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1. 发明专利

JPH10165132A AROMA COMPOSITION FOR FOOD 失效
公开(公告)号：JPH10165132A
公开(公告)日：1998-06-23
申请号：JP34669896
申请日：1996-12-10
申请人： SHIONO KORYO KAISHA , LION CORP , SODA AROMATIC
发明人： TSUNEYA TOMOYUKI , YOSHIDA FUMIO , ICHIMURA NOBUTOMO , ISHIHARA MASAKAZU , MASAJI YOSHINORI , UENAKA SHIGECHIKA , YAMAGISHI KEIICHI , TAKAHASHI HIDETOSHI
IPC分类号： A23L27/00 , A23L27/20 , C11B9/00 , A23L1/22 , A23L1/226
摘要： PROBLEM TO BE SOLVED: To obtain an aroma compsn. for food which is useful for juice drinks, etc., by compounding specific pentylcyclopropane carboxylic acid with the aroma compsn., thereby imparting fermentative sweetness and flavor having a ripe feel to spearmint-like and chocolate-like aromas and amplifying a natural feel. SOLUTION: The cis- and/or trans-2-pentylcyclopropane-1-carboxylic acid expressed by the formula is compounded at preferably 0.0001 to 10(wt.)% more preferably 0.0001 to 0.1% with this aroma compsn. The ratio of the cis body to the trans body is preferably higher in the cis body or the cis body alone is used for the aroma group (spearmint-like, etc.) for which the fermentative taste is requested.

2. 发明专利

JPH0517445A PYRIDINE DERIVATIVE AND PERFUME COMPOSITION CONTAINING THE SAME DERIVATIVE 失效
公开(公告)号：JPH0517445A
公开(公告)日：1993-01-26
申请号：JP17221491
申请日：1991-07-12
申请人： SHIONO KORYO KAISHA , LION CORP
发明人： ISHIHARA MASAKAZU , TSUNEYA TOMOYUKI , SHIGA MINORU , SATO HIROSHI , YAMAGISHI KEIICHI , YOSHIDA FUMIO
IPC分类号： A61K8/49 , A23L27/00 , A61Q13/00 , C07D213/06 , C07D213/16 , C07D213/50 , C07D213/78 , C11B9/00
摘要： PURPOSE:To obtain a pyridine derivative, having natural feeling, tastiness, etc., of natural spearmint essential oils and useful as a synthetic spearmint essential oil stably suppliable in constant quality at a low cost for perfumes in dentifrices, chewing gums, etc. CONSTITUTION:A compound expressed by formula I (R1 to R3 are as follows; when R1 is isopropenyl, R2 is n-propyl and R3 is H; when R1 is 1-butenyl, either of R2 and R3 is n-propyl and the other is H; when R1 is 1-propyl-1-propen-1-yl, R2 and R3 are H; when R1 is acetyl, R2 is n-propyl and R3 is H; when R1 is H, R2 is 1-methyl-1-propen-1-yl and R3 is H; when R1 is H, R2 is isopropenyl and R3 is n-butyl; when R1 is H, R2 is 1-propyl-1-propen-1-yl and R3 is H; when R1 is H, R2 is n-butyl and R3 is acetyl], e.g. 3-isopropenyl-4-propylpyridine. The exemplified compound can be produced from a compound expressed by formula II by passing through compounds expressed by formulas III and IV. Furthermore, the amount of the aforementioned compound added to a perfume composition is preferably about 1.0ppb to 10000ppm.

3. 发明专利

JPH04312573A PYRIDINE DERIVATIVE AND PERFUME COMPOSITION CONTAINING THE SAME DERIVATIVE 失效
公开(公告)号：JPH04312573A
公开(公告)日：1992-11-04
申请号：JP7879991
申请日：1991-04-11
申请人： SHIONO KORYO KAISHA , LION CORP
发明人： ISHIHARA MASAKAZU , TSUNEYA TOMOYUKI , SHIGA MINORU , SATO HIROSHI , YAMAGISHI KEIICHI , YOSHIDA FUMIO
IPC分类号： A61K8/49 , A61Q13/00 , C07D213/06 , C07D213/16 , C07D213/50 , C11B9/00
摘要： PURPOSE:To obtain a new derivative, capable of producing a spearmint essential oil, having natural feeling equal to that of natural products and useful as foods, cosmetics, etc., and stably supplying the spearmint essential oil of constant quality at a low cost. CONSTITUTION:A compound, e.g. 2-methyl-4-isopropenylpyridine expressed by formula I (R is isopropenyl when R is methyl or ethyl; isopropenyl or acetyl when R is isopropenyl; methyl when R is isopropyl; isopropenyl or isopropyl when R is acetyl). The aforementioned compound is obtained by converting methyl isonicotinate expressed by formula II once into a pyridinium salt, then reacting a Grignard reagent with the obtained pyridinium salt, providing a dihydropyridine derivative, subsequently reacting and dehydrogenating the resultant derivative in the presence of chloranil, then reacting the prepared compound with methylmagnesium bromide, affording an alcoholic derivative and subsequently dehydrating the alcoholic derivative in the presence of sulfuric acid.

