Caprate (10:0) (BioDeep_00000002198)

 

Secondary id: BioDeep_00000229630, BioDeep_00000400541, BioDeep_00000405291, BioDeep_00000860736

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product BioNovoGene_Lab2019 Volatile Flavor Compounds


代谢物信息卡片


decanoic acid

化学式: C10H20O2 (172.14632200000003)
中文名称: 癸酸(C10:0), 正癸酸, 癸酸
谱图信息: 最多检出来源 Homo sapiens(feces) 0.04%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Caprate (10:0). BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/caprate_(10:0) (retrieved 2024-11-22) (BioDeep RN: BioDeep_00000002198). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CCCCCCCCCC(=O)O
InChI: InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)

描述信息

Capric acid, also known as decanoic acid is a C10 saturated fatty acid. It is a member of the series of fatty acids found in oils and animal fats. The names of caproic, caprylic, and capric acids are all derived from the word caper (Latin for goat). These fatty acids are light yellowish transparent oily liquids with a sweaty, unpleasant aroma that is reminiscent of goats. Capric acid is used in the manufacture of esters for artificial fruit flavors and perfumes. It is also used as an intermediate in chemical syntheses. Capric acid is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals. Capric acid occurs naturally in coconut oil (about 10\\\\\\%) and palm kernel oil (about 4\\\\\\%), otherwise it is uncommon in typical seed oils. It is found in the milk of various mammals and to a lesser extent in other animal fats. Capric acid, caproic acid (a C6:0 fatty acid) and caprylic acid (a C8:0 fatty acid) account for about 15\\\\\\% of the fatty acids in goat milk fat (PMID 16747831). Capric acid may be responsible for the mitochondrial proliferation associated with the ketogenic diet, which may occur via PPARgamma receptor agonism and the targeting of genes involved in mitochondrial biogenesis (PMIDL 24383952).
Widespread in plant oils and as glycerides in seed oilsand is also present in apple, apricot, banana, morello cherry, citrus fruits, cheese, butter, white wine, Japanese whiskey, peated malt, wort and scallops. It is used as a defoamer, lubricant and citrus fruit coating. Salts (Na, K, Mg, Ca, Al) used as binders, emulsifiers and anticaking agents in food manuf. Decanoic acid is found in many foods, some of which are radish (variety), meatball, phyllo dough, and american shad.

Decanoic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=334-48-5 (retrieved 2024-06-29) (CAS RN: 334-48-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Decanoic acid, a component of medium chain triclycerides, is a brain-penetrant and non-competitive inhibitor of AMPA receptor. Decanoic acid has antiseizure effects[1][2][3].
Decanoic acid, a component of medium chain triclycerides, is a brain-penetrant and non-competitive inhibitor of AMPA receptor. Decanoic acid has antiseizure effects[1][2][3].
Decanoic acid, a component of medium chain triclycerides, is a brain-penetrant and non-competitive inhibitor of AMPA receptor. Decanoic acid has antiseizure effects[1][2][3].

同义名列表

39 个代谢物同义名

Decanoic acid, sodium salt; 1-Nonanecarboxylic acid; 1-Nonanecarboxylate; Sodium decanoate; n-Decanoic acid; CH3-[CH2]8-COOH; Sodium caprate; N-Decylic acid; N-Capric acid; Decanoic acid; Caprynic acid; N-Decoic acid; Caprinic acid; Kaprinsaeure; Decylic acid; Lunac 10-95; N-Decanoate; Capric acid; Decoic acid; Dekansaeure; Lunac 10-98; Prifac 2906; N-Decylate; Prifac 296; Emery 659; N-Caprate; Caprinate; Decanoate; N-Decoate; Caprynate; FA(10:0); Decylate; Caprate; Decoate; C10:0; 10:0; Decanoic acid; Decanoic acid; Decanoic acid



数据库引用编号

31 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(5)

BioCyc(0)

PlantCyc(0)

代谢反应

37 个相关的代谢反应过程信息。

Reactome(28)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(9)

PharmGKB(0)

