CN101190873B - 三十烷醇的制备方法 - Google Patents
三十烷醇的制备方法 Download PDFInfo
- Publication number
- CN101190873B CN101190873B CN2006100488523A CN200610048852A CN101190873B CN 101190873 B CN101190873 B CN 101190873B CN 2006100488523 A CN2006100488523 A CN 2006100488523A CN 200610048852 A CN200610048852 A CN 200610048852A CN 101190873 B CN101190873 B CN 101190873B
- Authority
- CN
- China
- Prior art keywords
- weight
- silica gel
- column chromatography
- filter residue
- normal hexane
- 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.)
- Active
Links
- REZQBEBOWJAQKS-UHFFFAOYSA-N triacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title abstract description 12
- 239000007787 solid Substances 0.000 claims abstract description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 8
- 241000221079 Euphorbia <genus> Species 0.000 claims abstract description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000004440 column chromatography Methods 0.000 claims abstract description 6
- 239000000741 silica gel Substances 0.000 claims abstract description 6
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 6
- 241000196324 Embryophyta Species 0.000 claims abstract description 5
- 239000013078 crystal Substances 0.000 claims abstract description 5
- 239000000706 filtrate Substances 0.000 claims abstract description 4
- 239000003208 petroleum Substances 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000284 extract Substances 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 7
- 239000003480 eluent Substances 0.000 claims description 5
- 238000005238 degreasing Methods 0.000 claims description 3
- 238000010828 elution Methods 0.000 claims description 3
- 239000006210 lotion Substances 0.000 claims description 3
- 235000012054 meals Nutrition 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 238000010898 silica gel chromatography Methods 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 235000005205 Pinus Nutrition 0.000 claims description 2
- 241000218602 Pinus <genus> Species 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 238000000605 extraction Methods 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 9
- 239000000843 powder Substances 0.000 abstract 1
- 238000005516 engineering process Methods 0.000 description 3
- 229960001109 policosanol Drugs 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ZYURHZPYMFLWSH-UHFFFAOYSA-N octacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC ZYURHZPYMFLWSH-UHFFFAOYSA-N 0.000 description 2
- 208000006820 Arthralgia Diseases 0.000 description 1
