JP2512400B2 - Methyl-4,6-0- [3- (1-methylcyclohexen-4-yl) butylidene] -D-glycoside - Google Patents
Methyl-4,6-0- [3- (1-methylcyclohexen-4-yl) butylidene] -D-glycosideInfo
- Publication number
- JP2512400B2 JP2512400B2 JP62287072A JP28707287A JP2512400B2 JP 2512400 B2 JP2512400 B2 JP 2512400B2 JP 62287072 A JP62287072 A JP 62287072A JP 28707287 A JP28707287 A JP 28707287A JP 2512400 B2 JP2512400 B2 JP 2512400B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- methyl
- formula
- butylidene
- methylcyclohexen
- 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 - Fee Related
Links
Landscapes
- Seasonings (AREA)
- Saccharide Compounds (AREA)
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
Description
【発明の詳細な説明】 (産業上の利用分野) 本発明は、それ自体実質的に無臭の化合物であって、
香料の保留剤として極めて優れた保留効果を有する従来
文献未記載の新規化合物に関する。又、本発明は上記式
(1)化合物の利用並びにその製法にも関する。DETAILED DESCRIPTION OF THE INVENTION Industrial Field of the Invention The present invention is a compound substantially odorless in itself,
The present invention relates to a novel compound which has not been described in the prior art and has an extremely excellent retaining effect as a retaining agent for perfumes. The present invention also relates to the use of the compound of the above formula (1) and a method for producing the same.
更に詳しくは、本発明は下記式(1) 但し式中、波線はアクシアル又はエカトリアル結合を
示す、 で表される従来文献未記載の新規化合物のメチル4,6
−0−[3−(1−メチルシクロヘキセン−4−イル)
ブチリデン]−D−グリコシドに関する。More specifically, the present invention provides the following formula (1) However, in the formula, the wavy line indicates an axial or equatorial bond. Methyl 4,6 of a novel compound represented by
-0- [3- (1-methylcyclohexen-4-yl)
Butylidene] -D-glycoside.
更に本発明は、該式(1)化合物が極めて優れた香料
の保留特性を有し、該式(1)化合物を有効成分として
含有する調合香料組成物の保留剤として極めて有用な新
規な香料組成物にも関する。Further, the present invention provides a novel perfume composition which is extremely useful as a retaining agent for a prepared perfume composition containing the compound of the formula (1) as an active ingredient, in which the compound of the formula (1) has an extremely excellent perfume retaining property. Also related to things.
更に又、該式(1)化合物の製法にも関する。 Furthermore, it also relates to a process for producing the compound of formula (1).
(従来の技術) 天然香料、合成香料は一般に揮発性が高いからこれら
の香料を調合して得られる調合香料は、経時的に調合香
料成分中のより揮発性の高い成分が揮発し、調合香料の
成分バランスがくずれ香調が著しく変化する場合があ
る。(Prior Art) Since natural fragrances and synthetic fragrances are generally highly volatile, a compounded fragrance obtained by compounding these fragrances is a compounded fragrance in which the more volatile component of the compounded fragrance evaporates over time. The component balance may be lost and the fragrance tone may change significantly.
従来、この様な変化を防ぐために、香料物質の揮発性
あるいは保留性を調整する各種保留剤が香料に有効成分
として配合し利用されている。Conventionally, in order to prevent such a change, various holding agents for adjusting the volatility or holding ability of the fragrance substance have been used by blending it as an active ingredient in the fragrance.
上記の保留剤として、通常例えば、ジエチルフタレー
ト、ベンジルベンゾエート、トリエチルシトレート、ジ
エチレングリコールモノエチルエーテル、イソプロピル
ミリステート、プロピレングリコール、ジプロピレング
リコールなどが利用されている。As the above retaining agent, for example, diethyl phthalate, benzyl benzoate, triethyl citrate, diethylene glycol monoethyl ether, isopropyl myristate, propylene glycol, dipropylene glycol, etc. are usually used.
