WO2020069754A1 - Verfahren zur herstellung von caryophyllenoxid - Google Patents
Verfahren zur herstellung von caryophyllenoxidInfo
- Publication number
- WO2020069754A1 WO2020069754A1 PCT/EP2018/077140 EP2018077140W WO2020069754A1 WO 2020069754 A1 WO2020069754 A1 WO 2020069754A1 EP 2018077140 W EP2018077140 W EP 2018077140W WO 2020069754 A1 WO2020069754 A1 WO 2020069754A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- mixture
- caryophyllene
- range
- fraction
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
- C07D303/06—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms in which the oxirane rings are condensed with a carbocyclic ring system having three or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/06—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the liquid phase
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Definitions
- the present invention relates to a process for the oxidation of beta-caryophylls with oxygen, in particular atmospheric oxygen, which dispenses with the use of catalysts, enzymes and solvents.
- the oxidation takes place at a temperature of 60 to 150 ° C in a period of 10 to 60 hours and the product is purified by distillation and optional crystallization.
- the present invention provides a mixture comprising caryophyllene oxides and their use as a flavor and / or fragrance.
- the present invention also relates to products and semi-finished goods comprising the mixture according to the invention.
- Beta-caryophyllene is a widely used sesquiterpene, which among other things occurs in cinnamon, pepper and cloves and is contained in a variety of flavors and cosmetic preparations. Autoxidation slowly converts beta-caryophyllene into the corresponding beta-caryophyllene oxides as well as other oxidized degradation products.
- beta-caryophyllene oxide For use in the flavoring industry, a highly pure beta-caryophyllene oxide is currently used which only contains the 1 R, 4R, 6R, 10S-beta-caryophyllene oxide CAS [1 139-30-6] in a purity of> 95%. This quality has long been used in a variety of flavors. So far nothing is known about the sensory properties of other isomers.
- Natural caryophyllene oxide is usually produced by enzymatic oxidation of caryophyllene with the help of hydrogen peroxide. This product is relatively expensive and it would also be desirable to convert the process to a variant, if possible, without the aid of hydrogen peroxide.
- a temperature in a range from 110 to 150 ° C, preferably in a range from 1 15 to 125 ° C, and
- step (iii) distilling the reaction mixture obtained from step (i) or (ii) to obtain a fraction comprising caryophyllene oxides;
- oxygen or atmospheric oxygen is used as the only oxidizing agent; in particular, no oxidizing agents such as peracids or hydrogen peroxide are used in step (i).
- no catalysts, in particular no organometallic compounds are used.
- the method according to the invention can be used without reservations in terms of food technology and law, since no reagents are used which are not suitable for use in foods or cosmetics. It also advantageously does not require any unusual process steps or procedures, so that it can be carried out without problems in conventional systems.
- the reagents used are procedurally unproblematic and harmless to health. The process is based on the use of renewable raw materials without the use of organometallic reagents or special oxidizing agents.
- step (i) can also produce undesired peroxides. Therefore, in step (ii) the reaction mixture from step (i) is optionally heated so that existing peroxides are destroyed. In this case, it may be useful to determine the peroxide number (POZ) of the reaction mixture before and / or after performing step (ii), as will be explained further below.
- POZ peroxide number
- step (i) of the process according to the invention three different diastereoisomers of caryophyllene oxide, i.e. (1 R, 4R, 6R, 10S) -caryophyllene oxide [CAS 1 139-30-6] (compound (1)), (1 R, 4R, 6S, 10S) -socaryophyllene oxide [CAS 60594-22-1]
- step (i) a mixture of the compounds (1), (2) and (3)
- step (iii) comprises or consists of the compounds (1), (2) and (3).
- the oxidation in step (i) is carried out until a significant decrease in the reaction rate begins.
- the typical reaction time is between 10 and 60 hours, particularly preferably between 15 and 40 hours, depending on the reactor geometry, air inlet and filling level.
- the ratio of unreacted caryophyllene to the sum of all three caryophyllene oxides is preferably 4: 1 to 1: 4, particularly preferably 2: 1 to 1: 2.
