WO2003044143A1 - Procede servant a entretenir un arome et sa mise en application - Google Patents
Procede servant a entretenir un arome et sa mise en application Download PDFInfo
- Publication number
- WO2003044143A1 WO2003044143A1 PCT/JP2002/012196 JP0212196W WO03044143A1 WO 2003044143 A1 WO2003044143 A1 WO 2003044143A1 JP 0212196 W JP0212196 W JP 0212196W WO 03044143 A1 WO03044143 A1 WO 03044143A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- cyclic tetrasaccharide
- fragrance
- aroma
- substance
- cyclic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 73
- -1 cyclic tetrasaccharide Chemical class 0.000 claims abstract description 248
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
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- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
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- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
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- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 0.000 description 1
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Classifications
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- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- 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
-
- 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
- A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
-
- 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
- A61K8/60—Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
Definitions
- Utilization of various sugars has been proposed as a method of retaining aroma.
- a method proposed in Japanese Patent Publication No. 52-37062 in which oligosaccharides and aroma substances are mixed and then solidified.
- Crystallinity proposed in Japanese Unexamined Patent Publication (Kokai) No.8-26663 a method of producing a mixture of maltose (anhydrous maltose) and an oily odorant.
- There is a method for producing an inclusion compound of cyclodextrin and a fragrance substance which is proposed in Japanese Patent Publication No. 5-9886.
- these methods may have a low or poor retention of odorants, or may be limited to oily odorants, or may have a secondary effect on the resulting mixture. Issues such as solubility during processing remain.
- cyclic tetrasaccharide refers to a cyclic tetrasaccharide or a saccharide containing a saccharide other than the saccharide derivative of the cyclic tetrasaccharide in addition to the cyclic tetrasaccharide.
- the ratio at which the cyclic tetrasaccharide or the mixture of the cyclic tetrasaccharide and the carbohydrate derivative of the cyclic tetrasaccharide is added to the odorant is not particularly limited as long as the odorant can be retained.
- the cyclic tetrasaccharide as an anhydride 1 part by weight to 100,000 parts by weight, preferably 10 parts by weight to 5 parts by weight, per 1 part by weight of the odorant. , 000 parts by weight are suitable.
- the cyclic tetrasaccharide used in the aroma retainer of the present invention or a mixture of this cyclic tetrasaccharide and a saccharide derivative of the cyclic tetrasaccharide has a dietary fiber-like action
- the fragrance holding substance is suitable as a raw material for healthy foods, since it is expected that the fragrance will be retained for a long period of time, and that the cholesterol lowering effect for intestinal action will be reduced.
- starch partially decomposed product (trade name “Pine Index # 4”, manufactured by Matsutani Chemical Co., Ltd.) 4.0 w / V%
- yeast extract (trade name “Asahi Mist”, (produced by Asahi Breweries, Ltd.) 1 8 w / V%, dicalcium phosphate 0.1 wV%, monosodium phosphate '12 hydrate 0.06 w / V%, magnesium sulfate '7 hydrate 0.0
- a liquid medium consisting of 5 wV% and water was placed in a 500 ml Erlenmeyer flask at 100 OmI, sterilized in an autoclave at 121 ° C for 20 minutes, cooled, and cooled.
- Bacillus globisporus C9 (FERMBP — 7143) was inoculated, and cultured with shaking at 27 ° C and 230 rpm for 48 hours to form a seed culture. Use a medium with the same composition as in the culture. Add about 20 L, heat sterilize, cool to a temperature of 27 ° C, inoculate 1 VV% of the seed culture, and keep the temperature at 27 ° C and pH 6.0 to 8.0. The cells were cultured with aeration and stirring for 48 hours.
- One unit of the activity of the monoisomaltosylglucosaccharide-forming enzyme was defined as the amount of the enzyme capable of producing 1 mol (male-mole) of maltose per minute under the above conditions.
- the enzymatic activity of Q? -Isomaltosylglucosaccharide-forming enzyme means a unit measured as described above.
- This crude enzyme solution was subjected to ion exchange chromatography (gel volume 1, OOO ml) using “Sepabeads FP—DA 13” gel manufactured by Mitsubishi Chemical Corporation. At this time, neither isomaltosyl glucosaccharide-forming enzyme nor Q? -Isomaltosyltransferase was eluted in the non-adsorbed fraction without adsorbing on the Sepabeads FP-DAI 3 gel. . This fraction was dialyzed against 10 mM phosphate buffer (pH 7.0) containing 1 M ammonium sulfate, and the dialysate was centrifuged to remove impurities.
