Arachidonyl alcohol
(Synonyms: (all-Z)-5,8,11,14-Eicosatetraen-1-ol) 目录号 : GC39340
A polyunsaturated fatty alcohol
Cas No.:13487-46-2
Sample solution is provided at 25 µL, 10mM.
Quality Control & SDS
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- Purity: >96.00%
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- Datasheet
Arachidonyl alcohol is a polyunsaturated fatty alcohol produced by the reduction of arachidonic acid .1,2 It has been used as a substrate in the synthesis of various ether lipids.
1.Nagao, T., Watanabe, Y., Tanaka, S., et al.Microbial conversion of arachidonic acid to arachidonyl alcohol by a new Acinetobacter speciesJ. Am. Oil Chem. Soc.891663-1671(2012) 2.Natarajan, V., and Schmid, H.H.Substrate specificities in ether lipid biosynthesis. Metabolism of polyunsaturated fatty acids and alcohols by rat brain microsomesBiochem. Biophys. Res. Commun.79(2)411-416(1977)
| Cas No. | 13487-46-2 | SDF | |
| 别名 | (all-Z)-5,8,11,14-Eicosatetraen-1-ol | ||
| Canonical SMILES | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCO | ||
| 分子式 | C20H34O | 分子量 | 290.48 |
| 溶解度 | DMSO: 250 mg/mL (860.64 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.4426 mL | 17.2129 mL | 34.4258 mL |
| 5 mM | 0.6885 mL | 3.4426 mL | 6.8852 mL |
| 10 mM | 0.3443 mL | 1.7213 mL | 3.4426 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Unique analogues of anandamide: arachidonyl ethers and carbamates and norarachidonyl carbamates and ureas
J Med Chem 1999 Jun 3;42(11):1975-81.PMID:10354405DOI:10.1021/jm980711w.
To examine the effect of changing the amide bond of anandamide (5, AN) to a less hydrolyzable moiety, analogues 1a-1l, 2a-2c, 3a-3c, and 4a-4h were synthesized from commercially available Arachidonyl alcohol or arachidonic acid and tested for their pharmacological activity. Arachidonyl ethers 1a-1k were obtained through the coupling of the arachidonyl mesylate (6) (generated from the mesylation of Arachidonyl alcohol) with the appropriate alcohol in potassium hydroxide. Arachidonyl ether 1l was obtained through the phase-transfer coupling of Arachidonyl alcohol with 2-(2-iodoethoxy)tetrahydropyran (which was generated from its bromide) followed by cleavage of the tetrahydropyran group with Dowex resin. Arachidonyl carbamates 2a-2c were obtained through the coupling of Arachidonyl alcohol with the appropriate isocyanates. Norarachidonyl carbamates 3a-3c and ureas 4a-4h were obtained through the coupling of the norarachidonyl isocyanate (generated from arachidonic acid using diphenyl phosphorazidate and triethylamine upon heating) with the appropriate alcohols and amines, respectively. AN analogues 1-3 have shown poor binding affinities to the CB1 receptor and fail to produce significant pharmacological effect at doses up to 30 mg/kg. Several ether analogues 1 were also evaluated in the CB2 binding assay and were found to be of low affinity. However, norarachidonyl urea analogues 4 have shown generally good binding affinities to the CB1 receptor (Ki = 55-746 nM) and pharmacological activity with AN-like profiles. The most potent analogue of this series is the 2-fluoroethyl analogue 4f which binds 2 times better than AN and was more active in several mouse behavioral assays. It was also observed that urea analogues 4a and 4g, which have weak binding affinities to the CB1 receptor (Ki = 436 and 347 nM, respectively), produced surprisingly potent pharmacological activity. These urea analogues have also shown hydrolytic stability toward the amidase enzymes, responsible for the primary degradation pathway of anandamide, in binding affinity assays in the absence of the enzyme inhibitor PMSF.
Synthesis and CB1 receptor activities of novel Arachidonyl alcohol derivatives
Bioorg Med Chem Lett 2004 Jun 21;14(12):3231-4.PMID:15149681DOI:10.1016/j.bmcl.2004.03.093.
Novel derivatives of Arachidonyl alcohol were synthesized and evaluated for their CB1 receptor activity by [(35)S]GTP(gamma)S assay using rat cerebellar membranes.
Synthesis of lysophosphatidylethanolamine analogs that inhibit renin activity
J Med Chem 1975 Dec;18(12):1184-90.PMID:1195274DOI:10.1021/jm00246a003.
A series of lysophosphatidylethanolamine analogs containing saturated and methylene-interrupted cis-olefinic fatty chains was synthesized by phosphorylation and phosphonylation of respective fatty alcohols. Arachidonyl- and linolenylphosphorylethanolamines (12, 13), arachidonyl (2-phthalimidoethyl)phosphonate (17), and arachidonyl (2-aminoethyl)phosphonate (18) were found to be effective inhibitors of the renin-renin substrate reaction in vitro; lysophosphatidylethanolamine analogs 14-16 of lesser unsaturation were either weakly active or inactive. In a preliminary study, intramuscular administration of 25 mg/kg/day of arachidonyl (2-aminoethyl)phosphonate (18) to the hypertensive rat caused pronounced reduction (50 mm) in blood pressure within 3 days; upon continued dosage (15 mg/kg/day) of 18 for an additional 4 days, plasma renin activity was found to be 16 ng/0.1 ml/15 hr as compared with 69 ng/0.1 ml/15 hr before initial drug administration. Arachidonic acid (3), Arachidonyl alcohol (8), and several corresponding tetraenoid ester, amide, mesylate, and glyceryl ether derivatives (4-7, 10, 11), that are not phosphate or phosphonate esters, were found to exhibit negligible or modest inhibition of renin activity in vitro.