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Article(id=1200147951118025635, tenantId=1146029695717560320, journalId=1190317699101192196, issueId=1200147945191469403, articleNumber=1001-2494(2024)12-1093-07, orderNo=null, doi=10.11669/cpj.2024.12.004, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1673452800000, receivedDateStr=2023-01-12, revisedDate=null, revisedDateStr=null, acceptedDate=null, acceptedDateStr=null, onlineDate=1764067169216, onlineDateStr=2025-11-25, pubDate=1718985600000, pubDateStr=2024-06-22, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1764067169216, onlineIssueDateStr=2025-11-25, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1764067169216, creator=13701087609, updateTime=1764067169216, updator=13701087609, issue=Issue{id=1200147945191469403, tenantId=1146029695717560320, journalId=1190317699101192196, year='2024', volume='59', issue='12', pageStart='1065', pageEnd='1170', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1764067167804, creator=13701087609, updateTime=1764067403507, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1200148933856035173, tenantId=1146029695717560320, journalId=1190317699101192196, issueId=1200147945191469403, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1200148933856035174, tenantId=1146029695717560320, journalId=1190317699101192196, issueId=1200147945191469403, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=1093, endPage=1099, ext={EN=ArticleExt(id=1200147951365489587, articleId=1200147951118025635, tenantId=1146029695717560320, journalId=1190317699101192196, language=EN, title=Synthesis of Phytanetriol as a Lipid Cubic Liquid Crystal Excipient, columnId=null, journalTitle=Chinese Pharmaceutical Journal, columnName=null, runingTitle=null, highlight=null, articleAbstract=

OBJECTIVE To synthesize phytanetriol by epoxidation/ring-opening reaction under catalyst-free conditions using phytol as raw material, low concentration of hydrogen peroxide as oxidant, and formic acid as oxygen carrier. METHODS The effects of the molar ratios of formic acid and hydrogen peroxide to phytol, reaction temperature, and reaction time on the yield of phytanetriol were investigated using a single-factor test and verified by 3-batch reproducibility. The chromatographic purity and structure of phytanetriol were analyzed by gas-mass spectrometry, infrared spectroscopy, and nuclear magnetic resonance spectrometry. RESULTS The optimal conditions for the epoxidation reaction system were n(HCOOH):n(H2O2):n(phytol)=5∶1.3∶1, temperature 55 ℃, and reaction time 2 h. The optimal conditions for the ring-opening reaction system were pH=13, temperature 105 ℃, and reaction time 0.5 h. The phytanetriol synthesis process had a yield of 86.6% in the validated experiments. The chromatographic purity was 94.6%. CONCLUSION The synthesis process is stable and can produce phytanetriol with controllable quality and better purity than commercially available products.

, correspAuthors=Rui ZHANG, authorNote=null, correspAuthorsNote=null, copyrightStatement=null, copyrightOwner=null, extLink=null, articleAbsUrl=null, sourceXml=null, magXml=null, pdfUrl=null, pdf=null, pdfFileSize=null, pdfExtLink=null, richHtmlUrl=null, mobilePdfUrl=null, reviewReport=null, pdfFirstPage=null, abstractGraph=null, abstractGraphContent=null, abstractVideo=null, citation=null, cebUrl=null, magXmlContent=null, mapNumber=null, authorCompany=null, fund=null, authors=null, authorsList=Xinquan RAO, Rui ZHANG), CN=ArticleExt(id=1200147953139679248, articleId=1200147951118025635, tenantId=1146029695717560320, journalId=1190317699101192196, language=CN, title=脂质立方液晶辅料植烷三醇的合成研究, columnId=1190352405612040510, journalTitle=中国药学杂志, columnName=论著, runingTitle=null, highlight=null, articleAbstract=

目的 建立以植醇为原料,低浓度的过氧化氢为氧化剂,甲酸为载氧剂,在无催化剂的条件下,通过环氧化/开环反应合成植烷三醇的方法。方法 采用单因素试验,考察甲酸、过氧化氢与植醇的摩尔比、反应温度和时间对植烷三醇收率的影响,并进行3批次重复性验证。用气-质联用仪、红外光谱仪以及核磁共振波谱仪对植烷三醇的色谱纯度和结构进行了分析。结果 最佳工艺条件确定为:环氧化反应体系最佳条件为n(HCOOH)-n(H2O2)n-n(植醇)=5∶1.3∶1,温度55 ℃,时间2 h;开环反应体系最佳条件为pH值13,温度105 ℃,时间0.5 h。经验证实验,该法植烷三醇合成工艺产率可达86.6%,色谱纯度为94.6%。结论 所建立的合成方法工艺稳定,质量可控,并且所合成的植烷三醇纯度优于市售产品。

