JPS6157804B2 - - Google Patents
Info
- Publication number
- JPS6157804B2 JPS6157804B2 JP54062717A JP6271779A JPS6157804B2 JP S6157804 B2 JPS6157804 B2 JP S6157804B2 JP 54062717 A JP54062717 A JP 54062717A JP 6271779 A JP6271779 A JP 6271779A JP S6157804 B2 JPS6157804 B2 JP S6157804B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- butanediol
- group
- threo
- compound
- 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.)
- Expired
Links
- 239000000796 flavoring agent Substances 0.000 claims description 10
- 235000019634 flavors Nutrition 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- -1 2,3-butanediol ester Chemical class 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000002085 persistent effect Effects 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 15
- GIZSHQYTTBQKOQ-UHFFFAOYSA-N threo-Syringoylglycerol Chemical compound COC1=CC(C(O)C(O)CO)=CC(OC)=C1O GIZSHQYTTBQKOQ-UHFFFAOYSA-N 0.000 description 10
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical class CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical group O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 5
- 241000220223 Fragaria Species 0.000 description 5
- 235000016623 Fragaria vesca Nutrition 0.000 description 5
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 5
- 244000288157 Passiflora edulis Species 0.000 description 5
- 235000000370 Passiflora edulis Nutrition 0.000 description 5
- 235000013399 edible fruits Nutrition 0.000 description 5
- CUXUOVQPLZEURD-UHFFFAOYSA-N 3-butanoyloxybutan-2-yl butanoate Chemical compound CCCC(=O)OC(C)C(C)OC(=O)CCC CUXUOVQPLZEURD-UHFFFAOYSA-N 0.000 description 4
- CMZLDPHMYGCLEY-UHFFFAOYSA-N 3-hydroxybutan-2-yl butanoate Chemical compound CCCC(=O)OC(C)C(C)O CMZLDPHMYGCLEY-UHFFFAOYSA-N 0.000 description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
- 235000004936 Bromus mango Nutrition 0.000 description 3
- 240000007228 Mangifera indica Species 0.000 description 3
- 235000014826 Mangifera indica Nutrition 0.000 description 3
- 235000009184 Spondias indica Nutrition 0.000 description 3
- OUFWGHRGNHLGEN-UHFFFAOYSA-N 3-hydroxybutan-2-yl 2-methylbutanoate Chemical compound CC(C(=O)OC(C)C(C)O)CC OUFWGHRGNHLGEN-UHFFFAOYSA-N 0.000 description 2
- BCWWODMTUXMSAB-UHFFFAOYSA-N 3-hydroxybutan-2-yl acetate Chemical compound CC(O)C(C)OC(C)=O BCWWODMTUXMSAB-UHFFFAOYSA-N 0.000 description 2
