Etherolenic Acid
(Synonyms: (9Z,11E,1'E,3'Z)-12-(1',3'-hexadenyloxy)-9,11-Dodecadienoic Acid) 目录号 : GC47312
A divinyl ether oxylipin
Cas No.:2247927-22-4
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
Etherolenic acid is a divinyl ether oxylipin.1,2 It is a metabolite of linolenic acid that is formed in plants via 13-lipoxygenase-mediated formation of 13(S)-HpOTrE followed by conversion to the divinyl ether by divinyl ether synthase.
1.Grechkin, A.N., Fazliev, F.N., and Mukhtarova, L.S.The lipoxygenase pathway in garlic (Allium sativum L.) bulbs: Detection of the novel divinyl ether oxylipinsFEBS Letters371159-162(1995) 2.Hamberg, M.Biosynthesis of new divinyl ether oxylipins in Ranunculus plantsLipids37(4)427-433(2002)
| Cas No. | 2247927-22-4 | SDF | |
| 别名 | (9Z,11E,1'E,3'Z)-12-(1',3'-hexadenyloxy)-9,11-Dodecadienoic Acid | ||
| Canonical SMILES | CC/C=C\C=C\O/C=C/C=C\CCCCCCCC(O)=O | ||
| 分子式 | C18H28O3 | 分子量 | 292.4 |
| 溶解度 | Ethanol: soluble | 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 | 3.42 mL | 17.0999 mL | 34.1997 mL |
| 5 mM | 0.684 mL | 3.42 mL | 6.8399 mL |
| 10 mM | 0.342 mL | 1.71 mL | 3.42 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。
Antimicrobial Activity of Geometric Isomers of Etherolenic Acid-the Products of Plant Lipoxygenase Cascade
Dokl Biochem Biophys 2018 May;480(1):139-142.PMID:30008094DOI:10.1134/S1607672918030031.
Data on the influence of the double bond geometry on the antimicrobial properties of different isomers of Etherolenic Acid against phytopathogenic bacteria are presented. (ω5Z)-Etherolenic acid possesses bactericidal properties against Xanthomonas campestris ssp. vesicatoria, Pseudomonas syringae ssp. tomato, Pectobacterium atrosepticum SCRI1043; the etherolenic and (11Z)-etherolenic acids possess only bacteriostatic properties.
On the mechanism of biosynthesis of divinyl ether oxylipins by enzyme from garlic bulbs
Eur J Biochem 1997 Apr 1;245(1):137-42.PMID:9128734DOI:10.1111/j.1432-1033.1997.00137.x.
The microsomal fraction of homogenate of garlic (Allium sativum L.) bulbs contains a divinyl ether synthase which catalyzes conversion of (9Z,11E,13S)-13-hydroperoxy-9, 11-octadecadienoic acid and (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatri eno ic acid into (9Z,11E,1'E,)-12-(1'-hexenyloxy)-9,11-dodecadienoic acid (Etherolenic Acid) and (9Z,11E,1'E,3'Z)-12-(1',3'-hexadienyloxy)-9,11-dode cadienoic acid (Etherolenic Acid), respectively. Two isomers of Etherolenic Acid were isolated. As shown by NMR spectrometry, the double bond configurations of these compounds were (9E,11E,1'E) and (9Z,11Z,1'E). Experiments with linoleic acid (13R,S)-hydroperoxide demonstrated that the S enantiomer was a much better substrate for the divinyl ether synthase compared to the R enantiomer. Incubation of (9Z,11E,13S)-[18O2]hydroperoxy-9,11-octadecadienoic acid led to the formation of Etherolenic Acid which retained 18O in the ether oxygen. An intermediary role of an epoxyallylic cation in Etherolenic Acid biosynthesis is postulated.
Separation of divinyl ether fatty acid isomers by micellar electrokinetic chromatography
Electrophoresis 2001 Apr;22(6):1163-9.PMID:11358142DOI:10.1002/1522-2683()22:6<1163::AID-ELPS1163>3.0.CO;2-M.
A micellar electrokinetic chromatography (MEKC) method has been developed for the direct resolution of divinyl ether type of hydrophobic fatty acid isomers. The fatty acid isomers resolved include colneleic acid (CL), colnelenic acid (CLn), 14(Z)-etheroleic acid (14(Z)-EL), 14(Z)-etherolenic acid (14(Z)-Eln), 11(Z)-etheroleic acid (11(Z)-EL), 11(Z)-etherolenic acid (11(Z)-Eln), etheroleic acid (EL) and Etherolenic Acid (Eln). These fatty acid isomers differ in number, position and spatial arrangement of the double bonds and the position of the ether oxygen. A central composite design was employed for the optimization of the key variables of the separation, namely the concentrations of sodium dodecyl sulfate (SDS) and organic modifiers. The use of micelles combined with an organic modifier in the background electrolyte made it possible to dissolve and separate relatively hydrophobic fatty acid isomers, and to achieve high separation efficiency. Using heptakis-(2,3-dimethyl-6-sulfato)-beta-cyclodextrin (HDMS-beta-CD) as a buffer additive, complete separation of the examined eight divinyl ethers was achieved. Separation efficiencies up to 5 x 10(5) theoretical plates/m were achieved under optimized conditions. Direct UV was applied for detection of the fatty acids. The results were compared with those obtained from high-performance liquid chromatography (HPLC) separation.
The lipoxygenase pathway in garlic (Allium sativum L.) bulbs: detection of the novel divinyl ether oxylipins
FEBS Lett 1995 Sep 4;371(2):159-62.PMID:7672118DOI:10.1016/0014-5793(95)00895-g.
Incubations of [1-14C]linoleic acid or [1-14C]-(9Z,11E, 13S)-13-hydropero xy-9,11-octadecadienoic acid (13-HPOD) with juice of garlic bulbs lead to the formation of one predominant labelled product, viz., the novel divinyl ether (9Z,11E, 1'E)-12-(1'-hexenyloxy)-9,11-dodecadienoic acid ('etheroleic acid'). With lesser efficiency [1-14C]alpha-linolenic acid or [1-14C](9Z,11E, 13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid (13-HPOT) are converted in this way into (9Z,11E,1'E,1'E,3'Z)-12-(1',3'-hexadienyloxy)-9,11- dodecadienoic acid ('Etherolenic Acid'). Thus, garlic bulbs possess the activity of a new 13-hydroperoxide-specific divinyl ether synthase.