- step (i) takes place in a period of from 10 to 60 hours, preferably 15 to 40 hours and / or in which the reaction in step (i) takes place until the ratio of unreacted beta-caryophyllene to the sum of compounds (1), (2) and (3) is 4: 1 to 1: 4, preferably 2: 1 to 1: 2.
- the ratio of caryophylls to caryophyllene oxides is preferably determined by gas chromatography with a flame ionization detector (GC FID) in GC-FID area percentages.
- GC FID flame ionization detector
- the following setup can be used for this, for example: Agilent 6890 (Agilent Technologies, Santa Clara, USA) Column type: DB-wax (length, 20 m; inner diameter, 0, 18 mm; film, 0, 18 miti); Flow rate: 1.3 ml min -1 (17 min) - 0.5 ml min -1 - 3.0 ml min -1 ; Injector, split ratio 1/70, temperature program (injector): 80 ° C - 12 ° C / s - 250 ° C; Temperature program (oven): 60 ° C - 9 ° C / min - 240 ° C; Carrier gas, H2; Detector, FID, 275 ° C (Ag
- step (i) the amount of oxygen or air supplied in step (i) is also important. It has been shown that if the air volume is too low, the yield is often too low, whereas higher ones Air quantities lead to the formation of by-products or decomposition of the resulting desired products.
- step (i) gassing is carried out with pure oxygen or preferably with ambient air and / or the amount of oxygen or air supplied is in a range from 10 to 1000 l / h per kg Starting material, preferably in a range from 15 to 500 l / h per kg of starting material, particularly preferably in a range from 20 to 150 l / h per kg of starting material, very particularly preferably in a range from 20 to 100 l / h per kg of starting material .
- undesired peroxides can be formed in the oxidation in step (i). These can be destroyed by optional step (ii). It may be useful to determine the peroxide number of the reaction mixture to ensure that the amount of peroxides present is below a certain limit.
- step (ii) the reaction mixture obtained from step (i) is heated to 110 to 150 ° C., preferably 115 to 125 ° C., for 1 to 3 hours and / or wherein in step (ii) the reaction mixture obtained from step (i) is heated to 110 to 150 ° C., preferably 115 to 125 ° C., until the peroxide number of the reaction mixture is less than 30 meq O / kg, preferably less than Is 20 meq O / kg.
- step (ii) If the temperature ranges mentioned in step (ii) are observed, the content of the desired caryophyllenoxides is largely retained. If higher temperatures are used, the peroxides decompose faster, but there are considerable losses in the yield of caryophyllenoxides.
- the peroxide number (POZ) represents a measure of the content of peroxidic functional groups in the reaction mixture. It is given in milliequivalents of oxygen per kg of the reaction mixture (meq O / kg). The peroxide number is preferably determined by the Wheeler method.
- a co-solvent is preferably added to the reaction mixture, which ensures the stirrability of the distillation bottoms and thereby makes the distillation easier and more efficient.
- Polyethylene glycol (PEG) in particular PEG 600, in a ratio of 3: 1 to 1: 1 (mixture containing caryophyllene oxide to PEG 600) has proven to be particularly preferred here.
- a process as described above is therefore particularly preferred in which a co-solvent is added in step (iii) before the distillation of the reaction mixture obtained from step (i) or (ii), preferably polyethylene glycol, in particular PEG 600, and / or wherein the co-solvent is added in a ratio of 3: 1 to 1: 1 reaction mixture from step (i) or (ii) to the co-solvent.
- a co-solvent is added in step (iii) before the distillation of the reaction mixture obtained from step (i) or (ii), preferably polyethylene glycol, in particular PEG 600, and / or wherein the co-solvent is added in a ratio of 3: 1 to 1: 1 reaction mixture from step (i) or (ii) to the co-solvent.
- the mixture is then distilled in order to separate the non-volatile polymer components.
- the vacuum applied should preferably be between 1 and 5 mbar.
- a fraction with low-boiling components top temperature between ⁇ 100 ° C. at 3-5 mbar) is particularly preferably removed beforehand. The distillation is complete when a top temperature of 130 ° C to 160 ° C at 1 - 5 mbar is reached.
- step (iii) is carried out at a pressure of 1 to 5 mbar and the fraction comprising caryophyllene oxides at a top temperature in a range from 100 to 160 ° C., preferably 100 to 130 ° C is obtained, and optionally a flow at a head temperature of 75 ° C to ⁇ 100 ° C and a pressure of 3 to 5 mbar is obtained and discarded.