- the monoisomaltosylglucosaccharide-forming enzyme fraction obtained in Example A-2 was dialyzed against a 10 mM phosphate buffer (pH 7.0) containing 1 M ammonium sulfate, and the dialysate was centrifuged. After removing the insoluble matter, the mixture was subjected to hydrophobic chromatography (gel amount: 350 mI) using “Buty I-Toyopear I” 65 M gel manufactured by Tosoh Corporation. This enzyme was adsorbed on a “Butyl I-Toyopear I” 6550 M gel and eluted with a linear gradient of ammonium sulfate from 1 M to 0 M.
- the obtained sugar solution is applied to a column (gel amount: about 2250 L) packed with an ion exchange resin “Amberlite CR-1310 (Na type)” manufactured by Organo, and the column temperature is set to 60 ° C.
- the chromatographic separation was carried out at a flow rate of about 45 LZh. Determine the sugar composition of the eluate using standard HPLC As a result, a fraction having a purity of the cyclic tetrasaccharide of about 98 o / o or more was collected.
- Example B-3 Preparation of hydrous cyclic tetrasaccharide crystal>
- the cyclic tetrasaccharide fraction having a purity of about 98 o / o or more obtained by the above method is concentrated to a solid concentration of about 50% with an evaporator, and then about 5 kg of the concentrated sugar solution is removed from a cylindrical plastic.
- the solution was placed in a container and crystallized by lowering the temperature from 65 ° C to 20 ° C in about 20 hours while gently rotating, whereby a white crystalline powder was obtained. Subsequently, the crystals were separated using a centrifugal filter, and 1,360 g of the crystalline material was recovered as a wet weight. Further, it was dried at 60 ° C.
- the cyclic tetrasaccharide 5-hydrated crystal powder obtained by the method of Example B-3 was placed in a glass container, and the glass container was kept in an oil bath kept at 140 ° C. in advance for 30 minutes, and heated. Dried.
- this powder was measured by X-ray diffraction, the main diffraction angle (2S) was determined. 8.3. , 16.6 °, 17.0 °, and 18.2 ° were obtained.
- the water content of this powder was measured by the force-Fischer method and found to be about 2.7%, indicating that one molecule of cyclic tetrasaccharide contained one molecule of water.
- Example B-5 Preparation of crystalline anhydrous cyclic tetrasaccharide>
- the cyclic tetrasaccharide crystalline powder obtained by the method of Example B-3 was vacuum dried at a temperature of 120 ° C. for 16 hours.
- the main diffraction angles (20) were 10.8, 14.7 °, 15.0 °, 15.7 and 2 1.5.
- a diffraction spectrum characterized by the following was obtained.
- the water content of this powder was measured by the Karl-Fischer method, and it was found that the water content was about 0.2%, which was substantially anhydrous.
- Example B-5 Preparation of amorphous anhydrous cyclic tetrasaccharide>
- Anhydrous cyclic tetrasaccharide is used, and as a control, a commercially available branched cyclodextrin (trade name “Iso-Elite P”, sold by Maruha Corporation) and described in JP-A-9-111284
- Example C Ethanol-bearing crystalline anhydrous cyclic tetrasaccharide, ethanol-bearing branched cyclodextrin, ethanol-bearing anhydrous trehalose or ethanol-bearing dextrin prepared by the method of Example 11 were used. Immediately after the preparation, about 0.5 g of each was precisely weighed and placed in a 20-ml glass vial, and allowed to stand at normal pressure and room temperature to volatilize ethanol.
- Example C-1 3 Preparation of fragrance retentate with crystalline anhydrous cyclic tetrasaccharide>
- the crystalline anhydrous cyclic tetrasaccharide has the function of retaining various liquid odorous substances such as alcohols, esters, ethers, essential oils, and organic acids.
- various aromatic substances can be prepared by using the crystalline anhydrous cyclic tetrasaccharide.
- An amorphous anhydrous cyclic tetrasaccharide was used, and a commercially available branched cyclodextrin (trade name “Iso-Elite P”, sold by Maruha Corporation) was used as a control.
- the alcohol was extracted, and citronellol or phenethyl alcohol in getyl ether was attached to DB-5 Capillari-Ichiram (0.25 mm x 30 m) (available from GL Sciences Corporation). Quantified by gas chromatography using a Shimadzu GC-14B gas chromatograph.
