CAS: 24696-26-2; C16-Ceramide

该化合物是一种在细胞结构和信号中发挥关键作用的长链脂肪酸(六十二氮酸),它与长链脂肪脊椎相连,有助于保持阻隔功能和水分.此外,对致癌剂进行研究,以了解其在皮肤紊乱和其他健康条件下的潜在治疗用途.由于其结构特性,C16-Ceramide还可以影响脂质木筏的形成,并在某些疾病的病理学和病理学中发挥作用.

结构式图片

相似化合物

124753-97-5 54164-50-0 121459-09-4

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ECHA物质C&L通报

上下游产品

D-erythro-3-O-Benzoyl-N-palmitoyl-sphingosin (2S,3R,4E)-2-amino-4-°Ctadecene-1,3-diol 4-nitrophenyl palmitate (2S,3R,4E)-1,3-benzylidene-2-(hexadecanoylamido)-4-°Ctadecene-1,3-diol1-OTBDPS ceramide (2S,3R,4E)-1-(triphenylmethyl)-2-(hexadecanamido)-4-°Ctadecene-1,3-diol (2S,3R,4E)-3-benzoyl-2-(hexadecanamido)-4-°Ctadecene-1,3-diol Benzoic acid (E)-(R)-1-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-hexadecanoylamino-ethyl]-hexadec-2-enyl ester

合成工艺路线路线简述

    📜正十四烷基三苯基溴化膦置于吡啶,4-二甲氨基吡啶,Sodium Tetrahydroborate,Sodium Periodate,正丁基锂,Sodium Azide,4-甲基苯磺酸吡啶,溶剂黄146,二苯二硫醚体系中,用 四氢呋喃,1,4-二氧六环,吡啶,甲醇,正己烷,二氯甲烷,环己烷,水,N,N-二甲基甲酰胺,异丙醇 用作溶剂,化学反应 265.25H,反应生成N-棕榈酰神经鞘氨醇
    参考文献:从d-葡萄糖高度立体选择性地合成2(S),3(R),4E-和2(S),3(R),4Z-N-十四烷酰基鞘氨醇
    标题:从d-葡萄糖高度立体选择性地合成2(S),3(R),4E-和2(S),3(R),4Z-N-十四烷酰基鞘氨醇
    摘要:摘要从1,2:5,6-Di-O-异亚丙基-α-开始,分十步完成了4-E-和4-Z-D-赤型神经酰胺的合成,总产率约为20-30%. D-葡萄糖呋喃糖.使用e-和z-5-脱氧-1,2-O-异亚丙基-5-C-十四叉基-α-D-木呋喃糖作为关键中间体.
    Doi:10.1016/0008-6215(86)84010-1

    海关参考信息

    专利信息


    专利号:US-9643915-B2
    优先权日:2013-03-15
    标题:Methods for the synthesis of sphingomyelins and dihydrosphingomyelins
    发明人:ONICIU DANIELA CARMEN; HECKHOFF STEFAN; OSWALD BENOIT; REBMANN PETER; PEER ANDREAS; GONZALEZ MIGUEL; SAUTER PATRIK
    权利人:CERENIS THERAPEUTICS HOLDING SA
    摘要:The present invention includes methods for the synthesis of sphingomyelins and dihydrosphingomyelins. The present invention also includes methods for the synthesis of sphingosines and dihydrosphingosines. The present invention further includes methods for the synthesis of ceramides and dihydroceramides.

    专利号:US-9708354-B2
    优先权日:2013-03-15
    标 题:Methods for the synthesis of sphingomyelins and dihydrosphingomyelins
    发明人:ONICIU DANIELA CARMEN; HECKHOFF STEFAN; OSWALD BENOIT; REBMANN PETER; PEER ANDREAS; GONZALEZ MIGUEL; SAUTER PATRIK
    权利人:CERENIS THERAPEUTICS HOLDING SA
    摘要:The present invention includes methods for the synthesis of sphingomyelins and dihydrosphingomyelins. The present invention also includes methods for the synthesis of sphingosines and dihydrosphingosines. The present invention further includes methods for the synthesis of ceramides and dihydroceramides.

    专利号:US-9546161-B2
    优先权日:2001-07-16
    标题:Synthesis of UDP-glucose: N-acylsphingosine glucosyl transferase inhibitors
    发明人:HIRTH BRADFORD H; SIEGEL CRAIG
    权利人:GENZYME CORP
    摘要:Disclosed is a novel enantiomeric synthesis ceramide-like inhibitors of UDP-glucose: N-acylsphingosine glucosyltransferase. Also disclosed are novel intermediates formed during the synthesis.

