und 3% trans, trans-Photocitra! A) zu obiger Kornposition verändert deren sensorische Eigenschaften in Richtung einer schaligen, grünen Hesperiden-Note, wobei besonders die starke Ester-Note in angenehm überraschender Weise modifiziert, d. h. zurückgedrängt wird.The addition of 5% o Photocitral mixture (58% Photocitral, 16% Photocitral B, 6% epi-Photocitral A and 3% trans, trans-Photocitra! A) to the above grain position changes their sensory properties in Direction of a peeled, green Hesperiden note, whereby the strong ester note in particular is pleasant surprisingly modified, d. H. is pushed back.
Die Verwertung der Erfindung kann durch gesetzliche Bestimmungen, insbesondere durch das Lebensmittelgesetz, beschränkt sein.The exploitation of the invention can be made possible by legal provisions, in particular by the Food Act, be limited.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1479372A CH572339A5 (en) | 1972-10-10 | 1972-10-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2347454A1 DE2347454A1 (en) | 1974-04-25 |
| DE2347454C2 true DE2347454C2 (en) | 1982-07-15 |
Family
ID=4403878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2347454A Expired DE2347454C2 (en) | 1972-10-10 | 1973-09-20 | Process for the production of flavor compositions |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5727085B2 (en) |
| CH (1) | CH572339A5 (en) |
| DE (1) | DE2347454C2 (en) |
| FR (1) | FR2205340B1 (en) |
| GB (1) | GB1401747A (en) |
| NL (1) | NL176834C (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4543203A (en) * | 1983-03-10 | 1985-09-24 | International Flavors & Fragrances Inc. | 2-Isopropenyl-1,5-dimethyl-cyclopentane carboxaldehyde |
| JPS622776U (en) * | 1985-06-21 | 1987-01-09 | ||
| EP1424071B1 (en) * | 2001-08-08 | 2008-08-20 | Shiseido Company Limited | Perfume compositions |
-
1972
- 1972-10-10 CH CH1479372A patent/CH572339A5/xx not_active IP Right Cessation
-
1973
- 1973-09-20 DE DE2347454A patent/DE2347454C2/en not_active Expired
- 1973-09-28 NL NLAANVRAGE7313419,A patent/NL176834C/en not_active IP Right Cessation
- 1973-10-08 FR FR7335864A patent/FR2205340B1/fr not_active Expired
- 1973-10-08 JP JP11318173A patent/JPS5727085B2/ja not_active Expired
- 1973-10-09 GB GB4708673A patent/GB1401747A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4971152A (en) | 1974-07-10 |
| FR2205340A1 (en) | 1974-05-31 |
| NL176834C (en) | 1985-06-17 |
| JPS5727085B2 (en) | 1982-06-08 |
| NL176834B (en) | 1985-01-16 |
| CH572339A5 (en) | 1976-02-13 |
| FR2205340B1 (en) | 1977-03-11 |
| GB1401747A (en) | 1975-07-30 |
| DE2347454A1 (en) | 1974-04-25 |
| NL7313419A (en) | 1974-04-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |