Determine the necessary mass, volume, or concentration for preparing a solution.
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Basic Description
| Synonyms | OXOAMINE | HONO2 | Methyllinolenate | NSC 607759 | (Z,Z,Z)-9,12,15-Octadecatrienoic acid, methyl ester | AC-33780 | Q27237155 | Linolenic acid methyl ester | METHYL LINOLENATE [USP-RS] | AS-56871 | D91234 | METHYL CIS,CIS,CIS-OCTADECA-9,12,15-TRIENOATE | |
|---|---|
| Specifications & Purity | ≥99% |
| Biochemical and Physiological Mechanisms | Methyl linolenic acid is a polyunsaturated fatty acid (PUFA) used to study the oxidation/peroxidation reaction mechanism of unsaturated fatty acids. We are studying methyl linolenic acid as a potential skin whitening agent with anti melanogenic activity. |
| Storage Temp | Store at -20°C,Argon charged |
| Shipped In | Ice chest + Ice pads |
Associated Targets(Human)
A498 (42825 Activities)
CAKI-1 (44928 Activities)
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CCRF-CEM (65223 Activities)
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COLO 205 (50209 Activities)
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DLD-1 (17511 Activities)
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DMS-273 (14108 Activities)
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HL-60 (67320 Activities)
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HT-29 (80576 Activities)
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K562 (73714 Activities)
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KM12 (47707 Activities)
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MCF7 (126967 Activities)
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MOLT-4 (49676 Activities)
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OVCAR-3 (48710 Activities)
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OVCAR-4 (44535 Activities)
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OVCAR-5 (45555 Activities)
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OVCAR-8 (47708 Activities)
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RPMI-8226 (44974 Activities)
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SF-295 (48000 Activities)
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SK-MEL-2 (46422 Activities)
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SK-MEL-28 (48833 Activities)
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SK-MEL-5 (47095 Activities)
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SK-OV-3 (52876 Activities)
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SN12C (47755 Activities)
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SNB-19 (46794 Activities)
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U-251 (51189 Activities)
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UACC-257 (46019 Activities)
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UACC-62 (47335 Activities)
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UO-31 (46270 Activities)
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XF498 (12972 Activities)
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A549 (127892 Activities)
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NCI/ADR-RES (33767 Activities)
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EKVX (44102 Activities)
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NCI-H322M (45589 Activities)
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HCC 2998 (41480 Activities)
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HCT-116 (91556 Activities)
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HOP-18 (11577 Activities)
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HOP-92 (41141 Activities)
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NCI-H460 (60772 Activities)
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SF-268 (49410 Activities)
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IGROV-1 (47897 Activities)
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LOX IMVI (44321 Activities)
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HOP-62 (47048 Activities)
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M19-MEL (15326 Activities)
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Malme-3M (44254 Activities)
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SNB-75 (44215 Activities)
