JPS6256142B2 - - Google Patents
Info
- Publication number
- JPS6256142B2 JPS6256142B2 JP60026831A JP2683185A JPS6256142B2 JP S6256142 B2 JPS6256142 B2 JP S6256142B2 JP 60026831 A JP60026831 A JP 60026831A JP 2683185 A JP2683185 A JP 2683185A JP S6256142 B2 JPS6256142 B2 JP S6256142B2
- Authority
- JP
- Japan
- Prior art keywords
- sorbitol
- oleic acid
- monoester
- diester
- enzyme
- 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
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 13
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 11
- 239000000600 sorbitol Substances 0.000 claims description 11
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 9
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 9
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 9
- 239000005642 Oleic acid Substances 0.000 claims description 9
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 9
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 9
- -1 9-octadecenoyl group Chemical group 0.000 claims description 8
- 229940049964 oleate Drugs 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 11
- 150000005690 diesters Chemical class 0.000 description 10
- 108090000790 Enzymes Proteins 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229940088598 enzyme Drugs 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 102000004882 Lipase Human genes 0.000 description 6
- 108090001060 Lipase Proteins 0.000 description 6
- 239000004367 Lipase Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 235000019421 lipase Nutrition 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WERKSKAQRVDLDW-ANOHMWSOSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO WERKSKAQRVDLDW-ANOHMWSOSA-N 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000588881 Chromobacterium Species 0.000 description 1
- 241000159512 Geotrichum Species 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 108010019160 Pancreatin Proteins 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000235527 Rhizopus Species 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 241000179532 [Candida] cylindracea Species 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229940079919 digestives enzyme preparation Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 229940055695 pancreatin Drugs 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- 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
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
【発明の詳細な説明】
本発明は、式、
の新規ソルビトールオレイン酸エステルに関す
る。式中、R1はオレイン酸から誘導されるアシ
ル基、すなわち９−オクタデセノイル基を表し、
R2はR1と同じか、または水素を表す。DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the formula: The present invention relates to a novel sorbitol oleate ester. In the formula, R 1 represents an acyl group derived from oleic acid, that is, a 9-octadecenoyl group,
R 2 is the same as R 1 or represents hydrogen.
炭水化物、特にシヨ糖やソルビタンの脂肪酸エ
ステルは代表的な非イオン界面活性剤であり、そ
れ自体およびその分解産物が毒性を有しないため
食品添加物として、また化粧品や医薬品の乳化剤
等として広く使われている。これらの工業的製造
法はいずれも加熱工程を含むため、加熱により生
成物が着色したり、複雑な混合物となるなどの欠
点を持つている。特にソルビトールは、従来のよ
うな純化学的方法によるエステル交換反応では分
子内脱水してソルビタン、ソルバイトになり、純
枠なソルビトールの高級脂肪酸エステルの合成は
困難である。 Carbohydrates, especially sucrose and sorbitan fatty acid esters, are typical nonionic surfactants, and because they themselves and their decomposition products are nontoxic, they are widely used as food additives and as emulsifiers in cosmetics and pharmaceuticals. ing. Since all of these industrial production methods involve a heating step, they have drawbacks such as coloring of the product due to heating and the formation of a complex mixture. In particular, sorbitol undergoes intramolecular dehydration into sorbitan and sorbite through transesterification using conventional pure chemical methods, making it difficult to synthesize pure higher fatty acid esters of sorbitol.
本発明者らは、酵素リパーゼを使用し、高級脂
肪酸と炭水化物とから生化学的に炭水化物高級脂
肪酸エステルを合成する方法を開発し、この方法
をソルビトールとオレイン酸との反応に試みたと
ころ、ソルビトールを環化させないでエステル化
することができた。生成物はモノエステルとジエ
ステルが主体であり、一級OH基の反応性が二級
OH基に比較して特異的に非常に高いことが特徴
であり、生成物を分別することによつて前記式で
表されるソルビトールモノオレイン酸エステルお
よびソルビトールジオレイン酸エステルを単離す
ることに成功した。 The present inventors developed a method for biochemically synthesizing carbohydrate higher fatty acid esters from higher fatty acids and carbohydrates using the enzyme lipase, and tried this method for the reaction of sorbitol and oleic acid. could be esterified without cyclization. The products are mainly monoesters and diesters, and the reactivity of the primary OH group is
It is characterized by a very high specificity compared to the OH group, and by fractionating the product, it is possible to isolate sorbitol monooleate and sorbitol dioleate represented by the above formula. Successful.