393 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

  • Shang Li, Junyu Zhai, Weiwei Chu, Xueying Geng, Dongshuang Wang, Luwei Jiao, Gang Lu, Wai-Yee Chan, Kang Sun, Yun Sun, Zi-Jiang Chen, Yanzhi Du. Alleviation of Limosilactobacillus reuteri in polycystic ovary syndrome protects against circadian dysrhythmia-induced dyslipidemia via capric acid and GALR1 signaling. NPJ biofilms and microbiomes. 2023 Jul; 9(1):47. doi: 10.1038/s41522-023-00415-2. [PMID: 37422471]
  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Huyen Tran, Eitaro Aihara, Faiz Ahmad Mohammed, Hongchang Qu, Andrew Riley, Yuan Su, Xianyin Lai, Siyuan Huang, Aktham Aburub, Jack Jia Hua Chen, Olivia Hope Vitale, Yanbin Lao, Selina Estwick, Zhonghua Qi, Mohamed E H ElSayed. In Vivo Mechanism of Action of Sodium Caprate for Improving the Intestinal Absorption of a GLP1/GIP Coagonist Peptide. Molecular pharmaceutics. 2023 02; 20(2):929-941. doi: 10.1021/acs.molpharmaceut.2c00443. [PMID: 36592951]
  • Cigdem Sahin, Lilia Magomedova, Thais A M Ferreira, Jiabao Liu, Jens Tiefenbach, Priscilla S Alves, Fellipe J G Queiroz, Andressa S de Oliveira, Mousumi Bhattacharyya, Julie Grouleff, Patrícia C N Nogueira, Edilberto R Silveira, Daniel C Moreira, José Roberto Souza de Almeida Leite, Guilherme D Brand, David Uehling, Gennady Poda, Henry Krause, Carolyn L Cummins, Luiz A S Romeiro. Phenolic Lipids Derived from Cashew Nut Shell Liquid to Treat Metabolic Diseases. Journal of medicinal chemistry. 2022 02; 65(3):1961-1978. doi: 10.1021/acs.jmedchem.1c01542. [PMID: 35089724]
  • Ruimin Miao, Fanqi Jin, Zhigao Wang, Weijia Lu, Junhong Liu, Xinyang Li, Rui Xue Zhang. Oral delivery of decanoic acid conjugated plant protein shell incorporating hybrid nanosystem leverage intestinal absorption of polyphenols. Biomaterials. 2022 02; 281(?):121373. doi: 10.1016/j.biomaterials.2022.121373. [PMID: 35063742]
  • Staffan Berg, Lillevi Kärrberg, Denny Suljovic, Frank Seeliger, Magnus Söderberg, Marta Perez-Alcazar, Natalie Van Zuydam, Bertil Abrahamsson, Andreas M Hugerth, Nigel Davies, Christel A S Bergström. Impact of Intestinal Concentration and Colloidal Structure on the Permeation-Enhancing Efficiency of Sodium Caprate in the Rat. Molecular pharmaceutics. 2022 01; 19(1):200-212. doi: 10.1021/acs.molpharmaceut.1c00724. [PMID: 34928160]
  • Rosita Kneiszl, Shakhawath Hossain, Per Larsson. In Silico-Based Experiments on Mechanistic Interactions between Several Intestinal Permeation Enhancers with a Lipid Bilayer Model. Molecular pharmaceutics. 2022 01; 19(1):124-137. doi: 10.1021/acs.molpharmaceut.1c00689. [PMID: 34913341]
  • Huijuan Zheng, Weilin Liu, Shuibing Yang. Carboxymethyl chitosan coated medium-chain fatty acid nanoliposomes: structure, composition, stability and in vitro release investigation. Food & function. 2021 Oct; 12(20):9947-9954. doi: 10.1039/d1fo01985f. [PMID: 34492679]
  • Julián Paul Martínez-Galán, Catalina María Ontibón-Echeverri, Mariana Campos Costa, Alexander Batista-Duharte, Vinicius Guerso Batista, Victoria Mesa, Rubens Monti, Ariela Veloso de Paula, Amanda Martins Baviera. Enzymatic synthesis of capric acid-rich structured lipids and their effects on mice with high-fat diet-induced obesity. Food research international (Ottawa, Ont.). 2021 10; 148(?):110602. doi: 10.1016/j.foodres.2021.110602. [PMID: 34507747]
  • Jens V Andersen, Emil W Westi, Emil Jakobsen, Nerea Urruticoechea, Karin Borges, Blanca I Aldana. Astrocyte metabolism of the medium-chain fatty acids octanoic acid and decanoic acid promotes GABA synthesis in neurons via elevated glutamine supply. Molecular brain. 2021 09; 14(1):132. doi: 10.1186/s13041-021-00842-2. [PMID: 34479615]
  • Jakub Suchodolski, Daria Derkacz, Przemysław Bernat, Anna Krasowska. Capric acid secreted by Saccharomyces boulardii influences the susceptibility of Candida albicans to fluconazole and amphotericin B. Scientific reports. 2021 03; 11(1):6519. doi: 10.1038/s41598-021-86012-9. [PMID: 33753842]
  • Witek Kwiatkowski, Radoslaw Bomba, Pavel Afanasyev, Daniel Boehringer, Roland Riek, Jason Greenwald. Prebiotic Peptide Synthesis and Spontaneous Amyloid Formation Inside a Proto-Cellular Compartment. Angewandte Chemie (International ed. in English). 2021 03; 60(10):5561-5568. doi: 10.1002/anie.202015352. [PMID: 33325627]
  • Xiumei Wang, Xiaoxu Zhao, Xiaoli Qin, Zexin Zhao, Bo Yang, Yonghua Wang. Immobilized MAS1 Lipase-catalyzed Synthesis of n-3 PUFA-rich Triacylglycerols in Deep Eutectic Solvents. Journal of oleo science. 2021 Feb; 70(2):227-236. doi: 10.5650/jos.ess20200. [PMID: 33456003]