- the distillate can be used in the crystallization in step (iv) without further working up.
- the distillate obtained can alternatively be mixed with water in a ratio of about 3: 1 (distillate: water).
- the water is then distilled off again at 85-95 ° C. and 100-500 mbar. This procedure can be repeated if necessary.
- a process as described above is therefore also preferred in which the fraction comprising caryophyllene oxides obtained in step (iii) before the crystallization in step (iv) is stirred with water in a ratio of 4: 1 to 2: 1 fraction comprising caryophyllene oxides to water are added and the water is then distilled off, preferably at a temperature in a range from 85 to 95 ° C. and at a pressure from 100 to 500 mbar.
- step (iv) of the process according to the invention the distillate is recrystallized with a mixture of short-chain alcohols (e.g. methanol, ethanol, n-propanol, iso-propanol) and water.
- a ratio of distillate from step (iii) to alcohol / water of 3: 1 to 1: 3 is preferred, particularly preferably 2: 1 to 1: 2.
- Particularly good results are achieved when ethanol or isopropanol is used for the recrystallization.
- step (iv) the fraction comprising caryophyllene oxides from step (iii) is recrystallized with a mixture of alcohols with 1 to 3 carbons, preferably ethanol and / or isopropanol, and water, preferably wherein a ratio of 3: 1 to 1: 3, preferably 2: 1 to 1: 2, fraction comprising caryophyllene oxides from step (iii) to the Mixture of alcohols with 1 to 3 carbons and water is used.
- the ratio relates to the weight used in each case.
- composition of the mixture of alcohols with 1 to 3 carbons and water is preferably between 3: 1 and 1: 3, particularly preferably between 3: 1 and 1: 1 alcohol mixture to water.
- the ratio relates to the weight used in each case.
- step (i) of the process according to the invention it is also possible to use an enriched fraction containing caryophyllene - which can be obtained by distillation from cloves or clove leaves - which also contains alpha-humulene in addition to beta-caryophylls. If such a fraction is used as starting material in the process according to the invention, a mixture of oxidation products which is particularly advantageous in terms of sensors is produced.
- a mixture of oxidation products which is particularly advantageous in terms of sensors is produced.
- (1 R, 3E, 7E, 1 1 R) -epoxyhumulen [CAS 19888-34-7] compound (4)
- the present invention therefore also relates to a process as described above, wherein the beta-caryophyllene used in step (i) in a mixture comprising 60 to 95% beta-caryophyllene and 2 to 20% alpha-humulene, preferably 85 to 95% beta Caryophylls and 4 to 15% alpha humulene.
- the content of beta-caryophylls and alpha-humules in the mixture used is preferably determined by gas chromatography with a flame ionization detector (GC FID) in GC-FID area percentages.
- GC FID flame ionization detector
- step (iii) comprises 75 to 90% of compound (1), 4 to 12% of compound (2), 0.1 to 5% of compound (3) and 0.1 to 5% of compound (4), preferably 80 to 90% of compound (1), 6 to 10% of compound (2), 0.2 to 3% of compound (3) and 0.5 to 3% of compound (4) consists.
- the percentages are preferably determined by gas chromatography with a flame ionization detector (GC FID) in GC-FID area percentages.
- GC FID flame ionization detector
- the present invention therefore also relates to a mixture, preferably a crystalline mixture, comprising or consisting of compounds (1), (2) and (3), preferably prepared or prepared by a process as described above, or a mixture comprising or consisting of compounds ( 1), (2), (3) and (4), preferably produced or producible by a process as described above, preferably wherein the mixture 75 to 90% of compound (1), 4 to 12% of compound (2), 0, 1 to 5% of compound (3) and 0.1 to 5% of compound (4), preferably 80 to 90% of compound (1), 6 to 10% of compound (2), 0.2 to 3% of compound (3) and Contains or consists of 0.5 to 3% of compound (4).
- the percentages are preferably determined by gas chromatography with a flame ionization detector (GC FID) in GC-FID area percentages.