更に、近年には単独で稀釈剤、保留剤および安定化剤
等の効果を同時に兼ね備える種々の化合物が香料調整剤
として提案されている。これらの化合物として、例えば
2−エチルヘキシルベンゾエート、3−フエニルプロピ
ル−2−エチルブチレート(特開昭55-133303)、例え
ば、ベンジルフエノキシアセテート、ベンジル−3−フ
エノキシプロピオネート(特開昭55-133304)、例えば
エチレングリコールジベンゾエート、ジエチレングリコ
ールジベンゾエート(特開昭55-133305)、例えばジヘ
キシルタータレート、トリヘキシルシトレート(特開昭
55-133306)などが提案されている。Furthermore, in recent years, various compounds which have the effects of a diluent, a retaining agent, a stabilizer, etc., alone at the same time have been proposed as perfume conditioners. Examples of these compounds include 2-ethylhexylbenzoate, 3-phenylpropyl-2-ethylbutyrate (JP-A-55-133303), for example, benzylphenoxyacetate, benzyl-3-phenoxypropionate (special 55-133304), for example, ethylene glycol dibenzoate, diethylene glycol dibenzoate (JP-A-55-133305), such as dihexyl tartrate, trihexyl citrate (JP-A-55-133305).
55-133306) and the like have been proposed.
(発明が解決しようとする問題点) 従来利用されている上述のジエチルフタレート・・・
・・・・・・・・ジプロピレングリコール類は、いずれ
も香料の保留効果は、必ずしも満足できるものではな
い。(Problems to be Solved by the Invention) The above-mentioned conventionally used diethyl phthalate ...
・ ・ ・ ・ ・ ・ ・ ・ The dipropylene glycols are not always satisfactory in the effect of retaining the fragrance.
又、上記の特許公開公報に記載される化合物類も、香
料の保留効果としては、満足できるものではない。In addition, the compounds described in the above-mentioned patent publications are not satisfactory as the effect of retaining the fragrance.
更に上記の特開昭60-188037、特開昭60-188039及び特
公昭56-44055に記載されているメチル−4,6−0−ベン
ジリデン−α,D−グリコピラノシドが、甘味剤の合成中
間体として利用できること或いは該化合物のエーテル又
はエステル誘導体を合成する方法について記載されてい
るが、本発明の式(1)新規化合物及びその製法につい
ては、全く言及されていないし、更に香料の保留特性に
ついては、全然記載も示唆もされていない。Further, the methyl-4,6-0-benzylidene-α, D-glycopyranoside described in JP-A-60-188037, JP-A-60-188039 and JP-B-56-44055 is a synthetic intermediate for sweeteners. However, no mention is made of the novel compound of formula (1) of the present invention and its production method, and the retention property of the perfume is not mentioned. , Neither described nor suggested at all.
(問題点を解決するための手段) 本発明者らは、上記事情にかんがみ、香料及び調合香
料の保留剤として有用な新しいタイプの保留剤を開発す
べく鋭意研究した結果、従来文献未記載の上記式(1)
新規化合物の合成に成功し、且つ該化合物が実質的に無
臭で化学的にも安定であるとともに皮膚安全性に優れ、
各種香料ならびにこれらの調合香料の保留剤として極め
て優れた保留効果を有することを発見した。更に上記式
(1)化合物が容易に合成できることも発見した。(Means for Solving Problems) In view of the above circumstances, the present inventors have earnestly studied to develop a new type of holding agent useful as a holding agent for perfumes and mixed perfumes, and as a result, have not been described in the conventional literature. Formula (1) above
Succeeded in synthesizing a new compound, and the compound is substantially odorless, chemically stable and excellent in skin safety,
It has been discovered that it has an extremely excellent holding effect as a holding agent for various flavors and their mixed flavors. Further, it was discovered that the compound of the above formula (1) can be easily synthesized.
従って、本発明の目的は、従来文献未記載の上記式
(1)新規化合物及びその製法を提供するにある。又、
本発明は、該式(1)化合物を香料ならびにこれらの調
合香料組成物に有効成分として含有することを特徴とす
る新規な香料組成物を提供するにある。Therefore, an object of the present invention is to provide a novel compound of the above formula (1) which has not been described in the prior art and a method for producing the same. or,
The present invention provides a novel perfume composition characterized by containing the compound of formula (1) as an active ingredient in a perfume and a prepared perfume composition thereof.