  • Partha Dabke, Graham Brogden, Hassan Y Naim, Anibh M Das. Ketogenic Diet: Impact on Cellular Lipids in Hippocampal Murine Neurons. Nutrients. 2020 Dec; 12(12):. doi: 10.3390/nu12123870. [PMID: 33352829]
  • Partha Dabke, Anibh M Das. Mechanism of Action of Ketogenic Diet Treatment: Impact of Decanoic Acid and Beta-Hydroxybutyrate on Sirtuins and Energy Metabolism in Hippocampal Murine Neurons. Nutrients. 2020 Aug; 12(8):. doi: 10.3390/nu12082379. [PMID: 32784510]
  • Mohamad Nasir Shafiee, Catharine A Ortori, David A Barrett, Nigel P Mongan, Jafaru Abu, William Atiomo. Lipidomic Biomarkers in Polycystic Ovary Syndrome and Endometrial Cancer. International journal of molecular sciences. 2020 Jul; 21(13):. doi: 10.3390/ijms21134753. [PMID: 32635401]
  • Caroline Twarog, Kai Liu, Peter J O'Brien, Kenneth A Dawson, Elias Fattal, Brigitte Illel, David J Brayden. A head-to-head Caco-2 assay comparison of the mechanisms of action of the intestinal permeation enhancers: SNAC and sodium caprate (C10). European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2020 Jul; 152(?):95-107. doi: 10.1016/j.ejpb.2020.04.023. [PMID: 32387703]
  • Seyedeh Maedeh Majidi, Mohammad Reza Hadjmohammadi. Hydrophobic borneol-based natural deep eutectic solvents as a green extraction media for air-assisted liquid-liquid micro-extraction of warfarin in biological samples. Journal of chromatography. A. 2020 Jun; 1621(?):461030. doi: 10.1016/j.chroma.2020.461030. [PMID: 32192705]
  • Abbey E Wilson, Darrell L Sparks, Katrina K Knott, Scott Willard, Ashli Brown. Simultaneous choice bioassays accompanied by physiological changes identify civetone and decanoic acid as pheromone candidates for giant pandas. Zoo biology. 2020 May; 39(3):176-185. doi: 10.1002/zoo.21532. [PMID: 31919913]
  • Meryem Köse, Thanigaimalai Pillaiyar, Vigneshwaran Namasivayam, Elisabetta De Filippo, Katharina Sylvester, Trond Ulven, Ivar von Kügelgen, Christa E Müller. An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights. Journal of medicinal chemistry. 2020 03; 63(5):2391-2410. doi: 10.1021/acs.jmedchem.9b01339. [PMID: 31721581]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Hubertine M E Willems, Jeremy S Stultz, Molly E Coltrane, Jabez P Fortwendel, Brian M Peters. Disparate Candida albicans Biofilm Formation in Clinical Lipid Emulsions Due to Capric Acid-Mediated Inhibition. Antimicrobial agents and chemotherapy. 2019 11; 63(11):. doi: 10.1128/aac.01394-19. [PMID: 31405860]
  • Julie Enderlin, Anna Loussouarn, Jean-François Benoist, Blandine Dozières-Puyravel, Stéphane Auvin. Absence of increased blood decanoic acid levels in children with epilepsy treated with classic ketogenic diet. Epileptic disorders : international epilepsy journal with videotape. 2019 Aug; 21(4):366-369. doi: 10.1684/epd.2019.1079. [PMID: 31366451]
  • Sung Ill Jang, Seok Jeong, Don Haeng Lee, Kun Na, Sugeun Yang, Dong Ki Lee. Safety Evaluation of Paclitaxel-Eluting Biliary Metal Stent with Sodium Caprate in Porcine Biliary Tract. Gut and liver. 2019 04; 13(4):471-478. doi: 10.5009/gnl18454. [PMID: 30970427]
  • Chunxiao Ren, Qiqi Zhou, Wutai Guan, Xiaofeng Lin, Yijiang Wang, Hanqing Song, Yinzhi Zhang. Immune Response of Piglets Receiving Mixture of Formic and Propionic Acid Alone or with Either Capric Acid or Bacillus Licheniformis after Escherichia coli Challenge. BioMed research international. 2019; 2019(?):6416187. doi: 10.1155/2019/6416187. [PMID: 31019970]
  • Yawen Li, Angelina Angelova, Jianwen Liu, Vasil M Garamus, Na Li, Markus Drechsler, Yabin Gong, Aihua Zou. In situ phase transition of microemulsions for parenteral injection yielding lyotropic liquid crystalline carriers of the antitumor drug bufalin. Colloids and surfaces. B, Biointerfaces. 2019 Jan; 173(?):217-225. doi: 10.1016/j.colsurfb.2018.09.023. [PMID: 30296646]
  • A Yu Lyudinina, G E Ivankova, E R Bojko. Priority use of medium-chain fatty acids during high-intensity exercise in cross-country skiers. Journal of the International Society of Sports Nutrition. 2018 Dec; 15(1):57. doi: 10.1186/s12970-018-0265-4. [PMID: 30526607]
  • Tim Erkens, Ruud Bueters, Marjolein van Heerden, Filip Cuyckens, Rob Vreeken, Nick Goeminne, Lieve Lammens. Translational safety biomarkers of colonic barrier integrity in the rat. Journal of applied toxicology : JAT. 2018 10; 38(10):1282-1292. doi: 10.1002/jat.3639. [PMID: 29781175]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • John P Gleeson, Jesús M Frías, Sinéad M Ryan, David J Brayden. Sodium caprate enables the blood pressure-lowering effect of Ile-Pro-Pro and Leu-Lys-Pro in spontaneously hypertensive rats by indirectly overcoming PepT1 inhibition. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2018 Jul; 128(?):179-187. doi: 10.1016/j.ejpb.2018.04.021. [PMID: 29684535]