, correspAuthors=张锐, authorNote=null, correspAuthorsNote=
*张锐,男,博士,教授 研究方向:药用辅料的设计与评价 Tel:(0791)87118658
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饶信权,男,硕士研究生 研究方向:药物化学

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饶信权,男,硕士研究生 研究方向:药物化学

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饶信权,男,硕士研究生 研究方向:药物化学

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articleId=1200147951118025635, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[1], rfOrder=0, authorNames=KIM J H, journalName=null, refType=null, unstructuredReference=KIM J H. Moisturizing cosmetic composition and its manufacturing method: Korea, KR172329[P]. 2016-12-16., articleTitle=Moisturizing cosmetic composition and its manufacturing method: Korea, KR172329, refAbstract=null), Reference(id=1200823837630780398, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1200147951118025635, doi=null, pmid=null, pmcid=null, year=2022, volume=10, issue=15, pageStart=2781, pageEnd=2819, url=null, language=null, rfNumber=[2], rfOrder=1, authorNames=ABOUREHAB M A S, ANSARI M J, SINGH A, journalName=J Mater Chem B, refType=null, unstructuredReference=ABOUREHAB M A S, ANSARI M J, SINGH A, et al. Cubosomes as an emerging platform for drug delivery: a review of the state of the art[J]. J Mater Chem B, 2022, 10(15): 2781-2819., articleTitle=Cubosomes as an emerging platform for drug delivery: a review of the state of the art, refAbstract=null), Reference(id=1200823837697889263, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1200147951118025635, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[3], rfOrder=2, authorNames=MORI T, SHIONO M, FUJITA Y, journalName=null, refType=null, unstructuredReference=MORI T, SHIONO M, FUJITA Y, et al. Phytanetriol: Japan, JP198577927[P]. 1985-04-11., articleTitle=Phytanetriol: Japan, JP198577927, refAbstract=null), Reference(id=1200823837760803824, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1200147951118025635, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[4], rfOrder=3, authorNames=MUELLER T, PAUST J, journalName=null, refType=null, unstructuredReference=MUELLER T, PAUST J. One-step process for the preparation of 3,7,11,15-tetramethyl-1,2,3-trihydroxyhexadecane: Germany, DE19604723[P]. 1996-02-09., articleTitle=One-step process for the preparation of 3,7,11,15-tetramethyl-1,2,3-trihydroxyhexadecane: Germany, DE19604723, refAbstract=null), Reference(id=1200823837836301297, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1200147951118025635, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[5], rfOrder=4, authorNames=CHEN P, LU C, YE W, journalName=null, refType=null, unstructuredReference=CHEN P, LU C, YE W. Process for one-step synthesis of 3,7,11,15-tetramethylhexadecane-1,2,3-triol: China, CN141433[P]. 2003-07-03., articleTitle=Process for one-step synthesis of 3,7,11,15-tetramethylhexadecane-1,2,3-triol: China, CN141433, refAbstract=null), Reference(id=1200823837895021554, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1200147951118025635, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[6], rfOrder=5, authorNames=IWASAKI H, journalName=null, refType=null, unstructuredReference=IWASAKI H. Preparation of phytanetriol: Japan, JP317719[P]. 2000-10-18., articleTitle=Preparation of phytanetriol: Japan, JP317719, refAbstract=null), Reference(id=1200823837978907635, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1200147951118025635, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[7], rfOrder=6, authorNames=IWASAKI H, journalName=null, refType=null, unstructuredReference=IWASAKI H. Preparation of phytanetriol from 1,2-epoxy-3,7,11,15-tetramethylhexadecan-3-ol: Japan, JP324557[P]. 2001-10-23., articleTitle=Preparation of phytanetriol from 1,2-epoxy-3,7,11,15-tetramethylhexadecan-3-ol: Japan, JP324557, refAbstract=null), Reference(id=1200823838046016500, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1200147951118025635, doi=null, pmid=null, pmcid=null, year=2004, volume=null, issue=4, pageStart=26, pageEnd=29, url=null, language=null, rfNumber=[8], rfOrder=7, authorNames=MISIUNAS A, TALAIKYTE Z, NAIURA G, journalName=Biologija, refType=null, unstructuredReference=MISIUNAS A, TALAIKYTE Z, NAIURA G, et al. Raman and infrared spectroscopic study of phytanetriol and phytanetriol-water cubic phases[J]. Biologija, 2004(4): 26-29., articleTitle=Raman and infrared spectroscopic study of phytanetriol and phytanetriol-water cubic phases, refAbstract=null), Reference(id=1200823838108931061, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1200147951118025635, doi=null, pmid=null, pmcid=null, year=2005, volume=62, issue=4/5, pageStart=945, pageEnd=957, url=null, language=null, rfNumber=[9], rfOrder=8, authorNames=MISIUNAS A, NIAURA G, TALAIKYTE Z, journalName=Spectrochim Acta A, refType=null, unstructuredReference=MISIUNAS A, NIAURA G, TALAIKYTE Z, et al. Infrared and Raman bands of phytanetriol as markers of hydrogen bonding and interchain interaction[J]. Spectrochim Acta A, 2005, 62 (4/5): 945-957., articleTitle=Infrared and Raman bands of phytanetriol as markers of hydrogen bonding and interchain interaction, refAbstract=null), Reference(id=1200823839258170358, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1200147951118025635, doi=null, pmid=null, pmcid=null, year=2020, volume=36, issue=31, pageStart=9132, pageEnd=9141, url=null, language=null, rfNumber=[10], rfOrder=9, authorNames=VALLOORAN J J, DUSS M, ANSORGE P, journalName=Langmuir, refType=null, unstructuredReference=VALLOORAN J J, DUSS M, ANSORGE P, et al. Stereochemical purity can induce a new crystalline mesophase in phytanetriol lipids[J]. Langmuir, 2020, 36(31): 9132-9141., articleTitle=Stereochemical purity can induce a new crystalline mesophase in phytanetriol lipids, refAbstract=null), Reference(id=1200823839342056439, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1200147951118025635, doi=null, pmid=null, pmcid=null, year=2007, volume=null, issue=null, pageStart=178, pageEnd=null, url=null, language=null, rfNumber=[11], rfOrder=10, authorNames=ZHANG Z G, journalName=Synthesis and Design of Fine Organic (精细有机合成与设计), refType=null, unstructuredReference=ZHANG Z G. Synthesis and Design of Fine Organic (精细有机合成与设计)[M]. Vol 2. Beijing: Chemical Industry Press, 2007: 178., articleTitle=null, refAbstract=null), Reference(id=1200823839413359608, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1200147951118025635, doi=null, pmid=null, pmcid=null, year=2019, volume=54, issue=9, pageStart=726, pageEnd=733, url=null, language=null, rfNumber=[12], rfOrder=11, authorNames=SHAN Q Q, JIANG X J, GUI S Y, journalName=Chin Pharm J(中国药学杂志), refType=null, unstructuredReference=SHAN Q Q, JIANG X J, GUI S Y. Preparation and in vitro evaluation of triptolide-loaded cubic liquid crystals[J]. 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Effects of mole ratio of formic acid to phytol feeding on the yield of phytanetriol

