Caproic acid (BioDeep_00000002191)

 

Secondary id: BioDeep_00000229603, BioDeep_00000405296, BioDeep_00000405855, BioDeep_00000861084, BioDeep_00000872171

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


代谢物信息卡片


Hexanoic acid, sodium salt, 1-(11)C-labeled

化学式: C6H12O2 (116.08372519999999)
中文名称: 己酸-1,2-13C2, 己酸, 正己酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.4%

分子结构信息

SMILES: C(=O)(O)CCCCC
InChI: InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)

描述信息

Caproic acid, also known as hexanoic acid or C6:0, is a medium-chain fatty acid. Medium-chain fatty acids (MCFA) are fatty acids with aliphatic tails of 6 to 12 carbons, which can form medium-chain triglycerides. Caproic acid is a colourless oily liquid that smells like cheese with an overlying waxy or barnyard odor like that of goats or other barnyard animals. Its name comes from the Latin word capra, meaning "goat". Two other fatty acids are named after goats: caprylic acid (C8) and capric acid (C10). Along with caproic acid, they account for 15\\% of the fat in goats milk. Caproic acid is a fatty acid found naturally in various animal fats and oils. While generally more abundant in animals, caproic acid is found in all organisms ranging from bacteria to plants to animals. Caproic acid is one of the chemicals that gives the decomposing fleshy seed coat of the ginkgo fruit its characteristic unpleasant odor. It is also one of the components of vanilla and cheese. Industrially, the primary use of caproic acid is in the manufacture of its esters for use as artificial flavors and in the manufacture of hexyl derivatives, such as hexylphenols. Caproic acid has been associated with medium chain acyl-CoA dehydrogenase deficiency, which is an inborn error of metabolism. As a relatively volatile organic compound, caproic acid has been identified as a fecal biomarker of Clostridium difficile infection (PMID: 30986230).
Present in apple, wine grapes, butter, licorice and cheeses, e.g. blue cheeses, Cheddar cheese, Swiss cheese, feta cheese, gruyere de comte cheese, etcand is) also present in a few essential oils and fruital aromas. Secondary product of butyric acid fermentation. Flavouring ingredient
KEIO_ID C035

同义名列表

55 个代谢物同义名

Hexanoic acid, sodium salt, 1-(11)C-labeled; Hexanoic acid, manganese (2+) salt; Hexanoic acid, sodium salt (1:1); Hexanoic acid, rhodium (2+) salt; Hexanoic acid, copper (2+) salt; Hexanoic acid, nickel (2+) salt; Hexanoic acid, potassium salt; Hexanoic acid, calcium salt; Hexanoic acid, sodium salt; Hexanoic acid, barium salt; Caproic acid sodium salt; 1-Pentanecarboxylic acid; Pentanecarboxylic acid; Bismuth(III)hexanoate; 1-Pentanecarboxylate; Calcium N-hexanoate; Pentanecarboxylate; Calcium hexanoate; Pentylformic acid; Butylacetic acid; Sodium capronate; Sodium hexanoate; Pentiformic acid; 1-Hexanoic acid; Sodium caproate; n-Hexanoic acid; CH3-[CH2]4-COOH; N-Caproic acid; N-Hexylic acid; Capronic acid; HEXANOIC ACID; N-Hexoic acid; Pentylformate; Caproic acid; Pentiformate; Hexylic acid; Butylacetate; 1-Hexanoate; N-Hexanoate; Hexoic acid; N-Hexylate; N-Caproate; Capronate; Bi(ohex)3; N-Hexoate; Hexanoate; Caproate; Hexylate; FA(6:0); Hexoate; C6:0; 6:0; Hexanoic acid; Hexanoic acid; Hexanoic acid



数据库引用编号

33 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

18 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(18)

PharmGKB(0)

