CAS: 79551-86-3; 20-Hete

该化合物是一种信号分子,影响血管收缩,细胞扩散和吸附等过程;通过细胞色素P450酶(特别是CYP4A和CYP4F)的行动合成,在各种组织,包括肾脏和大脑中发现.该物质因其在心血管健康中的作用和对高血压和癌症等疾病的潜在影响,引起了研究的兴趣.其CAS编号79551-86-3用于在化学数据库和监管环境中识别其化合物.

英文名称20-Hete
中文名称20-羟基二十碳-5Z,8Z,11Z,14Z-四烯酸
IUPAC名称(5Z,8Z,11Z,14Z)-20-Hydroxyicosa-5,8,11,14-tetraenoic acid
其它别名5,8,11,14-Eicosatetraenoicacid, 20-hydroxy-, (all-Z)-; 20-HETE; 20-Hydroxy-5,8,11,14-eicosatetraenoicacid; 20-Hydroxyarachidonic acid; 20-Hydroxyeicosa-5(Z),14(Z)-dienoic acid; 20-Hydroxyeicosa-5Z,8Z,11Z,14Z-tetraenoic acid; 20-Hydroxyeicosatetraenoicacid; w-Hydroxyarachidonic acid
CAS编号79551-86-3
MFCD编号:MFCD00171542
分子式:C20H32O3分子量:320.47
产品CID: 1789848
产品分类分析化学 → 食品安全 → 脂肪酸、脂肪酸甲酯

相似结构搜索
InChIKey: NNDIXBJHNLFJJP-DTLRTWKJSA-N
1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10-
计算化学: 氢键受体数3.0氢键供体数2.0可旋转键数15.0

物理性质

沸点482.0±33.0 °C at 760 mmHg
闪点259.4±21.9 °C
密度1.0±0.1 g/cm3
pKa:4.75±0.10(预测)
PSA:57.53
LogP:4.91
折射率1.515
蒸汽压0.0±2.7 mmHg at 25°C
溶解性0.1 M Na2Co3: 2 mg/mL; DMF: Miscible; DMSO: Miscible; Ethanol: Miscible; Pbs Ph 7.2: 0.8 mg/mL
外观形态粉末
储存条件-20°C
产品应用该化合物是一种细胞色素P450衍生的细胞类动物,它调节血管音质,肾功能和炎症. 临床研究显示,20-EHTE在老鼠和老鼠模型中促进血管收缩,将血压提高15-25毫米HG,在高强度菌株中将血壓提高15-25毫米HG.这些数据还刺激了肌肉平稳扩散和内皮功能失调,有助于血管改造. 在肾脏研究中,20HETE抑制作用将鼠鼠标模型中的异血细胞复发损伤减少30-40%.此外,20EHETE能增强XENOGRAFT鼠模型中的肿瘤血管成因,将肿瘤生长率提高20-50 % , 表明肿瘤在癌症发展过程中的作用. 这些数据突出了其在心血管,肾和癌症病理学中的多方面生物活动.

上下游产品

合成工艺路线路线简述

1286736-37-5 = 79551-86-3
反应条件:1.1 Reagents: Lithium Hydroxide Solvents: Tetrahydrofuran,Water; 16 H,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 2
标题:Synthesis And Functional Pharmacological Effects On Human Bronchi Of 20-Hydroxyeicosatetraenoic Acid
作者:Proteau-Gagne,A.; St-Jean,F.; Morin,C.; Gendron,L.; Rousseau,E.; Et Al
参考文献:Chemistry Of Natural Compounds 日期:2011 卷标:46(6) 页码:841-847]

506-32-1 = 79551-86-3
反应条件:1.1 Solvents: Ethanol; 5 D,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; 2 H,Rt
标题:Preparation Of 20-Hete Using Multifunctional Enzyme Type 2-Negative Starmerella Bombicola
作者:Van Bogaert,Inge; Zhang,Guodong; Yang,Jun; Liu,Jun-Yan; Ye,Yonghao; Et Al
参考文献:Journal Of Lipid Research 日期:2013 卷标:54(11) 页码:3215-3219]

506-32-1 = 79551-86-3
反应条件:1.1 Reagents: Glucose Solvents: Ethanol,Water; 96 H,30 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; 12 H,25 °C
标题:Immobilization Of Candida Bombicola Cells On Free-Standing Organic-Gold Nanoparticle Membranes And Their Use As Enzyme Sources In Biotransformations
作者:Phadtare,Sumant; Shah,Sachin; Prabhune,Asmita; Wadgaonkar,Prakash P.; Sastry,Murali
参考文献:Biotechnology Progress 日期:2004 卷标:20(6) 页码:1817-1824]