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Yield n(HCOOH)-n(phytol)
2∶1 3∶1 4∶1 5∶1 6∶1
% 5.7 10.8 29.1 84.0 78.3
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甲酸与植醇投料摩尔比对植烷三醇收率的影响

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Yield n(HCOOH)-n(phytol)
2∶1 3∶1 4∶1 5∶1 6∶1
% 5.7 10.8 29.1 84.0 78.3
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Effects of mole ratio of hydrogen peroxide to phytolon feeding on the yield of phytanetriol

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Yield n(H2O2)-n(phytol)
1.2∶1 1.3∶1 1.4∶1 1.5∶1 1.6∶1 1.7∶1 1.8∶1
% 66.9 81.9 80.7 80.4 79.5 78.0 67.8
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H2O2与植醇投料摩尔比对植烷三醇收率的影响

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Yield n(H2O2)-n(phytol)
1.2∶1 1.3∶1 1.4∶1 1.5∶1 1.6∶1 1.7∶1 1.8∶1
% 66.9 81.9 80.7 80.4 79.5 78.0 67.8
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Effects of epoxidation reaction time on the yield of phytanetriol

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Yield t/h
1 1.5 2 2.5 3
% 68.1 69.6 86.4 81.9 83.4
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环氧化反应时间对植烷三醇收率的影响

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Yield t/h
1 1.5 2 2.5 3
% 68.1 69.6 86.4 81.9 83.4
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Effects of epoxidation reaction temperature on the yield of phytanetriol

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Yield T/℃
45 50 55 60 65
% 81.3 77.4 86.4 87.0 83.4
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环氧化反应温度对植烷三醇收率的影响

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Yield T/℃
45 50 55 60 65
% 81.3 77.4 86.4 87.0 83.4
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Effects of pH of ring-opening reaction on the yield of phytanetriol

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Yield pH
9 10 11 12 13
% 4.5 15.0 21.6 20.1 78.0
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开环反应pH对植烷三醇收率的影响

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Yield pH
9 10 11 12 13
% 4.5 15.0 21.6 20.1 78.0
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Effects of ring-opening reaction temperature on the yield of phytanetriol

