Determine the necessary mass, volume, or concentration for preparing a solution.
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analytical standard, Moligand™ Analytical standard,Moligand™ for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Protected from light,Store at -20°C,Argon charged Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 18 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
This analyticalstandard can also be used as follows: Optimization of capillary zone electrophoresis procedurecoupled with direct absorption UV detection (CZE-UV) to determine eicosapentaenoicacid and docosahexaenoic acids after their methylation in 10 different samplesof commercial omega-3 supplements Simultaneous determination of eicosapentaenoic acid,docosahexaenoic acid, and arachidonic acid in human plasma samples by high-performanceliquid chromatography-electrochemical detection (HPLC-ECD) Separation, identification, and quantification of eicosapentaenoicacid, docosahexaenoic acid, and arachidonic acid in human plasma samples by high-performanceliquid chromatography combined with tandem mass spectrometry (HPLC-MS/MS)
| ALogP | 5.6 |
|---|
| Canonical Smiles | CCC=CCC=CCC=CCC=CCC=CCCCC(=O)O |
|---|---|
| IUPAC Name | (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid |
| InChIKey | JAZBEHYOTPTENJ-JLNKQSITSA-N |
| INCHI | 1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15- |
| Isomeric SMILES | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O |
| WGK Germany | 3 |
| UN Number | 3265 |
| Molecular Weight | 302.45 |
| Beilstein | 1714433 |
| Reaxy-Rn | 8989326 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8989326&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Fatty Acyls |
| Subclass | Fatty acids and conjugates |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Long-chain fatty acids |
| Alternative Parents | Unsaturated fatty acids Straight chain fatty acids Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Long-chain fatty acid - Unsaturated fatty acid - Straight chain fatty acid - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. |
| External Descriptors | Unsaturated fatty acids |
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Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
| Certificate of Analysis | Jun 08, 2026 | E100927 | |
| Certificate of Analysis | Jun 08, 2026 | E100927 | |
| Certificate of Analysis | May 20, 2026 | E100927 | |
| Certificate of Analysis | Jan 21, 2026 | E100927 | |
| Certificate of Analysis | Aug 21, 2024 | E100927 | |
| Certificate of Analysis | Aug 21, 2024 | E100927 | |
| Certificate of Analysis | Jul 09, 2024 | E100927 | |
| Certificate of Analysis | Jul 09, 2024 | E100927 | |
| Certificate of Analysis | Jul 22, 2022 | E100927 | |
| Certificate of Analysis | Jul 22, 2022 | E100927 | |
| Certificate of Analysis | Feb 11, 2022 | E100927 | |
| Certificate of Analysis | Jan 27, 2022 | E100927 |
| Sensitivity | Light sensitive,Air sensitive,Heat sensitive |
|---|---|
| Refractive Index | 1.4977 |
| Flash Point(°F) | 199.4 °F |
| Flash Point(°C) | 93℃ |
| Melt Point(°C) | -54--53°C |
| Molecular Weight | 302.500 g/mol |
| XLogP3 | 5.600 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 13 |
| Exact Mass | 302.225 Da |
| Monoisotopic Mass | 302.225 Da |
| Topological Polar Surface Area | 37.300 Ų |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Complexity | 398.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 5 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 5 |
| Covalently-Bonded Unit Count | 1 |
| 1. Lei Zhang, Peng Shi, Lin Zhang, Yajun Wang, Jilin Xu, Xiaojun Yan, Kai Liao. (2023) Molecular Characterization and Expression Response of Ghrelin, GLP-1 and PYY to Fasting, Dietary Lipid, and Fatty Acids in Silver Pomfret (Pampus argenteus). Fishes, 8 (3): (170). [PMID:] [10.3390/fishes8030170] |
| 2. Xin-Nan Teng, Shu-Chang Wang, Liaqat Zeb, Yue-Sheng Dong, Zhi-Long Xiu. (2023) Two-Step Enzymolysis of Antarctic Krill for Simultaneous Preparation of Value-Added Oil and Enzymolysate. Marine Drugs, 21 (1): (47). [PMID:36662220] [10.3390/md21010047] |
| 3. Jie Cheng, Yuling Li, Yunjun Wang, Jing Zhang, Tuanqi Sun, Li Zhang, Yinlong Guo. (2022) Quaterization Derivatization with Bis(Pyridine) Iodine Tetrafluoroboride: High-Sensitivity Mass Spectrometric Analysis of Unsaturated Fatty Acids in Human Thyroid Tissues. ANALYTICAL CHEMISTRY, [PMID:35916214] [10.1021/acs.analchem.2c01519] |