本発明の下記式(1) 但し式中、波線はアクシアル又はエカトリアル結合を
示す、 で表されるメチル4,6−0−[3−(1−メチルシク
ロヘキセン−4−イル)ブチリデン]−D−グリコシド
を合成するには、例えば、 下記式(2) 但し式中、波線はアクシアル又はエカトリアル結合を
示す、 で表されるメチル−Dグリコシドを有機溶媒中、酸の
存在下に下記式(3) で表されるリモネンアルデヒドジメチルアセタールと反
応させることにより容易に合成することができる。The following formula (1) of the present invention However, in the formula, the wavy line represents an axial or equatorial bond. To synthesize methyl 4,6-0- [3- (1-methylcyclohexen-4-yl) butylidene] -D-glycoside represented by, for example, , The following formula (2) However, in the formula, the wavy line represents an axial or equatorial bond. The methyl-D glycoside represented by the following formula (3) in the presence of an acid in an organic solvent It can be easily synthesized by reacting with limonene aldehyde dimethyl acetal represented by
本発明の上記式(1)化合物を合成する方法を工程図
で示すと以下の様に表すことができる。The method for synthesizing the compound of the above formula (1) of the present invention can be represented as follows when shown in a process diagram.
本発明の式(1)化合物を合成する態様を上記工程図
の例に従って、以下に詳細に述べる。 The mode for synthesizing the compound of formula (1) of the present invention will be described in detail below with reference to the example of the above process chart.
本発明の式(1)化合物の合成に必要な式(2)のメ
チル−D−グリコシドに包含される化合物としては、例
えば、メチル−α,或いはβ,D−グルコピラノシド、メ
チル−α,或いはβ,D−ガラクトピラノシド、メチル−
α,或いはβ,D−マンノピラノシドなどのごときメチル
6炭糖類を例示することができる。Examples of the compound included in the methyl-D-glycoside of the formula (2) necessary for synthesizing the compound of the formula (1) of the present invention include, for example, methyl-α or β, D-glucopyranoside, methyl-α, or β. , D-galactopyranoside, methyl-
Examples thereof include methyl hexacarbon sugars such as α or β, D-mannopyranoside.
これらのピラノシド類は、市場で容易に入手可能な化
合物である。又、式(3)化合物も市場で容易に入手で
きる化合物であり、所望により容易に合成することも可
能である。These pyranosides are readily available compounds on the market. The compound of formula (3) is also a compound that can be easily obtained on the market, and can be easily synthesized if desired.
本発明の式(1)化合物を合成するには、例えば式
(2)化合物を有機溶媒中、酸の存在下に式(3)化合
物と接触せしめることにより容易に安価且つ工業的に合
成することができる。この反応の温度は、適宜に選択変
更することができるが例えば、約40〜約150℃程度の温
度範囲を好しく例示することができる。又、反応時間
も、適宜に選択して行うことができるが、例えば通常約
1〜約6時間程度の範囲の反応時間で行うことができ
る。To synthesize the compound of formula (1) of the present invention, for example, the compound of formula (2) can be easily and inexpensively and industrially synthesized by contacting the compound of formula (3) with the compound in the presence of an acid in an organic solvent. You can The temperature of this reaction can be appropriately selected and changed, but a temperature range of about 40 to about 150 ° C. can be preferably exemplified. Further, the reaction time can be appropriately selected and carried out, but, for example, the reaction time is usually in the range of about 1 to about 6 hours.
