EP4003058A1 - Compositions de vanilline naturelle - Google Patents

Compositions de vanilline naturelle

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Publication number
EP4003058A1
EP4003058A1 EP20746221.9A EP20746221A EP4003058A1 EP 4003058 A1 EP4003058 A1 EP 4003058A1 EP 20746221 A EP20746221 A EP 20746221A EP 4003058 A1 EP4003058 A1 EP 4003058A1
Authority
EP
European Patent Office
Prior art keywords
equal
composition
ppm
natural vanillin
hydroxy
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.)
Pending
Application number
EP20746221.9A
Other languages
German (de)
English (en)
French (fr)
Inventor
Laurent Garel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Specialty Operations France SAS
Original Assignee
Rhodia Operations SAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rhodia Operations SAS filed Critical Rhodia Operations SAS
Publication of EP4003058A1 publication Critical patent/EP4003058A1/fr
Pending legal-status Critical Current

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Classifications

    • 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
    • A23L27/204—Aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • C07C47/58—Vanillin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K10/00—Animal feeding-stuffs
    • A23K10/30—Animal feeding-stuffs from material of plant origin, e.g. roots, seeds or hay; from material of fungal origin, e.g. mushrooms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/111—Aromatic compounds
    • 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
    • A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
    • A23L27/11—Natural spices, flavouring agents or condiments; Extracts thereof obtained by solvent extraction
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • C07C45/83—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation by extractive distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2072—Aldehydes-ketones
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/30—Extraction of the material
    • A61K2236/37—Extraction at elevated pressure or temperature, e.g. pressurized solvent extraction [PSE], supercritical carbon dioxide extraction or subcritical water extraction