- the retention of aroma was low in lavender oil and phenethyl alcohol as a whole, but among the four carbohydrates, the residual ratio of crystalline anhydrous cyclic tetrasaccharide and amorphous anhydrous cyclic tetrasaccharide was low. Is relatively high, and the hydrated cyclic tetrasaccharide crystals also show higher values than the branched cyclodextrin as a control, and it was judged that all the cyclic tetrasaccharides had a retaining effect. .
- the obtained dried product was pulverized by a pulverizer to obtain an aroma-containing powder containing grapefruit oil.
- This product has a high ability to retain grapefruit oil (holding action), and also has a high retention of grapefruit oil and is a stable fragrance-containing substance. It is a flavoring agent for foods, cosmetics, pharmaceuticals, daily necessities, etc. It was found that it could be used advantageously.
- Example C-17
- This product is a coffee beverage that has a stable fragrance of coffee over a long period of time, is dissolved by pouring hot water, and has an excellent fragrance and moderate sweetness derived from trehalose. It can be easily consumed and can be easily used as a raw material for producing coffee-containing beverages and various coffee-containing confectioneries.
- Example C-1 9 ⁇ Tea holdings>
- 30 parts by weight of grapefruit juice powder produced by spray drying is 50 parts by weight of a commercially available maltose (available from Hayashibara Shoji Co., Ltd., registered trademark “San Malto S”), and 10 parts by weight of anhydrous crystalline maltitol Parts by weight, 10 parts by weight of an aroma containing grapefruit oil prepared by the method of Example C-16, 0.65 parts by weight of citric anhydride, 0.5 parts by weight of pullulan, and 0.5 parts by weight of lingic acid.
- a commercially available maltose available from Hayashibara Shoji Co., Ltd., registered trademark “San Malto S”
- 10 parts by weight of anhydrous crystalline maltitol Parts by weight 10 parts by weight of an aroma containing grapefruit oil prepared by the method of Example C-16, 0.65 parts by weight of citric anhydride, 0.5 parts by weight of pullulan, and 0.5 parts by weight of lingic acid.
- Example C 1 g or 2 g of the ethanol-containing crystalline anhydrous cyclic tetrasaccharide prepared by the method of Example 1 was weighed and packed in a gas-permeable paper bag. It was sealed with a bag and packaged to prepare a disinfectant. When using this product, open the aluminum laminate bag and take out the breathable paper bag to release the retained ethanol gradually. It can be advantageously used as Z or fungicide. Also, since this product is composed of ethanol and cyclic tetrasaccharide, it does not show toxicity even if taken orally or adheres to skin or mucous membranes. It can be advantageously used as a bacteriostatic and / or fungicide for packed lunches and prepared dishes.
- Bacillus subtilis (ATCC 6633 strain), which is a typical microorganism as a resident bacterium, was prepared using the bactericide composed of the ethanol-retained crystalline anhydrous cyclic tetrasaccharide prepared above.
- the Sta Hiroko Cassadreus (S taph y I ococcusaureus) (ATCC 653 8 strain), Candida azolebicans (C andidaa I bicans) (ATCC 1023 1 strain), and Aspergillus niger (A spergi I 1 usniger) (ATCC 164 04)
- a test for investigating the bactericidal activity of the strain was performed as follows.
- a spore-containing solution obtained by suspending in a medium having the same composition as that obtained by filtration and filtering was used as a test bacterial solution.
- 1.5 ml of each test orchid was impregnated into an absorption pad (4.7 mm in diameter, sold by Advantech Toyo Co., Ltd.), and then allowed to stand at 25 ° C for 30 minutes to absorb the bacteria-containing absorption pad.
- Sealed in the above aluminum laminated bag '' Open the disinfectant immediately after preparation and after storage for 30 days at 25 ° C, and remove the disinfectant in the air-permeable paper bag inside.
- the paper bag (1 g or
- Table 6 shows the changes in the viable cell count of each strain used in the test when stored for 24 hours in the presence of a fungicide.
- the bactericide consisting of ethanol-bearing crystalline anhydrous cyclic tetrasaccharide placed in a breathable paper bag releases ethanol at a sustained rate.
- the test bacterium and Z or its spores absorbed in the absorbent pad are completely killed within 24 hours, and in a closed container of about 6 L in volume. It was confirmed that the microorganisms were completely killed.