  • Joanne Heade, Sam Maher, Sinead B Bleiel, David J Brayden. Labrasol® and Salts of Medium-Chain Fatty Acids Can Be Combined in Low Concentrations to Increase the Permeability of a Macromolecule Marker Across Isolated Rat Intestinal Mucosae. Journal of pharmaceutical sciences. 2018 06; 107(6):1648-1655. doi: 10.1016/j.xphs.2018.02.012. [PMID: 29462634]
  • Cristina Caleja, Lillian Barros, João C M Barreira, Ana Ciric, Marina Sokovic, Ricardo C Calhelha, M Beatriz, P P Oliveira, Isabel C F R Ferreira. Suitability of lemon balm (Melissa officinalis L.) extract rich in rosmarinic acid as a potential enhancer of functional properties in cupcakes. Food chemistry. 2018 Jun; 250(?):67-74. doi: 10.1016/j.foodchem.2018.01.034. [PMID: 29412929]
  • Changwon Yang, Whasun Lim, Fuller W Bazer, Gwonhwa Song. Decanoic acid suppresses proliferation and invasiveness of human trophoblast cells by disrupting mitochondrial function. Toxicology and applied pharmacology. 2018 01; 339(?):121-132. doi: 10.1016/j.taap.2017.12.009. [PMID: 29248464]
  • Jitka Čejková, Martin M Hanczyc, František Štěpánek. Multi-Armed Droplets as Shape-Changing Protocells. Artificial life. 2018; 24(1):71-79. doi: 10.1162/artl_a_00255. [PMID: 29369709]
  • Najla Bentrad, Rabéa Gaceb-Terrak, Fatma Rahmania. Identification and evaluation of antibacterial agents present in lipophilic fractions isolated from sub-products of Phoenix dactilyfera. Natural product research. 2017 Nov; 31(21):2544-2548. doi: 10.1080/14786419.2017.1314282. [PMID: 28403631]
  • Elakkiya Venugopal, Govindarajan Ramadoss, Kannan Krishnan, Sujith Subash Eranezhath, Amitava Bhattacharyya, Selvakumar Rajendran. Stimulation of human osteoblast cells (MG63) proliferation using decanoic acid and isopropyl amine fractions of Wattakaka volubilis leaves. The Journal of pharmacy and pharmacology. 2017 Nov; 69(11):1578-1591. doi: 10.1111/jphp.12801. [PMID: 28809438]
  • J Li, X-W Xie, H Zhou, B Wang, M-J Zhang, F-Y Tang. Metabolic profiling reveals new serum biomarkers of lupus nephritis. Lupus. 2017 Oct; 26(11):1166-1173. doi: 10.1177/0961203317694256. [PMID: 28420061]
  • Michael C Wamberg, Pernille L Pedersen, Philipp M G Löffler, Anders N Albertsen, Sarah E Maurer, Kent A Nielsen, Pierre-Alain Monnard. Synthesis of Lipophilic Guanine N-9 Derivatives: Membrane Anchoring of Nucleobases Tailored to Fatty Acid Vesicles. Bioconjugate chemistry. 2017 07; 28(7):1893-1905. doi: 10.1021/acs.bioconjchem.7b00228. [PMID: 28587449]
  • Mario M Müller, Roland Lehmann, Tilman E Klassert, Stella Reifenstein, Theresia Conrad, Christoph Moore, Anna Kuhn, Andrea Behnert, Reinhard Guthke, Dominik Driesch, Hortense Slevogt. Global analysis of glycoproteins identifies markers of endotoxin tolerant monocytes and GPR84 as a modulator of TNFα expression. Scientific reports. 2017 04; 7(1):838. doi: 10.1038/s41598-017-00828-y. [PMID: 28404994]
  • Bo Kyeong Yoon, Joshua A Jackman, Min Chul Kim, Tun Naw Sut, Nam-Joon Cho. Correlating Membrane Morphological Responses with Micellar Aggregation Behavior of Capric Acid and Monocaprin. Langmuir : the ACS journal of surfaces and colloids. 2017 03; 33(11):2750-2759. doi: 10.1021/acs.langmuir.6b03944. [PMID: 28263610]
  • F G Dupuy, S P Fernández Bordín, B Maggio, R G Oliveira. Hexagonal phase with ordered acyl chains formed by a short chain asymmetric ceramide. Colloids and surfaces. B, Biointerfaces. 2017 Jan; 149(?):89-96. doi: 10.1016/j.colsurfb.2016.10.009. [PMID: 27736726]
  • E A Sphakova, V N Sorokoumov, A V Akenti’ev, K V Derkach, T B Tennikova, A O Shpakov. THE RELATIONSHIP BETWEEN PHYSICAL-CHEMICAL CHARACTERISTICS AND BIOLOGICAL ACTIVITY OF PEPTIDE 562—572 OF LUTEINIZING HORMONE RECEPTOR MODIFIED BY DECANOYL RADICALS AT THE N- AND C-TERMINI. Tsitologiia. 2017 ; 59(2):133-9. doi: . [PMID: 30199161]
  • Rojeet Shrestha, Ken-Ichi Hirano, Akira Suzuki, Satoshi Yamaguchi, Yusuke Miura, Yi-Fan Chen, Masahiro Mizuta, Hitoshi Chiba, Shu-Ping Hui. Change in Plasma Total, Esterified and Non-esterified Capric Acid Concentrations during a Short-term Oral Administration of Synthetic Tricaprin in Dogs. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2017; 33(11):1297-1303. doi: 10.2116/analsci.33.1297. [PMID: 29129871]