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Yield T/℃
65 75 85 95 105
% 81.6 84.9 82.8 78.6 89.6
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开环反应温度对植烷三醇收率的影响

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Yield T/℃
65 75 85 95 105
% 81.6 84.9 82.8 78.6 89.6
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Effects of ring-opening reaction time on the yield of phytanetriol

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Yield t/min
20 30 40 50 60
% 73.5 78.6 72.0 70.8 74.1
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开环反应时间对植烷三醇收率的影响

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Yield t/min
20 30 40 50 60
% 73.5 78.6 72.0 70.8 74.1
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脂质立方液晶辅料植烷三醇的合成研究
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饶信权 , 张锐 *
中国药学杂志 | 论著 2024,59(12): 1093-1099
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中国药学杂志 | 论著 2024, 59(12): 1093-1099
脂质立方液晶辅料植烷三醇的合成研究
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饶信权, 张锐*
作者信息
  • 江西中医药大学, 现代中药制剂教育部重点实验室, 南昌 330004

    • 饶信权,男,硕士研究生 研究方向:药物化学

通讯作者:

*张锐,男,博士,教授 研究方向:药用辅料的设计与评价 Tel:(0791)87118658
Synthesis of Phytanetriol as a Lipid Cubic Liquid Crystal Excipient
Xinquan RAO, Rui ZHANG*
Affiliations
  • Key Laboratory of Modern Preparation of Chinese Medicine, Jiangxi University of Chinese Medicine, Nanchang 330004, China
出版时间: 2024-06-22 doi: 10.11669/cpj.2024.12.004
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摘要
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目的 建立以植醇为原料,低浓度的过氧化氢为氧化剂,甲酸为载氧剂,在无催化剂的条件下,通过环氧化/开环反应合成植烷三醇的方法。方法 采用单因素试验,考察甲酸、过氧化氢与植醇的摩尔比、反应温度和时间对植烷三醇收率的影响,并进行3批次重复性验证。用气-质联用仪、红外光谱仪以及核磁共振波谱仪对植烷三醇的色谱纯度和结构进行了分析。结果 最佳工艺条件确定为:环氧化反应体系最佳条件为n(HCOOH)-n(H2O2)n-n(植醇)=5∶1.3∶1,温度55 ℃,时间2 h;开环反应体系最佳条件为pH值13,温度105 ℃,时间0.5 h。经验证实验,该法植烷三醇合成工艺产率可达86.6%,色谱纯度为94.6%。结论 所建立的合成方法工艺稳定,质量可控,并且所合成的植烷三醇纯度优于市售产品。

脂质立方液晶  /  植烷三醇  /  过氧化氢  /  环氧化反应  /  开环反应

OBJECTIVE To synthesize phytanetriol by epoxidation/ring-opening reaction under catalyst-free conditions using phytol as raw material, low concentration of hydrogen peroxide as oxidant, and formic acid as oxygen carrier. METHODS The effects of the molar ratios of formic acid and hydrogen peroxide to phytol, reaction temperature, and reaction time on the yield of phytanetriol were investigated using a single-factor test and verified by 3-batch reproducibility. The chromatographic purity and structure of phytanetriol were analyzed by gas-mass spectrometry, infrared spectroscopy, and nuclear magnetic resonance spectrometry. RESULTS The optimal conditions for the epoxidation reaction system were n(HCOOH):n(H2O2):n(phytol)=5∶1.3∶1, temperature 55 ℃, and reaction time 2 h. The optimal conditions for the ring-opening reaction system were pH=13, temperature 105 ℃, and reaction time 0.5 h. The phytanetriol synthesis process had a yield of 86.6% in the validated experiments. The chromatographic purity was 94.6%. CONCLUSION The synthesis process is stable and can produce phytanetriol with controllable quality and better purity than commercially available products.