上記反応に使用する有機溶媒としては、例えばジメチ
ルホルムアミド、ジクロルエタン、酢酸エチル、ベンゼ
ン、トルエン、シクロヘキサンなどを好しく例示するこ
とができる。これら有機溶媒の使用量には、特別の制限
はなく適宜選択して行うことができるが、例えば、式
(2)化合物に対して約1〜約5重量倍程度の範囲を例
示することができる。又、式(3)化合物の使用量とし
ては、例えば、式(2)化合物1モルに対して約0.5〜
約2モル程度の範囲が例示できる。又、使用する酸とし
ては、例えばp−トルエンスルホン酸、硫酸、リン酸な
どを好ましく例示することができる。これらの酸の使用
量としては、例えば式(2)化合物に対して、例えば約
0.1〜約5重量%程度の範囲の使用量を例示できる。反
応は、所望により減圧下に行うことができる。減圧の程
度は、適宜に選択変更できるが、通常、例えば約10〜約
60mmHg程度の範囲で行われる。Preferable examples of the organic solvent used in the above reaction include dimethylformamide, dichloroethane, ethyl acetate, benzene, toluene and cyclohexane. The amount of these organic solvents used is not particularly limited and may be appropriately selected. For example, the amount may be about 1 to about 5 times the weight of the compound of the formula (2). . The amount of the compound of formula (3) used is, for example, about 0.5 to 1 mol of the compound of formula (2).
A range of about 2 mol can be exemplified. As the acid to be used, for example, p-toluenesulfonic acid, sulfuric acid, phosphoric acid and the like can be preferably exemplified. The amount of these acids to be used is, for example, about
The amount used may be in the range of about 0.1 to about 5% by weight. The reaction can be carried out under reduced pressure if desired. The degree of reduced pressure can be appropriately selected and changed, but usually, for example, about 10 to about
It is performed in the range of about 60 mmHg.
反応終了後は、例えば、反応液中に炭酸ナトリウムの
ごときアルカリの適当量を加え、減圧下に溶媒を留去し
て、本発明の式(1)化合物を容易に得ることができ
る。又、必要によりカラムクロマトのごとき手段を用い
て精製することもできる。After completion of the reaction, for example, an appropriate amount of alkali such as sodium carbonate is added to the reaction solution and the solvent is distilled off under reduced pressure to easily obtain the compound of formula (1) of the present invention. If necessary, it can be purified by using a means such as column chromatography.
かくして、上述の様にして得られる上記式(1)のメ
チル4,6−0−[3−(1−メチルシクロヘキセン−4
−イル)ブチリデン]−D−グリコシドに包含される化
合物としては、メチル−4,6−0−[3−(1−メチル
シクロヘキセン−1−イル)ブチリデン]−α,或いは
β,D−グルコピラノシド、メチル−4,6−0−[3−
(1−メチルシクロヘキセン−1−イル)ブチリデン]
−α,或いはβ,D−ガラクトピラノシド、メチル−4,6
−0−[3−(1−メチルシクロヘキセン−1−イル)
ブチリデン]−α,或いはβ,D−マンノピラノシドなど
を挙げることができる。Thus, methyl 4,6-0- [3- (1-methylcyclohexene-4) of the above formula (1) obtained as described above is obtained.
-Yl) Butylidene] -D-glycoside includes compounds such as methyl-4,6-0- [3- (1-methylcyclohexen-1-yl) butylidene] -α, or β, D-glucopyranoside. Methyl-4,6-0- [3-
(1-Methylcyclohexen-1-yl) butylidene]
-Α, or β, D-galactopyranoside, methyl-4,6
-0- [3- (1-methylcyclohexen-1-yl)
Butylidene] -α, or β, D-mannopyranoside.
これら式(1)化合物は、香料ならびに調合香料組成
物の保留剤として、従来にはない優れた効果を有し、そ
の使用量としては、特別限定されることなく適宜選択し
て使用することができるが、例えば調合香料組成物の場
合にあっては、約5〜約50重量%程度の範囲、好しくは
約10〜約30重量%程度の範囲の使用量を例示することが
できる。These compounds of formula (1) have an excellent effect which has never been obtained as a holding agent for perfumes and prepared perfume compositions, and the amount used is not particularly limited and may be appropriately selected and used. However, for example, in the case of a prepared fragrance composition, the amount used is in the range of about 5 to about 50% by weight, preferably about 10 to about 30% by weight.
以下に本発明の実施態様について、実施例をあけで更
に詳細に説明する。Hereinafter, embodiments of the present invention will be described in more detail with reference to examples.