- 244000241257 Cucumis melo Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 241000122904 Mucuna Species 0.000 description 1
- 235000008540 Mucuna pruriens var utilis Nutrition 0.000 description 1
- 244000003220 Mucuna pruriens var. utilis Species 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 201000001881 impotence Diseases 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000019384 rice bran wax Nutrition 0.000 description 1
- 239000004170 rice bran wax Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Landscapes
- Medicines Containing Plant Substances (AREA)
Abstract
本发明涉及一种已有化合物的制备工艺。本发明所述的三十烷醇的制备方法由以下步骤组成：一、以大戟科大戟属植物全株植物粗粉为原料，用体积百分比浓度为60-90％的乙醇或甲醇或丙酮，在50-80℃的温度下进行热回流提取，提取液浓缩成浸膏；二、按照浸膏重量的1-6倍加水进行溶解，不溶物先加入其两倍重量以上的石油醚搅拌脱脂，滤过，滤渣加入其两倍重量以上的氯仿，搅拌溶解，滤过，弃滤渣，滤液蒸馏回收溶剂，得固形物；三、所述固形物拌入一倍重量以上的柱层析硅胶，上硅胶柱层析，先用正己烷作为洗脱剂洗脱，再用正己烷∶醋酸乙酯为100∶3-10的洗脱剂作梯度洗脱，收集含5-10％醋酸乙酯的洗脱液，回收溶剂，得固体物，用醋酸乙酯重结晶，得鳞片状结晶。
Description
技术领域
本发明涉及一种已有化合物的制备工艺。
背景技术
中国专利申请号03113007.0公开了“一种米糠活性物质二十八烷醇和三十烷醇的制备方法”，以粗米糠蜡为原料，采用以异丙醇为溶剂的萃取法对粗米糠蜡进行脱油精制得精糠蜡；采用超声波水解米糠蜡制得脂肪醇、脂肪酸盐混合物；采用丙酮萃取法进行醇、酸分离，对混合脂肪醇进行提取和精制；最后采用分子蒸馏技术分离二十八烷醇、三十烷醇。
中国专利申请号85103562公开了“一种三十烷醇提纯的新方法”，是从天然资源如蜂蜡中制备高纯三十烷醇的简便纯化方法，该法能制得二十八烷醇含量极低的高纯度的三十烷醇CH3(CH2)28CH2OH.该法在前人关于萃取，皂化，分离工艺后，加进了混合溶剂保温结晶法，使三十烷醇纯度在95％以上，其中二十八烷醇含量为0～2.74％，收率为0.26～5％。
三十烷醇分子式为C30H62O，结构式为CH3-(CH2)28-CH2-OH，先前的报道是从油麻藤属植物Mucuna aterrima叶和茎中分离出，并用于植物生长调节剂(Manisa A，et，al，phytochemistry 1996，42，997)。
在现有技术中三十烷醇已经有大量的报道，其报道均集中在三十烷醇用于蔬菜、水果、植物和粮食作物的生长调节剂和营养剂，也有报道其作为农药。本申请人提出了三十烷醇作为制备人用药方面的用途。由此可见，三十烷醇的用途正在日益扩大，而其新的制备方法也亟待研究。
发明内容
本发明的目的旨在提供一种以大戟科植物为原料制备三十烷醇的方法。
本发明所述的三十烷醇的制备方法由以下步骤组成：
一、以大戟科大戟属植物全株植物粗粉为原料，用体积百分比浓度为60-90％的乙醇或甲醇或丙酮，在50-80℃的温度下进行热回流提取，提取液浓缩成浸膏；
二、按照浸膏重量的1-6倍加水进行溶解，不溶物先加入其两倍重量以上的石油醚搅拌脱脂，反复处理两次以上，滤过，滤渣加入其两倍重量以上的氯仿，搅拌溶解，滤过，弃滤渣，滤液蒸馏回收溶剂，得固形物；
三、所述固形物拌入一倍重量以上的柱层析硅胶，上硅胶柱层析，先用正己烷作为洗脱剂洗脱，洗液弃之，再用正己烷∶醋酸乙酯为100∶3-10的洗脱剂作梯度洗脱，收集含5-10％醋酸乙酯的洗脱液，回收溶剂，得固体物，用醋酸乙酯重结晶，得鳞片状结晶。
所述的大戟科大戟属植物为土瓜狼毒、大狼毒、小狼毒或鸡肠狼毒；步骤二中所述的石油醚的量和氯仿的量一般不超过10倍；步骤三中所述的拌固形物的柱层析硅胶的量为1-3倍。
本发明提供了一种从植物中获得三十烷醇的方法，增加了已知化合物三十烷醇的获得途径。
具体实施方式
实施例：
土瓜狼毒为大戟科植物Eupborbia pinus Le’V1。本品尚无现代的科研报告，仅见“滇南本草”记载：味苦，麻，性温，有毒。主治筋骨疼痛，手足痿软，毒气流于经络的一切诸疮，无不神效。
取土瓜狼毒粗粉2kg，加入常规量的体积浓度为80％的乙醇热回流提取3次，每次2小时，减压回收乙醇，得浸膏210g，置烧杯中加5倍量的水搅拌溶解，得不溶物98g。加入5倍重量的石油醚搅拌脱脂，反复处理三次，滤过，滤渣加入其5倍重量的氯仿，搅拌溶解，滤过，弃滤渣，滤液蒸馏回收氯仿，得固形物；加入固形物同等重量的柱层析硅胶，拌匀，上硅胶柱层析，先用正己烷洗脱，洗液弃之，再用正己烷∶醋酸乙酯为100∶3-10的洗脱剂作梯度洗脱，收集含5-10％醋酸乙酯的洗脱液，回收溶剂，得到固体物，用醋酸乙酯重结晶，得鳞片状结晶。结晶熔点84-85℃，经紫外、红外、核磁共振质谱分析，所得鳞片状结晶物分子式为C30H62O，分子量为438，结构式为CH3-(CH2)28-CH2-OH。即三十烷醇。
Claims (1)
1.一种三十烷醇的制备方法，其特征在于由以下步骤组成：
一、以大戟科大戟属植物全株植物土瓜狼毒Eupborbia pinus Le′vl粗粉为原料，用体积百分比浓度为60-90％的乙醇或甲醇或丙酮，在50-80℃的温度下进行热回流提取，提取液浓缩成浸膏；