これらモノおよびジエステルは、従来のエステ
ル交換法や酸クロライドによるアシル化法では合
成できなかつた新規化合物であり、毒性のない食
品用、化粧品用および医薬品用非イオン界面活性
剤として有用であるばかりでなく、抗腫瘍性、免
疫賦活作用、抗菌性、植物生長抑制作用などの有
用な生物活性を有する。 These mono- and diesters are new compounds that could not be synthesized by conventional transesterification methods or acylation methods with acid chloride, and are useful as nonionic surfactants for food, cosmetics, and pharmaceuticals without toxicity. However, it has useful biological activities such as antitumor, immunostimulatory, antibacterial, and plant growth inhibitory effects.
本発明のソルビトールオレイン酸エステルは、
ソルビトールとオレイン酸とを、酵素の存在下イ
ンキユベートすることによつて製造することがで
きる。 The sorbitol oleate ester of the present invention is
It can be produced by incubating sorbitol and oleic acid in the presence of an enzyme.
酵素は、加水分解酵素、特にリパーゼが使用さ
れる。リパーゼには周知のように動物起源のもの
と、微生物由来のものとがあるが、そのいずれで
もよい。例えばブタすい臓由来のもの、微生物由
来のものとして、Aspergillus、Rhizopus、
Pseudomonas、Enterobacterium、
Chromobacterium、Geotrichum、Penicillium、
Mucor、Candida属などの微生物由来のものがあ
る。これら酵素は必ずしも単離して用いる必要は
なく、例えばパンクレアチンのような粗酵素のま
まで、またはリパーゼを含む市販酵素製剤をその
まま使用することができる。 As the enzyme, a hydrolytic enzyme, especially a lipase, is used. As is well known, there are lipases of animal origin and those of microbial origin; either of these may be used. For example, those derived from pig pancreas, those derived from microorganisms, Aspergillus, Rhizopus,
Pseudomonas, Enterobacterium,
Chromobacterium, Geotrichum, Penicillium,
Some are derived from microorganisms such as Mucor and Candida. These enzymes do not necessarily need to be isolated and used; for example, crude enzymes such as pancreatin or commercially available enzyme preparations containing lipase can be used as they are.
酵素の添加量は酵素の由来、種類、力価などに
よつて異なるが、要するに反応混合液が所定の酵
素活性を含んでいればよい。 The amount of enzyme added varies depending on the origin, type, potency, etc. of the enzyme, but it is sufficient as long as the reaction mixture contains a predetermined enzyme activity.
この反応は可逆反応であるので、ある程度反応
が進行した後平衡に達する。この状態で反応を止
め、常法により反応液からソルビトールオレイン
酸エステルを分離し精製し、未反応脂肪酸を回収
することができる。 Since this reaction is reversible, equilibrium is reached after the reaction progresses to some extent. The reaction is stopped in this state, and sorbitol oleate is separated and purified from the reaction solution by a conventional method, and unreacted fatty acids can be recovered.
モノエステルとジエステルとの分離は、例えば
分取ゲルパーミエーシヨンクロマトグラフイーに
よつて実施することができる。 Separation of monoester and diester can be carried out, for example, by preparative gel permeation chromatography.
実施例 １
市販リパーゼ製剤（Candida Cylindracea由来
のリパーゼMY、名糖産業）12ｇをPH5.4のリン酸
緩衝液６に溶解し、除菌フイルターにて除菌
し、10のジヤーフアーメンターに仕込む。Example 1 12 g of a commercially available lipase preparation (Lipase MY derived from Candida Cylindracea, Meito Sangyo) was dissolved in phosphate buffer 6 of pH 5.4, sterilized with a sterilization filter, and charged into 10 jars. .
その後ソルビトール（和光純薬試薬一級）
109.3ｇを仕込み、35℃にて溶解する。 Then sorbitol (Wako Pure Chemicals Reagent Grade 1)
Charge 109.3g and dissolve at 35℃.
