DUB OM HTO (BioDeep_00000000894)

 

Secondary id: BioDeep_00000861806

PANOMIX_OTCML-2023


代谢物信息卡片


(Z)-9-octadecenoic acid, methyl ester;methyl (Z)-9-octadecenoate;methyl cis-9-octadecenoate;methyl-cis-oleate

化学式: C19H36O2 (296.2715156)
中文名称: 油酸甲酯
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 2.84%

分子结构信息

SMILES: C(=C/CCCCCCCC)/CCCCCCCC(OC)=O
InChI: InChI=1S/C19H36O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h10-11H,3-9,12-18H2,1-2H3/b11-10-

描述信息

Oleic acid methyl ester is a clear to amber liquid. Insoluble in water. (NTP, 1992)
Methyl oleate is a fatty acid methyl ester resulting from the formal condensation of the carboxy group of oleic acid with methanol. It is functionally related to an oleic acid.
Methyl oleate is a natural product found in Anchietea pyrifolia, Lepidium meyenii, and other organisms with data available.
Methyl oleate is a fatty acid methyl ester (FAME). Methyl oleate substantially improves the antioxidation ability but markedly impaired the antiwear capacity of zinc dialkyldithiophosphate (ZDDP)[1].
Methyl oleate is a fatty acid methyl ester (FAME). Methyl oleate substantially improves the antioxidation ability but markedly impaired the antiwear capacity of zinc dialkyldithiophosphate (ZDDP)[1].

同义名列表

63 个代谢物同义名

(Z)-9-octadecenoic acid, methyl ester;methyl (Z)-9-octadecenoate;methyl cis-9-octadecenoate;methyl-cis-oleate; Methyl Oleate, Pharmaceutical Secondary Standard; Certified Reference Material; 9-Octadecenoic acid (9Z)-, methyl ester, sulfurized, copper-treated; 9-Octadecenoic acid (Z)-, methyl ester, sulfurized, copper-treated; Methyl oleate, United States Pharmacopeia (USP) Reference Standard; 9-octadecenoic acid, methyl ester, (9E)-; 9-Octadecenoic acid (9Z)-, methyl ester; cis-9-Octyldecenoic acid, methyl ester; 9-OCTADECENOIC ACID(CIS), METHYL ESTER; 9-Octadecenoic acid (Z)-, methyl ester; Octadecenoic acid methyl ester, 9-(Z)-; cis-9-Octadecenoic acid, methyl ester; (Z)-9-Octadecenoic acid, methyl ester; 9-octadecenoic acid, methyl ester (Z); 1B317D43-CBCA-4348-B5B9-4687B6A3C698; cis-9-octadecenoic acid methyl ester; Methyl oleate, technical grade, 70\\%; (Z)-9-Octadecenoic acid methyl ester; Methyl oleate, analytical standard; Oleic acid, methyl ester, cis-; OLEIC ACID METHYL ESTER (CIS); Methyl (9Z)-9-octadecenoate #; Methyl 9-octadecenoate, cis-; Methyl (9Z)-octadec-9-enoate; methyl (Z)-octadec-9-enoate; cis-Methyl oleic acid ester; Methyl 9-(Z)-octadecenoate; Methyl (Z)-9-octadecenoate; Methyl cis-9-octadecenoate; (Z)-9-Methyl octadecenoate; methyl oleate, (E)-isomer; Methyl Oleate, 99per cent; Methyl oleate, tech grade; Oleic acid, methyl ester; Methyl Z-9-octadecenoate; oleic acid methyl ester; Emery, oleic acid ester; Oleic acid-methyl ester; METHYL OLEATE (USP-RS); METHYL OLEATE [USP-RS]; Methyl 9-octadecenoate; METHYL OLEATE [INCI]; METHYL OLEATE [HSDB]; Methyl oleate, 99\\%; Methyl (Z)-9-oleate; methyl-cis-oleate; AEC METHYL OLEATE; Edenor Me 90/95V; Oleic acid, cis-; methyl elaidate; methyl oleoate; Exceparl M-OL; WLN: 9U8VO1-C; Methyl oleate; Edenor MeTiO5; methyl oleat; methyloleate; Tox21_200225; DUB OM HTO; AI3-00651; SFE 19:1; C19H36O2; methyl octadec-9-enoate



