JPS6248652B2 - - Google Patents
Info
- Publication number
- JPS6248652B2 JPS6248652B2 JP7257079A JP7257079A JPS6248652B2 JP S6248652 B2 JPS6248652 B2 JP S6248652B2 JP 7257079 A JP7257079 A JP 7257079A JP 7257079 A JP7257079 A JP 7257079A JP S6248652 B2 JPS6248652 B2 JP S6248652B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- ether
- creams
- naalh
- och
- 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
- -1 2-butyloctane-1,8-diol compound Chemical class 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 11
- 239000006071 cream Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 210000003491 skin Anatomy 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- 239000002537 cosmetic Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229910010082 LiAlH Inorganic materials 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- OWCLRJQYKBAMOL-UHFFFAOYSA-N 2-butyloctanedioic acid Chemical compound CCCCC(C(O)=O)CCCCCC(O)=O OWCLRJQYKBAMOL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
- 235000011613 Pinus brutia Nutrition 0.000 description 2
- 241000018646 Pinus brutia Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- 231100000344 non-irritating Toxicity 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FQUNIRQTMOERKP-UHFFFAOYSA-N 2-butyloctane-1,8-diol Chemical compound CCCCC(CO)CCCCCCO FQUNIRQTMOERKP-UHFFFAOYSA-N 0.000 description 1
- QULNVKABFWNUCW-UHFFFAOYSA-N 5-methylundecane Chemical compound CCCCCCC(C)CCCC QULNVKABFWNUCW-UHFFFAOYSA-N 0.000 description 1
- 229910010084 LiAlH4 Inorganic materials 0.000 description 1
- 229910019020 PtO2 Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003885 eye ointment Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000008269 hand cream Substances 0.000 description 1
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Inorganic materials [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000004482 other powder Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/345—Alcohols containing more than one hydroxy group
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
Description
【発明の詳細な説明】
本発明は化粧品、医薬品等の基剤として有用な
る新規な２―ブチルオクタン―１，８―ジオール
化合物に関する。さらに詳しくは、本発明は式
（）
で表わされる２―ブチルオクタン―１，８―ジ
オール化合物に関するものである。式（）で示
される本発明の化合物は例えば次のようにして製
造することが出来る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel 2-butyloctane-1,8-diol compound useful as a base for cosmetics, pharmaceuticals, etc. More specifically, the present invention describes the formula () This relates to a 2-butyloctane-1,8-diol compound represented by The compound of the present invention represented by formula () can be produced, for example, as follows.
式（）
で表わされるカルボン酸、あるいは（）のエ
ステル類または（）の酸ハライド類等のカルボ
ン酸の反応性誘導体を公知の手段で還元反応を行
なうことにより製造される。例えば還元剤として
は、
LiAlH4，LiAlH（OCH3）3，AlH3，ｉ―
Bu2AlH，NaAlH4，NaAlH2
（OCH2CH2OCH3）2，NaBH4―AlCl3，NaBH4―
BF3，BH3―（CH3）2S，LiBH4，BH3，NMa＋
ROH，LiAlH（Ｏ―ｔ―Bu）3，NaAlH
（OC2H5）3，NaAlH〔OCH2CH2N（CH3）2〕3，
NaBH4―LiBr，NaBH（OCH3）3
電解還元、Ru、Cu―Ba―CrO、ラネ―Ni、あ
るいはPtO2を触媒した接触還元等が用いられ
る。工業的には取扱いの簡単で危険性の少ないも
の例えば、NaAlH2（OCH2CH2OCH2）2，NaAlH
（OC2H5）3、アルコール中Naによる還元あるいは
Cu―Ba―CrOを触媒とする接触水素添加等が好
ましい。実験室的には例えば化合物（）または
そのエステルをテトラヒドロフラン、ジオキサン
等の有機溶媒中LiAlH4を用いて室温から還流ま
での温度で反応することにより化合物（）が好
収率で製造することができる。本発明の化合物
（）は文献未知の新規化合物であり、化粧品や
医薬品の外用基剤として優れた特徴を有し、また
（）を中間体として他の化粧品や医薬品の外用
基剤、合成潤滑油等の有用な原料にもなりうるも
のである。本発明方法で得られる化合物の用途面
での特徴を更に詳細にのべると、本発明で得られ
る化合物（）は皮膚粘膜に対して無刺激で化粧
品、医薬品等の軟膏、坐薬、クリーム、乳液等の
基剤として用い、これに薬物等を混合させて皮膚
より滲透させる溶剤に用いられる。例えば皮膚に
対して刺激がなく親和性が良好で触感にすぐれ、
すぐれた溶解能力と表皮に対しての滲透力がある
ためクリーム類の油相原料として栄養クリーム、
エモリントクリームに、また油溶性薬物の卓越し
た皮膚学的媒液として薬用クリーム等に最適であ
る。その他化粧崩れを防ぎ過脂肪剤としてのパウ
ダー製品、皮膚保護剤、口紅の顔料色素の分散剤
としてのメーキヤツプクリーム、口紅製品、鉱油
の代りに用いると乳化が安定し髪をやわらかくし
て光沢を与えるのでヘヤーオイル、ヘヤークリー
ム製品、潤滑性にすぐれているためマツサージオ
イル、クリームのマツサージ製品、肌に対して非
常になめらかでべとつかないためハンドクリーム
製品、皮膚親和性および化学的安定性にすぐれて
いるため軟膏の油相成分として特に眼軟膏、坐薬
製品に用いられる等、その特異な性状により広範