| 4. Baoping Xiao, Yuanyuan Li, Yanqi Lin, Jingyu Lin, Lingyu Zhang, Daren Wu, Jun Zeng, Jian Li, Jing wen Liu, Guiling Li. (2021) Eicosapentaenoic acid (EPA) exhibits antioxidant activity via mitochondrial modulation. FOOD CHEMISTRY, [PMID:34710690] [10.1016/j.foodchem.2021.131389] |
| 5. Wen Zhang, An Bu, Qingyuan Ji, Luofu Min, Song Zhao, Yuxin Wang, Jing Chen. (2019) pKa-Directed Incorporation of Phosphonates into MOF-808 via Ligand Exchange: Stability and Adsorption Properties for Uranium. ACS Applied Materials & Interfaces, [PMID:31409065] [10.1021/acsami.9b10920] |
| 6. Qi Zhao, Jian Li, Yang Xu, Dandan Lv, Kanyasiri Rakariyatham, Dayong Zhou. (2019) Rapid extraction of free fatty acids from edible oil after accelerated storage based on amino-modified magnetic silica nanospheres. Analytical Methods, 11 (35): (4520-4527). [PMID:] [10.1039/C9AY01082C] |
| 7. Hongkai Xie, Dayong Zhou, Xiaopei Hu, Zhongyuan Liu, Liang Song, Beiwei Zhu. (2018) Changes in Lipid Profiles of Dried Clams (Mactra chinensis Philippi and Ruditapes philippinarum) during Accelerated Storage and Prediction of Shelf Life. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, [PMID:29965751] [10.1021/acs.jafc.8b03047] |
| 8. Wanpeng Ma, Wei Zhang, Yang Zhao, Helong Yu. (2016) Preparation and assessment of a self-healing material based on microcapsules filled with ethyl phenylacetate. JOURNAL OF APPLIED POLYMER SCIENCE, 133 (20): [PMID:] [10.1002/app.43430] |
| 9. Xiangyan Chen, Tianze Jiang, Yantao Li, Yifei Zhang, Jianqi Chen, Xia Zhao, Hai Yang. (2024) Carrageenan-ferrocene-eicosapentaenoic acid composite hydrogel induce ferroptosis and apoptosis for anti-tumor recurrence and metastasis. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, [PMID:39025181] [10.1016/j.ijbiomac.2024.133942] |
| 10. Youjun Wang, Yangmeijin Zhao, Yuxuan He, Chengxiang Ao, Yusheng Jiang, Yuanyong Tian, Hui Zhao, Hang Lu. (2024) Effect of three unsaturated fatty acids on the protein oxidation and structure of myofibrillar proteins from rainbow trout (Oncorhynchus mykiss). FOOD CHEMISTRY, [PMID:38653104] [10.1016/j.foodchem.2024.139403] |
| 11. Chen Fangquan, Tang Hu, Lin Junhao, Xiang Limin, Lu Yanjiao, Kang Rui, Tang Daolin, Liu Jiao. (2024) Macropinocytosis inhibits alkaliptosis in pancreatic cancer cells through fatty acid uptake. CARCINOGENESIS, [PMID:39008332] [10.1093/carcin/bgae045] |
| 12. Guo XiaoYu, Zhou Jianglu, Yu Hong, Cao Han, Li Xia, Hu Qing, Yu YunQiu. (2024) Serum lipidomic study of long-chain fatty acids in psoriasis patients prior to and after anti-IL-17A monoclonal antibody treatment by quantitative GC‒MS analysis with in situ extraction. Lipids in Health and Disease, 23 (1): (1-15). [PMID:38185620] [10.1186/s12944-023-01999-6] |
| 13. Feng Lijuan, Yu Shuping, Jin Weimei, Xiao Changyan, Qiao Yan, Yang Guangfeng. (2024) The role of hydroponic solution of Ulva fasciata in modulating the antibiotic resistance of Vibrio alginolyticus. JOURNAL OF APPLIED MICROBIOLOGY, [PMID:39533112] [10.1093/jambio/lxae281] |
| 14. Wen Xiao, Haihui Ren, Yueyi Zhang, Jiameng Han, Qiaorong Liu, Zunjian Zhang, Yuan Tian. (2025) Development of a pseudotargeted metabolomics approach for relative quantification of free fatty acid double-bond isomers in beagle plasma. JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, [PMID:40885032] [10.1016/j.jchromb.2025.124765] |
| 15. LiJie , NanWenshan , HuangXiaoli , MengHuali , WangShue , ZhengYan , LiYing , LiHui , ZhangZhiyue , DuLei , YinXiao , WuHao. (2024) Eicosapentaenoic acid induces macrophage Mox polarization to prevent diabetic cardiomyopathy. EMBO REPORTS, [PMID:39482491] [10.1038/s44319-024-00271-x] |
| 16. Jingyu Li, Bing Fang, Yao Wu, Yuhang Sun, Yue Liu, haina gao, Ming Zhang. (2025) Investigating the Neuroprotective Effects of Polyunsaturated Fatty Acids in Egg Yolk Phospholipids on Oxidative Damage in HT22 Cells. Food & Function, [PMID:40341910] [10.1039/D5FO00833F] |
| 17. Zhenghua Zheng, Na Liu, Weiping Ren, Mengjiao Liu, Ao Wang, Zujing Yang, Jingjie Hu, Zhenmin Bao, Wenqian Jiao. (2025) Endogenous LC-PUFA biosynthetic capability in dwarf surf clam Mulinia lateralis: characterization and functional analysis of fatty acyl elongases and a desaturase. BIOCHIMICA ET BIOPHYSICA ACTA-MOLECULAR AND CELL BIOLOGY OF LIPIDS, [PMID:40339787] [10.1016/j.bbalip.2025.159623] |
| 18. Yuling Tang, Xunjiao Wei, Yonghua Wang, Wen Chen. (2025) Human FABP7 selectively captures docosahexaenoic acid over eicosapentaenoic acid: A potential protein-based platform for affinity purification of ω-3 lipids. Food Bioscience, [PMID:] [10.1016/j.fbio.2025.107405] |
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