- a syrup, a mask, a cyclic tetrasaccharide or a mixture of the cyclic tetrasaccharide and a carbohydrate derivative of the cyclic tetrasaccharide with respect to an aroma substance is provided.
- a cyclic tetrasaccharide or a mixture of the cyclic tetrasaccharide and a carbohydrate derivative of the cyclic tetrasaccharide with respect to an aroma substance is provided.
- the scented substance of the present invention has a property of gradually evaporating scented substances ⁇ Since it has the property of releasing scented substances, it can be used not only as a sustained-release scented substance but also with a bactericidal action. In the case of having a bacterium, it can be advantageously used as a sustained-release bacteriostat and Z or a bactericide. As described above, the present invention is applied to a wide range of fields such as food, cosmetics, pharmaceuticals, or daily necessities. This is extremely useful in industrial fields, such as opening up applications to products with excellent retention and stability of odorants.
- Bacillus glo bisporus C9 (FERMBP—7143) described in the present specification was filed on April 25, 2000 by Izumi No. 1 1 Deposited at the National Institute of Advanced Industrial Science and Technology (AIST) Patent Microorganisms Depositary Center located at Chuo No. 6 and commissioned.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Birds (AREA)
- Nutrition Science (AREA)
- Dermatology (AREA)
- Medicinal Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
- Seasonings (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
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Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020047007680A KR101011552B1 (ko) | 2001-11-22 | 2002-11-21 | 향기의 유지방법 및 그 용도 |
US10/496,382 US20050013914A1 (en) | 2001-11-22 | 2002-11-21 | Method of sustaining aroma and use thereof |
EP02803561A EP1460123A4 (en) | 2001-11-22 | 2002-11-21 | PROCESS FOR AROMA-MAINTENANCE AND APPLICATION THEREOF |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2001358562 | 2001-11-22 | ||
JP2001-358562 | 2001-11-22 | ||
JP2002118439 | 2002-04-19 | ||
JP2002-118439 | 2002-04-19 | ||
JP2002-256070 | 2002-08-30 | ||
JP2002256070A JP4181829B2 (ja) | 2001-11-22 | 2002-08-30 | 香気の保持方法並びにその用途 |
Publications (1)
Publication Number | Publication Date |
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WO2003044143A1 true WO2003044143A1 (fr) | 2003-05-30 |
Family
ID=27347867
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2002/012196 WO2003044143A1 (fr) | 2001-11-22 | 2002-11-21 | Procede servant a entretenir un arome et sa mise en application |
Country Status (6)
Country | Link |
---|---|
US (1) | US20050013914A1 (ja) |
EP (1) | EP1460123A4 (ja) |
JP (1) | JP4181829B2 (ja) |
KR (1) | KR101011552B1 (ja) |
TW (1) | TW200300332A (ja) |
WO (1) | WO2003044143A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPWO2005007171A1 (ja) * | 2003-07-18 | 2007-09-20 | 株式会社林原生物化学研究所 | ミネラル吸収促進剤及びその用途 |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE0600887L (sv) * | 2006-04-24 | 2007-10-25 | Lyckeby Culinar Ab | Smakfrisättningsmaterial och dess användning i olika livsmedelsprodukter |
US9783325B1 (en) | 2010-08-07 | 2017-10-10 | Christy Booth Hierholzer | Bath water enhancing packet and method of use |
JP2012115205A (ja) * | 2010-11-30 | 2012-06-21 | Ogawa & Co Ltd | 粉末香味料及びその製造方法 |
JP2015519312A (ja) * | 2012-04-19 | 2015-07-09 | パーデュー・リサーチ・ファウンデーションPurdue Research Foundation | 高度分岐α−D−グルカン |
JP6412363B2 (ja) * | 2013-08-06 | 2018-10-24 | アース製薬株式会社 | 害虫誘引持続剤、害虫誘引剤及び害虫誘引方法 |
JP2021106571A (ja) | 2019-12-27 | 2021-07-29 | 三井製糖株式会社 | 顆粒の製造方法及び顆粒 |
