CAS: 6902-77-8; (1R,4As,7As)-Methyl 1-Hydroxy-7-(Hydroxymethyl)-1,4A,5,7A-Tetrahydrocyclopenta[c]Pyran-4-Carboxylate

该化合物是来自Cardenia Jasminoides的天然化合物,具有组织工程和伤口愈合应用的有力交叉特性,催化了凝胶,加强了生物材料的稳定性和机械强度,Genipin的生物活性和低毒性促进了生物医学和药物配方的使用.

结构式图片

相似化合物

24512-63-8 69977-52-2 206755-40-0

欧盟法规

REACH注册ECHA物质C&L通报

上下游产品

geniposide geniposide choline chloride genipin 1-O-β-D-isomaltoside cerbinal 1-methoxygenipin

合成工艺路线路线简述

    京尼平甙置于immobilized β-Glucosidase体系中,用 乙酸乙酯 作为反应溶剂,以63.08%的收率获得产物京尼平
    参考文献:固定化β-葡萄糖苷酶在两相水-有机系统中将栀子苷转化为京尼平
    标题:固定化β-葡萄糖苷酶在两相水-有机系统中将栀子苷转化为京尼平
    摘要:京尼平是京尼平苷的生物活性化合物,是一种天然交联剂.为改进京尼平的制备工艺,研究了在水-有机两相体系中固定化β-葡萄糖苷酶水解京尼平苷制备京尼平.β-葡萄糖苷酶以海藻酸钠为载体,采用交联包埋法固定化.最佳反应温度,Ph值和时间分别为55°C,4.5和2.5小时.为了减少京尼平水解和副产物产生,反应在包含乙酸乙酯和乙酸钠缓冲液的水-有机两相系统中进行.通过HPLC,Uv,Ir和NMR分析产物.京尼平的收率为47.81%,纯度超过98%(HPLC).
    DOI:10.3390/molecules16054295

    海关参考信息

    专利信息


    专利号:WO-2023044581-A1
    优先权日:2021-09-24
    标题 :Flow synthesis of porous collagen microparticles for versatile tissue engineering applications
    发明人:SINGH SUSHANT; SAMIEI EHSAN; GUENTHER AXEL; VERES TEODOR
    权利人:GOVERNING COUNCIL UNIV TORONTO; NAT RES COUNCIL CANADA; SINGH SUSHANT
    摘要:A microfluidic flow synthesis method for collagen-based microparticles. Macro-porous fibrillar microparticles of pure collagen and composite collagen-GAG were formed, where the particle size and porosity were controlled by the flow synthesis parameters such as precursor flow rates. Using human dermal fibroblasts (hDFB) and umbilical cord derives mesenchymal stem cells (ucMSC), the capacity of the presented collagen and collagen-GAG microparticles to serve as cell culture substrates has been shown, to enable casting of tissues, forming spheroids, and as shear-thinning bioinks for bioprinting. At high packing densities, jammed collagen-based microparticles along with cells constitute a shear-thinning bioink for extrusion bioprinting applications. Bioprinted constructs exhibit a high porosity matrix due to the space between the microparticles, facilitating macromolecular transport, and cell proliferation and migration.

    专利号:US-8771719-B2
    优先权日:2002-08-12
    标题 :Synthesis of a bone-polymer composite material
    发明人:SHIMP LAWRENCE A; WINTERBOTTOM JOHN M; BOYCE TODD M; KNAACK DAVID
    权利人:SHIMP LAWRENCE A; WINTERBOTTOM JOHN M; BOYCE TODD M; KNAACK DAVID; WARSAW ORTHOPEDIC INC
    摘要:A method of producing a bone-polymer composite. The method comprises the steps of providing a plurality of bone particles, combining the bone particles with a polymer precursor, and polymerizing the polymer precursor.

    专利号:US-8658711-B2
    优先权日:2010-09-29
    标题 :Process for the synthesis of methacrylate-derivatized type-1 collagen and derivatives thereof
    发明人:SHREIBER DAVID; GAUDET IAN
    权利人:SHREIBER DAVID; GAUDET IAN; UNIV RUTGERS
    摘要:Methods for synthesizing a methacrylate-derivatized type-I collagen in which methacrylic acid is reacted with a carboxylic acid activating reagent in the presence of a carbodiimide to form a methacrylic acid with an activated carboxylic acid group, which is then reacted with free amino groups on type-I collagen to form a collagen methacrylamide. Methacrylate-derivatized collagen, cross-linked collagens formed therefrom and products containing the cross-linked collagen are also disclosed.