  • Sara Crotti, Elisa Agnoletto, Gabriella Cancemi, Valerio Di Marco, Pietro Traldi, Salvatore Pucciarelli, Donato Nitti, Marco Agostini. Altered plasma levels of decanoic acid in colorectal cancer as a new diagnostic biomarker. Analytical and bioanalytical chemistry. 2016 Sep; 408(23):6321-8. doi: 10.1007/s00216-016-9743-1. [PMID: 27379390]
  • Weijia Chen, Shengnan Wei, Yang Yu, Huan Xue, Fan Yao, Ming Zhang, Jun Xiao, Grant M Hatch, Li Chen. Pretreatment of rats with increased bioavailable berberine attenuates cerebral ischemia-reperfusion injury via down regulation of adenosine-5'monophosphate kinase activity. European journal of pharmacology. 2016 May; 779(?):80-90. doi: 10.1016/j.ejphar.2016.03.015. [PMID: 26957053]
  • Pishan Chang, Katrin Augustin, Kim Boddum, Sophie Williams, Min Sun, John A Terschak, Jörg D Hardege, Philip E Chen, Matthew C Walker, Robin S B Williams. Seizure control by decanoic acid through direct AMPA receptor inhibition. Brain : a journal of neurology. 2016 Feb; 139(Pt 2):431-43. doi: 10.1093/brain/awv325. [PMID: 26608744]
  • Tomoki Abe, Katsuya Hirasaka, Shohei Kohno, Chisato Tomida, Marie Haruna, Takayuki Uchida, Ayako Ohno, Motoko Oarada, Shigetada Teshima-Kondo, Yuushi Okumura, Inho Choi, Toshiaki Aoyama, Junji Terao, Takeshi Nikawa. Capric Acid Up-Regulates UCP3 Expression without PDK4 Induction in Mouse C2C12 Myotubes. Journal of nutritional science and vitaminology. 2016; 62(1):32-9. doi: 10.3177/jnsv.62.32. [PMID: 27117849]
  • Bao Hui Lee, Inthrani Raja Indran, Huey Min Tan, Yu Li, Zhiwei Zhang, Jun Li, Eu-Leong Yong. A Dietary Medium-Chain Fatty Acid, Decanoic Acid, Inhibits Recruitment of Nur77 to the HSD3B2 Promoter In Vitro and Reverses Endocrine and Metabolic Abnormalities in a Rat Model of Polycystic Ovary Syndrome. Endocrinology. 2016 Jan; 157(1):382-94. doi: 10.1210/en.2015-1733. [PMID: 26465200]
  • Charles D Rutter, Shuyan Zhang, Christopher V Rao. Engineering Yarrowia lipolytica for production of medium-chain fatty acids. Applied microbiology and biotechnology. 2015 Sep; 99(17):7359-68. doi: 10.1007/s00253-015-6764-1. [PMID: 26129951]
  • Rojeet Shrestha, Shu-Ping Hui, Hiromitsu Imai, Satoru Hashimoto, Naoto Uemura, Seiji Takeda, Hirotoshi Fuda, Akira Suzuki, Satoshi Yamaguchi, Ken-Ichi Hirano, Hitoshi Chiba. Plasma capric acid concentrations in healthy subjects determined by high-performance liquid chromatography. Annals of clinical biochemistry. 2015 Sep; 52(Pt 5):588-96. doi: 10.1177/0004563215569081. [PMID: 25587197]
  • Dennis Fiorini, Deborah Pacetti, Rosita Gabbianelli, Serena Gabrielli, Roberto Ballini. A salting out system for improving the efficiency of the headspace solid-phase microextraction of short and medium chain free fatty acids. Journal of chromatography. A. 2015 Aug; 1409(?):282-7. doi: 10.1016/j.chroma.2015.07.051. [PMID: 26210111]
  • Keita Ikari, Yuka Sakuma, Takehiro Jimbo, Atsuji Kodama, Masayuki Imai, Pierre-Alain Monnard, Steen Rasmussen. Dynamics of fatty acid vesicles in response to pH stimuli. Soft matter. 2015 Aug; 11(31):6327-34. doi: 10.1039/c5sm01248a. [PMID: 26166464]
  • Jing Fu, Baogui Wang, Deming Gong, Cheng Zeng, Yihao Jiang, Zheling Zeng. Camphor Tree Seed Kernel Oil Reduces Body Fat Deposition and Improves Blood Lipids in Rats. Journal of food science. 2015 Aug; 80(8):H1912-7. doi: 10.1111/1750-3841.12943. [PMID: 26130050]
  • David J Brayden, Sam Maher, Bojlul Bahar, Edwin Walsh. Sodium caprate-induced increases in intestinal permeability and epithelial damage are prevented by misoprostol. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2015 Aug; 94(?):194-206. doi: 10.1016/j.ejpb.2015.05.013. [PMID: 26026287]
  • Santiago Garcia-Vallvé, Laura Guasch, Sarah Tomas-Hernández, Josep Maria del Bas, Vincent Ollendorff, Lluís Arola, Gerard Pujadas, Miquel Mulero. Peroxisome Proliferator-Activated Receptor γ (PPARγ) and Ligand Choreography: Newcomers Take the Stage. Journal of medicinal chemistry. 2015 Jul; 58(14):5381-94. doi: 10.1021/jm501155f. [PMID: 25734377]
  • Kervin O Evans, Joseph A Laszlo, David L Compton. Hydroxytyrosol and tyrosol esters partitioning into, location within, and effect on DOPC liposome bilayer behavior. Biochimica et biophysica acta. 2015 May; 1848(5):1175-82. doi: 10.1016/j.bbamem.2015.02.002. [PMID: 25687972]
  • María García-Díaz, Camilla Foged, Hanne Mørck Nielsen. Improved insulin loading in poly(lactic-co-glycolic) acid (PLGA) nanoparticles upon self-assembly with lipids. International journal of pharmaceutics. 2015 Mar; 482(1-2):84-91. doi: 10.1016/j.ijpharm.2014.11.047. [PMID: 25445991]