囲な応用面も開け製剤上価値あるものである。さ
らに本化合物は熱、光に安定で例えば150℃の温
度でも分解を生じにくい。本化合物は水に難溶
で、アルコール類、クロゝホルム、アセトン、エ
ーテル等の有機溶媒に可溶である。本物質は無色
透明の液体であり、引火点が高く、空気中に長期
放置しても酸化されることが少なく安定な化合物
である。以下実施例にて本発明の方法を説明する
がこれに限定されるものではない。 formula() It is produced by carrying out a reduction reaction of a carboxylic acid represented by, or a reactive derivative of a carboxylic acid such as an ester of () or an acid halide of () by a known method. For example, as reducing agents, LiAlH 4 , LiAlH(OCH 3 ) 3 , AlH 3 , i-
Bu 2 AlH, NaAlH 4 , NaAlH 2
(OCH 2 CH 2 OCH 3 ) 2 , NaBH 4 ―AlCl 3 , NaBH 4 ―
BF 3 , BH 3 ― (CH 3 ) 2 S, LiBH 4 , BH 3 , NMa+
ROH, LiAlH(O-t-Bu) 3 , NaAlH
(OC 2 H 5 ) 3 , NaAlH [OCH 2 CH 2 N(CH 3 ) 2 ] 3 ,
NaBH4 - LiBr, NaBH( OCH3 ) 3 electrolytic reduction, Ru, Cu-Ba-CrO, Raney-Ni, or PtO2 catalytic catalytic reduction are used. Industrially easy to handle and less dangerous e.g. NaAlH 2 (OCH 2 CH 2 OCH 2 ) 2 , NaAlH
(OC 2 H 5 ) 3 , reduction with Na in alcohol or
Catalytic hydrogenation using Cu--Ba--CrO as a catalyst is preferred. In the laboratory, for example, compound () can be produced in good yield by reacting compound () or its ester with LiAlH4 in an organic solvent such as tetrahydrofuran or dioxane at a temperature from room temperature to reflux. . The compound () of the present invention is a new compound unknown in the literature, and has excellent characteristics as an external base for cosmetics and pharmaceuticals.It can also be used as an intermediate for external bases for other cosmetics and pharmaceuticals, and as a synthetic lubricant. It can also be used as a useful raw material. To explain in more detail the usage characteristics of the compound obtained by the method of the present invention, the compound () obtained by the present invention is non-irritating to the skin and mucous membranes, and is used in cosmetics, pharmaceutical ointments, suppositories, creams, emulsions, etc. It is used as a base for medicines, etc., and is used as a solvent to be mixed with it to allow it to penetrate through the skin. For example, it is non-irritating to the skin, has good affinity, and has an excellent texture.
Due to its excellent dissolving ability and ability to penetrate the epidermis, it is used as a raw material for the oil phase of creams.
It is ideal for emollient creams, and as an excellent dermatological vehicle for oil-soluble drugs, it is ideal for medicated creams. Other powder products, skin protectants, makeup creams and lipstick products, used as a superfat agent to prevent makeup from falling off, makeup creams and lipstick products as a dispersing agent for lipstick pigments, and stabilize emulsification when used in place of mineral oil, making hair soft and shiny. Hair oil and hair cream products because of their excellent lubricity, pine surge oil because of their excellent lubricity, pine surge products that are creams, hand cream products because they are very smooth and non-sticky to the skin, and excellent skin affinity and chemical stability. Due to its unique properties, it is useful in a wide range of pharmaceutical applications, such as being used as an oil phase component of ointments, especially in eye ointments and suppository products. Furthermore, this compound is stable to heat and light, and does not easily decompose even at temperatures of, for example, 150°C. This compound is sparingly soluble in water and soluble in organic solvents such as alcohols, chloroform, acetone, and ether. This substance is a colorless and transparent liquid with a high flash point and is a stable compound with little oxidation even if left in the air for a long time. The method of the present invention will be explained below with reference to Examples, but is not limited thereto.