Definitions

  • the present invention relates to natural vanillin compositions comprising at least one compound selected from 4 - ((4-hydroxy-3-methoxybenzyl) oxy) -3 -methoxybenzaldehyde and 4- hydroxy-3 - (4-hydroxy-3 -methoxybenzyl) -5 -methoxybenzaldehyde.
  • the invention also relates to a process for obtaining natural vanillin compositions according to the invention.
  • Vanillin or 4-hydroxy-3-methoxybenzaldehyde, can be obtained by various methods known to those skilled in the art, and in particular by the following three routes:
  • ferulic acid used in which the fermentation substrate is ferulic acid.
  • the ferulic acid used can be of several origins, especially from rice or corn bran.
  • vanillin can also be prepared according to a route described as “biobased” in which the vanillin is obtained from eugenol or from lignin, one can cite in particular the documents US 2745796, DE 1132113 and the article entitled “Preparation of lignin ffom wood dust as vanillin source and comparison of different extraction method ”by Azadbakht et al. in International Journal of Biology and Biotechnology, 2004, vol 1, No 4, pp 535-537.
  • a first object of the present invention relates to a composition comprising natural vanillin and further comprising at least one compound chosen from 4 - ((4-hydroxy-3-methoxybenzyl) oxy) -3-methoxybenzaldehyde and 4-hydroxy- 3- (4-hydroxy-3-methoxybenzyl) -5-methoxybenzaldehyde.
  • Another aspect relates to a process for preparing a natural vanillin composition according to the invention comprising a stage (a) of ferulic acid fermentation and optionally a stage (b) of purification of the natural vanillin composition obtained at the outcome of step (a).
  • the present invention relates to the use of a natural vanillin composition as an aroma in the field of human and animal nutrition, of pharmacy, or as a perfume in the cosmetics and perfumery industry. and detergency.
  • natural vanillin can denote a flavoring substance according to article 9.2c) of regulation EC1334 / 2008, that is to say obtained by physical processes, enzymatic or microbiological from materials of plant, animal or microbiological origin taken as is or after their transformation for human consumption by one or more of the traditional processes for the preparation of foodstuffs.
  • a natural flavoring substance is a substance that is naturally occurring and has been identified in nature. The definitions given by the regulations in force in other countries or zones may also apply.
  • the term “natural vanillin” denotes vanillin obtained by a biotechnological process comprising the culture of a microorganism capable of allowing the transformation of a fermentation substrate into vanillin.
  • the microorganism can be wild or be genetically modified, in particular in order to improve the yield of vanillin or to avoid the formation of by-products.
  • it may be a ferulic acid fermentation process, as described in patent application EP 0885968.
  • Ferulic acid can be of any origin, in particular derived from rice bran or pulp of beet, wheat bran, bagasse, sugar cane or maize, in particular maize bran or maize fibers, in particular obtained from starches or nixtamalization units.
  • the present invention relates to a composition comprising natural vanillin and further comprising at least one compound selected from 4 - ((4-hydroxy-3-methoxybenzyl) oxy) -3-methoxybenzaldehyde and 4-hydroxy- 3- (4-hydroxy-3-methoxybenzyl) -5-methoxybenzaldehyde.
  • the composition according to the present invention comprises 4 - ((4-hydroxy-3-methoxybenzyl) oxy) -3-methoxybenzaldehyde and 4-hydroxy-3- (4-hydroxy-3-methoxybenzyl) -5-methoxybenzaldehyde.
  • the composition according to the present invention further comprises at least one compound chosen from vanillic alcohol, vanillic acid, acetovanillone, gaiacol and vinyl gaiacol.
  • the composition according to the present invention can comprise G acetovanillone and / or vinyl gaiacol.
  • the composition according to the present invention may further comprise at least one compound chosen from vanillic alcohol, vanillic acid and acetovanillone.
  • the composition according to the present invention has a natural vanillin content greater than or equal to 90%, preferably greater than 95%, very preferably greater than or equal to 99%. According to one particular aspect, the content of natural vanillin is greater than or equal to 99.5%.
  • the content by weight of 4 - ((4-hydroxy-3-methoxybenzyl) oxy) -3-methoxybenzaldehyde relative to the total weight of the composition is less than or equal to 10,000 ppm, preferably less than or equal to at 8,000 ppm, preferably less than or equal to 7,000 ppm, and very preferably less than or equal to 5,000 ppm.
  • the content by weight of 4 - ((4-hydroxy-3-methoxybenzyl) oxy) -3-methoxybenzaldehyde relative to the total weight of the composition is greater than or equal to 10 ppm, preferably greater than or equal to at 200 ppm, preferably greater than or equal to 500 ppm, and very preferably greater than or equal to 100 ppm.
  • the content by weight of 4 - ((4-hydroxy-3-methoxybenzyl) oxy) -3-methoxybenzaldehyde relative to the total weight of the composition is between 600 ppm and 2,500 ppm.
  • the content by weight of 4-hydroxy-3- (4-hydroxy-3-methoxybenzyl) -5-methoxybenzaldehyde relative to the total weight of the composition is less than or equal to 5000 ppm, preferably less than or equal to at 2500 ppm, preferably less than or equal to 1000 ppm and very preferably less than or equal to 900 ppm.
  • the content by weight of 4-hydroxy-3- (4-hydroxy-3-methoxybenzyl) - 5 -methoxybenzaldehyde relative to the total weight of the composition is greater than or equal to 10 ppm, preferably greater than or equal to 100 ppm, preferably greater than or equal to 200 ppm and very preferably greater than or equal to 300 ppm.
  • the content by weight of 4-hydroxy-3- (4-hydroxy-3-methoxybenzyl) -5-methoxybenzaldehyde relative to the total weight of the composition is between 400 ppm and 800 ppm.
  • the content by weight of vanillic alcohol relative to the total weight of the composition is less than or equal to 4000 ppm, preferably less than or equal to 2000 ppm, very preferably less than or equal to 1000 ppm, preferably less than or equal to equal to 800 ppm, preferably less than or equal to 600 ppm and very preferably less than or equal to 500 ppm.