(実施例) (1)メチル−4,6−0−[3−(1−メチルシクロヘ
キセン−4−イル)ブチリデン]−α,D−グルコピラノ
シドの合成。(Example) (1) Synthesis of methyl-4,6-0- [3- (1-methylcyclohexen-4-yl) butylidene] -α, D-glucopyranoside.
フラスコにメチル−α,D−グルコピラノシド10.5g(5
4.2ミリモル)、リモネンアルデヒドジメチルアセター
ル11.5g(54.2ミリモル)、ジメチルホルムアミド100m
l、p−トルエンスルホン酸0.2gを仕込み、30〜40mmHg
下、40℃にて3時間メタノールを留去しながら反応し
た。反応終了後、反応液中に炭酸ソーダ1gを加え、溶媒
を減圧下に留去し、残査を500gのシリカゲルを用いてカ
ラムクロマト精製(クロロホルム/メタノール=95/5)
し、13.3g(71.7%収率)の目的化合物を得た。1 H‐NMRδ(CDCl3)ppm 0.88(3H,d,J=5.9Hz) 1.1〜2.1(11H,m) 1.63(3H,S) 3.23〜4.69(8H,m) 3.42(3H,S) 4.75(1H,d,J=3.7Hz) 5.30(1H,brS) (2)メチル−4,6−0−[3−(1−メチルシクロヘ
キセン−4−イル)ブチリデン]−α,D−ガラクトピラ
ノシドの合成。Methyl-α, D-glucopyranoside 10.5 g (5
4.2 mmol), limonene aldehyde dimethyl acetal 11.5 g (54.2 mmol), dimethylformamide 100 m
l, p-toluenesulfonic acid 0.2g was charged, 30-40mmHg
The reaction was performed at 40 ° C. for 3 hours while distilling off methanol. After the reaction was completed, 1 g of sodium carbonate was added to the reaction solution, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using 500 g of silica gel (chloroform / methanol = 95/5).
Then, 13.3 g (71.7% yield) of the target compound was obtained. 1 H-NMRδ (CDCl 3 ) ppm 0.88 (3H, d, J = 5.9Hz) 1.1 to 2.1 (11H, m) 1.63 (3H, S) 3.23 to 4.69 (8H, m) 3.42 (3H, S) 4.75 ( 1H, d, J = 3.7Hz) 5.30 (1H, brS) (2) Methyl-4,6-0- [3- (1-methylcyclohexen-4-yl) butylidene] -α, D-galactopyranoside Synthesis of.
実施例(1)において、メチル−α,D−グルコノピラ
ノシドの代りにメチル−α,D−ガラクトピラノシド38.8
g(0.2モル)を用いた他は、実施例(1)と同様に行っ
て目的化合物42gを得た。(収率;64%)1 H‐NMR δ(CDCl3)ppm 0.88(3H,d,J=5.9Hz) 1.1〜2.1(11H,m) 1.63(3H,S) 3.23〜4.60(8H,m) 3.26(3H,S) 5.05(1H,d,J=3Hz) 5.36(1H,brS) (3)メチル−4,6−0−[3−(1−メチルシクロヘ
キセン−4−イル)ブチリデン]−α,D−マンノピラノ
シドの合成。In Example (1), methyl-α, D-galactopyranoside 38.8 was used instead of methyl-α, D-gluconopyranoside.
42 g of the target compound was obtained in the same manner as in Example (1) except that g (0.2 mol) was used. (Yield; 64%) 1 H-NMR δ (CDCl 3 ) ppm 0.88 (3H, d, J = 5.9Hz) 1.1 to 2.1 (11H, m) 1.63 (3H, S) 3.23 to 4.60 (8H, m) 3.26 (3H, S) 5.05 (1H, d, J = 3Hz) 5.36 (1H, brS) (3) Methyl-4,6-0- [3- (1-methylcyclohexen-4-yl) butylidene] -α , Synthesis of D-mannopyranoside.