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NCI-H226 (44470 Activities)
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NCI-H23 (49055 Activities)
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NCI-H522 (44358 Activities)
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SF-539 (44845 Activities)
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SW-620 (52400 Activities)
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Associated Targets(non-human)
P388 (20296 Activities)
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P388/ADR (1216 Activities)
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Names and Identifiers
| IUPAC Name | methyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate |
|---|---|
| INCHI | InChI=1S/C19H32O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h4-5,7-8,10-11H,3,6,9,12-18H2,1-2H3/b5-4-,8-7-,11-10- |
| InChi Key | DVWSXZIHSUZZKJ-YSTUJMKBSA-N |
| Canonical SMILES | CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OC |
| Isomeric SMILES | CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC |
| WGK Germany | 2 |
| PubChem CID | 5319706 |
| Molecular Weight | 292.46 |
| Beilstein | 1728194 |
| Reaxy-Rn | 1728194 |
Certificates
Certificate of Analysis(COA)
Enter Lot Number to search for COA:
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
 G2426492 | Certificate of Analysis | Aug 07, 2024 | M110076 |
| B2421565 | Certificate of Analysis | Feb 29, 2024 | M110076 |
| B2421564 | Certificate of Analysis | Feb 29, 2024 | M110076 |
| H2331673 | Certificate of Analysis | Sep 05, 2023 | M110076 |
| H2331678 | Certificate of Analysis | Sep 05, 2023 | M110076 |
| H2331677 | Certificate of Analysis | Sep 05, 2023 | M110076 |
| H2331676 | Certificate of Analysis | Sep 05, 2023 | M110076 |
| H2331675 | Certificate of Analysis | Sep 05, 2023 | M110076 |
| H2331674 | Certificate of Analysis | Sep 05, 2023 | M110076 |
| F2306836 | Certificate of Analysis | Jun 15, 2023 | M110076 |
| F2306786 | Certificate of Analysis | Jun 15, 2023 | M110076 |
| F1924047 | Certificate of Analysis | Apr 13, 2023 | M110076 |
| J2209511 | Certificate of Analysis | Oct 17, 2022 | M110076 |
| J2209512 | Certificate of Analysis | Oct 17, 2022 | M110076 |
| J2209508 | Certificate of Analysis | Oct 15, 2022 | M110076 |
| C2203078 | Certificate of Analysis | Mar 07, 2022 | M110076 |
| C2203072 | Certificate of Analysis | Mar 07, 2022 | M110076 |
Show more⌵
Chemical and Physical Properties
| Sensitivity | Light、Heat、Air sensitive |
|---|---|
| Refractive Index | 1.47 |
| Flash Point(°F) | 235.4 °F |
| Flash Point(°C) | 113 °C |
| Boil Point(°C) | 182°C |
Safety and Hazards(GHS)
| Signal | Warning |
|---|---|
| Hazard Statements | H319:Causes serious eye irritation H317:May cause an allergic skin reaction H400:Very toxic to aquatic life H410:Very toxic to aquatic life with long lasting effects |
| Precautionary Statements | P261:Avoid breathing dust/fume/gas/mist/vapors/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of water. P321:Specific treatment (see ... on this label). P501:Dispose of contents/container to ... P272:Contaminated work clothing should not be allowed out of the workplace. P333+P313:IF SKIN irritation or rash occurs: Get medical advice/attention. P362+P364:Take off contaminated clothing and wash it before reuse. P391:Collect spillage. P264+P265:Wash hands [and …] thoroughly after handling. Do not touch eyes. P337+P317:If eye irritation persists: Get medical help. |
| WGK Germany | 2 |
| Reaxy-Rn | 1728194 |
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Citations of This Product
| 1. Yuan Xue, JinXia Wang, Hong Yuan, Hui Li. (2023) Sulfonic acid-type hydrothermal carbon microspheres as stable, efficient catalysts for transesterification reactions. DIAMOND AND RELATED MATERIALS, 137 (110094). [PMID:] |
| 2. Hongxu Lu, Yanxia Liu, Wenyue Shen, Yang Zhou, Xiangwei Ma, Shibo Sun, Xiaoying Dong, Fengyun Ji, Huiyan Tong, Jianqiang Xu, Gaohong He, Weiping Xu. (2023) Yeast enrichment facilitated lipid removal and bioconversion by black soldier fly larvae in the food waste treatment. WASTE MANAGEMENT, 166 (152). [PMID:37172516] |
| 3. Yuan Xue, Xueling Zhao, Hong Yuan, Hui Li. (2022) Oxidation reaction mechanism of hydrothermal carbon microspheres with applications to transesterification after sulfonation. JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 98 (1): (66-76). [PMID:] |