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- GCNUJLSTRKUMRY-UHFFFAOYSA-N 3-acetyloxybutan-2-yl butanoate Chemical compound CCCC(=O)OC(C)C(C)OC(C)=O GCNUJLSTRKUMRY-UHFFFAOYSA-N 0.000 description 1
- SVBNKEDHNJDKOC-UHFFFAOYSA-N 3-hydroxybutan-2-yl hexanoate Chemical compound CCCCCC(=O)OC(C)C(C)O SVBNKEDHNJDKOC-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Landscapes
- Seasonings (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Description
本発明は新規な２，３―ブタンジオールエステ
ル類を有効成分として含有する持続性香気香味賦
与変調剤に関する。尚、本発明において、該エス
テルとは、そのスレオー体、エリスロー体、更に
それらの混合物を包含する呼称である。
更に詳しくは、本発明は下記式(1)、
但し式中、R1およびR2は、同一もしくは異つ
て、水素原子および−COR3よりなる群からえら
ばれた基を示し、ここでR3は水素原子およびC1
〜C10アルキル基よりなる群からえらばれた基を
示す、但し上記においてR1及びR2が共に水素原
子に関する。
本発明者は、ストロベリー、パツシヨンフルー
ツ、マンゴ、カバアの香気乃至香味成分について
研究を行つてきた。
その結果、上記式(1)で表わされる２，３―ブタ
ンジオールエステル類中、２，３―ブタンジオー
ル―モノ―ブチレート（ストロベリー、マンゴ、
パツシヨンフルーツ）、２，３―ブタンジオール
―モノ―メチルブチレート（ストロベリー）、
２，３―ブタンジオール―モノ―カプロエート
（ストロベリー、パツシヨンフルーツ）、２，３―
ブタンジオール―ジ―ブチレート（ストロベリ
ー、パツシヨンフルーツ）、２，３―ブタンジオ
ール―モノ―アセテート（カバア、マンゴ、パツ
シヨンフルーツ）、３―アセトキシ―２―ブチル
ブチレート（パツシヨンフルーツ）を、上記果実
類の香気乃至香味のキー・フレーバーとして、天
然のこれら果実類から抽出分離することに成功し
且つこれら化合物が合成可能であることを発見し
た。本発明者等の研究によれば天然に存在する上
記化合物は、いづれもスレオ―体及びエリスロ―
体の立体異性体の混合物として存在することがわ
かつた。
更に研究を進めた結果、上記果実類から抽出分
離された化合物を包含して、前記式(1)で表わされ
る２，３―ブタンジオールのアルキルおよびアル
ケニルエステル類が、上記果実類もしくはこれに
類似した香気乃至香味を呈し且つ合成可能であつ
て、更に、該式(1)化合物は優れた香気乃至香味持
続性を有し、持続性香気乃至香味賦与乃至変調剤
として注目すべき化合物であることを発見した。
斯して、上記式(1)化合物は、飲食物（嗜好品を
包含する）、石鹸、洗剤、化粧品類、保健、衛
生、医薬品類などの広い分野において優れた且つ
ユニークな持続性香気乃至香味賦与乃至変調剤と
して極めて有用であることを発見した。
従つて、本発明の目的は前記式(1)２，３―ブタ
ンジオールエステルを有効成分とする持続性香気
香味賦与乃至変調剤を提供するにある。
本発明の上記目的及び更に多くの他の目的なら
びに利点は、以下の記載から一層明らかとなるで
あろう。
本発明の下記式(1)
但し式中、R1及びR2は前記したと同義、は、
前述のとおり、スレオ―体、エリスロ―体及びこ
れらの混合物のいづれの形でも存在でき、本発明
の式(1)化合物に包含される。
上記式(1)において、R1および／又はR2が−
COR3である式(1)の化合物のR3の例としては、水
素原子のほかに、たとえばメチル、エチル、プロ
ピル、iso―プロピル、ｎ―ブチル、iso―ブチ
ル、tert―ブチル、sec―ブチル、ｎ―ペンチ
ル、iso―ペンチル、tert―ペンチル、ネオペンチ
ル、１―メチル―ブチル、１，２―ジメチルプロ
ピル、１―エチルブチル、１，２―ジメチルプロ
ピル、１―エチルプロピル、２―メチルブチル、
１―エチルプロピル、２―エチルヘキシル、など
の如きC1〜C10のアルキル基を、好ましく例示す
ることができる。
このような式(1)２，３―ブタンジオールエステ
ル類の具体例としては、例えば、以下に例示の如
き化合物をあげることができる。
(a) ２，３―ブタンジオール―モノアセテート
（スレオ―体／エリスロ―体１／１）
(b) ２，３―ブタンジオール―モノブチレート
（エリスロ―体）
(c) ２，３―ブタンジオール―モノ―２―メチル
ブチレート（エリスロ―体）
(d) ２，３―ブタンジオール―モノ―カブロエー
ト（エリスロ―体）
(e) ２，３―ブタンジオール―ジ―ブチレート
（エリスロ―体）
(f) ２，３―ブタンジオール―モノ―ブチレート
（スレオ―体／エリスロ―体＝１／１）
(g) ２，３―ブタンジオール―ジ―ブチレート
（スレオ―体／エリスロ―体＝１／１）
(h) ２，３―ブタンジオール―モノ―ブチレート
（スレオ―体）
(i) ２，３―ブタンジオール―ジ―ブチレート
（スレオ―体）
(j) ３―アセトキシ―２―ブチルブチレート（ス
レオ―体）
(k) ３―ブチロキシ―２―ブチルカプロエート
（スレオ―体）
上記例示化合物は透明油状物質であつて、その
沸点の数例を示すと下記のとおりである。
化合物番号 沸 点
(a) 59゜〜61℃／２mmHg
(b) 66゜〜67℃／２mmHg
(c) 55゜〜56℃／１mmHg
(d) 72゜〜73℃／２mmHg