- GC FID flame ionization detector
- the resulting product therefore differs in the specification from the products on the market that contain> 95% compound (1).
- the mixture according to the invention has an improved sensory profile compared to compound (1). It was also surprisingly found for the first time that the compound (2) is perceived to be significantly more intense than the compound (1) in terms of sensors, and that particularly advantageous notes are more pronounced in it.
- the present invention therefore also relates to the use of a mixture as described above as an odorant and / or flavoring agent or to the use of compound (2) as an odorant and / or flavoring agent.
- the mixture according to the invention or the compound (2) for producing, imparting or enhancing one or more taste and / or smell impressions selected from citrus, woody, grapefruit, tropical fruits, e.g. Mango, vegetables, e.g. Herbs, carrots, hops and green tea can be used.
- the mixture according to the invention can advantageously be used in a number of products and semi-finished goods as an odorant and / or flavoring.
- the invention therefore also relates to a cosmetic or pharmaceutical preparation or semi-finished product for nutrition, oral care or pleasure or for oral ingestion or for the manufacture of a cosmetic or pharmaceutical preparation for nutrition, oral care or pleasure or for oral ingestion comprising a mixture as described above.
- a preparation according to the invention preferably contains 0.05 to 50 ppm, particularly preferably 0.1 to 20 ppm of the mixture as described above.
- An inventive Semi-finished goods preferably contain 0.001 to 7.5 wt .-%, particularly preferably 0.01 to 5.0 wt .-% of the mixture as described above.
- Nutritional or pleasure preparations in the sense of the present invention are e.g. Baked goods (e.g. bread, dry biscuits, cakes, other pastries), confectionery (e.g. chocolates, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum), alcoholic or non-alcoholic drinks (e.g. coffee, tea, wine, wine-based drinks, beer, beer-based beverages, liqueurs, schnapps, brandies, fruit-based lemonades, isotonic drinks, soft drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations), instant drinks (e.g. instant cocoa drinks, instant tea drinks, instant coffee drinks), Meat products (e.g.
- Baked goods e.g. bread, dry biscuits, cakes, other pastries
- confectionery e.g. chocolates, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum
- alcoholic or non-alcoholic drinks e.g. coffee, tea, wine, wine-based drinks,
- vegetable preparations e.g. ketchup, sauces, dried vegetables, frozen vegetables, pre-cooked vegetables , pickled vegetables, boiled vegetables
- snack foods e.g. baked or fried potato chips or potato dough products, bread dough products, extrudates based on corn or peanut
- products based on fat and oil or emulsions thereof e.g. mayonnaise, tartar sauce, dressings, seasoning preparations
- other ready meals and soups e.g. dry soups, instant soups, pre-cooked soups
- spices, seasoning mixes and, in particular, seasonings which are used, for example, in the snack area.
- the preparations within the meaning of the invention can also be in the form of capsules, tablets (non-coated and coated tablets, for example with an enteric coating), coated tablets, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsions, as powders, as solutions, as pastes or as other swallowable or chewable preparations as food supplements.
- compositions intended for oral ingestion within the meaning of the present invention are preparations which, for example in the form of capsules, tablets (non-coated and coated tablets, for example with an enteric coating), coated tablets, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsions, as powder, as solutions, as pastes or as other swallowable or chewable Preparations are available and can be used as prescription, pharmacy or other medicinal products or as food supplements.
- Oral care preparations within the meaning of the present invention are, in particular, mouth and / or dental care products such as toothpastes, tooth gels, tooth powder, mouthwashes, chewing gums and other oral care products.
- cosmetic preparations are, for example, cosmetic preparations for application to the body or head, such as soaps, other cleaning or care products for the face or body, face creams, lotions or ointments, sunscreens, beard cleansing or care products , Shaving foams, soaps or gels, lipsticks or other lip cosmetics or lip care products.
- a preparation according to the invention or used for the production of such preparations, for example, as further constituents for preparations or semi-finished goods according to the invention which serve for nutrition or pleasure Water, mixtures of fresh or processed, vegetable or animal base or raw materials (e.g. raw, roasted, dried, fermented, smoked and / or cooked meat, bones, cartilage, fish, vegetables, fruits, herbs, nuts, vegetables or fruit juices or pastes or their mixtures), digestible or non-digestible carbohydrates (e.g.