  • Ahmed M A Moustafa, Jun Huang, Kerry N McPhedran, Hongbo Zeng, Mohamed Gamal El-Din. Probing the adsorption of weak acids on graphite using amplitude modulation-frequency modulation atomic force microscopy. Langmuir : the ACS journal of surfaces and colloids. 2015 Mar; 31(10):3069-75. doi: 10.1021/la5048968. [PMID: 25710305]
  • Piotr Wlaź, Katarzyna Socała, Dorota Nieoczym, Tomasz Żarnowski, Iwona Żarnowska, Stanisław J Czuczwar, Maciej Gasior. Acute anticonvulsant effects of capric acid in seizure tests in mice. Progress in neuro-psychopharmacology & biological psychiatry. 2015 Mar; 57(?):110-6. doi: 10.1016/j.pnpbp.2014.10.013. [PMID: 25445478]
  • Kazumi Hayama, Miki Takahashi, Motofumi Suzuki, Kunio Ezawa, Masatoshi Yamazaki, Taiji Matsukawa, Akinobu Kishi, Nobuya Sato, Shigeru Abe. [Anti-Candida activity of aroma candy and its protective activity against murine oral candidiasis]. Medical mycology journal. 2015; 56(1):J23-9. doi: 10.3314/mmj.56.j23. [PMID: 25855024]
  • Xuli Du, Jian Zhang, Yan Zhang, Shuang Li, Xia Lin, Xing Tang, Yu Zhang, Yanjiao Wang. Decanoic acid grafted oligochitosan nanoparticles as a carrier for insulin transport in the gastrointestinal tract. Carbohydrate polymers. 2014 Oct; 111(?):433-41. doi: 10.1016/j.carbpol.2014.04.048. [PMID: 25037372]
  • Lianying Zhang, Xiao-Min Ren, Bin Wan, Liang-Hong Guo. Structure-dependent binding and activation of perfluorinated compounds on human peroxisome proliferator-activated receptor γ. Toxicology and applied pharmacology. 2014 Sep; 279(3):275-283. doi: 10.1016/j.taap.2014.06.020. [PMID: 24998974]
  • David J Brayden, Edwin Walsh. Efficacious intestinal permeation enhancement induced by the sodium salt of 10-undecylenic acid, a medium chain fatty acid derivative. The AAPS journal. 2014 Sep; 16(5):1064-76. doi: 10.1208/s12248-014-9634-3. [PMID: 24961919]
  • A N Albertsen, S E Maurer, K A Nielsen, P-A Monnard. Transmission of photo-catalytic function in a self-replicating chemical system: in situ amphiphile production over two protocell generations. Chemical communications (Cambridge, England). 2014 Aug; 50(64):8989-92. doi: 10.1039/c4cc01543f. [PMID: 24983026]
  • Kristina Eisinger, Sabrina Krautbauer, Tobias Hebel, Gerd Schmitz, Charalampos Aslanidis, Gerhard Liebisch, Christa Buechler. Lipidomic analysis of the liver from high-fat diet induced obese mice identifies changes in multiple lipid classes. Experimental and molecular pathology. 2014 Aug; 97(1):37-43. doi: 10.1016/j.yexmp.2014.05.002. [PMID: 24830603]
  • Meng Zhaojie, Zhang Ming, Wei Shengnan, Bi Xiaojia, Grant M Hatch, Gu Jingkai, Chen Li. Amorphous solid dispersion of berberine with absorption enhancer demonstrates a remarkable hypoglycemic effect via improving its bioavailability. International journal of pharmaceutics. 2014 Jun; 467(1-2):50-9. doi: 10.1016/j.ijpharm.2014.03.017. [PMID: 24607213]
  • Shubin Dong, Jiacong Huang, Yannan Li, Jing Zhang, Shanzhi Lin, Zhixiang Zhang. Cloning, characterization, and expression analysis of acyl-acyl carrier protein (ACP)-thioesterase B from seeds of Chinese Spicehush (Lindera communis). Gene. 2014 May; 542(1):16-22. doi: 10.1016/j.gene.2014.03.028. [PMID: 24631366]
  • Sean David Hughes, Marta Kanabus, Glenn Anderson, Iain P Hargreaves, Tricia Rutherford, Maura O'Donnell, J Helen Cross, Shamima Rahman, Simon Eaton, Simon J R Heales. The ketogenic diet component decanoic acid increases mitochondrial citrate synthase and complex I activity in neuronal cells. Journal of neurochemistry. 2014 May; 129(3):426-33. doi: 10.1111/jnc.12646. [PMID: 24383952]
  • Carlos M Monreal, Amarpreet Chahal, Owen Rowland, Myron Smith, Morris Schnitzer. Metabolism of nC11 fatty acid fed to Trichoderma koningii and Penicillium janthinellum II: Production of intracellular and extracellular lipids. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2014; 49(12):955-65. doi: 10.1080/03601234.2014.951583. [PMID: 25310811]
  • Amarpreet Chahal, Carlos M Monreal, John Bissett, Owen Rowland, Myron L Smith, S Shea Miller. Metabolism of n-C10:0 and n-C11:0 fatty acids by Trichoderma koningii, Penicillium janthinellum and their mixed culture: I. Biomass and CO2 production, and allocation of intracellular lipids. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2014; 49(12):945-54. doi: 10.1080/03601234.2014.951581. [PMID: 25310810]
