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(5E,7Z,10Z,13Z,16Z,19Z)-4-Hydroxy-5,7,10,13,16,19-docosahexaenoic acid | 90906-40-4

中文名称
——
中文别名
——
英文名称
(5E,7Z,10Z,13Z,16Z,19Z)-4-Hydroxy-5,7,10,13,16,19-docosahexaenoic acid
英文别名
(5E,7Z,10Z,13Z,16Z,19Z)-4-hydroxydocosa-5,7,10,13,16,19-hexaenoic acid;(±)-4-hydroxy-5E,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid;4-hydroxy,5E,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid;4-HDHA;4-hydroxy-5E,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid;4-HDoHE
(5E,7Z,10Z,13Z,16Z,19Z)-4-Hydroxy-5,7,10,13,16,19-docosahexaenoic acid化学式
CAS
90906-40-4
化学式
C22H32O3
mdl
——
分子量
344.494
InChiKey
IFRKCNPQVIJFAQ-PQVBWYSWSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    502.3±50.0 °C(Predicted)
  • 密度:
    0.995±0.06 g/cm3(Predicted)
  • 溶解度:
    0.1 M Na2CO3:2 mg/mL; DMF:可混溶; DMSO:可混溶;乙醇:可混溶; PBS(pH 7.2):0.8 mg/mL

计算性质

  • 辛醇/水分配系数(LogP):
    5.1
  • 重原子数:
    25
  • 可旋转键数:
    14
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    0.41
  • 拓扑面积:
    57.5
  • 氢给体数:
    2
  • 氢受体数:
    3

安全信息

  • 储存条件:
    -20°C,密封保存于干燥处。

SDS

SDS:1d303e7470911814d2d4eb787e4fba49
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制备方法与用途

4-HDHA may serve as a marker for oxidative stress in the brain and retina, where DHA is a prevalent polyunsaturated fatty acid.

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
    —— 4-hydroxy,5E,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid γ-lactone 825632-99-3 C22H30O2 326.479
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量
    —— (4R,5E,7Z,10Z,13Z,16Z,19Z)-4-hydroxydocosa-5,7,10,13,16,19-hexaenoic acid —— C22H32O3 344.494
    —— (4S,5E,7Z,10Z,13Z,16Z,19Z)-4-hydroxydocosa-5,7,10,13,16,19-hexaenoic acid —— C22H32O3 344.494
    —— methyl (4S,5E,7Z,10Z,13Z,16Z,19Z)-4-hydroxydocosa-5,7,10,13,16,19-hexaenoate 1064009-76-2 C23H34O3 358.521
    —— methyl (5E,7Z,10Z,13Z,16Z,19Z)-4-hydroxydocosa-5,7,10,13,16,19-hexaenoate 872142-31-9 C23H34O3 358.521
    —— (5E,7Z,10Z,13Z,16Z,19Z)-4-methoxydocosa-5,7,10,13,16,19-hexaenoic acid —— C23H34O3 358.521
    —— methyl (5E,7Z,10Z,13Z,16Z,19Z)-4-methoxydocosa-5,7,10,13,16,19-hexaenoate 845673-71-4 C24H36O3 372.548
    —— 4-hydroxy-5E,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid methyl ester trimethylsilyl ether 825633-04-3 C26H42O3Si 430.703
    —— methyl (5E,7Z,10Z,13Z,16Z,19Z)-4-acetoxydocosa-5,7,10,13,16,19-hexaenoate —— C25H36O4 400.558
    —— (5E,7Z,10Z,13Z,16Z,19Z)-4-oxodocosa-5,7,10,13,16,19-hexaenoic acid —— C22H30O3 342.478

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Synthesis of docosahexaenoic acid derivatives designed as novel PPARγ agonists and antidiabetic agents
    摘要:
    To discover novel peroxisome proliferator-activated receptor gamma (PPAR gamma) agonists that Could be used as antidiabetic agents, we designed docosahexacnoic acid (DHA) derivatives (2 and 3), which have a hydrophilic substituent at the C(4)-position, based on the crystal structure of the ligand-binding pocket of PPAR gamma. These compounds were synthesized via iodolactolic as a key intermediate. We found that both DHA derivatives (2 and 3) showed PPAR gamma transactivation higher than, or comparable to, that of pioglitazone, which is a TZD derivative used as an antidiabetic agent. DHA derivatives related to these potent Compounds 2 and 3 were also synthesized to study structure-activity relationships. Furthermore, 4-OH DHA 2, which shows strong PPAR gamma transcriptional activity, was separated as an optically pure form. (c) 2005 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2005.07.074
  • 作为产物:
    参考文献:
    名称:
    Synthesis of docosahexaenoic acid derivatives designed as novel PPARγ agonists and antidiabetic agents
    摘要:
    To discover novel peroxisome proliferator-activated receptor gamma (PPAR gamma) agonists that Could be used as antidiabetic agents, we designed docosahexacnoic acid (DHA) derivatives (2 and 3), which have a hydrophilic substituent at the C(4)-position, based on the crystal structure of the ligand-binding pocket of PPAR gamma. These compounds were synthesized via iodolactolic as a key intermediate. We found that both DHA derivatives (2 and 3) showed PPAR gamma transactivation higher than, or comparable to, that of pioglitazone, which is a TZD derivative used as an antidiabetic agent. DHA derivatives related to these potent Compounds 2 and 3 were also synthesized to study structure-activity relationships. Furthermore, 4-OH DHA 2, which shows strong PPAR gamma transcriptional activity, was separated as an optically pure form. (c) 2005 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2005.07.074
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文献信息

