CAS: 54845-95-3; 15(S)-Hete

该化合物是主要通过15-光氧基因酶路径生产的芳烃酸的单氢酸代谢物,是炎症和免疫反应中的关键信号分子,影响细胞过程,如化毒,血管生成和血管变异.这个电子沙质在调节血清活性和血管功能方面的作用值得注意,使它成为炎症,心血管生物学和相关病理研究的宝贵化合物,其15位置的立体特性确保精确的生物互动,与其他HETE异构体区分开来. 15(S)-HETE由于其精密的活动以及生理和病理机制的相关性,广泛用于生物化学和药理学研究.

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(5Z,8Z,11Z,13E)-15(S)-hydroperoxyeicosa-5,8,11,13-tetraenoic acid (5Z,8Z,11Z,13E,15S)-15-hydroxy-5,8,11,13-eicosatetraenoic acid methyl ester 5-hexyl-1-ol tert-butyldimethylsilyl hex-5-yn-1-yl ether (5Z,8Z,11Z,13E,15S)-15-hydroxy-5,8,11,13-eicosatetraenoic acid methyl ester (2E,4S)-4-hydroxy-2-nonenal (5Z,8Z,11Z,13E)-15-oxo-5,8,11,13-eicosatetraenoic acid

合成工艺路线路线简述

  • 合成目标产物 15(S)-Hete 主要起始原料 15(S)-Hydroxy-(5Z,8Z,11Z,13E)-*eicosatet Raenoic Aci
  • 506-32-1 = 54845-95-3 + 71030-38-1 + 13222-49-6 + 83603-31-0 + 69371-38-6
    反应条件:1.1 Reagents: Oxygen Catalysts: Arachidonate Lipoxygenase Solvents: Water; 0 - 3 °C; 25 Min,35 Psi,< 5 °C1.2 Reagents: Sodium Borohydride; 60 - 90 Min,0 - 5 °C1.3 Reagents: Sulfuric Acid Solvents: Water; Ph 3
    标题:Manufacture Of (5Z,8Z,11Z,13E)(15S)-15-Hydroxyeicosa-5,8,11,13-Tetraenoic Acid Sodium Salt For Clinical Trials
    作者:Conrow,Raymond E.; Et Al
    参考文献:Organic Process Research & Development 日期:2011 卷标:15(1) 页码:301-304
📜15-羟基二十碳-5Z,8Z,11Z,13E-四烯酸置于sodium Tetrahydroborate,水,硫酸体系中,用 水 作为反应溶剂,以11.79 G的收率获得产物(15S,5Z,8Z,11Z,13E)-15-羟基二十碳四烯酸
参考文献:Manufacture Of (5Z,8Z,11Z,13E)(15S)-15-Hydroxyeicosa-5,8,11,13-Tetraenoic Acid Sodium Salt For Clinical Trials
标题:Manufacture Of (5Z,8Z,11Z,13E)(15S)-15-Hydroxyeicosa-5,8,11,13-Tetraenoic Acid Sodium Salt For Clinical Trials
摘要:A Robust Synthesis Of (5Z,8Z,11Z,13E)(15S)-15-Hydroxyeicosa-5,8,11,13-Tetraenoic Acid (15(S)-Hete) Sodium Salt Was Established,Utilising A Biooxidalion Process. Treatment Of Arachidonic Acid With Soybean Lipoxidase In 0.1 M Sodium Tetraborate Buffer Under Oxygen Pressure Resulted In Formation Of The Hydroperoxide,15(S)Hpete. Addition Of Sodium Borohydride To The Reaction Mixture Reduced The Hydroperoxide To 15(S)-Hete,Which Was Then Purified By Column Chromatography. 15(S)-Hete Sodium Salt Was Prepared By Treatment Of An Ethanol Solution Of Hete With Aqueous Sodium Hydrogen Carbonate. Multiple 10-G Batches Of 15(S)-Hete Sodium Salt With >98% Enantiomeric Excess And >98% Chemical Purity Were Prepared To Support Clinical Trials.
DOI:10.1021/op100244N

海关参考信息

专利信息


专利号:WO-2024075835-A1
优先权日:2022-10-07
标 题 :Action for suppressing any increase in body weight by aqueous extract of nannochloropsis algae
发明人:YANO ATSUSHI; UMEZU AKIRA; MITOME Kanoko; SASAKI YUKO; KAMEI ASUKA; SHIMADA KOSUKE; SHINOZAKI FUMIKA; SHIMOJIMA MIE; OHTA HIROYUKI; IWAI MASAKO; IHARA YUTA
权利人:PHYTOLIPID TECH CO LTD; KANAGAWA INSTITUTE OF INDUSTRIAL SCIENCE AND TECH; NIHON FILTER CO LTD
摘要:The present invention provides a novel application for Nannochloropsis algae. Specifically, an aqueous extract of Nannochloropsis algae is used in suppressing any increase in body weight or inhibiting any acceleration in synthesis of cholesterol.