次にオレイン酸（Extra Oleic90、日本油脂）
169.2ｇを滴下ロートにて徐々に滴下し、ミクロ
エマルジヨンを形成させる。 Next, oleic acid (Extra Oleic90, Nippon Oil & Fats)
Gradually drop 169.2 g using a dropping funnel to form a microemulsion.
回転数350rpm、温度35℃にて72時間インキユ
ベートする。反応混合物を凍結乾燥し、得られる
凍結乾燥物をクロロホルム抽出し、抽出液を減圧
濃縮する。クロロホルム抽出物をテトラヒドロフ
ラン（安定剤であるBHTを含まないもの）に溶
解し、3000rpmで遠心分離し、テトラドロフラン
可溶分とテトラヒドロフラン不溶分とに分ける。 Incubate for 72 hours at a rotation speed of 350 rpm and a temperature of 35°C. The reaction mixture is freeze-dried, the resulting freeze-dried product is extracted with chloroform, and the extract is concentrated under reduced pressure. The chloroform extract is dissolved in tetrahydrofuran (without the stabilizer BHT), centrifuged at 3000 rpm, and separated into a tetrahydrofuran-soluble fraction and a tetrahydrofuran-insoluble fraction.
テトラヒドロフラン可溶分について分取ゲルパ
ーミエーシヨンクロマトグラフイーにてモノエス
テル分画とジエステル分画とを分取し、それぞれ
を減圧濃縮してモノエステルおよびジエステルの
純品を得る。 A monoester fraction and a diester fraction are separated from the tetrahydrofuran soluble fraction by preparative gel permeation chromatography, and each is concentrated under reduced pressure to obtain pure monoester and diester fractions.
反応混合物のゲルパーミエーシヨンクロマトグ
ラフイーチヤートおよび分取範囲を第１図に、モ
ノエステルおよびジエステル単品の同じチヤート
を第２図に示す。 The gel permeation chromatography chart and preparative range of the reaction mixture are shown in FIG. 1, and the same charts for monoester and diester alone are shown in FIG.
モノエステル
構造式、
融点：70.5℃〜71.0℃
収量：64.30ｇ
元素分析：理論値 C64.57；H10.31
実験定 C64.13；H10.13
IR特性吸収（cm-1）：1720（RCOOR′）、1470
（CH2）、1060（Ｃ−Ｏ）、715（−CH2−）、
3300（OH）、1110（第二アルコール）、1050
（第一アルコール）；オレイン酸に基づく吸収
として3030（CHシヨルダーとして）、1660〜
1640（Ｃ＝Ｃ）、720（シス二重結合）
13CNMRシグナル帰属：
オレイン酸骨格炭素 CH3、−CH2−、14−38ppm
同 上 Ｃ＝Ｃ、135ppm
オレイン酸骨格炭素 Ｃ＝０、174ppm
ソルビトール骨格炭素、 62−78ppm
ジエステル
構造式
融点：58.5℃〜59.5℃
収量：33.18ｇ
元素分析：理論値 C70.98；H10.99
実験値 C71.10；H10.87
IR特性吸収（cm-1）：1720（RCOOR′）、1470
（CH2）、1060（Ｃ−Ｏ）、715（−CH2−）、
3300（OH）、1110（第二アルコール）、；オレ
イン酸に基づく吸収として3030（CHシヨルダ
ーとして）、1660〜1640（Ｃ＝Ｃ）、720（シス
二重結合）
13CNMRシグナル帰属：
オレイン酸骨格炭素 CH3、−CH2−、14−38ppm
同 上 Ｃ＝Ｃ、135ppm
同 上 Ｃ＝Ｏ、174ppm
ソルビトール骨格炭素、 62−78ppm
実施例 ２
実施例１において、オレイン酸169.2ｇの代わ
りにオレイン酸282.47ｇを用いた外は全く同様に
操作し、ソルビトールモノオレイン酸エステル
36.34ｇと、ソルビトールジオレイン酸エステル
76.66ｇを得た。Monoester structural formula, Melting point: 70.5℃～71.0℃ Yield: 64.30g Elemental analysis: Theoretical value C64.57; H10.31 Experimental determination C64.13; H10.13 IR characteristics Absorption (cm -1 ): 1720 (RCOOR'), 1470
( CH2 ), 1060(C-O), 715( -CH2- ),
3300 (OH), 1110 (secondary alcohol), 1050
(primary alcohol); 3030 as absorption based on oleic acid (as CH shoulder), 1660~
1640 (C=C), 720 (cis double bond) 13 CNMR signal assignment: Oleic acid backbone carbon CH 3 , -CH 2 -, 14-38ppm Same as above C=C, 135ppm Oleic acid backbone carbon C=0, 174ppm Sorbitol skeleton carbon, 62−78ppm diester structural formula Melting point: 58.5℃～59.5℃ Yield: 33.18g Elemental analysis: Theoretical value C70.98; H10.99 Experimental value C71.10; H10.87 IR characteristic absorption (cm -1 ): 1720 (RCOOR'), 1470