59 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

  • Rikard Fristedt, Vanessa Ruppert, Tania Trower, Janine Cooney, Rikard Landberg. Quantitation of circulating short-chain fatty acids in small volume blood samples from animals and humans. Talanta. 2024 May; 272(?):125743. doi: 10.1016/j.talanta.2024.125743. [PMID: 38382298]
  • Huiqin Shi, Wei Li, Hongyu Chen, Yao Meng, Huifang Wu, Jian Wang, Shuo Shen. Synthetic Microbial Community Members Interact to Metabolize Caproic Acid to Inhibit Potato Dry Rot Disease. International journal of molecular sciences. 2024 Apr; 25(8):. doi: 10.3390/ijms25084437. [PMID: 38674022]
  • Sergio Morales-Palomo, Clara Navarrete, José Luis Martínez, Cristina González-Fernández, Elia Tomás-Pejó. Transcriptomic profiling of an evolved Yarrowia lipolytica strain: tackling hexanoic acid fermentation to increase lipid production from short-chain fatty acids. Microbial cell factories. 2024 Apr; 23(1):101. doi: 10.1186/s12934-024-02367-4. [PMID: 38566056]
  • Yiming Ni, Liangyin Cai, Xiaojun Gou, Wenjie Li, Mingmei Zhou, Ying Huang. Therapeutic effect of Sanhua decoction on rats with middle cerebral artery occlusion and the associated changes in gut microbiota and short-chain fatty acids. PloS one. 2024; 19(2):e0298148. doi: 10.1371/journal.pone.0298148. [PMID: 38363776]
  • Hongbo Yuan, Bingke Shi, Zhuoni Wang, Genhong Qin, Hui Hou, Hongtao Tu, Li Wang. Exploration of the Biocontrol Activity of Bacillus atrophaeus Strain HF1 against Pear Valsa Canker Caused by Valsa pyri. International journal of molecular sciences. 2023 Oct; 24(20):. doi: 10.3390/ijms242015477. [PMID: 37895155]
  • Valentino Casolo, Marco Zancani, Elisa Pellegrini, Antonio Filippi, Sara Gargiulo, Dennis Konnerup, Piero Morandini, Ole Pedersen. Restricted O2 consumption in pea roots induced by hexanoic acid is linked to depletion of Krebs cycle substrates. Physiologia plantarum. 2023 Sep; 175(5):e14024. doi: 10.1111/ppl.14024. [PMID: 37882315]
  • Ji Wang, Yanhao Zhang, Shuo Dong, Wenhui Zha, Chao Liu, Yang Wang, Yuhao Jiang, Hanlei Xing, Xinsong Li. Bivalent mRNA vaccines against three SARS-CoV-2 variants mediated by new ionizable lipid nanoparticles. International journal of pharmaceutics. 2023 Jul; 642(?):123155. doi: 10.1016/j.ijpharm.2023.123155. [PMID: 37402442]
  • 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]
  • Tinh Van Nguyen, Tomeu Viver, Ilse Smets, Kristel Bernaerts, Karoline Faust, Rob Lavigne, Laurent Poughon, Claude-Gilles Dussap, Dirk Springael. Thermocaproicibacter melissae gen. nov., sp. nov., a thermophilic chain-elongating bacterium, producing n-caproate from polymeric carbohydrates. International journal of systematic and evolutionary microbiology. 2023 May; 73(5):. doi: 10.1099/ijsem.0.005893. [PMID: 37200213]
  • Ying He, Bang Cheng, Bing-Jian Guo, Zheng Huang, Jing-Hua Qin, Qian-Yi Wang, Lin-Lin Feng, Yun-Yuan Nong, Dan Zhu, Hong-Wei Guo, Zhi-Heng Su. Metabonomics and 16S rRNA gene sequencing to study the therapeutic mechanism of Danggui Sini decoction on collagen-induced rheumatoid arthritis rats with Cold Bi syndrome. Journal of pharmaceutical and biomedical analysis. 2023 Jan; 222(?):115109. doi: 10.1016/j.jpba.2022.115109. [PMID: 36270097]