WO2023054540A1 (ja) * | 2021-09-30 | 2023-04-06 | 株式会社林原 | 固形食品とその製造方法並びに固形食品の食感付与方法 |
JP7197743B1 (ja) * | 2022-07-15 | 2022-12-27 | Dm三井製糖株式会社 | 顆粒を製造する方法及び顆粒 |
Citations (6)
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JPS63181950A (ja) * | 1987-01-24 | 1988-07-27 | Yasushi Takahashi | 食酢及び/又は酢酸含有飼料 |
JPH06189737A (ja) * | 1992-12-25 | 1994-07-12 | Yamachiyuu Wasabi Kk | 残香性酒粕及びその製造方法 |
JPH07316204A (ja) * | 1994-05-23 | 1995-12-05 | Toshio Nakagawa | シクロマルトペンタオースおよびその誘導体 |
US5889179A (en) * | 1995-06-12 | 1999-03-30 | The United States Of America, As Represented By The Secretary Of Agriculture | Bacteria and enzymes for production of alternant fragments |
WO2000076472A1 (en) * | 1999-06-14 | 2000-12-21 | The Procter & Gamble Company | Anhydrous antiperspirant cream compositions having improved perfume longevity |
JP2001048765A (ja) * | 1999-05-28 | 2001-02-20 | Hayashibara Bijutsu Minto:Kk | 薫 香 |
Family Cites Families (4)
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US4816445A (en) * | 1984-06-21 | 1989-03-28 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Crystalline alpha-maltose |
WO2001090338A1 (en) * | 2000-05-22 | 2001-11-29 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | α-ISOMALTOSYLTRANSFERASE, PROCESS FOR PRODUCING THE SAME AND USE THEREOF |
TWI312369B (en) * | 2000-08-01 | 2009-07-21 | Hayashibara Biochem Lab | A-isomaltosylglucosaccharide synthase,process for producing the same and use thereof |
DE20220866U1 (de) * | 2002-02-13 | 2004-06-09 | Brose Fahrzeugteile Gmbh & Co. Kommanditgesellschaft, Coburg | Spindel- oder Schneckenantrieb für Verstelleinrichtungen in Kraftfahrzeugen |
-
2002
- 2002-08-30 JP JP2002256070A patent/JP4181829B2/ja not_active Expired - Lifetime
- 2002-11-21 EP EP02803561A patent/EP1460123A4/en not_active Withdrawn
- 2002-11-21 US US10/496,382 patent/US20050013914A1/en not_active Abandoned
- 2002-11-21 TW TW091133995A patent/TW200300332A/zh unknown
- 2002-11-21 KR KR1020047007680A patent/KR101011552B1/ko not_active IP Right Cessation
- 2002-11-21 WO PCT/JP2002/012196 patent/WO2003044143A1/ja active Application Filing
Patent Citations (6)
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JPS63181950A (ja) * | 1987-01-24 | 1988-07-27 | Yasushi Takahashi | 食酢及び/又は酢酸含有飼料 |
JPH06189737A (ja) * | 1992-12-25 | 1994-07-12 | Yamachiyuu Wasabi Kk | 残香性酒粕及びその製造方法 |
JPH07316204A (ja) * | 1994-05-23 | 1995-12-05 | Toshio Nakagawa | シクロマルトペンタオースおよびその誘導体 |
US5889179A (en) * | 1995-06-12 | 1999-03-30 | The United States Of America, As Represented By The Secretary Of Agriculture | Bacteria and enzymes for production of alternant fragments |
JP2001048765A (ja) * | 1999-05-28 | 2001-02-20 | Hayashibara Bijutsu Minto:Kk | 薫 香 |
WO2000076472A1 (en) * | 1999-06-14 | 2000-12-21 | The Procter & Gamble Company | Anhydrous antiperspirant cream compositions having improved perfume longevity |
Non-Patent Citations (1)
Title |
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See also references of EP1460123A4 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPWO2005007171A1 (ja) * | 2003-07-18 | 2007-09-20 | 株式会社林原生物化学研究所 | ミネラル吸収促進剤及びその用途 |
JP4702745B2 (ja) * | 2003-07-18 | 2011-06-15 | 株式会社林原生物化学研究所 | ミネラル吸収促進剤及びその用途 |
EP1652527A4 (en) * | 2003-07-18 | 2012-03-14 | Hayashibara Biochem Lab | MINERAL ABSORBENT AND ITS USE |
Also Published As
Publication number | Publication date |
---|---|
US20050013914A1 (en) | 2005-01-20 |
JP2004002620A (ja) | 2004-01-08 |
KR101011552B1 (ko) | 2011-01-31 |
EP1460123A1 (en) | 2004-09-22 |
TW200300332A (en) | 2003-06-01 |
JP4181829B2 (ja) | 2008-11-19 |
EP1460123A4 (en) | 2005-09-28 |
KR20040068141A (ko) | 2004-07-30 |
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