- taste-modulating substances eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate) or sodium glutamate (e.g. lecithins, diacylglycerols, gum arabic), stabilizers (e.g. carageenan, alginate), preservatives (e.g. benzoic acid, sorbic acid), antioxidants (e.g.
- tocopherol, ascorbic acid chelators
- organic or inorganic acidulants e.g. malic acid, acetic acid, Citro Nenoic acid, tartaric acid, phosphoric acid
- bitter substances e.g. quinine, caffeine, limonin, amarogentin, humolones, lupolones, catechins, tannins
- sweeteners e.g. saccharin, cyclamate, aspartame, neotame
- mineral salts e.g. sodium chloride, potassium chloride, magnesium chloride, Sodium phosphates
- substances that prevent enzymatic browning e.g.
- Dentifrices (as examples of oral care formulations according to the invention) generally comprise an abrasive system (abrasive or polishing agents) such as e.g. Silicas, calcium carbonates, calcium phosphates, aluminum oxides and / or hydroxylapatites, surface-active substances such as e.g. Sodium lauryl sulfate, sodium lauryl sarcosinate and / or cocamidopropyl betaine, humectants such as e.g. Glycerin and / or sorbitol, thickeners such as e.g.
- an abrasive system abrasive or polishing agents
- abrasive or polishing agents such as e.g. Silicas, calcium carbonates, calcium phosphates, aluminum oxides and / or hydroxylapatites
- surface-active substances such as e.g. Sodium lauryl sulfate, sodium lauryl sarcosinate and /
- Carboxy-methyl cellulose Carboxy-methyl cellulose, polyethylene glycols, carrageenan and / or Laponite®, sweeteners, such as e.g. Saccharin, taste corrections for unpleasant taste impressions or generally not unpleasant taste impressions, (possibly further) taste-modulating substances (e.g. inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as
- cooling agents such as Menthol, menthol derivatives (e.g. L-menthol, L-menthyl lactate, L-menthyl alkyl carbonates, menthone ketals, menthane carboxamides), 2,2,2-trialkylacetic acid amides (e.g. 2,2-diisopropylpropionic acid methyl amide), Icilin derivatives, stabilizers and active ingredients, e.g.
- Chewing gums (as another example of oral care formulations according to the invention) generally comprise a chewing gum base, i.e. a chewing mass that becomes plastic when chewing, different types of sugar, sugar substitutes, sweeteners, sugar alcohols, taste corrections or taste modulators for unpleasant or generally not unpleasant taste impressions, (possibly further) taste-modulating substances (e.g. inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate) how
- Emulsifiers (possibly other) flavors and stabilizers or odor correctors.
- Example 1 Oxidation of caryophylls to caryophyllene oxide (laboratory scale)
- the POZ is ⁇ 30 meq O / kg and the mixture is mixed with 450 g PEG 600 and distilled through a DN 30 column with 20 theoretical plates.
- a vacuum of 1 mbar is applied and the bottom temperature is slowly increased from 130 ° C to 225 ° C.
- a main fraction (280 g) is taken off at a head temperature between 100 - 103 ° C.
- the main fraction contains 78% caryophyllenoxide (1 R, 4R, 6R, 10S & 1 R, 4S, 6S, 10S or compounds (1) & (3)) as well as 12% isocaryophyllenoxide (compound (2)) and 10% epoxyhumulen ( Connection (4)).
- the main fraction is recrystallized from 140 ml of isopropanol and 70 ml of water, filtered off at 0 ° C., washed with isopropanol / water (2: 1) and dried to constant mass. 185.3 g of the composition (84.6% (1 R, 4R, 6R, 10S) -caryophyllene oxide [CAS 1 139-30-6]
- 600 kg of an enriched fraction containing caryophyllene from clove oil (containing 89.5% beta-caryophyllene and 8.2% alpha-humulene) are passed through an air gap of 16 m 3 / h for 30 h at 120 ° C (0 1, 2 mm) fumigated.
- a ratio of unreacted caryophyllene to the sum of all caryophyllene oxides formed was 1: 2.
- the mixture is then stirred at 125 ° C. for 2 h without any further air supply in order to destroy the peroxides formed before the distillation.