  • Chongrong Shen, Yanru Chen, Qiaoling Wang, Yingkai Sun, Huibin Lin, Mengshan Ni, Yufei Chen, Ling Zhang, Jiabin Jin, Xiayang Ying, Yuyao Zou, Xiaolin Wang, Yaorui Ye, Miaomiao Yuan, Nan Yin, Zhiwen Cao, Yifei Zhang, Weiqiong Gu, Weiqing Wang, Guang Ning, Jiqiu Wang, Shaoqian Zhao, Jie Hong, Ruixin Liu. Fecal short chain fatty acids modify therapeutic effects of sleeve gastrectomy. Frontiers in endocrinology. 2023; 14(?):1277035. doi: 10.3389/fendo.2023.1277035. [PMID: 38027127]
  • Zachary A Drum, Stephen M Lanno, Sara M Gregory, Serena J Shimshak, Mukshud Ahamed, Will Barr, Bethlehem Bekele, Alison Biester, Colleen Castro, Lauren Connolly, Nicole DelGaudio, William Humphrey, Helen Karimi, Sophie Karolczak, Tay-Shaun Lawrence, Andrew McCracken, Noah Miller-Medzon, Leah Murphy, Cameron Park, Sojeong Park, Chloe Qiu, Kevin Serra, Gigi Snyder, Alexa Strauss, Spencer Tang, Christina Vyzas, Joseph D Coolon. Genomics analysis of hexanoic acid exposure in Drosophila species. G3 (Bethesda, Md.). 2022 01; 12(1):. doi: 10.1093/g3journal/jkab354. [PMID: 34718544]
  • M N Caccalano, G Dilarri, C F C Zamuner, D S Domingues, H Ferreira. Hexanoic acid: a new potential substitute for copper-based agrochemicals against citrus canker. Journal of applied microbiology. 2021 Nov; 131(5):2488-2499. doi: 10.1111/jam.15125. [PMID: 34008224]
  • Ping Song, Hui Xu, Jixiu Zhang, Huatao Chen, Li Li, Yana Qu, Feng Lin, Qun Zhang. Functional analysis of indole 3-hexanoic acid as a novel auxin from Arabidopsis thaliana. Planta. 2021 Sep; 254(4):69. doi: 10.1007/s00425-021-03719-9. [PMID: 34498125]
  • Takahiro Mori, Kiyofumi Wanibuchi, Hiroyuki Morita, Ikuro Abe. Amide Bond Formation Using 4-Coumarate: CoA Ligase from Arabidopsis thaliana. Chemical & pharmaceutical bulletin. 2021 Aug; 69(8):717-720. doi: 10.1248/cpb.c21-00404. [PMID: 34053981]
  • David R Hall, Steven J Harte, Daniel P Bray, Dudley I Farman, Rob James, Celine X Silva, Michelle T Fountain. Hero Turned Villain: Identification of Components of the Sex Pheromone of the Tomato Bug, Nesidiocoris tenuis. Journal of chemical ecology. 2021 May; 47(4-5):394-405. doi: 10.1007/s10886-021-01270-1. [PMID: 33844148]
  • Mohamed El-Far, Madeleine Durand, Isabelle Turcotte, Etienne Larouche-Anctil, Mohamed Sylla, Sarah Zaidan, Carl Chartrand-Lefebvre, Rémi Bunet, Hardik Ramani, Manel Sadouni, Irina Boldeanu, Annie Chamberland, Sylvie Lesage, Jean-Guy Baril, Benoit Trottier, Réjean Thomas, Emmanuel Gonzalez, Ali Filali-Mouhim, Jean-Philippe Goulet, Jeffrey A Martinson, Seble Kassaye, Roksana Karim, Jorge R Kizer, Audrey L French, Stephen J Gange, Petronela Ancuta, Jean-Pierre Routy, David B Hanna, Robert C Kaplan, Nicolas Chomont, Alan L Landay, Cécile L Tremblay. Upregulated IL-32 Expression And Reduced Gut Short Chain Fatty Acid Caproic Acid in People Living With HIV With Subclinical Atherosclerosis. Frontiers in immunology. 2021; 12(?):664371. doi: 10.3389/fimmu.2021.664371. [PMID: 33936102]
  • Jacob Bejder, Gözde Gürdeniz, Cătălina Cuparencu, Frederikke Hall, Mikkel Gybel-Brask, Andreas Breenfeldt Andersen, Lars Ove Dragsted, Niels H Secher, Pär I Johansson, Nikolai Baastrup Nordsborg. An Untargeted Urine Metabolomics Approach for Autologous Blood Transfusion Detection. Medicine and science in sports and exercise. 2021 01; 53(1):236-243. doi: 10.1249/mss.0000000000002442. [PMID: 32694367]