专利号:WO-2024020091-A1
优先权日:2022-07-19
标 题 :Inhibitors of short-chain dehydrogenase activity for reducing glial fibrillary acidic protein levels
发明人:MARKOWITZ SANFORD; PIEPER ANDREW
权利人:UNIV CASE WESTERN RESERVE; THE US GOV AS REPRESENTED BY THE DEPARTMENT OF VETERAN AFFAIRS
摘要:A method of decreasing blood glial fibrillary acidic protein (GFAP) levels in a subject in need thereof includes administering to the subject a therapeutically effective amount of a 15-PGDH inhibitor. Astroglia cells are the major and perhaps most abundant cell types in the brain. In healthy brain, astrocytes help with providing structural and network support for neurons and interface with the brain vasculature, including the blood-brain-barrier. Functionally, astrocytes are involved with providing neurotrophic factors (such as glial derived neurotrophic factor (GDNF)), and cytokine/chemokine release that influences the global and local inflammatory response environments, as well as working closely with neurons involved in the glutamate-glutamine synthesis/recycling pathway.

专利号:WO-2024233563-A1
优先权日:2023-05-09
标 题:6,6-fused bicyclic amides and compositions for use as 15-prostaglandin dehydrogenase modulators
发明人:GREENMAN KEVIN LLOYD; WANG HUI-LING; WEIRES NICHOLAS ANTHONY; ALLEN JOHN G; AMEGADZIE ALBERT K; BOURBEAU MATTHEW P; LI KEXUE
权利人:AMGEN INC
摘要:The present disclosure provides novel 15-hydroxy-prostaglandin dehydrogenase inhibitors, pharmaceutical compositions comprising such compounds, and methods of using such compounds and compositions in treating 15-hydroxy-prostaglandin dehydrogenase-mediated disease. Also provided are methods of making such compounds and intermediates thereof. The compounds have a structure of Formula (I): or a pharmaceutically acceptable salt thereof; wherein is Formula (i) or Formula (ii) Further, the disclosure provides intermediates useful in the synthesis of compounds of Formula (I).

专利号:US-2024409557-A1
优先权日:2023-05-09
标 题 :5,6-fused and 6,6-fused bicyclic alcohols and ethers and compositions for use as 15-prostaglandin dehydrogenase modulators
发明人:GREENMAN KEVIN LLOYD; PICKRELL ALEXANDER J; LI KEXUE; AMEGADZIE ALBERT K; WANG HUI-LING; WEIRES NICHOLAS ANTHONY; ALLEN JOHN G; BOURBEAU MATTHEW P
权利人:AMGEN INC
摘要:The present disclosure provides novel 15-hydroxy-prostaglandin dehydrogenase inhibitors, pharmaceutical compositions comprising such compounds, and methods of using such compounds and compositions in treating 15-hydroxy-prostaglandin dehydrogenase-mediated disease. Also provided are methods of making such compounds and intermediates thereof. The compounds have a general Formula (A).Further, the disclosure provides intermediates useful in the synthesis of compounds of Formula (A).

专利号:US-11407837-B2
优先权日:2017-09-11
标 题 :GPCR binding proteins and synthesis thereof
发明人:GLANVILLE JACOB
权利人:TWIST BIOSCIENCE CORP
摘要:Provided herein are methods and compositions relating to G protein-coupled receptor (GPCR) libraries having nucleic acids encoding for a scaffold comprising a GPCR binding domain. Libraries described herein include variegated libraries comprising nucleic acids each encoding for a predetermined variant of at least one predetermined reference nucleic acid sequence. Further described herein are protein libraries generated when the nucleic acid libraries are translated. Further described herein are cell libraries expressing variegated nucleic acid libraries described herein.

专利号:NL-2023826-B1
优先权日:2019-09-12
标 题 :Photo biocatalytic synthesis of secondary fatty alcohols from unsaturated fatty acids

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主要参考文献

参考标题:Stereocontrolled Total Synthesis Of (5Z,8Z11Z,13E)(15S)-15-Hydroxyeicosa-5,8,11,13-Tetraenoic Acid (15S-Hete) And Analogues
作者:K. C. Nicolaou,Tamara Ladduwahetty,E. Michael Elisseou
摘要:A Novel And Stereoselective Synthesis Of 15S-Hete And A Number Of Analogues Based On Cui-Pd0 Coupling Reaction Is Described.

合成参考文献


参考文献:10.1007/bf02522975
摘要:Zhang LY, Hamberg M. Specificity of two lipoxygenases from rice: unusual regiospecificity of a lipoxygenase isoenzyme. Lipids. 1996 Aug;31(8):803–9. doi: 10.1007/bf02522975.
参考文献:10.1007/bf02562317
摘要:Kühn H, Heydeck D, Brinckman R, Trebus F. Regulation of cellular 15-lipoxygenase activity on pretranslational, translational, and posttranslational levels. Lipids. 1999;34 Suppl():S273–9. doi: 10.1007/bf02562317.
参考文献:10.1084/jem.20072329
摘要:Okuno T, Iizuka Y, Okazaki H, Yokomizo T, Taguchi R, Shimizu T. 12(S)-Hydroxyheptadeca-5Z, 8E, 10E-trienoic acid is a natural ligand for leukotriene B4 receptor 2. J Exp Med. 2008 Apr 14;205(4):759–66.
参考文献:10.1007/bf00918814
摘要:Morykwas MJ, Duell EA, Jennings DA, Ledbetter MS, White WL, Argenta LC. Arachidonic acid metabolites: effects on inflammation of fetal rabbit excisional wounds. Inflammation. 1992 Jun;16(3):251–8. doi: 10.1007/bf00918814.
参考文献:10.1007/bf01907914
摘要:Schrör K. Prostaglandins, other eicosanoids and endothelial cells. Basic Res Cardiol. 1985 Sep;80(5):502–14. doi: 10.1007/bf01907914.
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