506-32-1 = 79551-86-3 + 79551-85-2
反应条件:1.1 Reagents: Glucose Solvents: Ethanol,Water1.2 Reagents: Hydrochloric Acid Solvents: Water
标题:Transformation Of Arachidonic Acid To 19-Hydroxy- And 20-Hydroxy-Eicosatetraenoic Acids Using Candida Bombicola
作者:Prabhune,Asmita; Fox,Simon R.; Ratledge,Colin
参考文献:Biotechnology Letters 日期:2002 卷标:24(12) 页码:1041-1044]

86179-96-6 = 79551-86-3
反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Tetrahydrofuran,Water; 6 - 8 H,23 °C
标题:A Practical,Stereospecific Route To 18-,19-,And 20-Hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-Tetraenoic Acids (18-,19-,And 20-Hetes)
作者:Gopal,V. Raj; Jagadeesh,S. G.; Reddy,Y. Krishna; Bandyopadhyay,A.; Capdevila,Jorge H.; Et Al
参考文献:Tetrahedron Letters 日期:2004 卷标:45(12) 页码:2563-2565]

86179-96-6 = 79551-86-3
反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Tetrahydrofuran,Water; 0 °C; Overnight,Rt1.2 Reagents: Oxalic Acid Solvents: Water; Ph 5,Rt
标题:20-Hydroxyeicosatetraenoic Acid (20-Hete): Structural Determinants For Renal Vasoconstriction
作者:Yu,Ming; Alonso-Galicia,Magdalena; Sun,Cheng-Wen; Roman,Richard J.; Ono,Naoya; Et Al
参考文献:Bioorganic & Medicinal Chemistry 日期:2003 卷标:11(13) 页码:2803-2821]

86179-96-6 = 79551-86-3
反应条件:1.1 Reagents: Lithium Hydroxide Solvents: Tetrahydrofuran,Water; Overnight,Rt
标题:Chemical Synthesis And Biological Evaluation Of ω-Hydroxy Polyunsaturated Fatty Acids
作者:Hwang,Sung Hee; Wagner,Karen; Xu,Jian; Yang,Jun; Li,Xichun; Et Al
参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2017 卷标:27(3) 页码:620-625]

506-32-1 = 79551-86-3 + 79551-85-2
反应条件:1.1 Reagents: Glucose Catalysts: Octadecylamine,Cytochrome P450 Solvents: Ethanol,Water; 96 H,28 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; 12 H,25 °C
标题:Porous Alumina Membrane As A Support System For Candida Bombicola Cells And Their Use In Biotransformation Of Arachidonic Acid To 19-Hete And 20-Hete
作者:Sachin,Shah; Asmita,Prabhune; Sulabha,Kulkarni
参考文献:Research Journal Of Biotechnology 日期:2007 卷标:2(3) 页码:12-20

📜花生四烯酸置于human Cytochrome P450 4F11体系中,化学反应生成 20-羟基二十碳-5Z,8Z,11Z,14Z-四烯酸
参考文献:Human Cytochrome P450 4F11: Heterologous Expression In Bacteria,Purification,And Characterization Of Catalytic Function
标题:Human Cytochrome P450 4F11: Heterologous Expression In Bacteria,Purification,And Characterization Of Catalytic Function
摘要:Human Cytochrome P450 (P450) 4F11 Is Still Considered An "Orphan" Because Its Function Is Not Well Characterized. A Bacterial Expression System Was Developed For Human P450 4F11,Producing Similar To 230 Nmol P450 From A 3-1 Culture Of Escherichia Coli. P450 4F11 Was Purified And Utilized For Untargeted Substrate Searches In Human Liver Extract Using A Liquid Chromatography/mass Spectrometry-Based Metabolomic And Isotopic Labeling Approach (Tang Et Al.,2009 [19]). Four Fatty Acids-Palmitic,Oleic,Arachidonic,And Docosahexaenoic-Were Identified In Human Liver And Verified As Substrates Of P450 4F11. The Products Were Characterized As Omega-Hydroxylated Fatty Acids By Gas Chromatography-Mass Spectrometry Analysis Of Their Trimethylsilyl Derivatives. Kinetic Analysis Of The Oxidation Products Confirmed That The Fatty Acids Are Substrates Oxidized By P450 4F11. P450 4F11 Also Exhibited Low Activity For Some Drug N-Demethylation Reactions But None For Activation Of Several Pro-Carcinogens. (C) 2009 Elsevier Inc. All Rights Reserved.
DOI:10.1016/j.Abb.2009.11.017