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

72 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

  • Marta Martinez-Garcia, Wouter Van Hecke, Hilde Peeters, Dries Gabriels, Pieter Van der Weeën, Winnie Dejonghe, Yamini Satyawali. Methyl oleate for plant protection products formulations: Enzymatic synthesis, reaction kinetics and application testing. Journal of biotechnology. 2024 Jan; 379(?):78-86. doi: 10.1016/j.jbiotec.2023.12.004. [PMID: 38072327]
  • María Molina-Gutiérrez, Leonor Rodríguez-Sánchez, Carmen Doñoro, M Jesús Martínez, Alicia Prieto. Sustainable and Green Synthesis of Stanol Esters from Oil Wastes. Journal of agricultural and food chemistry. 2021 Jan; 69(1):286-293. doi: 10.1021/acs.jafc.0c06581. [PMID: 33375783]
  • Julien Peyrton, Clémence Chambaretaud, Luc Avérous. New Insight on the Study of the Kinetic of Biobased Polyurethanes Synthesis Based on Oleo-Chemistry. Molecules (Basel, Switzerland). 2019 Nov; 24(23):. doi: 10.3390/molecules24234332. [PMID: 31783536]
  • Juan Carlos de Haro, Daniel López-Pedrajas, Ángel Pérez, Juan Francisco Rodríguez, Manuel Carmona. Synthesis of rigid polyurethane foams from phosphorylated biopolyols. Environmental science and pollution research international. 2019 Feb; 26(4):3174-3183. doi: 10.1007/s11356-017-9765-z. [PMID: 28822032]
  • Todd Clark Brelje, Nicholas V Bhagroo, Laurence E Stout, Robert L Sorenson. Prolactin and oleic acid synergistically stimulate β-cell proliferation and growth in rat islets. Islets. 2017 07; 9(4):e1330234. doi: 10.1080/19382014.2017.1330234. [PMID: 28686504]
  • Hosni Sassi, Frank Delvigne, Tambi Kar, Jean-Marc Nicaud, Anne-Marie Crutz-Le Coq, Sebastien Steels, Patrick Fickers. Deciphering how LIP2 and POX2 promoters can optimally regulate recombinant protein production in the yeast Yarrowia lipolytica. Microbial cell factories. 2016 Sep; 15(1):159. doi: 10.1186/s12934-016-0558-8. [PMID: 27651221]
  • Hui Fan, Jonathan Smuts, Ling Bai, Phillip Walsh, Daniel W Armstrong, Kevin A Schug. Gas chromatography-vacuum ultraviolet spectroscopy for analysis of fatty acid methyl esters. Food chemistry. 2016 Mar; 194(?):265-71. doi: 10.1016/j.foodchem.2015.08.004. [PMID: 26471553]
  • Shiva Shanker Kaki, Sammaiah Arukali, Padmaja V Korlipara, R B N Prasad, Poornachandra Yedla, C Ganesh Kumar. Synthesis and biological evaluation of novel lipoamino acid derivatives. Bioorganic & medicinal chemistry letters. 2016 Jan; 26(1):209-12. doi: 10.1016/j.bmcl.2015.10.086. [PMID: 26586599]
  • Sara Santos, José Graça. Stereochemistry of C18 monounsaturated cork suberin acids determined by spectroscopic techniques including (1) H-NMR multiplet analysis of olefinic protons. Phytochemical analysis : PCA. 2014 May; 25(3):192-200. doi: 10.1002/pca.2491. [PMID: 24307616]
  • A B Seres, E Ducza, M Báthori, A Hunyadi, Z Béni, M Dékány, J Hajagos-Tóth, J Verli, Róbert Gáspár. Androgenic effect of honeybee drone milk in castrated rats: roles of methyl palmitate and methyl oleate. Journal of ethnopharmacology. 2014 Apr; 153(2):446-53. doi: 10.1016/j.jep.2014.02.050. [PMID: 24607508]
  • Arturo Morales, Susana Marmesat, M Carmen Dobarganes, Gloria Márquez-Ruiz, Joaquín Velasco. Evaporative light scattering detector in normal-phase high-performance liquid chromatography determination of FAME oxidation products. Journal of chromatography. A. 2012 Sep; 1254(?):62-70. doi: 10.1016/j.chroma.2012.07.028. [PMID: 22840820]