  • Marina Saresella, Ivana Marventano, Monica Barone, Francesca La Rosa, Federica Piancone, Laura Mendozzi, Alessia d'Arma, Valentina Rossi, Luigi Pugnetti, Gabriella Roda, Eleonora Casagni, Michele Dei Cas, Rita Paroni, Patrizia Brigidi, Silvia Turroni, Mario Clerici. Alterations in Circulating Fatty Acid Are Associated With Gut Microbiota Dysbiosis and Inflammation in Multiple Sclerosis. Frontiers in immunology. 2020; 11(?):1390. doi: 10.3389/fimmu.2020.01390. [PMID: 32733460]
  • Wyckliff P Omondi, Eunice A Owino, David Odongo, Joseph M Mwangangi, Baldwyn Torto, David P Tchouassi. Differential response to plant- and human-derived odorants in field surveillance of the dengue vector, Aedes aegypti. Acta tropica. 2019 Dec; 200(?):105163. doi: 10.1016/j.actatropica.2019.105163. [PMID: 31494122]
  • S M Lanno, J D Coolon. Derived esterase activity in Drosophila sechellia contributes to evolved octanoic acid resistance. Insect molecular biology. 2019 12; 28(6):798-806. doi: 10.1111/imb.12587. [PMID: 30977928]
  • Soshi Takahashi, Jun Saegusa, Akira Onishi, Akio Morinobu. Biomarkers identified by serum metabolomic analysis to predict biologic treatment response in rheumatoid arthritis patients. Rheumatology (Oxford, England). 2019 12; 58(12):2153-2161. doi: 10.1093/rheumatology/kez199. [PMID: 31143951]
  • Fei Shi, Xin Zhou, Miao-Miao Yao, Qian Zhou, Shu-Juan Ji, Yu Wang. Low-temperature stress-induced aroma loss by regulating fatty acid metabolism pathway in 'Nanguo' pear. Food chemistry. 2019 Nov; 297(?):124927. doi: 10.1016/j.foodchem.2019.05.201. [PMID: 31253294]
  • Jin Zhang, Sonja Bisch-Knaden, Richard A Fandino, Shuwei Yan, George F Obiero, Ewald Grosse-Wilde, Bill S Hansson, Markus Knaden. The olfactory coreceptor IR8a governs larval feces-mediated competition avoidance in a hawkmoth. Proceedings of the National Academy of Sciences of the United States of America. 2019 10; 116(43):21828-21833. doi: 10.1073/pnas.1913485116. [PMID: 31591212]
  • María José López-Galiano, Inmaculada García-Robles, Víctor Manuel Ruiz-Arroyo, Sara Sanchís Oltra, Marko Petek, Carolina Rausell, M Dolores Real. Colorado potato beetle chymotrypsin genes are differentially regulated in larval midgut in response to the plant defense inducer hexanoic acid or the Bacillus thuringiensis Cry3Aa toxin. Journal of invertebrate pathology. 2019 09; 166(?):107224. doi: 10.1016/j.jip.2019.107224. [PMID: 31362005]
  • Qianhong Ye, Shuang Cai, Shuai Wang, Xiangzhou Zeng, Changchuan Ye, Meixia Chen, Xiangfang Zeng, Shiyan Qiao. Maternal short and medium chain fatty acids supply during early pregnancy improves embryo survival through enhancing progesterone synthesis in rats. The Journal of nutritional biochemistry. 2019 07; 69(?):98-107. doi: 10.1016/j.jnutbio.2019.03.015. [PMID: 31063920]
  • Li-Chun Chen, Ke-Xian Chen, Xi-Ying Huang, Jian Lou, Jing-Yuan Li, Shao-Ping Deng. Vesicles from the self-assembly of the ultra-small fatty acids with amino acids under aqueous conditions. Colloids and surfaces. B, Biointerfaces. 2019 Jan; 173(?):69-76. doi: 10.1016/j.colsurfb.2018.07.007. [PMID: 30267956]