lipid cubic liquid crystal  /  phytanetriol  /  hydrogen peroxide  /  epoxidation reaction  /  ring-opening reaction
饶信权, 张锐. 脂质立方液晶辅料植烷三醇的合成研究. 中国药学杂志, 2024 , 59 (12) : 1093 -1099 . DOI: 10.11669/cpj.2024.12.004
Xinquan RAO, Rui ZHANG. Synthesis of Phytanetriol as a Lipid Cubic Liquid Crystal Excipient[J]. Chinese Pharmaceutical Journal, 2024 , 59 (12) : 1093 -1099 . DOI: 10.11669/cpj.2024.12.004
正文
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植烷三醇(3,7,11,15-四甲基-1,2,3-十六烷三醇,phytanetriol),是一种具有护发、保湿、防晒等多种功效的活性物质,是重要的化妆品原料;同时其又是一种双亲脂质材料,可作为脂溶性维生素的增溶剂,被广泛应用于功能饮料和其他保健品中,以增强及稳定维生素的活性[1]。近年来植烷三醇作为一种新型药物辅料,常被用于制备新型纳米制剂—脂质立方液晶。由于其结构中不含有酯键,在胃肠道中不降解,能够长时间保持立方液晶结构,可使药物免受降解并有利于药物缓慢长效释放[2]。因此,它的出现引发了制药行业的关注。
植烷三醇的制备方法较多,都是以植醇或异植醇为原料,将双键氧化为邻二羟基结构而制得。根据所采用的氧化剂的不同,主要可分为叔丁基过氧化氢法[3]、锇酸氧化法[4]、四氧化钌氧化法[5]、过氧化氢氧化法[6-7]。这些方法存在以下几个问题:其一,锇酸是剧毒品且生产成本高,废水处理必须进行大量严格的操作步骤,否则将带来严重的环境污染。其二,有些方法都使用了医药工业中所不希望看到的重金属催化剂,如Mori等[3]报道以V或Mo衍生物为催化剂,Iwasaki[6-7]报道以钨酸钠为催化剂,存在催化剂价格昂贵、重金属(毒性)残留等难题。其三,有的方法在后处理过程中还使用了甲苯等二类溶剂,存在溶剂残留的问题[5]。本研究改良了过氧化氢氧化法,采用价廉易得的甲酸/过氧化氢的无催化体系通过环氧化/开环反应,以植醇为原料制备植烷三醇,并结合单因素试验结果对该合成工艺进行优化,得到最佳合成条件,为制备符合药物辅料要求的植烷三醇及其工业化合成应用和国产替代提供了一定的基础和依据。
1 实验部分
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1.1 仪器与试剂
Spectrum 2傅里叶变换红外光谱仪(美国PerkinElmer公司);6890/5973C型气相色谱-质谱联用仪HP-5MS毛细管色谱柱(0.25 mm×30 m,0.25 μm)。(美国Agilent公司),配有MSD ChemStation D.01.02.16数据处理系统,NIST-20质谱数据库;LC3000N高效液相色谱仪(北京创新通恒公司);Alltech 3300蒸发光散射检测器(美国 Alltech 公司);AvanceⅡ 600 MHz核磁共振波谱仪(瑞士Bruker公司);KDL 2分子蒸馏仪(德国UIC公司)。
植醇(Lot#:BQC493,质量分数98%),上海毕得医药科技有限公司;植烷三醇(Lot#:C11558022异构体混合物),Macklin化工有限公司;植烷三醇(Lot#:A1809066,异构体混合物),上海阿拉丁生化科技股份有限公司;双氧水(H2O2,分析纯,质量分数30%);其他试剂均为市售分析纯。
1.2 方法
根据烯烃先经过环氧化反应再经过开环反应生成反式双羟基化合物的原理,可采用甲酸(HCOOH)为载氧剂,先将双键环氧化生成环氧化合物,再用碱水处理,得反式邻二醇。植烷三醇反应式及合成路线见图1。
在装有回流冷凝管、温度计、磁力搅拌子的100 mL三口瓶中加入20.00 g(67.44 mmoL)植醇和一定摩尔量甲酸,开动搅拌,油浴锅缓慢升温至一定温度后,缓慢滴加一定摩尔量30% H2O2至滴完,反应一定时间后,反应液溶于50 mL乙酸乙酯中,置于250 mL分液漏斗中用水(50 mL×3)洗涤有机层,并用pH试纸和淀粉碘化钾试纸监控水层中甲酸与双氧水的残留,以确保除去甲酸与双氧水;有机层经减压旋蒸除去乙酸乙酯。残渣加入50 mL一定pH值的KOH溶液反应一定时间,薄层色谱法(thin layer chromatography,TLC)[展开剂:V(石油醚)-V(乙酸乙酯)=7∶3]跟踪直到反应完全,用饱和食盐水洗涤至中性,无水Na2SO4干燥后减压旋蒸除去溶剂得到植烷三醇粗品。分子蒸馏收集200~202 ℃/3.33 kPa馏分,得无色透明液体,即为产品植烷三醇,对产品进行气相色谱-质谱联用仪(gas chromatography-mass spectrometry,GC-MS)、傅里叶变换红外光谱仪(fourier transform infrared spectrometer,FT-IR)和核磁共振波谱仪(nuclear magnetic resonance,NMR)分析。