二、按照浸膏重量的1-6倍加水进行溶解，不溶物先加入其2-10倍重量的石油醚搅拌脱脂，反复处理两次，滤过，滤渣加入其2-10倍重量的氯仿，搅拌溶解，滤过，弃滤渣，滤液蒸馏回收溶剂，得固形物；
三、所述固形物拌入1-3倍重量的柱层析硅胶，上硅胶柱层析，先用正己烷作为洗脱剂洗脱，洗液弃之，再用正己烷∶醋酸乙酯为100∶3-10的洗脱剂作梯度洗脱，收集含5-10％醋酸乙酯的洗脱液，回收溶剂，得固体物，用醋酸乙酯重结晶，得鳞片状结晶。
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2006100488523A CN101190873B (zh) | 2006-11-24 | 2006-11-24 | 三十烷醇的制备方法 |
| PCT/CN2007/002873 WO2008061428A1 (fr) | 2006-11-24 | 2007-09-30 | Formulations pharmaceutiques, utilisation et élaboration du triacontanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2006100488523A CN101190873B (zh) | 2006-11-24 | 2006-11-24 | 三十烷醇的制备方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101190873A CN101190873A (zh) | 2008-06-04 |
| CN101190873B true CN101190873B (zh) | 2010-09-29 |
Family
ID=39486093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2006100488523A Active CN101190873B (zh) | 2006-11-24 | 2006-11-24 | 三十烷醇的制备方法 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101190873B (zh) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106883100B (zh) * | 2017-02-07 | 2020-04-07 | 昆明龙津药业股份有限公司 | 一种三十烷醇晶型ⅰ及其制备方法 |
| CN113336628B (zh) * | 2021-04-16 | 2023-02-10 | 云南省中医中药研究院 | 一种二醇蔷薇烷、其制备方法及用途 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1439625A (zh) * | 2003-03-17 | 2003-09-03 | 江南大学 | 一种米糠活性物质二十八烷醇和三十烷醇的制备方法 |
| WO2005067903A1 (en) * | 2004-01-20 | 2005-07-28 | Panacea Biotec Ltd. | Pharmaceutical compositions comprising higher primary alcohols and ezetimibe and process of preparation thereof |
| CN1834079A (zh) * | 2006-04-18 | 2006-09-20 | 浙江大学 | 近临界水介质中米糠蜡无催化水解制备高级脂肪醇的方法 |
-
2006
- 2006-11-24 CN CN2006100488523A patent/CN101190873B/zh active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1439625A (zh) * | 2003-03-17 | 2003-09-03 | 江南大学 | 一种米糠活性物质二十八烷醇和三十烷醇的制备方法 |
| WO2005067903A1 (en) * | 2004-01-20 | 2005-07-28 | Panacea Biotec Ltd. | Pharmaceutical compositions comprising higher primary alcohols and ezetimibe and process of preparation thereof |
| CN1834079A (zh) * | 2006-04-18 | 2006-09-20 | 浙江大学 | 近临界水介质中米糠蜡无催化水解制备高级脂肪醇的方法 |
Non-Patent Citations (8)
| Title |
|---|
| 焦莹等.大戟属植物主要化学成分及其生理活性的研究进展.中草药21 2.1990,21(2),39-44. |
| 焦莹等.大戟属植物主要化学成分及其生理活性的研究进展.中草药21 2.1990,21(2),39-44. * |
| 赵奎君等.大狼毒化学成分的研究.中国中药杂志20 3.1995,20(3),169-170. |
| 赵奎君等.大狼毒化学成分的研究.中国中药杂志20 3.1995,20(3),169-170. * |
| 赵奎君等.狼毒类生药Jolkinolide B的HPLC分析.中国药科大学学报25 6.1994,25(6),332-334. |
| 赵奎君等.狼毒类生药Jolkinolide B的HPLC分析.中国药科大学学报25 6.1994,25(6),332-334. * |
| 阮汉利等.湖北大戟化学成分研究.中国中药杂志31 9.2006,31(9),742-744. |