  • Wei Wei, Zhonggui He, Jincheng Yang, Mengchi Sun, Jin Sun. Cytosine arabinoside prodrug designed to bind plasma serum albumin for drug delivery. Drug delivery and translational research. 2018 10; 8(5):1162-1170. doi: 10.1007/s13346-018-0534-4. [PMID: 29748833]
  • Lisa R Hoving, Marieke Heijink, Vanessa van Harmelen, Ko Willems van Dijk, Martin Giera. GC-MS Analysis of Short-Chain Fatty Acids in Feces, Cecum Content, and Blood Samples. Methods in molecular biology (Clifton, N.J.). 2018; 1730(?):247-256. doi: 10.1007/978-1-4939-7592-1_17. [PMID: 29363078]
  • R D Peyser, S M Lanno, S J Shimshak, J D Coolon. Analysis of cytochrome P450 contribution to evolved plant toxin resistance in Drosophila sechellia. Insect molecular biology. 2017 Dec; 26(6):715-720. doi: 10.1111/imb.12329. [PMID: 28703934]
  • Arnaud T Djami-Tchatchou, Efficient N Ncube, Paul A Steenkamp, Ian A Dubery. Similar, but different: structurally related azelaic acid and hexanoic acid trigger differential metabolomic and transcriptomic responses in tobacco cells. BMC plant biology. 2017 Nov; 17(1):227. doi: 10.1186/s12870-017-1157-5. [PMID: 29187153]
  • M José López-Galiano, Víctor Manuel Ruiz-Arroyo, Emma Fernández-Crespo, Carolina Rausell, M Dolores Real, Pilar García-Agustín, Carmen González-Bosch, Inmaculada García-Robles. Oxylipin mediated stress response of a miraculin-like protease inhibitor in Hexanoic acid primed eggplant plants infested by Colorado potato beetle. Journal of plant physiology. 2017 Aug; 215(?):59-64. doi: 10.1016/j.jplph.2017.04.013. [PMID: 28578135]
  • Jing Liu, Dujuan Zhao, Wenxiu He, Huiyuan Zhang, Zhonghao Li, Yuxia Luan. Nanoassemblies from amphiphilic cytarabine prodrug for leukemia targeted therapy. Journal of colloid and interface science. 2017 Feb; 487(?):239-249. doi: 10.1016/j.jcis.2016.10.041. [PMID: 27776282]
  • Yu V Holota, O O Holubenko, A M Ostapchuk, T M Serhiychuk, L V Zakordonets, G M Tolstanova. Fecal short-chain fatty acids at different time points after ceftriaxone administration in rats. Ukrainian biochemical journal. 2017 Jan; 89(1):50-8. doi: 10.15407/ubj89.01.050. [PMID: 29236389]
  • M Roostaei-Ali Mehr, P Parisoush. Effect of Different Levels of Silymarin and Caproic Acid on Storage of Ram Semen in Liquid Form. Reproduction in domestic animals = Zuchthygiene. 2016 Aug; 51(4):569-74. doi: 10.1111/rda.12721. [PMID: 27321767]
  • Byung-Chun Kim, Byoung Seung Jeon, Seil Kim, Hyunook Kim, Youngsoon Um, Byoung-In Sang. Caproiciproducens galactitolivorans gen. nov., sp. nov., a bacterium capable of producing caproic acid from galactitol, isolated from a wastewater treatment plant. International journal of systematic and evolutionary microbiology. 2015 Dec; 65(12):4902-4908. doi: 10.1099/ijsem.0.000665. [PMID: 26474980]
  • Alberto Caminero, Esther Nistal, Alexandra R Herrán, Jénifer Pérez-Andrés, Miguel A Ferrero, Luis Vaquero Ayala, Santiago Vivas, José M G Ruiz de Morales, Silvia M Albillos, Francisco Javier Casqueiro. Differences in gluten metabolism among healthy volunteers, coeliac disease patients and first-degree relatives. The British journal of nutrition. 2015 Oct; 114(8):1157-67. doi: 10.1017/s0007114515002767. [PMID: 26428276]