( CH2 ), 1060(C-O), 715( -CH2- ),
3300 (OH), 1110 (secondary alcohol),; 3030 (as CH shoulder) as absorption based on oleic acid, 1660-1640 (C=C), 720 (cis double bond) 13 CNMR signal assignment: Oleic acid skeleton Carbon CH3 , -CH2- , 14-38ppm Same as above C=C, 135ppm Same as above C=O, 174ppm Sorbitol skeleton carbon, 62-78ppm Example 2 In Example 1, oleic acid was used instead of 169.2g of oleic acid. The same procedure was carried out except that 282.47g of sorbitol monooleate was used.
36.34g and sorbitol dioleate ester
76.66g was obtained.
テトラヒドロフラン可溶分のゲルパーミエーシ
ヨンクロマトグラフイーのチヤートを第３図に、
精製後のモノエステルおよびジエステルの同じチ
ヤートを第４図に示す。 Figure 3 shows the chart of gel permeation chromatography of tetrahydrofuran soluble content.
The same chart of monoester and diester after purification is shown in FIG.
図面はゲルパーミエーシヨンクロマトグラフイ
ーのチヤートであり、第１図は実施例１のテトラ
ヒドロフラン可溶分、第２図は実施例１で得られ
たモノエステルおよびジエステル、第３図は実施
例２のテトラヒドロフラン可溶分、第４図は実施
例２で得られたモノエステルおよびジエステルの
チヤートである。
The drawings are charts of gel permeation chromatography; Fig. 1 shows the tetrahydrofuran soluble portion of Example 1, Fig. 2 shows the monoester and diester obtained in Example 1, and Fig. 3 shows Example 2. Fig. 4 is a chart of the monoester and diester obtained in Example 2.
Claims (1)
基、すなわち９−オクタデセノイル基を表し、
R2はR1と同じか、または水素を表す）の新規ソ
ルビトールオレイン酸エステル。[Claims] 1 formula, (In the formula, R 1 represents an acyl group derived from oleic acid, that is, a 9-octadecenoyl group,
A novel sorbitol oleate ester in which R 2 is the same as R 1 or represents hydrogen.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60026831A JPS61186347A (en) | 1985-02-14 | 1985-02-14 | Novel sorbitol oleic acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60026831A JPS61186347A (en) | 1985-02-14 | 1985-02-14 | Novel sorbitol oleic acid ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61186347A JPS61186347A (en) | 1986-08-20 |
| JPS6256142B2 true JPS6256142B2 (en) | 1987-11-24 |
Family
ID=12204211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60026831A Granted JPS61186347A (en) | 1985-02-14 | 1985-02-14 | Novel sorbitol oleic acid ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61186347A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2646439B1 (en) * | 1989-04-28 | 1994-02-11 | Gattefosse Sa | PROCESS FOR THE PREPARATION OF SUCROESTERS BY REACTION OF A SUGAR AND A FATTY ACID IN A SOLVENT MEDIUM AND IN THE PRESENCE OF AN ENZYME, AND SUCROESTERS THUS PREPARED |
| AU9762598A (en) * | 1998-03-13 | 2000-05-29 | Meiji Milk Products Co., Ltd. | Insecticide, acaricide, and antibacterial agent for plant |
| JP2011207987A (en) * | 2010-03-29 | 2011-10-20 | Sumitomo Chemical Co Ltd | Processing stabilizer for resin, resin composition containing the same, and method for improving processing stability of resin |
-
1985
- 1985-02-14 JP JP60026831A patent/JPS61186347A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61186347A (en) | 1986-08-20 |
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