実施例(1)においてメチル−α,D−グルコノピラノ
シドの代りにメチル−α,D−マンノピラノシド38.8g
(0.2モル)を用いた他は、実施例(1)と同様に行っ
て目的化合物44gを得た。(収率;67%)1 H‐NMR δ(CDCl3)ppm 0.86(3H,d,J=5.9Hz) 1.1〜2.1(11H,m) 1.16(3H,S) 3.23〜4.60(8H,m) 3.26(3H,S) 4.55(1H,d,J=2Hz) 5.25(1H,brS) (応用例) この応用例は、前記の実施例1〜3で得られた本発明
の化合物の香料の保留効果を示すものである。38.8 g of methyl-α, D-mannopyranoside instead of methyl-α, D-gluconopyranoside in Example (1)
44 g of the target compound was obtained in the same manner as in Example (1) except that (0.2 mol) was used. (Yield; 67%) 1 H-NMR δ (CDCl 3 ) ppm 0.86 (3H, d, J = 5.9Hz) 1.1 to 2.1 (11H, m) 1.16 (3H, S) 3.23 to 4.60 (8H, m) 3.26 (3H, S) 4.55 (1H, d, J = 2Hz) 5.25 (1H, brS) (Application Example) This application example is the retention of the fragrance of the compound of the present invention obtained in Examples 1 to 3 above. It shows the effect.
保留効果試験 後記の第1表に示す有効物質10種からなるモデル調合
香料90重量%と本発明の化合物または比較化合物を10重
量%とを均一に溶解混合した調合香料を調整し、これに
調合香料の4倍重量のエチルアルコールを添加して試料
とする。Retention effect test 90% by weight of a model compounded fragrance consisting of 10 kinds of active substances shown in Table 1 below and 10% by weight of a compound of the present invention or a comparative compound were uniformly dissolved and mixed to prepare a compounded fragrance. A sample is prepared by adding four times as much ethyl alcohol as the fragrance.
匂い紙(9cm×9cm,2.4g)にこの試料又はモデル調合
香料を0.5g塗布し、次いで温度25℃、湿度50%の恒温、
恒湿の部屋内で、調香技術者5名からなる判定者によ
り、塗布終了直後(0分)より50分、180分、300分後迄
の香りの変化の度合いを後記第2表の判定基準に従って
判定し、その結果を○,△,×,××で示した。0.5g of this sample or model blended fragrance was applied to odor paper (9cm x 9cm, 2.4g), and then a temperature of 25 ° C and a constant temperature of 50% humidity,
In a room with constant humidity, a judge consisting of 5 fragrance technicians determined the degree of fragrance change 50 minutes, 180 minutes, and 300 minutes after the end of application (0 minutes), as shown in Table 2 below. Judgment was made according to the standard, and the results are shown by ○, △, ×, and XX.
尚、保留効果の試験結果は第3表に示した。 The test results of the holding effect are shown in Table 3.
第3表から明らかなように、前記本発明の化合物の香
料の保留効果は、極めて良好であり、そして公知の保留
剤よりも著しく優れている。 As is evident from Table 3, the perfume retention effect of the compounds of the invention is very good and significantly better than known retention agents.
(効果) 本発明の上記式(1)化合物は、それ自体実質的に無
臭で化学的にも安定であるとともに皮膚安全性にも優れ
た従来文献未記載の新規化合物である。そして該化合物
が各種香料およびこれらの調合香料組成物の保留剤とし
て、極めて優れた効果を有し、該式(1)化合物を有効
成分として含有する新規な調合香料組成物を提供するこ
とができ且つ該組成物は、化粧品類、香粧品類、飲食品
類などの広い分野に於て利用できる有用な化合物であ
る。(Effect) The compound of the above formula (1) of the present invention is a novel compound which has not been described in the conventional literature and is substantially odorless per se, chemically stable, and excellent in skin safety. Then, the compound has a very excellent effect as a perfume and a retaining agent for these prepared flavoring compositions, and it is possible to provide a new prepared flavoring composition containing the compound of the formula (1) as an active ingredient. In addition, the composition is a useful compound that can be used in a wide range of fields such as cosmetics, cosmetics, foods and drinks.