- the POZ is ⁇ 30 meq O / kg and the mixture is mixed with 280 kg PEG 600 and distilled through a column with 20 theoretical plates.
- a final vacuum of 2 mbar is gradually applied and the bottom temperature is slowly increased to 170 ° C.
- a main fraction 180 kg is taken off at a head temperature between 105 - 15 ° C.
- the main fraction is heated to 80 ° C and 60 kg of water are added, which is then distilled off again at 500-100 mbar and 80-95 ° C. Then it is recrystallized with 300 l of ethanol / water (2: 1). The precipitate is pressed off at 5 ° C., washed with ethanol / water 2: 1 and until dried to constant mass.
- 85.3 kg of the composition 88.7% (1 R, 4R, 6R, 10S) -caryophyllene oxide [CAS 1 139-30-6] (compound (1)), 8.1%
- Example 4 Sensory Evaluation of the Mixture According to the Invention from Example 2
- Example of use 1 Thyme aroma - type white
- parts A and B are each premixed separately and thoroughly stirred together under vacuum at 25-30 ° C. for 30 minutes.
- Part C is premixed and added to A and B; D is added and the mixture is stirred well under vacuum at 25-30 ° C. for 30 minutes. After relaxation, the toothpaste is ready and can be filled.
- Example of use 4 melt extrudate with a carrot aroma
- Part A The matrix materials (Part A) are mixed and fed to an extruder.
- the aroma (Part B) is then metered in during the extrusion process.
- the melt extrudate obtained in this way can, for example, be added to a dry green or black tea base at 50 g / kg.
- Example of use 6 Spray-dried mango type composition
- the drinking water is placed in a container and the maltodextrin and the starch are dissolved in it.
- the aroma is then emulsified into the carrier solution using a Turrax.
- the temperature of the spray solution should not exceed 30 ° C.
- the mixture is then spray dried (target temperature input: 185-195 ° C, target temperature output: 70-75 ° C).
- Example of use 7 Aroma type green tea
- Example of use 8 Aroma type grapefruit
- Example of use 10 Sugar-free chewing gum
- Parts A to D are mixed and kneaded intensively.
- the raw mass can be processed into ready-to-eat chewing gum, for example in the form of thin strips.
- Example of use 12 instant drink
- the ingredients were mixed in the order given and made up to 100% with water.
- the mixtures are filled into glass bottles and carbonized.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
- Confectionery (AREA)
- Seasonings (AREA)
- Non-Alcoholic Beverages (AREA)
- Epoxy Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
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US17/282,436 US20210387959A1 (en) | 2018-10-05 | 2018-10-05 | Process for preparing caryophyllene oxide |
JP2021518741A JP2022513573A (ja) | 2018-10-05 | 2018-10-05 | カリオフィレンオキシド |
EP18785306.4A EP3860983A1 (de) | 2018-10-05 | 2018-10-05 | Verfahren zur herstellung von caryophyllenoxid |
BR112021006143-6A BR112021006143A2 (pt) | 2018-10-05 | 2018-10-05 | processo para produção de óxido de cariofileno |
PCT/EP2018/077140 WO2020069754A1 (de) | 2018-10-05 | 2018-10-05 | Verfahren zur herstellung von caryophyllenoxid |
CN201880098347.0A CN112789267B (zh) | 2018-10-05 | 2018-10-05 | 石竹烯氧化物 |
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PCT/EP2018/077140 WO2020069754A1 (de) | 2018-10-05 | 2018-10-05 | Verfahren zur herstellung von caryophyllenoxid |
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WO2020069754A1 true WO2020069754A1 (de) | 2020-04-09 |
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EP (1) | EP3860983A1 (de) |
JP (1) | JP2022513573A (de) |
CN (1) | CN112789267B (de) |
BR (1) | BR112021006143A2 (de) |
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Publication number | Publication date |
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US20210387959A1 (en) | 2021-12-16 |
CN112789267A (zh) | 2021-05-11 |
EP3860983A1 (de) | 2021-08-11 |
BR112021006143A2 (pt) | 2021-06-29 |
JP2022513573A (ja) | 2022-02-09 |
CN112789267B (zh) | 2024-09-03 |
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