  • Chenxing Sun, Yuan-Yuan Zhao, Jonathan M Curtis. A study of the ozonolysis of model lipids by electrospray ionization mass spectrometry. Rapid communications in mass spectrometry : RCM. 2012 Apr; 26(8):921-30. doi: 10.1002/rcm.6183. [PMID: 22396028]
  • Yang Liu, Huai-feng Yi, Yu Chen, Yu-long Wu, Ming-de Yang, Zeng Chen, Jun-mao Tong. [Column chromatography purification and analysis of biodiesel by transesterification]. Guang pu xue yu guang pu fen xi = Guang pu. 2012 Feb; 32(2):505-9. doi: ". [PMID: 22512199]
  • Shaheen Faizi, Shahina Fayyaz, Samina Bano, Erum Yawar Iqbal, Lubna, Humaira Siddiqi, Aneela Naz. Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae. Journal of agricultural and food chemistry. 2011 Sep; 59(17):9080-93. doi: 10.1021/jf201611b. [PMID: 21780738]
  • Dauenpen Meesapyodsuk, Xiao Qiu. A peroxygenase pathway involved in the biosynthesis of epoxy fatty acids in oat. Plant physiology. 2011 Sep; 157(1):454-63. doi: 10.1104/pp.111.178822. [PMID: 21784965]
  • Purabi Roy, Sarika Amdekar, Avnish Kumar, Vinod Singh. Preliminary study of the antioxidant properties of flowers and roots of Pyrostegia venusta (Ker Gawl) Miers. BMC complementary and alternative medicine. 2011 Aug; 11(?):69. doi: 10.1186/1472-6882-11-69. [PMID: 21861910]
  • Naoya Morinaga, Atsushi Maeda, Takayuki Mizuno, Masanori Bunya, Shigeo Sugihara, Akio Sugihara. Synthesis of fatty acid sterol esters using cholesterol esterase from Trichoderma sp. AS59. Enzyme and microbial technology. 2011 May; 48(6-7):498-504. doi: 10.1016/j.enzmictec.2011.02.007. [PMID: 22113022]
  • Ill-Min Chung, Min-A Yeo, Sun-Jin Kim, Hyung-In Moon. Anti-complement activity of essential oils from red and black rice bran. International journal of food sciences and nutrition. 2011 May; 62(3):215-8. doi: 10.3109/09637486.2010.503187. [PMID: 20673187]
  • Atanu Biswas, Brajendra K Sharma, Karl Vermillion, J L Willett, H N Cheng. Preparation of acetonides from soybean oil, methyl soyate, and fatty esters. Journal of agricultural and food chemistry. 2011 Apr; 59(7):3066-70. doi: 10.1021/jf1026229. [PMID: 21375297]
  • Jumat Salimon, Nadia Salih, Bashar Mudhaffar Abdullah. Improvement of physicochemical characteristics of monoepoxide linoleic acid ring opening for biolubricant base oil. Journal of biomedicine & biotechnology. 2011; 2011(?):196565. doi: 10.1155/2011/196565. [PMID: 22131799]
  • Jae Su Kim, Yeon Ho Je, En Ok Woo, Jong Sung Park. Persistence of Isaria fumosorosea (Hypocreales: Cordycipitaceae) SFP-198 conidia in corn oil-based suspension. Mycopathologia. 2011 Jan; 171(1):67-75. doi: 10.1007/s11046-010-9336-z. [PMID: 20571913]
  • Muchtaridi, Anas Subarnas, Anton Apriyantono, Resmi Mustarichie. Identification of compounds in the essential oil of nutmeg seeds (Myristica fragrans Houtt.) that inhibit locomotor activity in mice. International journal of molecular sciences. 2010 Nov; 11(11):4771-81. doi: 10.3390/ijms11114771. [PMID: 21151471]
  • T A Misharina, M B Terenina, N I Krikunova, I B Medvedeva. [Autooxidation of a mixture of lemon essential oils, methyl linolenoate, and methyl oleinate]. Prikladnaia biokhimiia i mikrobiologiia. 2010 Sep; 46(5):599-604. doi: ". [PMID: 21061607]
