CAS: 479-98-1; (2S,3R,4S,5S,6R)-2-(((1S,4Ar,5S,7As)-5-Hydroxy-7-(Hydroxymethyl)-1,4A,5,7A-Tetrahydrocyclopenta[c]Pyran-1-yl)Oxy)-6-(Hydroxymethyl)Tetrahydro-2H-Pyran-3,4,5-Triol

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CAS号11044-25-0 hexa-O-acetyl-a... | CAS号82504-05-0 penta-O-acetyl-...

合成工艺路线路线简述

  • 合成目标产物 Aucubin 主要起始原料 β-D-Glucopyranoside, (1S,4Ar,5S,7As)-5-(Acetyloxy)-7-[(Acetyloxy)Methyl]-1,4A,5,7A-Tetrahydrocyclopenta[c]Pyran-1-Yl, Tetraacetate (9CI)
  • (文献来源)合成步骤主要原料 β-D-Glucopyranoside, (1S,4Ar,5S,7As)-5-(Acetyloxy)-7-[(Acetyloxy)Methyl]-1,4A,5,7A-Tetrahydrocyclopenta[c]Pyran-1-Yl, Tetraacetate (9Ci)
📜(8S)-(-)-Hexaacetyl-7,8-Dihydro-8-Hydroxyaucubin置于吡啶,Sodium Methylate,三氯氧磷体系中,用 甲醇 作为反应溶剂,化学反应 14.0H,反应生成 桃叶珊瑚苷(杜仲甙)
参考文献:Weinges,Klaus; Ziegler,Hans Juergen,Liebigs Annalen Der Chemie,1990,# 7,P. 715-717
标题:Weinges,Klaus; Ziegler,Hans Juergen,Liebigs Annalen Der Chemie,1990,# 7,P. 715-717

海关参考信息

专利信息


专利号:US-4410710-A
优先权日:1981-09-25
标题 :Conversion of iridoids to prostaglandins
发明人：BERKOWITZ WILLIAM F; CHOUDHRY SATISH C; HRABIE JOSEPH A
权利人:UNIV CITY
摘要:Naturally occurring iridoids provide the starting material for a unique synthesis sequence to produce prostaglandin intermediates. The iridoid lactone is hydrogenated, converted to an acetal, and rings opened to introduce the carbonyl octenyl side chain in six steps. The intermediate can be converted to prostaglandin as previously demonstrated.

专利号:CN-113045531-A
优先权日:2021-03-31
标 题:A kind of method and extraction device for high-yield extraction and synthesis of aucubin aglycone

专利号:CN-104644461-B
优先权日:2015-01-23
标题:Application of compounds with collagen synthesis promoting activity in anti-aging cosmetics

专利号:CN-104644461-A
优先权日:2015-01-23
标题 :Application of compounds with collagen synthesis promoting activity in anti-aging cosmetics

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主要参考文献


1: Zhang L, Ma YL, Liu Y, Zu YG. Development and validation of high liquid performance chromatography-tandem mass spectrometry method for simultaneous determination of geniposidic acid and aucubin in rat plasma for pharmacokinetic study after oral administration of Du-zhong tea extract. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Jul 15;963:62-9. doi: 10.1016/j.jchromb.2014.04.033. Epub 2014 May 23. doi: 10.1371/journal.pone.0088017. eCollection 2014.
3: Lee HY, Lee GH, Lee MR, Kim HK, Kim NY, Kim SH, Lee YC, Kim HR, Chae HJ. Eucommia ulmoides Oliver extract, aucubin, and geniposide enhance lysosomal activity to regulate ER stress and hepatic lipid accumulation. PLoS One. 2013 Dec 11;8(12):e81349. doi: 10.1371/journal.pone.0081349. eCollection 2013.
4: Park KS. Aucubin, a naturally occurring iridoid glycoside inhibits TNF-α-induced inflammatory responses through suppression of NF-κB activation in 3T3-L1 adipocytes. Cytokine. 2013 Jun;62(3):407-12. doi: 10.1016/j.cyto.2013.04.005. Epub 2013 Apr 20. doi: 10.1002/chem.201203968. Epub 2013 Feb 28. Chinese. doi: 10.1007/s11033-012-1730-9. Epub 2012 Jul 19. doi: 10.1002/bmc.1748. Epub 2011 Nov 23.

合成参考文献


参考文献:10.3275/7859
摘要:Jiang YL, Ning Y, Liu YY, Wang Y, Zhang Z, Yin LM, Xu YD, Wei Y, Yang YQ. Effects of preventive acupuncture on streptozotocin-induced hyperglycemia in rats. Journal of Endocrinological Investigation. 2011 Jul 12;34(10):e355–61. doi: 10.3275/7859.
参考文献:10.1371/journal.pone.0021781
摘要:Kim Y, Hollenbaugh JA, Kim D, Kim B. Novel PI3K/Akt Inhibitors Screened by the Cytoprotective Function of Human Immunodeficiency Virus Type 1 Tat. PLoS ONE. 2011 Jul 12;6(7):e21781. doi: 10.1371/journal.pone.0021781.
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