Oleyl Anilide
(Synonyms: OA, Oleic Acid Anilide, Oleylanilide) 目录号 : GC44505An ACAT inhibitor
Cas No.:5429-85-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
AcylCoA:cholesterol acyltransferase (ACAT) is an intracellular cholesteryl ester synthase tied closely to the absorption of dietary cholesterol. Oleyl analide (OA) is a weak inhibitor of acylCoA:cholesterol acyltransferase (ACAT) with an IC50 of 26 µM. OA and the related glyceride dioleoyl phenylamino propane 1,2-diol have been linked to a syndrome of eosinophilia, excessive T-cell activation, and elevated interleukin-4 (IL-4), soluble IL-2R, and IL-5. The clinical consequences are an acute pulmonary inflammatory reaction followed by chronic neuropathy, myalgia, and autoimmune connective tissue disease, generally referred to as toxic oil syndrome (TOS). Aniline-denatured cooking oil is a source of OA associated with TOS.
| Cas No. | 5429-85-6 | SDF | |
| 别名 | OA, Oleic Acid Anilide, Oleylanilide | ||
| Canonical SMILES | CCCCCCCC/C=C\CCCCCCCC(=O)Nc1ccccc1 | ||
| 分子式 | C24H39NO | 分子量 | 357.6 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml | 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 | 2.7964 mL | 13.9821 mL | 27.9642 mL |
| 5 mM | 0.5593 mL | 2.7964 mL | 5.5928 mL |
| 10 mM | 0.2796 mL | 1.3982 mL | 2.7964 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。
Distribution of oleyl-anilide hydrolysing activity in rat and human tissues
Toxicology 1993 Jun 11;80(2-3):131-9.PMID:8327996DOI:10.1016/0300-483x(93)90176-s.
A method has been developed and tested for the measurement of anilide hydrolysing activity in rat tissues. A concentrated solution of labelled Oleyl Anilide in isopropanol is added to the tissue homogenates and after incubation, the chloroform/methanol extract of the samples is chromatographed on Silicagel TLC plates and the oleic acid radioactivity is measured. The activity is time-, homogenate- and temperature-dependent, the optimal pH for measurement is 8 and there is no significant spontaneous anilide degradation. In the rat, the activity is widely distributed, with highest protein specific activity in the adipose tissues. The tissue activities of a same animal are fairly well inter-correlated, with rats showing very low activity in all tissues compared with others presenting high overall activity. The levels of activity found can easily explain the fast elimination of anilides administered to rats and their scant toxic effects. Human adipose tissue samples showed a wide range of anilide hydrolase activities per gram of protein, in general lower than in rats and with some values very low. It is postulated that this lack of anilide-hydrolising capability in some humans may be related to the incidence of the toxic oil syndrome.
Factors associated with pathogenicity of oils related to the toxic oil syndrome epidemic in Spain
Epidemiology 1994 Jul;5(4):404-9.PMID:7918809DOI:10.1097/00001648-199407000-00005.
The toxic oil syndrome (TOS), which affected over 20,000 persons in Spain in 1981, has been linked to the consumption of aniline-denatured rapeseed oil, but the precise etiologic agent is still unknown. We attempted to validate the use of high concentrations of Oleyl Anilide as a marker for oils that contain (or contained) the causal agent. We compared the chemical compositions of oils obtained from ill (N = 59) and unaffected (N = 70) families in 1981. Case oils had higher concentrations of fatty acids and sterols in which rapeseed oil is particularly rich. In addition, case oils had more frequent and extensive contamination with Oleyl Anilide and other fatty acid anilides. We observed a dose-response effect; risk increased sharply with increasing concentrations of Oleyl Anilide, and no control oil had more than about 825 micrograms per liter of that compound. We conclude that high concentrations of Oleyl Anilide specifically mark oils that contain (or used to contain) the TOS etiologic agent.
Single step thin-layer chromatographic method for quantitation of enzymatic formation of fatty acid anilides
J Chromatogr B Biomed Sci Appl 1998 Feb 13;705(2):269-75.PMID:9521563DOI:10.1016/s0378-4347(97)00542-2.