  • Carlos Angulo, María de la O Leyva, Ivan Finiti, Jaime López-Cruz, Emma Fernández-Crespo, Pilar García-Agustín, Carmen González-Bosch. Role of dioxygenase α-DOX2 and SA in basal response and in hexanoic acid-induced resistance of tomato (Solanum lycopersicum) plants against Botrytis cinerea. Journal of plant physiology. 2015 Mar; 175(?):163-73. doi: 10.1016/j.jplph.2014.11.004. [PMID: 25543862]
  • Vicky De Preter, Kathleen Machiels, Marie Joossens, Ingrid Arijs, Christophe Matthys, Severine Vermeire, Paul Rutgeerts, Kristin Verbeke. Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar; 64(3):447-58. doi: 10.1136/gutjnl-2013-306423. [PMID: 24811995]
  • Catherine E Isom, Mark A Nanny, Ralph S Tanner. Improved conversion efficiencies for n-fatty acid reduction to primary alcohols by the solventogenic acetogen "Clostridium ragsdalei". Journal of industrial microbiology & biotechnology. 2015 Jan; 42(1):29-38. doi: 10.1007/s10295-014-1543-z. [PMID: 25410829]
  • Katherine E Meadows, Binoy Paulose Nadappuram, Patrick R Unwin. A new approach for the fabrication of microscale lipid bilayers at glass pipets: application to quantitative passive permeation visualization. Soft matter. 2014 Nov; 10(42):8433-41. doi: 10.1039/c3sm51406d. [PMID: 25221789]
  • Akira Sato, Hikaru Yamanaka, Keitaro Oe, Yoji Yamazaki, Keiichi Ebina. Novel fluorescently labeled peptide compounds for detection of oxidized low-density lipoprotein at high specificity. Chemical biology & drug design. 2014 Oct; 84(4):443-9. doi: 10.1111/cbdd.12333. [PMID: 24717143]
  • Ivan Finiti, María de la O Leyva, Begonya Vicedo, Rocío Gómez-Pastor, Jaime López-Cruz, Pilar García-Agustín, Maria Dolores Real, Carmen González-Bosch. Hexanoic acid protects tomato plants against Botrytis cinerea by priming defence responses and reducing oxidative stress. Molecular plant pathology. 2014 Aug; 15(6):550-62. doi: 10.1111/mpp.12112. [PMID: 24320938]
  • Buddhadev Layek, Manas K Haldar, Gitanjali Sharma, Lindsey Lipp, Sanku Mallik, Jagdish Singh. Hexanoic acid and polyethylene glycol double grafted amphiphilic chitosan for enhanced gene delivery: influence of hydrophobic and hydrophilic substitution degree. Molecular pharmaceutics. 2014 Mar; 11(3):982-94. doi: 10.1021/mp400633r. [PMID: 24499512]
  • Loredana Scalschi, Gemma Camañes, Eugenio Llorens, Emma Fernández-Crespo, María M López, Pilar García-Agustín, Begonya Vicedo. Resistance inducers modulate Pseudomonas syringae pv. tomato strain DC3000 response in tomato plants. PloS one. 2014; 9(9):e106429. doi: 10.1371/journal.pone.0106429. [PMID: 25244125]
  • M T Agler, C M Spirito, J G Usack, J J Werner, L T Angenent. Development of a highly specific and productive process for n-caproic acid production: applying lessons from methanogenic microbiomes. Water science and technology : a journal of the International Association on Water Pollution Research. 2014; 69(1):62-8. doi: 10.2166/wst.2013.549. [PMID: 24434969]
  • Inmaculada García-Robles, Camila Ochoa-Campuzano, Emma Fernández-Crespo, Gemma Camañes, Amparo C Martínez-Ramírez, Carmen González-Bosch, Pilar García-Agustín, Carolina Rausell, María Dolores Real. Combining hexanoic acid plant priming with Bacillus thuringiensis insecticidal activity against Colorado potato beetle. International journal of molecular sciences. 2013 Jun; 14(6):12138-56. doi: 10.3390/ijms140612138. [PMID: 23743826]