実施例 １
２―ブチルオクタン―１，８―ジオルの製造法
２―ブチルオクタン二酸2.3ｇを過剰のメタノ
ールに溶解させこれに濃H2SO4を触媒程度に加え
数時間還流させる。メタノールを留去後NaHCO3
水で冷時中和後エーテルで抽出し、Na2SO4で乾
燥後エーテルを留去し残留物を減圧蒸留してジメ
チルエステル体を得る。次にジメチルエステル体
を無水エタノール30mlを加え金属Na2ｇを徐々に
加えて還元する。還元後無水エタノール留去し水
を加えエーテルで抽出する。エーテルは無水
Na2SO4で乾燥し、エーテルを留去後、脱色、脱
臭して無色無臭の液状の２―ブチルオクタン―
１，８―ジオール（）を92％の収率で得た。Example 1 Method for producing 2-butyloctane-1,8-diol 2.3 g of 2-butyloctanedioic acid is dissolved in excess methanol, concentrated H 2 SO 4 is added to a catalytic level, and the mixture is refluxed for several hours. After distilling off methanol NaHCO 3
After cold neutralization with water, extraction with ether and drying over Na 2 SO 4 , the ether was distilled off and the residue was distilled under reduced pressure to obtain a dimethyl ester. Next, the dimethyl ester is reduced by adding 30 ml of absolute ethanol and gradually adding 2 g of metallic Na. After reduction, anhydrous ethanol is distilled off, water is added, and the mixture is extracted with ether. ether is anhydrous
After drying with Na 2 SO 4 and distilling off the ether, decolorization and deodorization yield a colorless and odorless liquid 2-butyl octane.
1,8-diol () was obtained with a yield of 92%.
水酸基価 553.0（計算値 555.5，
実施例 ２
２―ブチルオクタン―１，８―ジオールの製造
法
２―ブチルオクタン二酸のメチルエステル2.6
ｇをエーテル100mlに溶解させ、これに水素化リ
チウムアルミニウム1.0ｇのエーテル懸濁液50ml
を氷冷撹拌下滴下、滴下終了後氷冷下３時間、つ
いで室温で３時間撹拌後水で分解、エーテル層を
分取しさらに水層をエーテルで抽出する。抽出液
を合しNa2SO4で乾燥後溶媒留去すれば化合物
（）を82％の収率で得た。 Hydroxyl value 553.0 (calculated value 555.5, Example 2 Production method of 2-butyloctane-1,8-diol Methyl ester of 2-butyloctanedioic acid 2.6
Dissolve g in 100 ml of ether, and add 50 ml of ether suspension of 1.0 g of lithium aluminum hydride.
was added dropwise with ice-cooling and stirring, and after completion of the dropwise addition, the mixture was cooled with ice for 3 hours, then stirred at room temperature for 3 hours, and then decomposed with water, the ether layer was separated, and the aqueous layer was further extracted with ether. The extracts were combined, dried over Na 2 SO 4 , and the solvent was distilled off to obtain compound () with a yield of 82%.
水酸基価 554.0 Hydroxyl value 554.0
Claims (1)
ル化合物。[Claims] 1 Formula () A 2-butyloctane-1,8-diol compound represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7257079A JPS55164636A (en) | 1979-06-09 | 1979-06-09 | 2-butyloctane-1,8-diol compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7257079A JPS55164636A (en) | 1979-06-09 | 1979-06-09 | 2-butyloctane-1,8-diol compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55164636A JPS55164636A (en) | 1980-12-22 |
| JPS6248652B2 true JPS6248652B2 (en) | 1987-10-15 |
Family
ID=13493155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7257079A Granted JPS55164636A (en) | 1979-06-09 | 1979-06-09 | 2-butyloctane-1,8-diol compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55164636A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5618910A (en) * | 1979-07-24 | 1981-02-23 | Kanebo Ltd | Liquid hair cosmetic |
| JPS5622713A (en) * | 1979-08-01 | 1981-03-03 | Kanebo Ltd | Liquid hair cosmetic |
| WO1996028405A1 (en) * | 1995-03-10 | 1996-09-19 | Nitto Chemical Industry Co., Ltd. | Process for producing 1,2-ethanediol derivatives |
-
1979
- 1979-06-09 JP JP7257079A patent/JPS55164636A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55164636A (en) | 1980-12-22 |
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