| 4. Su Ji-Ling, Wang Juan, Fu Xiao-Na, Hou Li, Zhu Ping, Zhang Kai, Li Huo-Wang, Hou Ying, Liu Xiang-Yi, Xu Juan. (2022) Fatty acid composition and thermal characteristics of Malania oleifera seed oil. Advanced Composites and Hybrid Materials, 5 (2): (1268-1279). [PMID:] |
| 5. Yi-Tong Wang, Di Gao, Ya-Nan Zeng, Jun-Guo Li, Ai-Min Ji, Tian-Ji Liu, Shuang Cai, Wen-Jie Cong, Fu-Ping Wang, Qing Yu, Xiao-Man Wang, Zhen Fang. (2022) Efficient production of biodiesel with electric furnace dust impregnated in Na2CO3 solution. Journal of Cleaner Production, 330 (129772). [PMID:] |
References
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| 2. J T MacGregor,R E Wilson,W E Neff,E N Frankel. (1985-12-01) Mutagenicity tests of lipid oxidation products in Salmonella typhimurium: monohydroperoxides and secondary oxidation products of methyl linoleate and methyl linolenate.. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 23 ((12)): (1041-1047). [PMID:3908249] |
| 3. A A Gallon,W A Pryor. (1993-02-01) The identification of the allylic nitrite and nitro derivatives of methyl linoleate and methyl linolenate by negative chemical ionization mass spectroscopy.. Lipids, 28 ((2)): (125-133). [PMID:8441338] |
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| 6. S Satchithanandam,J Fritsche,J I Rader. (2001-06-22) Extension of AOAC Official Method 996.01 to the analysis of Standard Reference Material (SRM) 1846 and infant formulas.. Journal of AOAC International, 84 ((3)): (805-813). [PMID:11417645] |
| 7. Rosario Zamora,Francisco J Hidalgo. (2004-01-07) Comparative methyl linoleate and methyl linolenate oxidation in the presence of bovine serum albumin at several lipid/protein ratios.. Journal of agricultural and food chemistry, 51 ((16)): (4661-4667). [PMID:14705893] |
| 8. Saori Okuda,D Julian McClements,Eric A Decker. (2005-11-24) Impact of lipid physical state on the oxidation of methyl linolenate in oil-in-water emulsions.. Journal of agricultural and food chemistry, 53 ((24)): (9624-9628). [PMID:16302787] |
| 9. Muneyuki Maekawa,Kazuaki Kawai,Yoshikazu Takahashi,Hikaru Nakamura,Takumi Watanabe,Ryuichi Sawa,Kenji Hachisuka,Hiroshi Kasai. (2006-01-18) Identification of 4-oxo-2-hexenal and other direct mutagens formed in model lipid peroxidation reactions as dGuo adducts.. Chemical research in toxicology, 19 ((1)): (130-138). [PMID:16411666] |
| 10. Patrícia Baptista,Pedro Felizardo,José C Menezes,M Joana Neiva Correia. (2008-01-15) Multivariate near infrared spectroscopy models for predicting the methyl esters content in biodiesel.. Analytica chimica acta, 607 ((2)): (153-159). [PMID:18190803] |
| 11. Dan-Dan Feng,Yu-Feng Zhao,Zi-Qiang Luo,Damien J Keating,Chen Chen. (2008-02-07) Linoleic acid induces Ca2+-induced inactivation of voltage-dependent Ca2+ currents in rat pancreatic beta-cells.. The Journal of endocrinology, 196 ((2)): (377-384). [PMID:18252961] |
| 12. H P Vasantha Rupasinghe,Afsana Yasmin. (2010-01-30) Inhibition of oxidation of aqueous emulsions of omega-3 fatty acids and fish oil by phloretin and phloridzin.. Molecules (Basel, Switzerland), 15 ((1)): (251-257). [PMID:20110888] |
| 13. Yunbao Liu,Muraleedharan G Nair. (2010-06-23) An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds.. Journal of natural products, 73 ((7)): (1193-1195). [PMID:20565070] |
| 14. Sungran Huh,Young-Soo Kim,Eunsun Jung,Jihee Lim,Kwang Sun Jung,Myeong-Ok Kim,Jongsung Lee,Deokhoon Park. (2010-07-08) Melanogenesis inhibitory effect of fatty acid alkyl esters isolated from Oxalis triangularis.. Biological & pharmaceutical bulletin, 33 ((7)): (1242-1245). [PMID:20606321] |
| 15. T A Misharina,M B Terenina,N I Krikunova,I B Medvedeva. (2010-11-11) [Autooxidation of a mixture of lemon essential oils, methyl linolenoate, and methyl oleinate].. Prikladnaia biokhimiia i mikrobiologiia, 46 ((5)): (599-604). [PMID:21061607] |
| 16. Emmanuel Richaud,Ludmila Audouin,Bruno Fayolle,Jacques Verdu,Lyda Matisová-Rychlá,Jozef Rychlý. (2012-10-03) Rate constants of oxidation of unsaturated fatty esters studied by chemiluminescence.. Chemistry and physics of lipids, 165 ((7)): (753-759). [PMID:23026153] |
