WO2011110614A1 - Composés organiques - Google Patents

Composés organiques Download PDF

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Publication number
WO2011110614A1
WO2011110614A1 PCT/EP2011/053581 EP2011053581W WO2011110614A1 WO 2011110614 A1 WO2011110614 A1 WO 2011110614A1 EP 2011053581 W EP2011053581 W EP 2011053581W WO 2011110614 A1 WO2011110614 A1 WO 2011110614A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
propyl
compound
flavour
fragrance
Prior art date
Application number
PCT/EP2011/053581
Other languages
English (en)
Inventor
David C. Bom
Philip A. Christenson
Felix Flachsmann
Melanie Rizzi
Original Assignee
Givaudan Sa
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 Givaudan Sa filed Critical Givaudan Sa
Publication of WO2011110614A1 publication Critical patent/WO2011110614A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • C07D313/02—Seven-membered rings
    • C07D313/04—Seven-membered rings not condensed with other rings

Definitions

  • This disclosure relates to a new class of compounds possessing fruity peach odor notes and to flavour and fragrance compositions comprising them. This disclosure relates furthermore to a method of their production.
  • flavour and fragrance industry is always interested in new compounds that may enhance, improve, or modify the aroma and/or taste in a product.
  • compounds having unique organoleptic profiles suitable for use in a variety of products, including consumable and topically-applied products.
  • flavour of consumable products consists of two parts, namely aroma and taste.
  • the part that is perceived olfactively in the nasal cavity is described by the term "aroma”, whereas the part termed “taste” is used to describe the sensorial impact perceived in the mouth, and more particularly on the tongue.
  • n 1 or 2;
  • the "base material” includes all known odorant molecules selected from the extensive range of natural products and synthetic molecules currently available, such as essential oils, alcohols, aldehydes and ketones, ethers and acetals, esters and lactones, macrocycles and heterocycles, and/or in admixture with one or more ingredients or excipients conventionally used in conjunction with odorants in fragrance and flavour compositions, for example, carrier materials, and other auxiliary agents commonly used in the art.
  • “flavour compositions” means any composition comprising at least one compound of formula (I) and a base material suitable for consumables, e.g.
  • flavouring compounds such as ethylene glycol, propylene glycol, glycerol, triacetine, triethylcitrate, diethyl phthalate, dimethyl phthalate, benzylic alcohol, ethanol, and vegetal oils.
  • fragment composition means any composition comprising at least one compound of formula (I) and a base material suitable for consumer products, e.g. a diluent conventionally used in conjunction with odorants, such as dipropyleneglycol (DPG), iso propyl my ri state (IPM), triethylcitrate (TEC) and alcohol (e.g. ethanol).
  • a base material suitable for consumer products e.g. a diluent conventionally used in conjunction with odorants, such as dipropyleneglycol (DPG), iso propyl my ri state (IPM), triethylcitrate (TEC) and alcohol (e.g. ethanol).
  • DPG dipropyleneglycol
  • IPM iso propyl my ri state
  • TEC triethylcitrate
  • alcohol e.g. ethanol
  • - essential oils and extracts e.g. tree moss absolute, basil oil, fruit oils such as bergamot oil and mandarine oil, myrtle oil, palmarose oil, patchouli oil, petitgrain oil, jasmine oil, rose oil, sandalwood oil, wormwood oil, lavender oil or ylang-ylang oil;
  • - alcohols e.g. cinnamic alcohol, cis-3-hexenol, citronellol, EbanolTM, eugenol, farnesol, geraniol, Super uguetTM, linalool, menthol, nerol, phenylethyl alcohol, rhodinol, SandaloreTM, terpineol or TimberolTM;
  • - aldehydes and ketones e.g. anisaldehyde, cc-amylcinnamaldehyde, GeorgywoodTM, hydroxycitronellal, Iso E ® Super, Isoraldeine ® , Hedione ® , Lilial ® , maltol, Methyl cedryl ketone, methylionone, verbenone or vanillin; - ethers and acetals, e.g. Ambrox , geranyl methyl ether, rose oxide or
  • esters and lactones e.g. benzyl acetate, Cedryl acetate, ⁇ -decalactone, Helvetolide ® , ⁇ -undecalactone or Vetivenyl acetate;
  • heterocycles e.g. isobutylquinoline.
  • the compounds according to formula (I) may be used in a broad range of fragrance and flavour applications, e.g. in any field of fine and functional perfumery, such as perfumes, air care products, household products, laundry products, body care products, cosmetics and consumables, such as foodstuff and beverages.
  • the compounds can be employed in widely varying amounts, depending upon the specific application and on the nature and quantity of other ingredients.
  • the proportion is typically from 0.001 to 1 weight percent of the fragrance application.
  • compounds of formula (I) may be employed in a fabric softener in an amount of from 0.001 to 0.2 weight percent.
  • compounds of formula (I) may be used in fine perfumery in amounts of from 0.001 to 1 weight percent, in certain embodiments between 0.001 and 0.5 weight percent.
  • these values are given only by way of example, since the experienced perfumer may also achieve effects or may create novel accords with lower or higher concentrations.
  • the compounds of the formula (I) may be employed in the range from 0.001 % to 5% by weight, more particular from 0.1% to 1% by weight.
  • these values are given only by way of example, since the experienced flavourist may also achieve effects with lower or higher concentrations.
  • Flavoured applications for which the compounds of formula (I) are particularly suitable are foodstuffs and beverages such as yogurt, fruit juices, jams, carbonated beverages, chewing gum, candy, chocolate, chocolate fillings, flavoured waters, baked goods, toothpaste, mouthwash, ice cream, and cake icing.
  • foodstuffs and beverages such as yogurt, fruit juices, jams, carbonated beverages, chewing gum, candy, chocolate, chocolate fillings, flavoured waters, baked goods, toothpaste, mouthwash, ice cream, and cake icing.
  • This list of products is given by way of illustration and is not to be regarded as being in any way limiting.