(e) 52゜〜54℃／１mmHg
(f) 49゜〜50℃／１mmHg
(g) 54゜〜57℃／１mmHg
(h) 49゜〜50℃／１mmHg
(i) 54゜〜56℃／１mmHg
(j) 63゜〜66℃／２mmHg
(k) 70゜〜74℃／２mmHg
本発明の式(1)化合物は、例えば、下記のように
容易に且つ好収率で製造することができる。
下記式(2)、
で表わされる２，３―ブタンジオールを、下記式
(3)、
（R3CO）nX (3)
但し式中、R3は水素原子およびC1〜C10アルキ
ル基よりなる群からえらばれた基を示し、Ｘは−
OH、ハロゲン原子もしくは酸素原子を示し、こ
こでＸが−OHもしくはハロゲン原子の場合には
ｎ＝１であり、Ｘが酸素原子の場合にはｎ＝２で
ある、
で表わされるカルボン酸もしくはその官能性誘導
体と、触媒の存在下もしくは不存在下に、接触さ
せることにより、下記式(1)′及び／又は(1)″、
但し式中、R3は上記したと同義である、で表
わされる２，３―ブタンジオールエステル類を製
造することができる。
更に、式(1)化合物中、上記式(1)″で表わされる
ジエステル類は、式(1)化合物中、上記式(1)′のモ
ノエステル類からも製造することができる。例え
ば、下記式(1)′、
但し式中、R3は水素原子およびC1〜C10アルキ
ル基よりなる群からえらばれた基を示す、
で表わされる２，３―ブタンジオールモノエステ
ル類を、下記式(3)、
（R3CO）nX (3)
但し式中、R3、Ｘ及びｎは上記したと同義で
あり、ここでR3は上記式(1)′におけるR3と同一で
も異つていてもよい、
で表わされるカルボン酸もしくはその官能性誘導
体と、触媒の存在下もしくは不存在下に、接触さ
せることにより、下記式(1)″
但し式中、R3は上記したと同義であり、ここ
で、二つのR3は同一でも異つていてもよい、
で表わされる２，３―ブタンジオールエステル類
が製造できる。
上記式(2)の２，３―ブタンジオールは、DL―
体、メソ―体及びそれらの混合物のいづれであつ
てもよく、上記式(1)′のモノエステル類は、スレ
オ―体、エリスロ―体及びそれらの混合物のいづ
れであつてもよい。
上記製造例について図式的に示すと下記の如く
示すことができる。
The present invention relates to a long-lasting aroma and flavor imparting modulator containing a novel 2,3-butanediol ester as an active ingredient. In the present invention, the term ester includes its threo form, erythro form, and mixtures thereof. More specifically, the present invention is based on the following formula (1), However, in the formula, R 1 and R 2 are the same or different and represent a group selected from the group consisting of a hydrogen atom and -COR 3 , where R 3 is a hydrogen atom and a group consisting of C 1
˜C 10 alkyl group, with the proviso that in the above R 1 and R 2 both relate to a hydrogen atom. The present inventor has conducted research on aroma and flavor components of strawberry, passion fruit, mango, and kavaa. As a result, among the 2,3-butanediol esters represented by the above formula (1), 2,3-butanediol-mono-butyrate (strawberry, mango,
fruit), 2,3-butanediol-mono-methylbutyrate (strawberry),
2,3-butanediol-mono-caproate (strawberry, passion fruit), 2,3-
Butanediol-di-butyrate (strawberry, passion fruit), 2,3-butanediol-mono-acetate (kavaa, mango, passion fruit), 3-acetoxy-2-butyl butyrate (passion fruit), We have succeeded in extracting and separating the key flavors of the above-mentioned fruits from natural fruits, and have discovered that these compounds can be synthesized. According to the research conducted by the present inventors, the above-mentioned naturally occurring compounds are both threo-form and erythro-form.