| 17. Xian-Guo Zou,Jiang-Ning Hu,Man-Li Zhao,Xue-Mei Zhu,Hong-Yan Li,Xiao-Ru Liu,Rong Liu,Ze-Yuan Deng. (2014-10-10) Lipozyme RM IM-catalyzed acidolysis of Cinnamomum camphora seed oil with oleic acid to produce human milk fat substitutes enriched in medium-chain fatty acids.. Journal of agricultural and food chemistry, 62 ((43)): (10594-10603). [PMID:25298236] |
| 18. Oier Aizpurua-Olaizola,Markel Ormazabal,Asier Vallejo,Maitane Olivares,Patricia Navarro,Nestor Etxebarria,Aresatz Usobiaga. (2014-12-05) Optimization of supercritical fluid consecutive extractions of fatty acids and polyphenols from Vitis vinifera grape wastes.. Journal of food science, 80 ((1)): (E101-E107). [PMID:25471637] |
| 19. Zsuzsanna Grózer,Adél Tóth,Renáta Tóth,Anita Kecskeméti,Csaba Vágvölgyi,Joshua D Nosanchuk,András Szekeres,Attila Gácser. (2015-02-06) Candida parapsilosis produces prostaglandins from exogenous arachidonic acid and OLE2 is not required for their synthesis.. Virulence, 6 ((1)): (85-92). [PMID:25654274] |
| 20. Obie Farobie,Yukihiko Matsumura. (2015-05-26) A comparative study of biodiesel production using methanol, ethanol, and tert-butyl methyl ether (MTBE) under supercritical conditions.. Bioresource technology, 191 (306-311). [PMID:26004381] |
| 21. Anders Kullberg,Oscar Oz Ekholm,J Peter Slotte. (2015-11-05) Miscibility of Sphingomyelins and Phosphatidylcholines in Unsaturated Phosphatidylcholine Bilayers.. Biophysical journal, 109 ((9)): (1907-1916). [PMID:26536267] |
| 22. William Y Boadi,Peter A Iyere,Samuel E Adunyah. (2003-09-17) Effect of quercetin and genistein on copper- and iron-induced lipid peroxidation in methyl linolenate.. Journal of applied toxicology : JAT, 23 ((5)): (363-369). [PMID:12975775] |
| 23. Caroline P Baron,Lis Berner,Leif H Skibsted,Hanne H F Refsgaard. (2005-07-23) Evaluation of activity of selected antioxidants on proteins in solution and in emulsions.. Free radical research, 39 ((7)): (777-785). [PMID:16036358] |
| 24. G Márquez-Ruiz,F Holgado,M C García-Martínez,M C Dobarganes. (2007-08-21) A direct and fast method to monitor lipid oxidation progress in model fatty acid methyl esters by high-performance size-exclusion chromatography.. Journal of chromatography. A, 1165 ((1-2)): (122-127). [PMID:17706232] |
| 25. Philippe Lesot,Vincent Baillif,Isabelle Billault. (2008-03-11) Combined analysis of C-18 unsaturated fatty acids using natural abundance deuterium 2D NMR spectroscopy in chiral oriented solvents.. Analytical chemistry, 80 ((8)): (2963-2972). [PMID:18327921] |
| 26. Kevin Huvaere,Daniel R Cardoso,Paula Homem-de-Mello,Signe Westermann,Leif H Skibsted. (2010-04-10) Light-induced oxidation of unsaturated lipids as sensitized by flavins.. The journal of physical chemistry. B, 114 ((16)): (5583-5593). [PMID:20377218] |
| 27. G M Huber,H P V Rupasinghe. (2010-05-25) Phenolic profiles and antioxidant properties of apple skin extracts.. Journal of food science, 74 ((9)): (C693-C700). [PMID:20492102] |
| 28. Yuan Xue, JinXia Wang, Hong Yuan, Hui Li. (2023) Sulfonic acid-type hydrothermal carbon microspheres as stable, efficient catalysts for transesterification reactions. DIAMOND AND RELATED MATERIALS, 137 (110094). [PMID:] |
| 29. Hongxu Lu, Yanxia Liu, Wenyue Shen, Yang Zhou, Xiangwei Ma, Shibo Sun, Xiaoying Dong, Fengyun Ji, Huiyan Tong, Jianqiang Xu, Gaohong He, Weiping Xu. (2023) Yeast enrichment facilitated lipid removal and bioconversion by black soldier fly larvae in the food waste treatment. WASTE MANAGEMENT, 166 (152). [PMID:37172516] |
| 30. Yuan Xue, Xueling Zhao, Hong Yuan, Hui Li. (2022) Oxidation reaction mechanism of hydrothermal carbon microspheres with applications to transesterification after sulfonation. JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 98 (1): (66-76). [PMID:] |
| 31. Su Ji-Ling, Wang Juan, Fu Xiao-Na, Hou Li, Zhu Ping, Zhang Kai, Li Huo-Wang, Hou Ying, Liu Xiang-Yi, Xu Juan. (2022) Fatty acid composition and thermal characteristics of Malania oleifera seed oil. Advanced Composites and Hybrid Materials, 5 (2): (1268-1279). [PMID:] |
| 32. Yi-Tong Wang, Di Gao, Ya-Nan Zeng, Jun-Guo Li, Ai-Min Ji, Tian-Ji Liu, Shuang Cai, Wen-Jie Cong, Fu-Ping Wang, Qing Yu, Xiao-Man Wang, Zhen Fang. (2022) Efficient production of biodiesel with electric furnace dust impregnated in Na2CO3 solution. Journal of Cleaner Production, 330 (129772). [PMID:] |