  • the compounds as described hereinabove may be employed in a product base simply by directly mixing the compound of formula (1), a mixture thereof, or a flavour or fragrance composition with the product base, or they may, in an earlier step, be entrapped with an entrapment material, for example, polymers, capsules,
  • the compounds of formula (I) may be dissolved or dispersed in a carrier material, such as a fat, or enrobed with maltose-dextrin, gelatine, gum Arabic and the like. They may be mixed with the food ingredients ready to be prepared or mixed with one of the ingredients, and then mixed with the product base.
  • a carrier material such as a fat, or enrobed with maltose-dextrin, gelatine, gum Arabic and the like. They may be mixed with the food ingredients ready to be prepared or mixed with one of the ingredients, and then mixed with the product base.
  • the compounds of formula (I) may be chemically bonded to substrates, which are adapted to release the molecule upon application of an external stimulus such as light, enzyme, temperature, moisture, or the like, and then mixed with the product base.
  • a method of manufacturing a flavour or fragrance application comprising the incorporation of a compound of formula (I), as a flavour or fragrance ingredient, either by directly admixing the compound to the product base or by admixing a flavour or fragrance composition comprising a compound of formula (I), which may then be mixed with the product base, using conventional techniques and methods.
  • a method of manufacturing a flavour or fragrance application comprising the incorporation of a compound of formula (I), as a flavour or fragrance ingredient, either by directly admixing the compound to the product base or by admixing a flavour or fragrance composition comprising a compound of formula (I), which may then be mixed with the product base, using conventional techniques and methods.
  • a fragrance application comprising:
  • ..product base in conjunction with fragrance applications is meant a composition for use as a consumer product to fulfill specific actions, such as cleaning, softening, and caring or the like.
  • examples of such products include fine perfumery, e.g. perfume and eau de toilette; fabric care, household products and personal care products such as laundry care detergents, rinse conditioner, personal cleansing composition, detergent for dishwasher, surface cleaner; laundry products, e.g. softener, bleach, detergent; body care products, e.g. shampoo, shower gel; air care products and cosmetics, e.g. deodorant, vanishing creme.
  • This list of products is given by way of illustration and is not to be regarded as being in any way limiting.
  • flavour application comprising:
  • product base in conjunction with flavour applications is meant a consumable, not containing a compound of formula (I) as hereinabove defined.
  • consumable is meant a product such as foodstuffs and beverages, or personal care products that are intended to be introduced into the oral cavity of a human or animal and remain there for a certain period of time before being ingested or removed from the mouth.
  • Such products include compositions in their processed, partially processed or unprocessed state.
  • n 1 or 2;
  • the compounds of formula (I) comprise several chiral centres and as such may exist as a mixture of stereoisomers, or they may be resolved as isomerically pure forms.
  • Resolving stereoisomers adds to the complexity of manufacture and purification of these compounds and so it is preferred to use the compounds as mixtures of their stereoisomers simply for economic reasons. However, if it is desired to prepare individual stereoisomers, this may be achieved according to methods known in the art, e.g. preparative HPLC and GC, crystallization or stereoselective synthesis.
  • compounds of formula (I) selected from the group consisting of 6-(2-(4-methylcyclohex-3-enyl)propyl)tetrahydro-2H-pyran-2-one, 6-(2-(4- methylcyclohexyl)propyl)tetrahydro-2H-pyran-2-one, 7-(2-(4-methylcyclohex-3- enyl)propyl)oxepan-2-one and 7- ⁇ 2-(4-methylcycIohexyl)propyl)oxepan-2-one.
  • the compounds of formula (I) may be prepared by Baeyer-Villiger oxidation starting from the corresponding olefine under conditions known to the person skilled in the art.
  • the corresponding olefins may be prepared by radical addition of the corresponding cycloalkanone to limonene (e.g. (+)-!imonene), as described for example by Iwahama, T. et al. ⁇ Chem Comm. 2000, 23, 2317-2318).
  • Example 1 6-(2- (4-methyl cy clohex-3-enyI) pro py I )tetra hyd ro-2 H -py ran-2-one
  • dichloromethane (about 84 mf) was added in portions over 5 minutes at 0° C. After stirring five minutes the reaction was warmed to ambient temperature at which point it began refluxing. The reaction was cooled in the ice bath to control the exotherm. After five minutes, the reaction was warmed to room temperature at which point no further rise in temperature was observed. After 3hours, sodium sulfite (42 g) was added and the reaction was stirred overnight. The next morning the contents were poured onto a pad of silica gel (about 300 g) and the pad was washed with 3:2 hexane/EtOAc (1500 ml). The solvent was evaporated providing a crude, clear oil.
  • This oil was dissolved in a small amount of dichloromethane and purified by flash chromatography on silica gel using a gradient of 100% hexane to 50:50 hexane/EtOAc. The product containing fractions were concentrated and the resulting oil was distilled under high vacuum (1 mbar) to remove last traces of solvent. After distillation a total of 10.8 g (32.6%) was obtained as a clear oil. Based on NMR and GC/MS it was clear that it was a mixture of diastereoisomers.
  • Odour description cooked peach, apricot, creamy, mango, tropical, slightly soapy.
  • Example 3 Perfuming composition suitable for a body care product parts by weight
  • fragrance composition above may be used, for example, in shampoo or body wash applications.
  • Example 4 tropical fruit flavor compositions
  • the compounds of formula (I), in particular 6-(2-(4-methyIcyclohex-3-enyl)propyl)tetrahydro-2H-pyran-2-one, has differentiating value, especially for ripe, tropical fruit flavors without sulfur containing components.
  • MCT medium chain triglycerides (e.g. Captex ® 355 from ABITEC Corporation) 4) 2-(5-methyl-5-vinyltetrahydrofuran-2-yl)propan-2-ol