KBr液膜法:称取适量光谱纯KBr固体将其放入研钵中,将KBr固体研磨至细小颗粒,然后将细小颗粒用傅立叶红外光谱仪配套的磨具将其压制成两片圆形的KBr薄片。用微量进样器的针头沾一些合成的植烷三醇(已纯化)在其中一片圆形的KBr薄片表面用为微量进样器针头轻轻铺开,其上铺上一层植烷三醇液膜。取未铺植烷三醇的圆形的KBr薄片先放入傅立叶红外光谱仪中扣除背景值,然后再放入已铺上植烷三醇液膜的圆形的KBr薄片,启动仪器进行检测。
2 结果与讨论
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2.1 甲酸与植醇投料摩尔比对植烷三醇收率的影响
不同投料摩尔比对植烷三醇收率的影响见表1。
由表1可知,随着甲酸与植醇的摩尔比升高,植烷三醇合成产率是先升高后趋近稳定。在甲酸与植醇的摩尔比为5∶1时,植烷三醇的合成产率最大。其原因可能是当甲酸用量少时,植醇的羟基未能被酯化保护,导致植醇的羟基被氧化为醛或羧酸等副产物,使得植烷三醇的合成产率低,故选择n(HCOOH)-n(植醇)=5∶1为宜。
2.2 H2O2与植醇投料摩尔比对植烷三醇收率的影响
不同投料摩尔比对植烷三醇收率的影响见表2。
由表2可知,随着H2O2与植醇的摩尔比升高,植烷三醇合成产率先升高,然后趋近稳定。当n(H2O2)-n(植醇)=1.3∶1时,植烷三醇合成产率最大,此后改变双氧水用量对其合成产率无显著影响。当H2O2与植醇的摩尔比超过1.8∶1后,收率明显下降。其原因可能是氧化剂的量越大,氧化的能力越强,随着氧化剂氧化能力的增大,植醇部分被氧化成醛或羧酸,同时其他副反应也相应增多,从而导致植烷三醇的收率降低。故选择n(H2O2)-n(植醇)=1.3∶1为宜。
2.3 环氧化反应时间对植烷三醇收率的影响
不同环氧化反应时间对植烷三醇收率的影响见表3。由表3可见,植烷三醇的收率随环氧化反应时间的增加而增大,但在反应2 h后收率基本不变,因此,选择反应时间2 h较适宜。
2.4 环氧化反应温度对植烷三醇收率的影响
不同环氧化温度对植烷三醇收率的影响见表4。由表4可见,环氧化反应温度低于55 ℃时,植烷三醇的收率低,高于60 ℃后收率也有所下降,其原因可能是低温时 H2O2反应活性低,随着温度的升高反应活性增大,但是反应温度过高,H2O2的分解速度增快,所以温度高于60 ℃后收率有所下降。故选择55 ℃为最佳反应温度。
2.5 开环反应pH对植烷三醇收率的影响
不同pH对植烷三醇收率的影响见表5。
由表5可见,当pH较低时,不容易发生环氧化合物的开环反应,导致植烷三醇合成产率不高。但当pH值=13时,其合成产率有显著增大。因此,在反应液中加入KOH溶液,控制pH值约为13。
2.6 开环反应温度对植烷三醇收率的影响
不同开环反应温度对植烷三醇收率的影响见表6。由表6所见,当开环反应温度在65~95 ℃时,植烷三醇的合成产率变化不大,但当温度达到105 ℃时,植烷三醇的合成产率增大。其原因可能为,当开环反应温度在65~95 ℃时,虽然开环反应可以发生,但是反应不完全,而当温度达到105 ℃时反应较为彻底,故此温度下植烷三醇合成产率增大。因此,选择以开环反应温度105 ℃为宜。
2.7 开环反应时间对植烷三醇收率的影响
不同开环反应时间对植烷三醇收率的影响见表7。由表7可见,开环反应时间对植烷三醇合成产率影响不显著,故选择30 min为开环反应时间。
2.8 验证性实验
依据单因素试验考察的结果,将植烷三醇的合成工艺条件确定为环氧化反应n(HCOOH)-n(H2O2)-n(植醇)=5∶1.3∶1,反应温度55 ℃,反应时间2 h;开环反应pH=13,反应温度105 ℃,反应时间0.5 h。具体操作见“1.2”项下。平行合成实验3次得到平均产率为86.6%标准偏差(SD)值为1.54。
2.9 放大实验
为进一步验证工艺的合理性和有效性,按“2.8”项下条件,将所建立的植烷三醇的合成工艺进行了初步放大实验,具体放大实验过程如下:在装有回流冷凝管、温度计、磁力搅拌子的1 L三口瓶中加入227.00 g(765.5 mmol)植醇和176.14 g(3 826.5 mmol)甲酸,开动搅拌,油浴锅缓慢升温至55 ℃,用250 mL恒压漏斗滴加130.14 g(994.9 mmol)双氧水,以一滴一滴的速度滴加至完全,反应液溶于600 mL乙酸乙酯中,置于1 L分液漏斗中用水(600 mL×3)洗涤,并用pH试纸和淀粉碘化钾试纸监控水层中甲酸与双氧水的残留,以确保除去甲酸与双氧水,有机层经减压旋蒸除去乙酸乙酯。有机相残渣加入500 mL pH值=13的KOH溶液105 ℃回流0.5 h,TLC〔展开剂:V(石油醚)-V(乙酸乙酯)=7∶3〕监控直到反应完全,用饱和食盐水洗涤至中性,无水Na2SO4干燥后减压旋蒸除去溶剂得到植烷三醇粗品。分子蒸馏收集200~202 ℃/3.33 kPa馏分,得无色透明液体218 g,即为产品植烷三醇,产率86.2%。
2.10 结构表征
2.10.1 GC-MS定性表征产物及测定其色谱纯度