It was found that it exists as a mixture of stereoisomers. As a result of further research, we found that the alkyl and alkenyl esters of 2,3-butanediol represented by the formula (1) above, including compounds extracted and separated from the above fruits, are derived from the above fruits or similar thereto. The compound of formula (1) exhibits a pleasant aroma or flavor and can be synthesized, and furthermore, the compound of formula (1) has excellent aroma or flavor persistence and is a compound that should be noted as a persistent aroma or flavor imparting or modulating agent. discovered. Thus, the compound of formula (1) above has an excellent and unique long-lasting aroma or flavor in a wide range of fields such as food and beverages (including luxury goods), soaps, detergents, cosmetics, health, hygiene, and pharmaceuticals. It has been discovered that it is extremely useful as an imparting or modulating agent. Therefore, an object of the present invention is to provide a persistent aroma and flavor imparting or flavor modulating agent containing the 2,3-butanediol ester of formula (1) as an active ingredient. The above objects and many other objects and advantages of the present invention will become more apparent from the following description. The following formula (1) of the present invention However, in the formula, R 1 and R 2 have the same meanings as above, and
As mentioned above, it can exist in any of the forms of threo-form, erythro-form and mixtures thereof, which are included in the compound of formula (1) of the present invention. In the above formula (1), R 1 and/or R 2 are -
Examples of R 3 in the compound of formula (1) which is COR 3 include, in addition to a hydrogen atom, methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, sec-butyl. , n-pentyl, iso-pentyl, tert-pentyl, neopentyl, 1-methyl-butyl, 1,2-dimethylpropyl, 1-ethylbutyl, 1,2-dimethylpropyl, 1-ethylpropyl, 2-methylbutyl,
Preferred examples include C1 to C10 alkyl groups such as 1 -ethylpropyl, 2-ethylhexyl, and the like. Specific examples of such 2,3-butanediol esters of formula (1) include the following compounds. (a) 2,3-butanediol monoacetate (threo form/erythro form 1/1) (b) 2,3-butanediol monobutyrate (erythro form) (c) 2,3-butanediol Mono-2-methylbutyrate (erythro form) (d) 2,3-butanediol-mono-cabroate (erythro form) (e) 2,3-butanediol-dibutyrate (erythro form) (f ) 2,3-butanediol-mono-butyrate (threo-form/erythro-form = 1/1) (g) 2,3-butanediol-di-butyrate (threo-form/erythro-form = 1/1) (h) 2,3-butanediol-mono-butyrate (threo form) (i) 2,3-butanediol-di-butyrate (threo form) (j) 3-acetoxy-2-butylbutyrate (threo form) (k) 3-Butyloxy-2-butylcaproate (threo-form) The above-mentioned exemplified compound is a transparent oily substance, and some examples of its boiling points are as follows. Compound number Boiling point (a) 59°~61°C/2mmHg (b) 66°~67°C/2mmHg (c) 55°~56°C/1mmHg (d) 72°~73°C/2mmHg (e) 52°~ 54°C/1mmHg (f) 49°~50°C/1mmHg (g) 54°~57°C/1mmHg (h) 49°~50°C/1mmHg (i) 54°~56°C/1mmHg (j) 63°~ 66°C/2mmHg (k) 70° to 74°C/2mmHg The compound of formula (1) of the present invention can be produced easily and in a good yield, for example, as described below. The following formula (2), 2,3-butanediol represented by the following formula
(3), (R 3 CO) nX (3) However, in the formula, R 3 represents a group selected from the group consisting of a hydrogen atom and a C 1 to C 10 alkyl group, and X is -
OH, a halogen atom or an oxygen atom, where n=1 when X is -OH or a halogen atom, and n=2 when X is an oxygen atom, or a carboxylic acid thereof; By contacting with a functional derivative in the presence or absence of a catalyst, the following formula (1)′ and/or (1)″, However, 2,3-butanediol esters represented by the formula, in which R 3 has the same meaning as described above, can be produced. Furthermore, the diesters represented by the above formula (1)'' in the formula (1) compound can also be produced from the monoesters of the above formula (1)' in the formula (1) compound. For example, the following Equation (1)′, However, in the formula, R3 represents a group selected from the group consisting of a hydrogen atom and a C1 to C10 alkyl group. 2,3-butanediol monoesters represented by the following formula (3), (R 3 CO) nX (3) However, in the formula, R 3 , X and n have the same meanings as above, and R 3 may be the same or different from R 3 in the above formula (1)′. By contacting the represented carboxylic acid or its functional derivative in the presence or absence of a catalyst, the following formula (1)'' However, in the formula, R 3 has the same meaning as described above, and two R 3s may be the same or different. A 2,3-butanediol ester represented by the following can be produced. 2,3-butanediol of the above formula (2) is DL-
The monoester of formula (1)' may be either a threo-isomer, an erythro-isomer or a mixture thereof. The above production example can be diagrammatically shown as follows.