  • Arjen VanDoorn, Mario Kallenbach, Alejandro A Borquez, Ian T Baldwin, Gustavo Bonaventure. Rapid modification of the insect elicitor N-linolenoyl-glutamate via a lipoxygenase-mediated mechanism on Nicotiana attenuata leaves. BMC plant biology. 2010 Aug; 10(?):164. doi: 10.1186/1471-2229-10-164. [PMID: 20696061]
  • Ru Yang, Mengxing Su, Min Li, Jianchun Zhang, Xinmin Hao, Hua Zhang. One-pot process combining transesterification and selective hydrogenation for biodiesel production from starting material of high degree of unsaturation. Bioresource technology. 2010 Aug; 101(15):5903-9. doi: 10.1016/j.biortech.2010.02.095. [PMID: 20231090]
  • L M Ovsepian, G V Kazarian, A V Zakharian, G V Zakarian, M V L'vov. [Effect of cysteine lithium salt on lipid peroxidation in the model of dopaminergic system disorder]. Eksperimental'naia i klinicheskaia farmakologiia. 2010 Jul; 73(7):16-8. doi: . [PMID: 20821974]
  • Kevin Huvaere, Daniel R Cardoso, Paula Homem-de-Mello, Signe Westermann, Leif H Skibsted. Light-induced oxidation of unsaturated lipids as sensitized by flavins. The journal of physical chemistry. B. 2010 Apr; 114(16):5583-93. doi: 10.1021/jp9121744. [PMID: 20377218]
  • Gino A Kurian, Srilalitha Suryanarayanan, Archana Raman, Jose Padikkala. Antioxidant effects of ethyl acetate extract of Desmodium gangeticum root on myocardial ischemia reperfusion injury in rat hearts. Chinese medicine. 2010 Jan; 5(?):3. doi: 10.1186/1749-8546-5-3. [PMID: 20180993]
  • Sabreen F Fostok, Rima A Ezzeddine, Fadia R Homaidan, Jamal A Al-Saghir, Ralph G Salloum, Najat A Saliba, Rabih S Talhouk. Interleukin-6 and Cyclooxygenase-2 downregulation by fatty-acid fractions of Ranunculus constantinopolitanus. BMC complementary and alternative medicine. 2009 Nov; 9(?):44. doi: 10.1186/1472-6882-9-44. [PMID: 19917107]
  • Catherine M Klapperich, Cassandra L Noack, Jessica D Kaufman, Lin Zhu, Laetitia Bonnaillie, Richard P Wool. A novel biocompatible adhesive incorporating plant-derived monomers. Journal of biomedical materials research. Part A. 2009 Nov; 91(2):378-84. doi: 10.1002/jbm.a.32250. [PMID: 18980208]
  • Atanu Biswas, Brajendra K Sharma, Kenneth M Doll, Sevim Z Erhan, Julious L Willett, H N Cheng. Synthesis of an amine-oleate derivative using an ionic liquid catalyst. Journal of agricultural and food chemistry. 2009 Sep; 57(18):8136-41. doi: 10.1021/jf901401s. [PMID: 19719124]
  • Thaddao Waraho, Vladimiro Cardenia, Maria T Rodriguez-Estrada, D Julian McClements, Eric A Decker. Prooxidant mechanisms of free fatty acids in stripped soybean oil-in-water emulsions. Journal of agricultural and food chemistry. 2009 Aug; 57(15):7112-7. doi: 10.1021/jf901270m. [PMID: 19572645]
  • Satoshi Yoshida, Qin-Zeng Zhang, Shu Sakuyama, Satoshi Matsushima. Metabolism of fatty acids and lipid hydroperoxides in human body monitoring with Fourier transform Infrared Spectroscopy. Lipids in health and disease. 2009 Jul; 8(?):28. doi: 10.1186/1476-511x-8-28. [PMID: 19627618]
  • Lei Guo, Guo Qing Li. Olfactory perception of oviposition-deterring fatty acids and their methyl esters by the Asian corn borer, Ostrinia furnacalis. Journal of insect science (Online). 2009; 9(?):1-9. doi: 10.1673/031.009.6701. [PMID: 20053122]
  • Bassie B Marvey. Extrudate versus powder silica alumina as support for Re₂O₇ catalyst in the metathesis of seed oil-derivatives - a comparison. International journal of molecular sciences. 2009 Jan; 10(1):213-220. doi: 10.3390/ijms10010213. [PMID: 19333442]