海关参考信息

2901210000-乙烯
2901220000-丙烯
2905121000-正丙醇
2905130000-正丁醇
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专利信息

专利号:US-11001783-B2
优先权日:2016-08-16
标题:Synthesis and use of Ï‰-hydroxylated polyunsaturated fatty acids
发明人：ZHANG GUODONG; HAMMOCK BRUCE; HWANG SUNG HEE; WANG WEICANG
权利人:UNIV CALIFORNIA; UNIV MASSACHUSETTS
摘要:The present invention provides a synthetic chemical method for preparing Ï‰-hydroxylated polyunsaturated fatty acids (PUFAs) including 20-hydroxyeicosatetraenoic acid (20-HETE), 20-hydroxyeicosapentaenoic acid (20-HEPE), and 22-hydroxydocosahexaenoic acid (22-HDoHE) and a method of use thereof for treating cancer and macular degeneration.

专利号:EP-4028533-A1
优先权日:2019-09-12
标题 :Photo biocatalytic synthesis of secondary fatty alcohols from unsaturated fatty acids

专利号:US-2019270950-A1
优先权日:2016-08-16
标题:Synthesis and use of omega-hydroxylated polyunsaturated fatty acids

专利号:US-2020332224-A1
优先权日:2016-08-16
标题:Synthesis and use of omega-hydroxylated polyunsaturated fatty acids

专利号:US-8415400-B2
优先权日:2003-05-16
标题:Cross-linked ionic core micelles
发明人：BRONICH TATIANA K; KABANOV ALEXANDER V
权利人:BRONICH TATIANA K; KABANOV ALEXANDER V; UNIV NEBRASKA
摘要:The present invention provides polymer micelles with cross-linked ionic cores as delivery vehicles for therapeutics, diagnostics, nucleic acids, proteins, small molecules and the like. The present invention provides additionally methods of synthesis and uses for such micelles.

专利号:WO-2018035208-A1
优先权日:2016-08-16
标题 :Synthesis and use of omega-hydroxylated polyunsaturated fatty acids

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主要参考文献

1: Jarrar Y, Almansour M, Ahmad MA, Al-Najjar BO, Al-Doaiss AA, Shilbayeh SAR, Lee SJ. Simvastatin inhibits 20-Hydroxyeicosatetraenoic acid formation: docking and in vitro assay. BMC Pharmacol Toxicol. 2025 Aug 18;26(1):151. doi: 10.1186/s40360-025-00976-2.
15:1607845. doi: 10.3389/fcimb.2025.1607845.
3: Hou YN, Liu SJ, Chen F, Wang S, Song SY, Yang WQ, Li LM. 20-HETE: Its potential role in physiological and pathophysiological processes. Biochem Pharmacol. 2025 Aug

合成参考文献

参考文献:10.1159/000189154
摘要:Schwartzman ML, da Silva JL, Lin F, Nishimura M, Abraham NG. Cytochrome P450 4A expression and arachidonic acid omega-hydroxylation in the kidney of the spontaneously hypertensive rat. Nephron. 1996;73(4):652–63. doi: 10.1159/000189154.
参考文献:10.1006/mvre.2002.2409
摘要:Frisbee JC, Lombard JH. Parenchymal tissue cytochrome P450 4A enzymes contribute to oxygen-induced alterations in skeletal muscle arteriolar tone. Microvasc Res. 2002 May;63(3):340–3. doi: 10.1006/mvre.2002.2409.
摘要:Hacein-Bey L, Harder DR, Meier HT, Varelas PN, Miyata N, Lauer KK, Cusick JF, Roman RJ. Reversal of delayed vasospasm by TS-011 in the dual hemorrhage dog model of subarachnoid hemorrhage. AJNR Am J Neuroradiol. 2006 Jun;27(6):1350–4.
参考文献:10.1152/ajpheart.00349.2006
摘要:Fang X, Faraci FM, Kaduce TL, Harmon S, Modrick ML, Hu S, Moore SA, Falck JR, Weintraub NL, Spector AA. 20-Hydroxyeicosatetraenoic acid is a potent dilator of mouse basilar artery: role of cyclooxygenase. American Journal of Physiology-Heart and Circulatory Physiology. 2006 Nov;291(5):H2301–7. doi: 10.1152/ajpheart.00349.2006.
参考文献:10.1097/fjc.0b013e318160b415
摘要:Berezan DJ, Dunn KM, Falck JR, Davidge ST. Aging increases cytochrome P450 4A modulation of alpha1-adrenergic vasoconstriction in mesenteric arteries. J Cardiovasc Pharmacol. 2008 Mar;51(3):327–30. doi: 10.1097/fjc.0b013e318160b415.