| 阮汉利等.湖北大戟化学成分研究.中国中药杂志31 9.2006,31(9),742-744. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101190873A (zh) | 2008-06-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1935820B (zh) | 无患子总皂苷的制备方法 | |
| US9884884B2 (en) | Compound extracted from husk and fruit stem of xanthoceras sobifolia and its extracting method and use thereof | |
| CN101999493B (zh) | 一种植物保健凉茶的制备方法 | |
| CN111978158A (zh) | 一种从工业大麻中提取纯化次大麻二酚的方法 | |
| CN110467521A (zh) | 一种以工业大麻为原料的大麻二酚（cbd）分离纯化方法 | |
| CN103040882B (zh) | 紫果西番莲茎及叶提取物及其药物组合物与抗抑郁作用 | |
| CN111848362A (zh) | 一种超声提取结合动态轴向压缩柱系统制备高纯度大麻二酚的方法 | |
| CN112500448B (zh) | 从百合科葱属植物中提取拉肖皂苷元的方法 | |
| CN101190873B (zh) | 三十烷醇的制备方法 | |
| CN111848358A (zh) | 一种大孔树脂富集结合动态轴向压缩柱系统制备高纯度大麻二酚的方法 | |
| CN107298642B (zh) | 一种6-姜烯酚的提取纯化方法 | |
| CN1651383A (zh) | 天然结晶姜酚的制备方法 | |
| CN101880301B (zh) | 一种制备芍药苷提取物的方法 | |
| CN113209165A (zh) | 一种大叶蒟提取物及其制备方法与应用 | |
| CN115010618B (zh) | 一种可降尿酸的金色酰胺醇酯分离纯化方法及其应用 | |
| CN103739490B (zh) | 一种从菝葜或其同属植物中提取纯化绿原酸的方法 | |
| KR100715206B1 (ko) | 참당귀로부터 데쿨시놀을 고수율로 제조하는 방법 | |
| CN111171106A (zh) | 一种24-羟基硬脂醇甘草亭酸酯的制备方法 | |
| CN102127131A (zh) | 一种梓醇的提取方法 | |
| CN102432419B (zh) | 从紫茎泽兰中提取分离β-榄香烯的方法 | |
| CN101974008B (zh) | 小八角莲中提取纯化鬼臼毒素的工艺 | |
| CN114671755A (zh) | 一种高含量玛咖烯的制备方法 | |
| CN107510773A (zh) | 一种纯植物提取液及其制备方法 | |
| CN104119410B (zh) | 一种从杜仲果中制备桃叶珊瑚苷单体的工艺方法 | |
| EP1732875B1 (en) | Process for isolation of hepatoprotective agent "oleanolic acid" from lantana camara |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| ASS | Succession or assignment of patent right |
Owner name: KUNMING LONGJIN PHARMACEUTICAL CO., LTD. Free format text: FORMER OWNER: FAN XIANE Effective date: 20111130 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 650228 KUNMING, YUNNAN PROVINCE TO: 650101 KUNMING, YUNNAN PROVINCE |
|
| TR01 | Transfer of patent right |
Effective date of registration: 20111130 Address after: 650101 No. 2188, Gao Lu, Kunming, Yunnan Patentee after: Kunming Longjin Pharmaceutical Co., Ltd. Address before: 650228, Yunnan City, Kunming province road under the five pile of Kunming Long Jin Pharmaceutical Co., Ltd. Patentee before: Fan Xiane |
|
| CP02 | Change in the address of a patent holder |
Address after: 650500 No. 789, Lanmao Road, majinpu sub district office, Kunming high tech Zone, Wuhua District, Kunming, Yunnan Province Patentee after: KUNMING LONGJIN PHARMACEUTICAL Co.,Ltd. Address before: No. 2188, Kegao Road, Kunming, Yunnan 650101 Patentee before: KUNMING LONGJIN PHARMACEUTICAL Co.,Ltd. |
|
| CP02 | Change in the address of a patent holder |