The activity of the enzyme involved in catalyzing the formation of fatty acid anilides can be measured by quantitating the fatty acid anilides formed. We have shown earlier that oleic acid is the most preferred substrate among other fatty acids studied for the conjugation with aniline. The reaction product (Oleyl Anilide) could be separated by thin-layer chromatography (TLC) and then quantified by reversed-phase high-performance liquid chromatography (HPLC). Using [1-(14)C]oleic acid as substrate, the fatty acid anilide forming activity can be determined in a single step by TLC analysis. The conventional TLC methods used for the separation of the fatty acid esters, however, could not resolve Oleyl Anilide from the residual [1-(14)C]oleic acid. Therefore, a simple and reliable TLC method was developed for the separation of Oleyl Anilide from oleic acid using a freshly prepared solvent consisting of petroleum ether-ethyl acetate-ammonium hydroxide (80:20:1, v/v). Using this solvent system the relative flow (Rf) values were found to be 0.54 for Oleyl Anilide and 0.34 for aniline, whereas oleic acid remained at the origin. The TLC procedure developed in the present study could be used to determine the fatty acid anilide forming activity using [1-(14)C]oleic or other fatty acids as substrate and was also found suitable for the analysis of fatty acid anilides from the biological samples.
Epidemiologic evidence for a new class of compounds associated with toxic oil syndrome
Epidemiology 1999 Mar;10(2):130-4.PMID:10069247doi
Toxic oil syndrome appeared in epidemic form in Spain in 1981. Epidemiologic studies have demonstrated that illness was caused by consumption of rapeseed oil that had been denatured with aniline. Chemical analyses of oil specimens conducted in conjunction with epidemiologic studies have established that consumption of specific oils containing fatty acid anilide contaminants was associated with increased risk for disease. New chemical analytic methods identified a family of compounds, the di-fatty acid esters of phenylamino propane-diol, and one of these compounds, the 1,2-di-oleyl ester of 3-(N-phenylamino)-1,2-propanediol (DPAP), has been found to be more strongly associated with disease status than the fatty acid anilides. We found the odds ratio for exposure to DPAP (OR = 26.4, 95% CI = 6.4-76.3) is much higher than the odds ratio for exposure to Oleyl Anilide (OR = 4.1, 95% CI = 2.2-7.8), implying that exposure to DPAP was a more relevant risk factor for development of toxic oil syndrome than exposure to Oleyl Anilide. In this paper, we review and present analyses of data from multiple studies of the possible etiologic role of DPAP in toxic oil syndrome. The presence of DPAP in oil collected from affected and unaffected households was a more specific correlate of case relatedness than was the presence of fatty acid anilides, and it was equally sensitive. Moreover, DPAP was found in oil from the only refinery whose oil was clearly associated with illness.
Toxic oil syndrome: traceback of the toxic oil and evidence for a point source epidemic
Food Chem Toxicol 1996 Mar;34(3):251-7.PMID:8621106DOI:10.1016/0278-6915(95)00111-5.
Rapeseed oil denatured with aniline was the vehicle of the causal agent of the toxic oil syndrome (TOS) epidemic that occurred in Spain in 1981. Although the precise aetiologic agent remains unknown, researchers established that increasing concentrations of Oleyl Anilide and other fatty acid anilides were associated with an increased risk for disease. To examine the hypothesis that 5-litre plastic containers of rapeseed oil associated with TOS, and which contained Oleyl Anilide had a characteristic shape, we measured fatty acid, sterol and fatty acid anilide levels in oil from containers of different shapes. We identified 1673 bottles of oil that had been collected during the Spanish Government's oil exchange programme and linked these bottles to people with TOS as reported in the official government census of patients with TOS. Although rapeseed oil (identified by the presence of brassicasterol) was found in 798 (47.7%) of the 1673 bottles examined, contamination with fatty acid anilide occurred in only 329 (19.6%) of the 1673 bottles and 319 (97%) of the 329 were oil containers of the shape sold by RAELCA, an oil company in Madrid. The first aniline-denatured oil that RAELCA had purchased to be refined specifically for distribution was refined at the ITH refinery of Seville, and this oil has been most directly associated with the epidemic. Previous work has shown that the only toxic oil linked to a specific refinery was that associated with rapeseed oil from the ITH refinery in Seville, and the epidemic began shortly after this oil was delivered to RAELCA for retail sale. On the basis of these findings, we conclude that oil refined by ITH and distributed by RAELCA was the principal, and probably the only, oil responsible for the TOS epidemic. Information about the history and treatment of this oil may yield important clues towards identifying the aetiologic agent of TOS.