【表】
ロ〓体もしくはそれ ロ〓体もしくはそれ
らの混合物〕 らの混合物〓
[Table] 〓 or 〓 〓 or mixture thereof〓〓 Mixture of these〓
Claims (1)
て、水素原子および−COR3よりなる群からえら
ばれた基を示し、ここでR3は水素原子およびC1
〜C10アルキル基よりなる群からえらばれた基を
示す、但し上記においてR1及びR2が共に水素原
子の場合を除く、 で表わされる２，３―ブタンジオールエステル類
を有効成分として含有することを特徴とする持続
性香気香味賦与乃至変調剤。[Claims] 1. The following formula (1), However, in the formula, R 1 and R 2 are the same or different and represent a group selected from the group consisting of a hydrogen atom and -COR 3 , where R 3 is a hydrogen atom and a group consisting of C 1
A group selected from the group consisting of ~C 10 alkyl groups, except when R 1 and R 2 are both hydrogen atoms, containing as an active ingredient a 2,3-butanediol ester represented by A persistent aroma and flavor imparting or modulating agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6271779A JPS55154940A (en) | 1979-05-23 | 1979-05-23 | 2,3-butanediol ester, its preparation and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6271779A JPS55154940A (en) | 1979-05-23 | 1979-05-23 | 2,3-butanediol ester, its preparation and use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55154940A JPS55154940A (en) | 1980-12-02 |
| JPS6157804B2 true JPS6157804B2 (en) | 1986-12-09 |
Family
ID=13208363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6271779A Granted JPS55154940A (en) | 1979-05-23 | 1979-05-23 | 2,3-butanediol ester, its preparation and use |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55154940A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011161197A1 (en) | 2010-06-23 | 2011-12-29 | Surgiceye Gmbh | Device and method for combined optical and nuclear image acquisition |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4419280A (en) * | 1980-08-07 | 1983-12-06 | International Flavors & Fragrances Inc. | 1-Ethoxy-1-ethanol acetate and uses thereof for augmenting or enhancing aroma or taste of consumable materials |
| EP1043968B1 (en) * | 1998-10-26 | 2004-09-15 | Firmenich Sa | Antimicrobial perfume compositions |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS518210A (en) * | 1974-07-11 | 1976-01-23 | Kuraray Co | |
| JPS5212122A (en) * | 1975-07-18 | 1977-01-29 | Mitsui Toatsu Chem Inc | Process for preparation of glycolester |
| JPS52139014A (en) * | 1976-05-11 | 1977-11-19 | Mitsui Toatsu Chem Inc | Synthesis of carboxylic acid glycol esters |
-
1979
- 1979-05-23 JP JP6271779A patent/JPS55154940A/en active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS518210A (en) * | 1974-07-11 | 1976-01-23 | Kuraray Co | |
| JPS5212122A (en) * | 1975-07-18 | 1977-01-29 | Mitsui Toatsu Chem Inc | Process for preparation of glycolester |
| JPS52139014A (en) * | 1976-05-11 | 1977-11-19 | Mitsui Toatsu Chem Inc | Synthesis of carboxylic acid glycol esters |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011161197A1 (en) | 2010-06-23 | 2011-12-29 | Surgiceye Gmbh | Device and method for combined optical and nuclear image acquisition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55154940A (en) | 1980-12-02 |
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