  • Avery Sengupta, Mahua Ghosh, Dipak K Bhattacharyya. Antioxidative effect of rice bran oil and medium chain fatty acid rich rice bran oil in arsenite induced oxidative stress in rats. Journal of oleo science. 2014; 63(11):1117-24. doi: 10.5650/jos.ess14128. [PMID: 25354877]
  • Michael Shilling, Laurie Matt, Evelyn Rubin, Mark Paul Visitacion, Nairmeen A Haller, Scott F Grey, Christopher J Woolverton. Antimicrobial effects of virgin coconut oil and its medium-chain fatty acids on Clostridium difficile. Journal of medicinal food. 2013 Dec; 16(12):1079-85. doi: 10.1089/jmf.2012.0303. [PMID: 24328700]
  • Ying Chen, Xinmin Liu, Ruile Pan, Xiaoxin Zhu, André Steinmetz, Yonghong Liao, Ning Wang, Bo Peng, Qi Chang. Intestinal transport of 3,6'-disinapoylsucrose, a major active component of Polygala tenuifolia, using Caco-2 cell monolayer and in situ rat intestinal perfusion models. Planta medica. 2013 Oct; 79(15):1434-9. doi: 10.1055/s-0033-1350794. [PMID: 24043590]
  • Dongjiao Fan, Xiaorong Wu, Wenna Dong, Wei Sun, Jinzhuo Li, Xing Tang. Enhancement by sodium caprate and sodium deoxycholate of the gastrointestinal absorption of berberine chloride in rats. Drug development and industrial pharmacy. 2013 Sep; 39(9):1447-56. doi: 10.3109/03639045.2012.723219. [PMID: 23020091]
  • Lorna J Smith, Ysobel Roby, Jane R Allison, Wilfred F van Gunsteren. Molecular dynamics simulations of barley and maize lipid transfer proteins show different ligand binding preferences in agreement with experimental data. Biochemistry. 2013 Jul; 52(30):5029-38. doi: 10.1021/bi4006573. [PMID: 23834513]
  • Ping Liu, Andriy Chernyshov, Tarek Najdi, Yao Fu, Julie Dickerson, Suzanne Sandmeyer, Laura Jarboe. Membrane stress caused by octanoic acid in Saccharomyces cerevisiae. Applied microbiology and biotechnology. 2013 Apr; 97(7):3239-51. doi: 10.1007/s00253-013-4773-5. [PMID: 23435986]
  • Makiko Washiyama, Naoya Koizumi, Makiko Fujii, Masuo Kondoh, Kiyohito Yagi, Yoshiteru Watanabe. Percolation analysis in electrical conductivity of Madin-Darby canine kidney and Caco-2 cells by permeation-enhancing agents. Biological & pharmaceutical bulletin. 2013; 36(3):384-9. doi: 10.1248/bpb.b12-00786. [PMID: 23449326]
  • Wei Zhou, Kun Ming Qin, Jin Jun Shan, Wen Zheng Ju, Shi Jia Liu, Bao Chang Cai, Liu Qing Di. Improvement of intestinal absorption of forsythoside A in weeping forsythia extract by various absorption enhancers based on tight junctions. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2012 Dec; 20(1):47-58. doi: 10.1016/j.phymed.2012.09.014. [PMID: 23089157]
  • Wei-pu Zhang, Wei-bin Ruan, Yun-ying Deng, Yu-bao Gao. Potential antagonistic effects of nine natural fatty acids against Meloidogyne incognita. Journal of agricultural and food chemistry. 2012 Nov; 60(46):11631-7. doi: 10.1021/jf3036885. [PMID: 23121218]
  • Ming Zhang, Xiaoyan Lv, Jing Li, Zhaojie Meng, Qiujing Wang, WenGuang Chang, Wei Li, Li Chen, Yanjun Liu. Sodium caprate augments the hypoglycemic effect of berberine via AMPK in inhibiting hepatic gluconeogenesis. Molecular and cellular endocrinology. 2012 Nov; 363(1-2):122-30. doi: 10.1016/j.mce.2012.08.006. [PMID: 22922125]
  • Yiran Ma, Li Zhang, Xinyi Zhao, Qi Shen. Analysis of daidzein in nanoparticles after oral co-administration with sodium caprate to rats by ultra-performance liquid chromatography-quadrupole-time-of-flight mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Oct; 907(?):21-6. doi: 10.1016/j.jchromb.2012.08.026. [PMID: 23010479]
  • G Del Vecchio, C Tscheik, K Tenz, H C Helms, L Winkler, R Blasig, I E Blasig. Sodium caprate transiently opens claudin-5-containing barriers at tight junctions of epithelial and endothelial cells. Molecular pharmaceutics. 2012 Sep; 9(9):2523-33. doi: 10.1021/mp3001414. [PMID: 22827574]
  • Hiraku Onishi, Yu Imura, Minoru Uchida, Yoshiharu Machida. Enhancement potential of sucrose laurate (L-1695) on intestinal absorption of water-soluble high molecular weight compounds. Current drug delivery. 2012 Sep; 9(5):487-94. doi: 10.2174/156720112802650699. [PMID: 22520068]
  • Joost Groen, David W Deamer, Alexander Kros, Pascale Ehrenfreund. Polycyclic aromatic hydrocarbons as plausible prebiotic membrane components. Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life. 2012 Aug; 42(4):295-306. doi: 10.1007/s11084-012-9292-3. [PMID: 22798228]
  • John J Sheehan, Kristin R Reilly, Dong-Jing Fu, Larry Alphs. Comparison of the peak-to-trough fluctuation in plasma concentration of long-acting injectable antipsychotics and their oral equivalents. Innovations in clinical neuroscience. 2012 Jul; 9(7-8):17-23. doi: NULL. [PMID: 22984648]