  • M C Fernandez-Cerejido, F Bastida, J Menendez. The effect of several adjuvants on glufosinate effectiveness in Conyza species. Communications in agricultural and applied biological sciences. 2009; 74(2):525-32. doi: ". [PMID: 20222614]
  • Marie Zarevúcka, Zdeněk Wimmer. Plant products for pharmacology: application of enzymes in their transformations. International journal of molecular sciences. 2008 Dec; 9(12):2447-2473. doi: 10.3390/ijms9122447. [PMID: 19330086]
  • Mariusz Kepczyński, Kinga Nawalany, Marta Kumorek, Agnieszka Kobierska, Barbara Jachimska, Maria Nowakowska. Which physical and structural factors of liposome carriers control their drug-loading efficiency?. Chemistry and physics of lipids. 2008 Sep; 155(1):7-15. doi: 10.1016/j.chemphyslip.2008.05.174. [PMID: 18590712]
  • Atanu Biswas, Brajendra K Sharma, J L Willett, Atanu Advaryu, S Z Erhan, H N Cheng. Azide derivatives of soybean oil and fatty esters. Journal of agricultural and food chemistry. 2008 Jul; 56(14):5611-6. doi: 10.1021/jf800123t. [PMID: 18558698]
  • Jyunichi Kawata, Munekazu Kameda, Mitsuo Miyazawa. Cyclooxygenase-2 inhibitory effects and composition of the volatile oil from the dried roots of Lithospermum erythrorhizon. Journal of natural medicines. 2008 Apr; 62(2):239-43. doi: 10.1007/s11418-007-0221-0. [PMID: 18404332]
  • Guoguang Liu, Xiaohua Kong, Hayley Wan, Suresh Narine. Production of 9-hydroxynonanoic Acid from methyl oleate and conversion into lactone monomers for the synthesis of biodegradable polylactones. Biomacromolecules. 2008 Mar; 9(3):949-53. doi: 10.1021/bm7012235. [PMID: 18271512]
  • James D Vasta, Bernard Fried, Joseph Sherma. High performance thin layer chromatographic analysis of neutral lipids in the urine of BALB/c mice infected with Echinostoma caproni. Parasitology research. 2008 Mar; 102(4):625-9. doi: 10.1007/s00436-007-0798-y. [PMID: 18040717]
  • G Márquez-Ruiz, F Holgado, M C García-Martínez, M C Dobarganes. 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. 2007 Sep; 1165(1-2):122-7. doi: 10.1016/j.chroma.2007.08.001. [PMID: 17706232]
  • Muhammad Ishtiaq Ch, Yang F Wen, YiYu Cheng. Gas chromatographic/mass spectrometric analysis of the essential oil of Houttuynia cordata Thunb by using on-column methylation with tetramethylammonium acetate. Journal of AOAC International. 2007 Jan; 90(1):60-7. doi: . [PMID: 17373437]
  • Ivan Tubert-Brohman, Orlando Acevedo, William L Jorgensen. Elucidation of hydrolysis mechanisms for fatty acid amide hydrolase and its Lys142Ala variant via QM/MM simulations. Journal of the American Chemical Society. 2006 Dec; 128(51):16904-13. doi: 10.1021/ja065863s. [PMID: 17177441]
  • V A Men'shov, L N Shishkina. [Effect of hydrophobicity of yeast cell envelope on the rate of autooxidation of methyloleate]. Biofizika. 2006 May; 51(3):491-8. doi: ". [PMID: 16808349]
  • L N Shishkina, N V Khrustova. [The kinetic characteristics of lipids of animal tissues in autooxidation reactions]. Biofizika. 2006 Mar; 51(2):340-6. doi: ". [PMID: 16637343]
  • Xiao Yi Li, Leif A Eriksson. Photoreaction of skin-sensitizing trimethyl psoralen with lipid membrane models. Photochemistry and photobiology. 2005 Sep; 81(5):1153-60. doi: 10.1562/2005-03-21-ra-467. [PMID: 15882092]
  • Katrin Sinderhauf, Wolfgang Schwack. Photodegradation of phosmet in wool wax models and on sheep wool: determination of wool wax bound phosmet by means of isotope ratio mass spectrometry. Journal of agricultural and food chemistry. 2005 Jun; 53(12):4873-9. doi: 10.1021/jf047834b. [PMID: 15941329]