4. 发明专利

JP2003169626A DAIRY PRODUCT FLAVOR 审中-公开
公开(公告)号：JP2003169626A
公开(公告)日：2003-06-17
申请号：JP2001370821
申请日：2001-12-05
申请人： SHIONO KORYO KAISHA
发明人： FUJIMURA TAICHIRO , NOHAYASHI YOSHIKAZU , NAKAMOTO HIDEKI , ISHIHARA MASAKAZU
IPC分类号： A23L27/10 , C11B9/00 , A23L1/221
摘要： PROBLEM TO BE SOLVED: To provide a dairy product flavor having tasting properties such as a spread with extensibility and impartment of a voluminous feeling, raw milk flavor improving effects or fermentation flavor improving effects on masking of skimmilk powder and impartment of a light taste, an aftertaste with a good cutoff and a raw milk feeling and further connected to effective utilization of a waste whey. SOLUTION: This dairy product flavor is obtained by bringing a whey into contact with an adsorbent and then eluting adsorbed ingredients from the adsorbent with an ethyl alcohol solution. COPYRIGHT: (C)2003,JPO

5. 发明专利

JP2002322489A PERFUME COMPRISING (5S)- OR (5R)-5-METHYL-5-(4-METHYL-3- PENTENYL)-4,5-DIHYDRO-2(3H)-FURANONE, METHOD FOR PRODUCING THE SAME AND PERFUME COMPOSITION INCLUDING THE SAME 失效
公开(公告)号：JP2002322489A
公开(公告)日：2002-11-08
申请号：JP2001129380
申请日：2001-04-26
申请人： SHIONO KORYO KAISHA
发明人： KITAURA TARO , ENDO HIROKATSU , KONDO TOMOHIRO , ISHIHARA MASAKAZU
IPC分类号： C07D307/33 , C11B9/00
摘要： PROBLEM TO BE SOLVED: To establish an efficient production method (asymmetric synthesis) for a naturally occurring and optically active perfume substance, and to provide a perfume composition including the same. SOLUTION: This perfume consists of (5S)-5-methyl-5-(4-methyl-3-pentenyl)-4,5- dihydro-2(3H)-franone or (5R)-5-methyl-5-(4-methyl-3-pentenyl)-4,5-dihydro-2(3H)- franone. The method for producing the perfume and the perfume composition comprising at least one of the above two perfumes are provided.

6. 发明专利

JPH119220A PRODUCTION OF NATURAL MILK FLAVOR 失效
公开(公告)号：JPH119220A
公开(公告)日：1999-01-19
申请号：JP18178197
申请日：1997-06-23
申请人： SHIONO KORYO KAISHA
发明人： YOSHIKAWA HIROSHI , ISHIHARA MASAKAZU
IPC分类号： A23C9/00 , A23L27/10 , A23L1/221
摘要： PROBLEM TO BE SOLVED: To enable the simple obtaining of the subject flavor, having a light taste and an aftertaste good in cutoff, capable of imparting natural flavor and taste and excellent in impartment of especially a raw milky feeling by bringing a cow's milk into contact with an adsorbent and then eluting the adsorbed component from the adsorbent with an ethyl alcohol solution. SOLUTION: A cow's milk is brought into contact with an adsorbent (preferably a packing for reversed phase chromatography such as a chemically bound type silica gel or a porous polymer) and the adsorbed component is then eluted from the adsorbent with an ethyl alcohol solution (preferably 99.5% ethyl alcohol or 95% ethyl alcohol). The cow's milk is preferably a homogenized and high- temperature sterilized milk having 3.5-4.2% milk fat component is preferred or the cow's milk retaining a raw milk feeling is preferably used. The contact of the cow's milk with the adsorbent is preferably conducted at 10-30 deg.C temperature and 1-200 liquid passage speed SV of the cow's milk by a method for packing the adsorbent and passing the cow's milk therethrough. The contact time may usually be 0.5-3 hr.

7. 发明专利

JPH0978081A PERFUME COMPOSITION 失效
公开(公告)号：JPH0978081A
公开(公告)日：1997-03-25
申请号：JP26068795
申请日：1995-09-12
申请人： SHIONO KORYO KAISHA
发明人： ISHIHARA MASAKAZU , KITAURA TARO , KAWAI TETSUO , FUNABASHI YOZO , YONETANI TAKESHI , OMI HIROYUKI
IPC分类号： A61K8/49 , A61Q13/00 , C11B9/00 , A61K7/46
摘要： PROBLEM TO BE SOLVED: To obtain a perfume composition, comprising a specific 1- alkylpyrrolidine, having excellent aroma and flavor characteristics such as a dried cuttlefishlike, a crustaceous, a cornlike, a Welsh oniony, an orange floral, an ambery and a fresh citrous ones and useful as foods and drinks, cosmetics, etc. SOLUTION: This perfume composition comprises one or more of 1- alkylpyrrolidines of the formula (R is ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, 2-methylbutyl or 3-methylbutyl) such as 1-ethylpyrrolidine. The amount of the blended 1-alkylpyrrolidines is preferably within the range of 0.00001-10wt.% based on the total amount of the perfume composition.