    专利号:US-2024336559-A1
    优先权日:2021-10-06
    标 题 :Anti-fungals compounds targeting the synthesis of fungal sphingolipids
    发明人:OJIMA IWAO; HARANAHALLI KRUPANANDAN; DEL POETA MAURIZIO; GARG ASHNA
    权利人:UNIV NEW YORK STATE RES FOUND
    摘要:The present invention provides a compound having the structure: n n n n n n n n n n n n wherein n R 3 , R 4 , R 5 , R 6 , and R 7 are each independently, H, halogen, CN, —CF 3 , —OCF 3 , —NO 2 , alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, —OH, —OAc, —OR 13 , —COR 13 , —CH 2 OR 13 , —SH, —SR 13 , —SO 2 R 13 , —NH 2 , —NHR 13 , —NR 14 R 15 , —NHCOR 12 , or —CONR 14 R 15 ; n R 9 , R 10 , R 11 , and R 12 are each independently, H, CN, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, —OAc, —COR 13 , —SH, —SR 13 , —SO 2 R 13 , —NH 2 , —NHR 13 , —NR 14 R 15 , —NHCOR 12 , or —CONR 14 R 15 ;n wherein each occurrence of R 13 is independently alkyl, alkenyl, alkynyl, aryl, or heteroaryl, wherein each occurrence of R 14 is independently —H, alkyl, alkenyl, alkynyl, aryl, or heteroaryl, wherein each occurrence of R 15 is independently —H, alkyl, alkenyl, alkynyl, aryl, or heteroaryl, n n wherein when R 14 is methyl, R 15 is not methyl; n wherein at least one of R 9 , R 10 , R 11 , and R 12 is not H; n wherein at least one of R 3 , R 4 , R 5 , R 6 , and R 7 is not H.

    专利号:EP-1239813-B1
    优先权日:1999-12-23
    标题:Extract of blue-green alga spirulina and the use thereof in cosmetic skin-care and body care agents
    发明人:SCHLOTMANN KORDULA; WALDMANN-LAUE MARIANNE; JASSOY CLAUDIA; KAETEN MELANIE; KOEHLER EVA-MARIA; PULZ OTTO; KURTH ELKE
    权利人:HENKEL KGAA
    摘要:The invention relates to an aqueous or aqueous-alcoholic extract of the blue-green algal taxon Spirulina, characterized in that it contains at least 10 wt. % magnesium in relation to the dry weight of said extract. The inventive blue-green alga extract is an efficacious component for stimulating intracellular synthesis of ATP and matrix proteins and differentiation of keratinozytes. The blue-green alga extract is used in topical preparations for cleaning and cosmetic care of the skin and hair, in addition to the production of agents for dermatological treatment of the skin.

    专利号:US-12325678-B2
    优先权日:2017-06-16
    标 题 :Anti-fungals compounds targeting the synthesis of fungal sphingolipids
    发明人:OJIMA IWAO; DEL POETA MAURIZIO; LAZZARINI CRISTINA; HARANAHALLI KRUPANANDAN; SUN YI
    权利人:UNIV NEW YORK STATE RES FOUND
    摘要:The present invention provides a compound having the structure: n nand use of the compound for inhibiting the growth of or killing.

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    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    合成参考文献


    参考文献:10.1046/j.1523-1747.1999.00633.x
    摘要:Di Marzio L, Cinque B, De Simone C, Cifone MG. Effect of the Lactic Acid BacteriumStreptococcus thermophilus on Ceramide Levels in Human KeratinocytesIn Vitro and Stratum Corneum In Vivo. Journal of Investigative Dermatology. 1999 Jul;113(1):98–106. doi: 10.1046/j.1523-1747.1999.00633.x.
    参考文献:10.1007/s12072-021-10231-5
    摘要:Hao Z, Tao K, Wu K, Luo Y, Lu Y, Li B, Shi P, Wang P, Zeng X, Lin Y. Alterations of gut microbiome and metabolite profiles in choledocholithiasis concurrent with cholangitis. Hepatology International. 2021 Jul 27;16(2):447–62. doi: 10.1007/s12072-021-10231-5.
    参考文献:10.1034/j.1600-0625.2003.00051.x
    摘要:Di Marzio L, Centi C, Cinque B, Masci S, Giuliani M, Arcieri A, Zicari L, De Simone C, Cifone MG. Effect of the lactic acid bacterium Streptococcus thermophilus on stratum corneum ceramide levels and signs and symptoms of atopic dermatitis patients. Experimental Dermatology. 2003 Sep 09;12(5):615–20. doi: 10.1034/j.1600-0625.2003.00051.x.
    参考文献:10.1074/jbc.m302531200
    摘要:Deguchi H, Yegneswaran S, Griffin JH. Sphingolipids as Bioactive Regulators of Thrombin Generation. Journal of Biological Chemistry. 2004 Mar;279(13):12036–42. doi: 10.1074/jbc.m302531200.
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