  • Jacqueline Destain, Patrick Fickers, Frédéric Weekers, Benoît Moreau, Philippe Thonart. Utilization of methyloleate in production of microbial lipase. Applied biochemistry and biotechnology. 2005; 121-124(?):269-77. doi: 10.1385/abab:121:1-3:0269. [PMID: 15917605]
  • Katrin Sinderhauf, Wolfgang Schwack. Photodegradation chemistry of the insecticide phosmet in lipid models and in the presence of wool wax, employing a 15N-labeled compound. Journal of agricultural and food chemistry. 2004 Dec; 52(26):8046-52. doi: 10.1021/jf048537+. [PMID: 15612794]
  • J Menéndez, F Bastida. The correlation of the spraying volume with herbicide adherence and herbicide penetration in glyphosate treatments. Communications in agricultural and applied biological sciences. 2004; 69(4):815-20. doi: ". [PMID: 15756875]
  • Ahmet C Gören, Gökhan Bilsel, Mehmet Altun, Fatih Satil, Tuncay Dirmenci. Fatty acid composition of seeds of Satureja thymbra and S. cuneifolia. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2003 Jul; 58(7-8):502-4. doi: 10.1515/znc-2003-7-810. [PMID: 12939035]
  • C Cecutti, D Agius, B Caussade, A Gaset. Fate in the soil of an oil additive of plant origin. Pest management science. 2002 Dec; 58(12):1236-42. doi: 10.1002/ps.587. [PMID: 12476997]
  • Jia-Rong Duan, Isabelle Billault, Françoise Mabon, Richard Robins. Natural deuterium distribution in fatty acids isolated from peanut seed oil: a site-specific study by quantitative 2H NMR spectroscopy. Chembiochem : a European journal of chemical biology. 2002 Aug; 3(8):752-9. doi: 10.1002/1439-7633(20020802)3:8<752::aid-cbic752>3.0.co;2-g. [PMID: 12203973]
  • Robert J Bartelt, Allard A Cossé, Richard J Petroski, David K Weaver. Cuticular hydrocarbons and novel alkenediol iacetates from wheat stem sawfly (Cephus cinctus): natural oxidation to pheromone components. Journal of chemical ecology. 2002 Feb; 28(2):385-405. doi: 10.1023/a:1017994410538. [PMID: 11925075]
  • B H Chen, Y C Chen. Formation of polycyclic aromatic hydrocarbons in the smoke from heated model lipids and food lipids. Journal of agricultural and food chemistry. 2001 Nov; 49(11):5238-43. doi: 10.1021/jf0106906. [PMID: 11714310]
  • N Weber, P Weitkamp, K D Mukherjee. Steryl and stanyl esters of fatty acids by solvent-free esterification and transesterification in vacuo using lipases from Rhizomucor miehei, Candida antarctica, and Carica papaya. Journal of agricultural and food chemistry. 2001 Nov; 49(11):5210-6. doi: 10.1021/jf0107407. [PMID: 11714305]
  • I S Chen, H F Chen, M J Cheng, Y L Chang, C M Teng, I Tsutomu, J J Chen, I L Tsai. Quinoline alkaloids and other constituents of Melicope semecarpifolia with antiplatelet aggregation activity. Journal of natural products. 2001 Sep; 64(9):1143-7. doi: 10.1021/np010122k. [PMID: 11575945]
  • M Buchgraber, F Ulberth. Determination of trans octadecenoic acids by silver-ion chromatography-gas liquid chromatography: an intercomparison of methods. Journal of AOAC International. 2001 Sep; 84(5):1490-8. doi: ". [PMID: 11601469]
  • V Roginsky, T Barsukova. Superoxide dismutase inhibits lipid peroxidation in micelles. Chemistry and physics of lipids. 2001 May; 111(1):87-91. doi: 10.1016/s0009-3084(01)00148-7. [PMID: 11438286]