GC-MS:HP-5MS毛细管色谱柱(0.25 mm×30 m,0.25 μm)。升温程序:起始温度200 ℃,保持3 min,以10 ℃·min-1速率升至250 ℃,5 min;进样口温度250 ℃,进样量1 μL,分流比20∶1;载气:高纯氦气,流速1 mL·min-1;质谱接口温度280 ℃;电子轰击(EI)离子源;电子能量70 eV;离子源温度230 ℃;四极杆温度150 ℃;扫描范围:m/z 10~500全扫描,溶剂延时3 min。检测到一保留时间为8.715 min的单峰,色谱峰纯度为94.6%(面积归一化法计算含量),采用NIST20质谱数据库进行谱图匹配,确定为植烷三醇,匹配度91。质谱图见图2,可见m/z(%)分别为:269.3(29%),125.1(48%),111(73%),105.1(96%),97.1(84%),85.1(41%),83.1(87%),71.1(97%),69.1(90%),57.1(90%),55.1(57%),43.1(100%),41.1(32%)。
2.10.2 产物的红外光谱表征
产物的红外光谱图(KBr液膜法)见图3。波数:3 391(s,νO-H),2 953(s,νC-H),2 926(s,νC-H),2 869(s,νC-H),1 463(s,νC-H),1 377(s, νC-H),1 090(m,νC-O),1 090(m,νC-O),与文献[8-9]数据一致。
2.10.3 产物的核磁共振谱表征
称取适量合成的植烷三醇(已纯化)于核磁管中,加入氘代氯仿配置成1 mg·mL-1浓度溶液用核磁共振波谱仪进行氢谱和碳谱的扫描。1H-NMR(600 MHz,CDCl3),化学位移δ:0.86~0.91(m, 12H),1.00~1.59(m, 24H),2.54~2.61(m, 3H)3.50(d, 1H),3.79(d, 2H)。产物1H-NMR谱图(图4),烯氢峰消失。谱图数据与文献[10]报道一致。
13C-NMR(150 MHz, CDCl3)δ:76.87, 76.20, 75.30, 74.77, 74.75, 74.63, 74.61, 63.44, 63.27, 39.74, 39.37, 38.46, 37.77, 37.68, 37.57, 37.44, 37.40, 37.29, 32.81, 32.79, 27.99, 24.82, 24.80, 24.19, 23.57, 22.73, 22.64, 22.31, 21.05, 20.99, 19.75, 19.72, 19.68, 19.66, 19.62, 19.59。产物的13C-NMR谱图(图5)与原料植醇相比, 烯碳峰消失;谱图数据与文献[10]报道一致。
2.11 与市售产品对比实验
GC/MS不能对植烷三醇中的异构体进行有效的分离。为了有效的对比所合成植烷三醇与市售产品的纯度差异,本研究建立了新的HPLC/ELSD的分离方法,色谱条件:色谱柱:Alltech C18(4.6 mm×250 mm,5 μm);流动相:90%乙腈-水等度洗脱;柱温:30 ℃;样品浓度1 mg·min-1;进样量:10 μL;ELSD漂移管温度为60 ℃;氮气流速1.6 L·min-1。色谱图见图6,由图6可见,本研究所合成的植烷三醇为单一色谱峰,而市售产品呈现明显的双峰(标称为异构体混合物),说明本工艺合成的植烷三醇纯度较高。
3 讨论
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本研究以植醇为原料,采用价廉易得的低浓度过氧化氢作为氧化剂,甲酸作为载氧剂,通过环氧化/开环反应合成了植烷三醇,通过GC-MS、FT-IR和NMR确定了植烷三醇的色谱纯度和结构。排除了使用高质量分数过氧化氢在工业化生产中的不安全因素,反应过程不使用任何催化剂,实现合成工艺的绿色化,有效地降低了生产成本。同时,氧化剂反应生成水,对环境污染较小。因此,本工艺具有放大经济性,对环境友好,实施条件简单,无须高压高温装置,便于进行规模化连续生产。为此后合成植烷三醇的工业化应用实现进口替代[11-12]提供了一定的基础和依据。
基金
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  • 国家自然科学基金项目资助(82360702)
  • 国家自然科学基金项目资助(81560579)
  • 国家自然科学基金项目资助(81160523)
  • 江西省教育厅科技项目资助(GJJ14609)
  • 江西中医药大学校级科技创新团队发展项目资助(CXTD22005)
  • 江西中医药大学校级科技创新团队发展项目资助(20045252300403)
文献
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参考文献 引证文献
排序方式：
[1]
KIM J H. Moisturizing cosmetic composition and its manufacturing method: Korea, KR172329[P]. 2016-12-16.
[2]
ABOUREHAB M A S, ANSARI M J, SINGH A, et al. Cubosomes as an emerging platform for drug delivery: a review of the state of the art[J]. J Mater Chem B, 2022, 10(15): 2781-2819.
[3]
MORI T, SHIONO M, FUJITA Y, et al. Phytanetriol: Japan, JP198577927[P]. 1985-04-11.
[4]