8. 发明专利

JPS6486884A PRODUCTION OF UNSATURATED ALDEHYDE UTILIZING ENZYME FROM SEA ALGAE 失效
公开(公告)号：JPS6486884A
公开(公告)日：1989-03-31
申请号：JP24538687
申请日：1987-09-29
申请人： SHIONO KORYO KAISHA
发明人： KAWAI TETSUO , KAJIWARA TADAHIKO , ISHIHARA MASAKAZU , TSUNEYA TOMOYUKI , HATANAKA AKIKAZU , IRIE MAMORU
IPC分类号： C12P7/24 , C07C45/41
摘要： PURPOSE:To produce an unsaturated aldehyde enzymatically through a shortened and simplified process of high safety, by allowing a crude enzyme solution prepared from a sea algae to act on the corresponding carboxylic acid. CONSTITUTION:An unsaturated fatty acid is allowed to react with a crude enzyme solution or a powder containing the same prepared from a sea algae to produce an unsaturated aldehyde which has the same chemical structure as of the substrate, but has a 1 less carbon number than the substrate on the carboxyl side. The reaction is preferably carried out at 20-35 deg.C for 1-2hr. The pH of the reaction mixture is preferably in the neutral zone.

9. 发明专利

JPS6056930A NOVEL BICYCLO(4.3.0)NONANE COMPOUND 失效
公开(公告)号：JPS6056930A
公开(公告)日：1985-04-02
申请号：JP16602083
申请日：1983-09-08
申请人： SHIONO KORYO KAISHA
发明人： ISHIHARA MASAKAZU , TSUNEYA TOMOYUKI , SHIGA MINORU
IPC分类号： A23L27/29 , A61K8/34 , A61K8/35 , A61Q13/00 , C07C1/00 , C07C13/465 , C07C27/00 , C07C35/32 , C07C45/00 , C07C49/633 , C07C67/00 , C11B9/00 , C12P7/02 , C12P7/26
摘要： NEW MATERIAL:The compound of formula I (R1 is H and R2 and R3 together form a C-C bond, or R1 and R2 together form oxo and R3 is H, or R1 and R3 are H and R2 is OH, or R1 is H and R2 and R3 are OH). EXAMPLE:2,2,6,7-Tetramethylbicyclo[4.3.0]nonane-4,7,9-triene. USE:A raw material of perfumery and a component of perfumery. It has unique perfume, e.g. rush-like flavor, damascone fragrance, flavor of the pulp of citric fruit, or tropical fruit fragrance having strong grassy smell. Although it has weak flavor, a combined use of the compound increases the astringent smell of the fruit juice. Especially, a synergistic effect and an excellent effect to improve, modify and increase the flavor of a perfumery composition, can be attained by the combined use of two or more kinds of the compounds. PREPARATION:The compound of formula I wherein R1 is H and R2 and R3 together form a C-C bond can be produced by reacting the dehydro-beta-ionol of formula II with 5% aqueous solution of citric acid.

10. 发明专利

JPS56120678A NOVEL LACTONE OF OCTANOIC ACID 失效
公开(公告)号：JPS56120678A
公开(公告)日：1981-09-22
申请号：JP2484080
申请日：1980-02-28
申请人： SHIONO KORYO KAISHA
发明人： TSUNEYA TOMOYUKI , ISHIHARA MASAKAZU , SHIODA HARUYASU , SHIGA MINORU
IPC分类号： A23L27/20 , A24B3/12 , A61K8/49 , A61Q13/00 , C07D307/32 , C07D307/33 , C11B9/00
摘要： NEW MATERIAL:A lactone of octanoic acid expressed by the formula (R is alkyl group having one or two 4C straight chain double bonds having a methyl group at the gamma-position). EXAMPLE:Lactone of 7-methyl-4-hydroxy-5-octenoic acid. USE:Useful as a raw material for a perfume having a unique aroma, particularly exhibiting an effect more than expected on addition in combination with two or more types thereof and useful for improving, modifying and enhancing the aroma of various perfume compositions. PROCESS:Monoethyl malonate and methylene chloride are reacted with a Grignard reagent, and the reaction solution is cooled. An acid chloride solution is methylene chloride and hydrochloric acid are added to the resultant cooled solution, and the mixture is extracted with methylene chloride. The resultant ketoester is dropped to sodium ethoxide, and sodium iodide is added thereto and reacted, and the reaction product is hydrolyzed with caustic soda and decarboxylated. Sodium boron hydride is then dropped and the reaction mixture is cooled, adjusted to weakly acidic and extracted with toluene to afford the exemplified substance.

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