  • D E Breithaupt, W Schwack. Photoinduced addition of the fungicide anilazine to cyclohexene and methyl oleate as model compounds of plant cuticle constituents. Chemosphere. 2000 Nov; 41(9):1401-6. doi: 10.1016/s0045-6535(99)90553-2. [PMID: 11057576]
  • Y Matsumura, C Satake, M Egami, T Mori. Interaction of gum arabic, maltodextrin and pullulan with lipids in emulsions. Bioscience, biotechnology, and biochemistry. 2000 Sep; 64(9):1827-35. doi: 10.1271/bbb.64.1827. [PMID: 11055384]
  • V V Kalytka, H V Donchenko. [Antioxidant activity of the drug distinol in vitro]. Ukrainskii biokhimicheskii zhurnal (1978). 1995 Jul; 67(4):87-92. doi: . [PMID: 8553479]
  • M H Lee, J W Park. Lipid peroxidation products mediate damage of superoxide dismutase. Biochemistry and molecular biology international. 1995 Apr; 35(5):1093-102. doi: ". [PMID: 7549928]
  • V V Kaytka, H V Donchenko. [Antioxidant properties of products of the interaction of amino acids with carbohydrates under conditions of the Maillard reaction]. Ukrainskii biokhimicheskii zhurnal (1978). 1995 Mar; 67(2):71-5. doi: ". [PMID: 8592789]
  • M Geoffroy, P Lambelet, P Richert. Radical intermediates and antioxidants: an ESR study of radicals formed on carnosic acid in the presence of oxidized lipids. Free radical research. 1994 Sep; 21(4):247-58. doi: 10.3109/10715769409056576. [PMID: 7827696]
  • L N Shishkina, Iu P Taran, S V Eliseeva, V G Bulgakov. [The effect of 6-methyluracil on oxidative reactions in model systems of varying degrees of complexity]. Izvestiia Akademii nauk. Seriia biologicheskaia. 1992 May; ?(3):350-7. doi: ". [PMID: 1304850]
  • E B Burlakova, N M Storozhok, N G Khrapova. [Synergistic effect of antioxidants and phospholipids during oxidation of natural lipids]. Voprosy pitaniia. 1990 Jul; ?(4):53-8. doi: ". [PMID: 2244364]
  • E B Burlakova, N M Storozhok, N G Khrapova, V V Naumov, E N Kukhtina. [The study of the additive antioxidative activity of total natural lipid antioxidants]. Voprosy meditsinskoi khimii. 1990 Jul; 36(4):72-4. doi: ". [PMID: 2238537]
  • P W Wertz, D T Downing. Metabolism of topically applied fatty acid methyl esters in BALB/C mouse epidermis. Journal of dermatological science. 1990 Jan; 1(1):33-7. doi: 10.1016/0923-1811(90)90007-z. [PMID: 2078539]
  • B E Bihain, R J Deckelbaum, F T Yen, A M Gleeson, Y A Carpentier, L D Witte. Unesterified fatty acids inhibit the binding of low density lipoproteins to the human fibroblast low density lipoprotein receptor. The Journal of biological chemistry. 1989 Oct; 264(29):17316-21. doi: . [PMID: 2793857]
  • A R Merrill, H Aubry, P Proulx, A G Szabo. Relation between Ca2+ uptake and fluidity of brush-border membranes isolated from rabbit small intestine and incubated with fatty acids and methyl oleate. Biochimica et biophysica acta. 1987 Jan; 896(1):89-95. doi: 10.1016/0005-2736(87)90359-2. [PMID: 3790590]
  • S Yoshida, T Tamura, M Tamura, M Takeshita, H Terao, T Fujioka, T Itoga. Evidence for the presence of fatty acid methyl esters in human hepatoma tissue from a patient with hypercholesterolemia. Journal of applied biochemistry. 1984 Oct; 6(5-6):314-8. doi: ". [PMID: 6100292]
  • S J Engelsen, M Zatz. Stimulation of fatty acid methylation in human red cell membranes by phospholipase A2 activation. Biochimica et biophysica acta. 1982 Jun; 711(3):515-20. doi: 10.1016/0005-2760(82)90067-4. [PMID: 7104380]