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
  • Fats And Perfumes (AREA)
  • Seasonings (AREA)

Abstract

La présente invention concerne des composés de formule (I) où n est égal à 1 ou à 2 ; et la ligne pointillée représente avec la liaison carbone-carbone une liaison simple ou une double liaison. En outre, la présente invention concerne des compositions d'arômes et de parfums comprenant au moins un composé de formule (I) et l'une de leurs méthodes de production.
PCT/EP2011/053581 2010-03-11 2011-03-10 Composés organiques WO2011110614A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US31271110P 2010-03-11 2010-03-11
US61/312,711 2010-03-11

Publications (1)

Publication Number Publication Date
WO2011110614A1 true WO2011110614A1 (fr) 2011-09-15

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Family Applications (1)

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PCT/EP2011/053581 WO2011110614A1 (fr) 2010-03-11 2011-03-10 Composés organiques

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WO (1) WO2011110614A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111662262A (zh) * 2020-06-29 2020-09-15 怀宁大有医药科技有限公司 6-(4-((2-环己硫基乙基)氨基)苯基)四氢-2h-吡喃-2-酮的合成方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0513627A1 (fr) * 1991-05-15 1992-11-19 Givaudan-Roure (International) S.A. Dérivé de tétrahydro-alpha-pyrone, procédé pour sa préparation et compositions parfumantes et/ou aromatisantes le contenant

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0513627A1 (fr) * 1991-05-15 1992-11-19 Givaudan-Roure (International) S.A. Dérivé de tétrahydro-alpha-pyrone, procédé pour sa préparation et compositions parfumantes et/ou aromatisantes le contenant

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
IWAHAMA, T. ET AL., CHEM COMM., vol. 23, 2000, pages 2317 - 2318

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111662262A (zh) * 2020-06-29 2020-09-15 怀宁大有医药科技有限公司 6-(4-((2-环己硫基乙基)氨基)苯基)四氢-2h-吡喃-2-酮的合成方法
CN111662262B (zh) * 2020-06-29 2023-04-28 陕西大美化工科技有限公司 6-(4-((2-环己硫基乙基)氨基)苯基)四氢-2h-吡喃-2-酮的合成方法

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