  • the content by weight of vanillic alcohol relative to the total weight of the composition is greater than or equal to 1 ppm, preferably greater than or equal to 5 ppm, preferably greater than or equal to 10 ppm and very preferably greater than or equal to at 20 ppm.
  • the content by weight of vanillic alcohol relative to the total weight of the composition is between 50 ppm and 250 ppm.
  • the content by weight of vanillic acid relative to the total weight of the composition is less than or equal to 1000 ppm, preferably less than or equal to 700 ppm, preferably less than or equal to 500 ppm and very preferably less than or equal to at 200 ppm.
  • the content by weight of vanillic acid relative to the total weight of the composition is greater than or equal to 1 ppm, preferably greater than or equal to 5 ppm, preferably greater than or equal to 10 ppm and very preferably greater than or equal to at 20 ppm.
  • the content by weight of vanillic acid relative to the total weight of the composition is between 50 ppm and 100 ppm.
  • the content by weight of acetovanillone relative to the total weight of the composition is less than or equal to 1000 ppm, preferably less than or equal to 800 ppm, preferably less than or equal to 600 ppm and very preferably less than or equal to 500 ppm.
  • the content by weight of acetovanillone relative to the total weight of the composition is greater than or equal to 0.1 ppm, preferably greater than or equal to 5 ppm, preferably greater than or equal to 10 ppm and very preferably greater than or equal to at 20 ppm.
  • the content by weight of acetovanillone relative to the total weight of the composition is between 50 ppm and 400 ppm.
  • the content by weight of guaiacol relative to the total weight of the composition is less than or equal to 100 ppm, preferably less than or equal to 50 ppm, preferably less than or equal to 40 ppm and very preferably less than or equal to 20 ppm.
  • the content by weight of guaiacol relative to the total weight of the composition is greater than or equal to 0.01 ppm, preferably greater than or equal to 0.1 ppm, preferably greater than or equal to 1 ppm and very preferably greater than or equal to 10 ppm.
  • the vanillin composition does not include gaiacol.
  • the content by weight of vinyl gaiacol relative to the total weight of the composition is less than or equal to 100 ppm, preferably less than or equal to 50 ppm, preferably less than or equal to 40 ppm and very preferably less than or equal to at 20 ppm.
  • the content by weight of vinyl guaiacol relative to the total weight of the composition is greater than or equal to 0.01 ppm, preferably greater than or equal to 0.1 ppm, preferably greater than or equal to 1 ppm and very preferably greater than or equal to 10 ppm.
  • the vanillin composition does not comprise no vinyl gaiacol, in particular the vinyl gaiacol content is below the detection limits of liquid chromatography methods.
  • the composition according to the present invention is weakly colored.
  • the natural vanillin composition has a color less than or equal to 400 Hazen, preferably less than or equal to 200 Hazen, more preferably less than or equal to 100 Hazen, very preferably less than or equal to 50 Hazen and even more preferably less than or equal to equal to 20 Hazen.
  • the coloring is measured in an ethanolic solution at 10% by weight. Color measurements are performed with a Konica Minolta CM-5 spectrophotometer using a cuvette with an optical path of 10 mm.
  • the natural vanillin composition according to the present invention can be in crystalline or amorphous form, preferably crystalline.
  • the natural vanillin composition can be shaped as a powder, crystals, pearls, prills or scales.
  • the natural vanillin composition according to the present invention has a consistent organoleptic profile, in particular in terms of visual appearance, texture, taste or fragrance.
  • the composition according to the present invention does not exhibit false notes.
  • the organoleptic profile of the composition according to the present invention is at least equivalent to the organoleptic profile of the natural vanillin extracted from pods.
  • the natural vanillin composition according to the present invention is likely to contain other compounds. These compounds present in said composition are linked to the process for preparing natural vanillin. Mention may be made in particular, without however being exhaustive, of 4- (3-hydroxy-4-methoxybenzyl) -2-methoxyphenol, 4,4'-methylenebis (2-methoxyphenol), ferulic acid, dimers and / or trimers of vanillin.
  • Another aspect relates to a process for preparing a natural vanillin composition according to the invention, characterized in that it comprises a stage (a) of ferulic acid fermentation and optionally a stage (b) of purification of the ferulic acid. composition of crude natural vanillin obtained at the end of step (a).
  • step (a) of the process is a step of ferulic acid fermentation for the production of a crude composition of natural vanillin.
  • a crude composition of natural vanillin refers to a composition obtained at the end of the ferulic acid fermentation step.
  • the crude vanillin composition can be obtained after treatment of the aqueous fermentation medium.
  • the fermentation medium can be separated from the biomass, then the aqueous phase can be extracted with an appropriate solvent.
  • the composition of crude natural vanillin can be obtained at the end of the ferulic acid fermentation step, indirectly.
  • a liquid composition comprising natural vanillin, impurities and a large amount of solvent, typically a food solvent such as for example ethyl acetate is generally recovered.
  • the fermentation can be carried out as indicated in document EP 0885968.
  • the fermentation is generally carried out in an aqueous medium.
  • the mass concentration of natural vanillin is between 0.5 and 60%, preferably between 5% and 40% and even more preferably between 10 and 35% relative to the mass of the raw natural vanillin composition.
  • the crude natural vanillin composition used in step (a) may comprise at least one compound selected from 4 - ((4-hydroxy-3-methoxybenzyl) oxy) -3 -methoxybenzaldehyde and 4- hydroxy-3- (4- hydroxy-3-methoxybenzyl) -5 -methoxybenzaldehyde.
  • the crude vanillin composition may further comprise at least one compound selected from vanillic alcohol, vanillic acid, acetovanillone, gaiacol and vinyl gaiacol.
  • Step (b) is an optional step for purifying the composition obtained at the end of step (a). Alternatively, step (b) is not optional.