Claims (1)
す、 で表されるメチル−4,6−0−[3−(1−メチルシク
ロヘキセン−4−イル)ブチリデン]−D−グリコシ
ド。1. The following formula (1) However, in the formula, a wavy line represents an axial or equatorial bond, and is a methyl-4,6-0- [3- (1-methylcyclohexen-4-yl) butylidene] -D-glycoside represented by the following formula.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62287072A JP2512400B2 (en) | 1987-11-12 | 1987-11-12 | Methyl-4,6-0- [3- (1-methylcyclohexen-4-yl) butylidene] -D-glycoside |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62287072A JP2512400B2 (en) | 1987-11-12 | 1987-11-12 | Methyl-4,6-0- [3- (1-methylcyclohexen-4-yl) butylidene] -D-glycoside |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH01128992A JPH01128992A (en) | 1989-05-22 |
JP2512400B2 true JP2512400B2 (en) | 1996-07-03 |
Family
ID=17712690
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP62287072A Expired - Fee Related JP2512400B2 (en) | 1987-11-12 | 1987-11-12 | Methyl-4,6-0- [3- (1-methylcyclohexen-4-yl) butylidene] -D-glycoside |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP2512400B2 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5728371A (en) * | 1996-04-29 | 1998-03-17 | L'oreal, S.A. | Skin protection, fragrance enhancing and vitamin delivery composition |
DE19624051A1 (en) * | 1996-06-17 | 1997-12-18 | Henkel Kgaa | Perfume oil concentrates |
DE19718537A1 (en) * | 1997-05-02 | 1998-11-05 | Henkel Kgaa | Use of depot preparations for targeted fragrance release |
JPWO2021095741A1 (en) * | 2019-11-11 | 2021-05-20 |
-
1987
- 1987-11-12 JP JP62287072A patent/JP2512400B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JPH01128992A (en) | 1989-05-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2512400B2 (en) | Methyl-4,6-0- [3- (1-methylcyclohexen-4-yl) butylidene] -D-glycoside | |
JP2515261B2 (en) | Methyl-4,6-0-alkylidene-D-glycoside | |
JP2512401B2 (en) | Methyl-4,6-0- (7-hydroxy-3,7-dimethyl) octylidene-D-glycoside | |
JP3833347B2 (en) | Fragrance composition | |
US4504412A (en) | Cyclohexane derivatives in fragrance compositions | |
JPH0558040B2 (en) | ||
JP3271785B2 (en) | Fragrance composition containing 8-hydroxy-8-methylnonanal | |
JP4027471B2 (en) | Novel cyclohexylalkanols and perfume compositions containing the same | |
JP2746375B2 (en) | Methyl-4,6-0-alkylidene or cyclohexenylidene-D-glycoside | |
JPS5936990B2 (en) | Norbornane (-nene) derivatives, their production methods, and methods for imparting, modulating, or enhancing aromatic properties to fragrances and perfumed products | |
JP3462319B2 (en) | Fragrance composition | |
JPH0523278B2 (en) | ||
JP2960597B2 (en) | p-Mentane-2-alkyl-3,8-diol | |
JP2815893B2 (en) | Acetals of 3- and 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene-1-carboxaldehyde and perfume compositions containing the compounds | |
JP4159700B2 (en) | Cyclohexylmethanol | |
JP2000053675A (en) | Macrocyclic lactone compound, its production and perfume composition containing the compound | |
JP4707281B2 (en) | Optically active ester | |
CN108929227B (en) | Method for synthesizing aromatic benzyl ester by oxidizing and self-coupling benzyl halide | |
JP2794331B2 (en) | 3,7-decadiene-5-olides | |
JP2771241B2 (en) | Fragrance composition containing 3- and 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene-1-carboxaldehyde diethyl acetal | |
JP2727254B2 (en) | Lilac aldehyde derivative | |
JP5080776B2 (en) | Ester compound | |
JP2837520B2 (en) | A novel formate, a novel pseudopheromone of Pseudomonas chile, a method for producing the same, and a formate composition | |
JPS6379894A (en) | Methyl-4,6-0-3',4'-methylenedioxybenzylidene-alpha-d-gly-coside | |
JP2794333B2 (en) | Lilac alcohol derivative |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313117 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
LAPS | Cancellation because of no payment of annual fees |