MUELLER T, PAUST J. One-step process for the preparation of 3,7,11,15-tetramethyl-1,2,3-trihydroxyhexadecane: Germany, DE19604723[P]. 1996-02-09.
[5]
CHEN P, LU C, YE W. Process for one-step synthesis of 3,7,11,15-tetramethylhexadecane-1,2,3-triol: China, CN141433[P]. 2003-07-03.
[6]
IWASAKI H. Preparation of phytanetriol: Japan, JP317719[P]. 2000-10-18.
[7]
IWASAKI H. Preparation of phytanetriol from 1,2-epoxy-3,7,11,15-tetramethylhexadecan-3-ol: Japan, JP324557[P]. 2001-10-23.
[8]
MISIUNAS A, TALAIKYTE Z, NAIURA G, et al. Raman and infrared spectroscopic study of phytanetriol and phytanetriol-water cubic phases[J]. Biologija, 2004(4): 26-29.
[9]
MISIUNAS A, NIAURA G, TALAIKYTE Z, et al. Infrared and Raman bands of phytanetriol as markers of hydrogen bonding and interchain interaction[J]. Spectrochim Acta A, 2005, 62 (4/5): 945-957.
[10]
VALLOORAN J J, DUSS M, ANSORGE P, et al. Stereochemical purity can induce a new crystalline mesophase in phytanetriol lipids[J]. Langmuir, 2020, 36(31): 9132-9141.
[11]
ZHANG Z G. Synthesis and Design of Fine Organic (精细有机合成与设计)[M]. Vol 2. Beijing: Chemical Industry Press, 2007: 178.
[12]
SHAN Q Q, JIANG X J, GUI S Y. Preparation and in vitro evaluation of triptolide-loaded cubic liquid crystals[J]. Chin Pharm J(中国药学杂志), 2019, 54(9): 726-733.
2024年第59卷第12期
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doi: 10.11669/cpj.2024.12.004
  • 接收时间：2023-01-12
  • 首发时间：2025-11-25
  • 出版时间：2024-06-22
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  • 收稿日期：2023-01-12
基金
国家自然科学基金项目资助(82360702)
国家自然科学基金项目资助(81560579)
国家自然科学基金项目资助(81160523)
江西省教育厅科技项目资助(GJJ14609)
江西中医药大学校级科技创新团队发展项目资助(CXTD22005)
江西中医药大学校级科技创新团队发展项目资助(20045252300403)
作者信息
    江西中医药大学, 现代中药制剂教育部重点实验室, 南昌 330004

通讯作者:

*张锐,男,博士,教授 研究方向:药用辅料的设计与评价 Tel:(0791)87118658
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2种不同金属材料的力学参数
科
Family		 属数
Number of
genus		 种数
Number of
species		 占总种数比例
Percentage of
total species (%)		 属
Genus		 种数
Number of
species		 占总种数比例
Percentage of total
species (%)
鹅膏菌科Amanitaceae 2 11 5.26 鹅膏菌属 Amanita 10 4.78
小菇科 Mycenaceae 2 12 5.74 丝盖伞属 Inocybe 5 2.39
多孔菌科 Polyporaceae 8 14 6.70 蜡蘑属 Laccaria 5 2.39
红菇科 Russulaceae 3 23 11.00 小皮伞属 Marasmius 6 2.87
小菇属 Mycena 11 5.26
光柄菇属 Pluteus 5 2.39
红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
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