  • step (b) can comprise a liquid-liquid extraction as described in document EP 2791098, preferably the liquid-liquid extraction is carried out with a solvent compatible with agro-food applications.
  • Step (b) can also include at least one crystallization step.
  • the purification step can comprise an extraction with supercritical CO2.
  • step (b) can comprise a step in which the crude natural vanillin is evaporated as described in document EP 2948424 or a stripping step as described in document WO 2018/146210.
  • step (b) is an evaporation step in a scraped film evaporator or in a falling film evaporator.
  • this step allows the elimination of compounds less volatile than vanillin present in the raw natural vanillin composition obtained at the end of step (a).
  • the less volatile compounds are preferably chosen from vanillic alcohol, vanillic acid, acetovanillone and the heavy ones.
  • the term "heavy” refers to compounds less volatile than vanillin under the temperature and pressure conditions considered.
  • This embodiment is particularly advantageous in that it allows to purify a crude natural vanillin composition obtained at the end of step (a) and allows the preparation of a natural vanillin composition according to the present invention.
  • the content of impurities is particularly controlled and the composition of natural vanillin is very weakly colored.
  • the process according to the present invention is capable of limiting the content of 4 - ((4-hydroxy-3-methoxybenzyl) oxy) -3-methoxybenzaldehyde and 4-hydroxy-3- (4-hydroxy-3-methoxybenzyl) -5- methoxybenzaldehyde.
  • this embodiment makes it possible to avoid a stripping step in the presence of an entrainment gas and / or a vaporized liquid.
  • this process is interesting from an industrial point of view in that it is economically viable.
  • the temperature of the heat transfer fluid at which step (b) is carried out is generally greater than or equal to 130 ° C, preferably greater than or equal to 145 ° C. Generally the temperature of the heat transfer fluid is less than or equal to 230 ° C, preferably less than or equal to 180 ° C.
  • the pressure at which step (b) is carried out is generally greater than or equal to 0.4 mbar, preferably greater than or equal to 1 mbar. Generally the pressure is less than or equal to 75 mbar, preferably less than or equal to 8 mbar, and more preferably less than or equal to 4 mbar.
  • the mass concentration of natural vanillin in the crude natural vanillin composition used in step (b) is greater than or equal to 10%, preferably greater than or equal to 20%, more preferably greater than or equal to 30%, and again more preferably greater than or equal to 50% and very preferably greater than or equal to 70% relative to the total mass of the raw natural vanillin composition.
  • the method may include a step of concentrating the raw natural vanillin composition.
  • step (b) is carried out in the presence of at least one technical adjuvant, for example a thinner.
  • a thinner authorized by the regulations on food products can be added to natural vanillin.
  • the thinner can be added before step (b), in particular between step (a) and step (b).
  • the thinner can be added during step (b).
  • the plasticizer can be chosen from white mineral oils, in particular food, polyethylene glycol, in particular having an average molecular weight between 200 and 3000 g / mol, preferably between 600 and 1500 g / mol or castor oil plant.
  • step (b) is carried out under an inert atmosphere, in particular under argon, nitrogen or their mixtures.
  • Step (b) can also be carried out in oxygen-depleted air.
  • the oxygen content is less than or equal to 1%.
  • the evaporator makes it possible to recover a gaseous effluent containing the composition of evaporated natural vanillin, which is then condensed so as to recover a condensate of the composition of natural vanillin according to the invention.
  • the natural vanillin titer is greater than or equal to 90%, very preferably greater than 95%, even more preferably greater than or equal to 99%. According to one particular aspect, the vanillin titer is greater than or equal to 99.5%.
  • the natural vanillin condensate obtained at the end of step (b) of natural vanillin purification is weakly colored.
  • the natural vanillin condensate obtained at the end of step (b) is a natural vanillin composition according to the present invention.
  • this natural vanillin condensate, obtained at the end of step (b) exhibits conforming organoleptic properties, at least equivalent to those of natural vanillin extracted from pods or of synthetic vanillin.
  • the purification step (b) does not include a stripping step.
  • the process of the invention does not include the step of melting the natural vanillin composition prior to the evaporation step in a falling film or scraped film evaporator.
  • the natural vanillin composition is not crystallized between step (a) and step (b).
  • the process can also comprise an optional step (c) of shaping the natural vanillin composition obtained at the end of step (b), preferably by crystallization, more preferably by crystallization in a solvent. identified by the FEMA program GRAS TM .
  • the natural vanillin composition is crystallized or recrystallized from water or from a water / alcohol mixture, in particular ethanol.
  • the method according to the invention can be implemented in continuous mode operation or in batch mode operation.
  • the invention also relates to a natural vanillin composition which can be obtained according to the process described according to the present invention.
  • the present invention relates to the use of a natural vanillin composition as a flavoring in the field of human and animal food, pharmaceuticals, or as a perfume in the cosmetics industry, perfumery and detergency.
  • Example 1 A composition of crude natural vanillin is prepared from a fermentation carried out according to the procedure described in application EP 0885968. In addition to the solvent, the crude vanillin composition comprised the compounds of Table 1.
  • Example 2 A crude natural vanillin composition obtained according to the process of application EP 0885968 is subjected to purification by vacuum evaporation in the presence of castor oil, in a scraped film evaporator.
  • composition of natural vanillin according to the invention Properties of the composition of natural vanillin according to the invention:

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)
  • Fodder In General (AREA)
  • Seasonings (AREA)
  • Medicinal Preparation (AREA)
EP20746221.9A 2019-07-30 2020-07-30 Compositions de vanilline naturelle Pending EP4003058A1 (fr)

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FR1908643A FR3099477B1 (fr) 2019-07-30 2019-07-30 Compositions de vanilline naturelle
PCT/EP2020/071485 WO2021019001A1 (fr) 2019-07-30 2020-07-30 Compositions de vanilline naturelle

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EP (1) EP4003058A1 (ja)
JP (1) JP2022542935A (ja)
CN (1) CN114174253A (ja)
BR (1) BR112021026703A2 (ja)
FR (1) FR3099477B1 (ja)
MX (1) MX2022001168A (ja)
WO (1) WO2021019001A1 (ja)

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FR3120627B1 (fr) * 2021-03-15 2024-01-19 Rhodia Operations Procédé de purification de vanilline ou d’un dérivé de vanilline obtenus par un procédé biotechnologique
FR3120629B1 (fr) * 2021-03-15 2024-01-19 Rhodia Operations Procédé de purification de vanilline ou d’un dérivé de vanilline obtenus par un procédé biotechnologique

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Publication number Priority date Publication date Assignee Title
US2745796A (en) 1953-10-21 1956-05-15 Aschaffenburger Zellstoffwerke Method of recovering vanillin
DE1132113B (de) 1959-07-09 1962-06-28 Aschaffenburger Zellstoffwerke Verfahren zur Reinigung von Vanillin
CA2238215A1 (en) 1997-06-19 1998-12-19 Markus Wetli Process for the production of vanillin
CN101165168B (zh) * 2006-10-20 2010-05-12 上海爱普香料有限公司 一株链霉菌及利用其生物转化阿魏酸生产香兰素的方法
EP2157184B1 (en) * 2007-04-19 2020-11-18 Laboratorios Minkab, S.A. de C.V. Process for producing vanilin from microorganisms immobilized by surface culture
FR2981069B1 (fr) * 2011-10-06 2013-12-20 Rhodia Operations Procede de preparation d'un derive de vanilline
FR2984314B1 (fr) 2011-12-15 2014-01-17 Rhodia Operations Procede de purification de la vanilline par extraction liquide-liquide
DE14712214T1 (de) * 2013-01-24 2021-01-07 RHODIA OPéRATIONS Verfahren zur reinigung von natürlichem vanillin
US20170172184A1 (en) * 2014-02-12 2017-06-22 Evolva Sa Methods of Improving Production of Vanillin
FR3062652B1 (fr) 2017-02-08 2020-10-16 Rhodia Operations Procede de purification de la vanilline naturelle

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WO2021019001A1 (fr) 2021-02-04
JP2022542935A (ja) 2022-10-07
MX2022001168A (es) 2022-02-23
CN114174253A (zh) 2022-03-11
BR112021026703A2 (pt) 2022-02-15
US20220264922A1 (en) 2022-08-25
FR3099477B1 (fr) 2023-01-13
FR3099477A1 (fr) 2021-02-05

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