  • Mounika Chnadhapuram, Yella Reddy Sunkireddy. Preparation of palm olein enriched with medium chain fatty acids by lipase acidolysis. Food chemistry. 2012 May; 132(1):216-21. doi: 10.1016/j.foodchem.2011.10.059. [PMID: 26434283]
  • Avery Sengupta, Mahua Ghosh. Comparison of native and capric acid-enriched mustard oil effects on oxidative stress and antioxidant protection in rats. The British journal of nutrition. 2012 Mar; 107(6):845-9. doi: 10.1017/s0007114511003874. [PMID: 22040386]
  • Giselli Scaini, Kellen R Simon, Anelise M Tonin, Estela N B Busanello, Alana P Moura, Gustavo C Ferreira, Moacir Wajner, Emilio L Streck, Patrícia F Schuck. Toxicity of octanoate and decanoate in rat peripheral tissues: evidence of bioenergetic dysfunction and oxidative damage induction in liver and skeletal muscle. Molecular and cellular biochemistry. 2012 Feb; 361(1-2):329-35. doi: 10.1007/s11010-011-1119-4. [PMID: 22015654]
  • Amar Zellagui, Noureddine Gherraf, Segni Ladjel, Samir Hameurlaine. Chemical composition and antibacterial activity of the essential oils from Launaea resedifolia L. Organic and medicinal chemistry letters. 2012 Jan; 2(1):2. doi: 10.1186/2191-2858-2-2. [PMID: 22373506]
  • Rui F P Pereira, Maria J Tapia, Artur J M Valente, Hugh D Burrows. Effect of metal ion hydration on the interaction between sodium carboxylates and aluminum(III) or chromium(III) ions in aqueous solution. Langmuir : the ACS journal of surfaces and colloids. 2012 Jan; 28(1):168-77. doi: 10.1021/la2034164. [PMID: 22107111]
  • Raghu R V Malapaka, SokKean Khoo, Jifeng Zhang, Jang H Choi, X Edward Zhou, Yong Xu, Yinhan Gong, Jun Li, Eu-Leong Yong, Michael J Chalmers, Lin Chang, James H Resau, Patrick R Griffin, Y Eugene Chen, H Eric Xu. Identification and mechanism of 10-carbon fatty acid as modulating ligand of peroxisome proliferator-activated receptors. The Journal of biological chemistry. 2012 Jan; 287(1):183-195. doi: 10.1074/jbc.m111.294785. [PMID: 22039047]
  • Mengshu Wang, Bingxue Sun, Jiao Feng, Haihong Zhang, Bin Liu, Chun Li, Yan Chen, Yong Zhang, Wei Kong. Investigation of transport mechanism of exendin-4 across Madin Darby canine kidney cell monolayers. Biological & pharmaceutical bulletin. 2012; 35(5):745-52. doi: 10.1248/bpb.35.745. [PMID: 22687411]
  • Shigeharu Inouye, Miki Takahashi, Shigeru Abe. [Inhibitory activity of hydrosols prepared from 18 Japanese herbs of weak aromatic flavor against filamentous formation and growth of Candida albicans]. Medical mycology journal. 2012; 53(1):33-40. doi: 10.3314/mmj.53.33. [PMID: 22467129]
  • Eriko Harada, Jun Nakagawa, Tsunaki Asano, Masato Taoka, Hiroyuki Sorimachi, Yoshihiro Ito, Toshiro Aigaki, Takashi Matsuo. Functional evolution of duplicated odorant-binding protein genes, Obp57d and Obp57e, in Drosophila. PloS one. 2012; 7(1):e29710. doi: 10.1371/journal.pone.0029710. [PMID: 22238638]
  • Bianca Silva Ferreira, Lara Pereira Faza, Mireille Le Hyaric. A comparison of the physicochemical properties and fatty acid composition of indaiá (Attalea dubia) and Babassu (Orbignya phalerata) oils. TheScientificWorldJournal. 2012; 2012(?):532374. doi: 10.1100/2012/532374. [PMID: 22593692]
  • Wei-Luen Yu, William Ansari, Nathan G Schoepp, Michael J Hannon, Stephen P Mayfield, Michael D Burkart. Modifications of the metabolic pathways of lipid and triacylglycerol production in microalgae. Microbial cell factories. 2011 Nov; 10(?):91. doi: 10.1186/1475-2859-10-91. [PMID: 22047615]
  • Ingrid Elisia, David D Kitts. Quantification of hexanal as an index of lipid oxidation in human milk and association with antioxidant components. Journal of clinical biochemistry and nutrition. 2011 Nov; 49(3):147-52. doi: 10.3164/jcbn.10-142. [PMID: 22128211]
  • Raffaella Di Cagno, Maria De Angelis, Ilaria De Pasquale, Maurice Ndagijimana, Pamela Vernocchi, Patrizia Ricciuti, Francesca Gagliardi, Luca Laghi, Carmine Crecchio, Maria Elisabetta Guerzoni, Marco Gobbetti, Ruggiero Francavilla. Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC microbiology. 2011 Oct; 11(?):219. doi: 10.1186/1471-2180-11-219. [PMID: 21970810]
  • Takafumi Toyohara, Takehiro Suzuki, Yasutoshi Akiyama, Daisuke Yoshihara, Yoichi Takeuchi, Eikan Mishima, Koichi Kikuchi, Chitose Suzuki, Masayuki Tanemoto, Sadayoshi Ito, Shizuko Nagao, Tomoyoshi Soga, Takaaki Abe. Metabolomic profiling of the autosomal dominant polycystic kidney disease rat model. Clinical and experimental nephrology. 2011 Oct; 15(5):676-687. doi: 10.1007/s10157-011-0467-4. [PMID: 21695416]