    专利号:US-9567430-B2
    优先权日:2011-12-02
    标 题 :Enzymatic synthesis of poly(amine-co-esters) and methods of use thereof for gene delivery
    发明人:SALTZMAN W MARK; JIANG ZHAOZHONG; ZHOU JIANGBING; LIU JIE
    权利人:UNIV YALE
    摘要:Poly(amine-co-ester) polymers, methods of forming active agent-load nanoparticles therefrom, and methods of using the nanoparticles for drug delivery are disclosed. The nanoparticles can be coated with an agent that reduces surface charge, an agent that increases cell-specific targeting, or a combination thereof. Typically, the loaded nanoparticles are less toxic, more efficient at drug delivery, or a combination thereof compared to a control other transfection reagents. In some embodiments, the nanoparticles are suitable for in vivo delivery, and can be administered systemically to a subject to treat a disease or condition.

    专利号:WO-2013082529-A1
    优先权日:2011-12-02
    标题 :Enzymatic synthesis of poly(amine-co-esters) and methods of use thereof for gene delivery
    发明人:SALTZMAN W MARK; JIANG ZHAOZHONG; ZHOU JIANGBING
    权利人:UNIV YALE
    摘要:Poly(amine-co-ester) polymers, methods of forming active agent-load nanoparticies therefrom, and methods of using the nanoparticies for drug delivery are disclosed. The nanoparticies can be coated with an agent that reduces surface charge, an agent that increases cell-specific targeting, or a combination thereof. Typically, the loaded nanoparticies are less toxic, more efficient at drug delivery, or a combination thereof compared to a control other transfection reagents. In some embodiments, the nanoparticies are suitable for in vivo delivery, and can be administered systemically to a subject to treat a disease or condition.

    专利号:US-2018193528-A1
    优先权日:2014-07-24
    标 题 :Printable morphogenetic phase-specific chitosan-calcium-polyphosphate scaffold for bone repair
    发明人:MÜLLER WERNER ERNST LUDWIG GEORG; SCHRÖDER HEINRICH-CHRISTOPH WILHELM FRIEDRICH; WANG XIAOHONG
    权利人:MUELLER WERNER ERNST LUDWIG GEORG
    摘要:This invention concerns a formula for the synthesis of a printable hybrid material, formed of carboxymethyl chitosan (CMC) and polyphosphate (polyP). Both polymers are linked together by calcium ions. The inventive CMC-polyP material, in combination with alginate, is biocompatible, biodegradable and useful for three-dimensional (3D) printing and 3D cell printing (bioprinting). The CMC-polyP scaffold, hardened by exposure to calcium ions, is morphogenetically active and can be used in bone N tissue engineering, as a bio mimetic 3-phase scaffold that mimics and induces essential phases in bone repair, including blood clot formation and platelet degranulation (release of growth factors and cytokines) (Phase 1: initiation phase), calcium carbonate bioseed formation (Phase 2: nucleation) and expression/activation of bone alkaline phosphatase (Phase 3: hydroxyapatite-biomineral.
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    主要参考文献


    1: Shen XL, Liu H, Xiang H, Qin XM, Du GH, Tian JS. Combining biochemical with (1)H NMR-based metabolomics approach unravels the antidiabetic activity of genipin and its possible mechanism. J Pharm Biomed Anal. 2016 Jun 25;129:80-89. doi: 10.1016/j.jpba.2016.06.041. [Epub ahead of print] doi: 10.1016/j.fitote.2016.06.010. Epub 2016 Jun 23. doi: 10.1021/acs.jafc.6b01835. Epub 2016 Jun 30. doi: 10.1016/j.intimp.2016.05.011. [Epub ahead of print] doi: 10.1016/j.biomaterials.2016.04.012. Epub 2016 Apr 22. doi: 10.1038/srep24779.
    12: Fiamingo A, Campana-Filho SP. Structure, morphology and properties of genipin-crosslinked carboxymethylchitosan porous membranes. Carbohydr Polym. 2016 Jun 5;143:155-63. doi: 10.1016/j.carbpol.2016.02.016. Epub 2016 Feb 8. doi: 10.1038/srep24429.
    14: Zhang Y, Wang QS, Yan K, Qi Y, Wang GF, Cui YL. Preparation, characterization, and evaluation of genipin crosslinked chitosan/gelatin three-dimensional scaffolds for liver tissue engineering applications. J Biomed Mater Res A. 2016 Aug;104(8):1863-70. doi: 10.1002/jbm.a.35717. Epub 2016 Mar 30. doi: 10.1016/j.msec.2015.12.085. Epub 2015 Dec 30. pii: E117. doi: 10.3390/ijms17010117.

    合成参考文献


    参考文献:10.1248/bpb.33.1343
    摘要:Cao H, Feng Q, Xu W, Li X, Kang Z, Ren Y, Du L. Genipin Induced Apoptosis Associated with Activation of the c-Jun NH2-Terminal Kinase and p53 Protein in HeLa Cells. Biological & Pharmaceutical Bulletin. 2010;33(8):1343–8. doi: 10.1248/bpb.33.1343.
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