  • Synthesis of polyconjugated fatty acids
    申请人:Smith William
    公开号:US20050014826A1
    公开(公告)日:2005-01-20
    The present invention relates to fatty acids. In particular, the present invention provides polyconjugated fatty acids, and methods of their synthesis and their use.
    本发明涉及脂肪酸。具体来说,本发明提供了多共轭脂肪酸,以及它们的合成方法和用途。
  • Synthesis of long chain n-3 and n-6 fatty acids having a photoactive conjugated tetraene group
    作者:Dmitry V. Kuklev、William L. Smith
    DOI:10.1016/j.chemphyslip.2004.02.006
    日期:2004.7
    Fatty acids of the n-3 and n-6 families containing a photoactive conjugated tetraene group near the carboxylate were prepared from several naturally occurring fatty acids by sequential iodolactonization and treatment with excess 1,8-diazabicyclo[5.4.0]undec-7-ene. The new conjugated fatty acids include 5E,7E,9E,11Z,14Z- and 5E,7E,9E,11E,14Z-eicosapentaenoic acids derived from arachidonic acid; 5E,7E
    通过顺序的碘代内酯化并用过量的1,8-二氮杂双环[5.4.0] undec-7-处理,由几种天然存在的脂肪酸制备n-3和n-6家族,其中的羧酸在羧酸酯附近包含一个光敏共轭四烯基团的脂肪酸。烯。新的共轭脂肪酸包括衍生自花生四烯酸的5E,7E,9E,11Z,14Z-和5E,7E,9E,11E,14Z-二十碳五烯酸。来自二十碳五烯酸的5E,7E,9E,11Z,14Z,17Z-和5E,7E,9E,11E,14Z,17Z-二十碳六烯酸; 和来自二十二碳六烯酸的4E,6E,8E,10Z,13Z,16Z,19Z-和4E,6E,8E,10E,13Z,16Z,19Z-二十二碳六烯酸。所有新合成的脂肪酸均通过UV,1H NMR和质谱进行了表征。这些新产品代表了亚甲基间断双键系统定向共轭的第一个例子。可以以克量和高产率(> 50%)合成产物。有趣的是,即使使用温和的条件和不同的合成方法,也无法合成在羧基附近具有
  • [EN] METHOD OF SYNTHESIZING A 5-OXO-CONJUGATED FATTY ACID<br/>[FR] PROCÉDÉ DE SYNTHÈSE D'UN ACIDE GRAS 5-OXO-CONJUGUÉ
    申请人:UNIV SYDDANSK
    公开号:WO2011131619A1
    公开(公告)日:2011-10-27
    There is provided a novel chemical synthetic method for the preparation of a 5-oxo-ETE and related compounds. The method is based on a short and efficient synthesis of 5-oxo-ETE from commercially available Arachidonic acid. The method is based on the surprising discovery that a 5-oxo-conjugated fatty acid may be efficiently converted into the corresponding 5-oxo-conjugated fatty acid by reaction with the Dess-Martin reagent (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one)in the presence of pyridine or a substituted pyridine.
    提供了一种新颖的化学合成方法,用于制备5-氧-ETE及相关化合物。该方法基于从商业可获得的花生四烯酸中短而高效地合成5-氧-ETE。该方法基于一个惊人的发现,即5-氧共轭脂肪酸可以通过与Dess-Martin试剂(1,1,1-三乙酰氧基-1,1-二氢-1,2-苯碘氧醇-3(1H)-酮)在吡啶或取代吡啶的存在下反应,高效地转化为相应的5-氧共轭脂肪酸。
  • THERAPEUTIC AGENT FOR ULCERATIVE COLITIS AND/OR CROHN'S DISEASE
    申请人:Yamamoto, Keiko
    公开号:EP1946754A1
    公开(公告)日:2008-07-23
    Disclosed is an agent for preventing or treating ulcerative colitis, Crohn's disease, and/or Behcet's disease. A therapeutic agent for ulcerative colitis, Crohn's disease, and/or Behcet's disease, comprising a polyunsaturated fatty acid derivative represented by the following formula (1) as an active ingredient.
    本发明公开了一种用于预防或治疗溃疡性结肠炎、克罗恩病和/或白塞氏病的制剂。一种治疗溃疡性结肠炎、克罗恩病和/或白塞氏病的药剂,由下式(1)代表的多不饱和脂肪酸衍生物作为活性成分组成。
  • Oils with anti-inflammatory activity containing natural specialized proresolving mediators and their precursors
    申请人:SOLUTEX NA LLC
    公开号:US10568858B2
    公开(公告)日:2020-02-25
    The present invention encompasses oils that have anti-inflammatory or resolution-stimulating activity that contain or are enriched with Specialized Proresolving Mediators (SPM) or SPM precursors, which originate from an oil obtained from organisms containing long chain omega-3 polyunsaturated fatty acids, such as fish, crustaceae, algae, and mollusks. The invention also encompasses a method for the production of these oils, and the utilization of the oils for nutritional supplements, pharmaceutical formulations, and cosmetic formulations, which can be employed for treating an inflammatory condition.
    本发明包括具有抗炎或刺激溶解活性的油类,这些油类含有或富含特化促溶解介质(SPM)或 SPM 前体,这些特化促溶解介质或 SPM 前体来源于从含有长链欧米加-3 多不饱和脂肪酸的生物(如鱼类、甲壳类、藻类和软体动物)中获得的油类。本发明还包括生产这些油的方法,以及将这些油用于营养补充剂、药物制剂和化妆品制剂的方法,这些制剂可用于治疗炎症。
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