  • Loredana Scalschi, Begonya Vicedo, Gemma Camañes, Emma Fernandez-Crespo, Leonor Lapeña, Carmen González-Bosch, Pilar García-Agustín. Hexanoic acid is a resistance inducer that protects tomato plants against Pseudomonas syringae by priming the jasmonic acid and salicylic acid pathways. Molecular plant pathology. 2013 May; 14(4):342-55. doi: 10.1111/mpp.12010. [PMID: 23279078]
  • 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]
  • Eugenio Llorens, Emma Fernández-Crespo, Begonya Vicedo, Leonor Lapeña, Pilar García-Agustín. Enhancement of the citrus immune system provides effective resistance against Alternaria brown spot disease. Journal of plant physiology. 2013 Jan; 170(2):146-54. doi: 10.1016/j.jplph.2012.09.018. [PMID: 23260526]
  • Hassiba Aoudia, Nikoletta Ntalli, Nadhem Aissani, R Yahiaoui-Zaidi, Pierluigi Caboni. Nematotoxic phenolic compounds from Melia azedarach against Meloidogyne incognita. Journal of agricultural and food chemistry. 2012 Nov; 60(47):11675-80. doi: 10.1021/jf3038874. [PMID: 23136941]
  • 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]
  • Pierre Daumar, Cindy A Wanger-Baumann, NagaVaraKishore Pillarsetty, Laura Fabrizio, Sean D Carlin, Oleg A Andreev, Yana K Reshetnyak, Jason S Lewis. Efficient (18)F-labeling of large 37-amino-acid pHLIP peptide analogues and their biological evaluation. Bioconjugate chemistry. 2012 Aug; 23(8):1557-66. doi: 10.1021/bc3000222. [PMID: 22784215]
  • Jake M Stout, Zakia Boubakir, Stephen J Ambrose, Randy W Purves, Jonathan E Page. The hexanoyl-CoA precursor for cannabinoid biosynthesis is formed by an acyl-activating enzyme in Cannabis sativa trichomes. The Plant journal : for cell and molecular biology. 2012 Aug; 71(3):353-65. doi: 10.1111/j.1365-313x.2012.04949.x. [PMID: 22353623]
  • Lv Wang, Claus Thagaard Christophersen, Michael Joseph Sorich, Jacobus Petrus Gerber, Manya Therese Angley, Michael Allan Conlon. Elevated fecal short chain fatty acid and ammonia concentrations in children with autism spectrum disorder. Digestive diseases and sciences. 2012 Aug; 57(8):2096-102. doi: 10.1007/s10620-012-2167-7. [PMID: 22535281]
  • R A Reimer, X Pelletier, I G Carabin, M R Lyon, R J Gahler, S Wood. Faecal short chain fatty acids in healthy subjects participating in a randomised controlled trial examining a soluble highly viscous polysaccharide versus control. Journal of human nutrition and dietetics : the official journal of the British Dietetic Association. 2012 Aug; 25(4):373-7. doi: 10.1111/j.1365-277x.2012.01230.x. [PMID: 22320902]
  • Marina Himanen, Petr Prochazka, Kari Hänninen, Aimo Oikari. Phytotoxicity of low-weight carboxylic acids. Chemosphere. 2012 Jul; 88(4):426-31. doi: 10.1016/j.chemosphere.2012.02.058. [PMID: 22440635]
  • Noelia Luque, Ana Ballesteros-Gómez, Stefan van Leeuwen, Soledad Rubio. A simple and rapid extraction method for sensitive determination of perfluoroalkyl substances in blood serum suitable for exposure evaluation. Journal of chromatography. A. 2012 Apr; 1235(?):84-91. doi: 10.1016/j.chroma.2012.02.055. [PMID: 22420956]
  • Man-Ho Oh, Hyoung Seok Kim, Xia Wu, Steven D Clouse, Raymond E Zielinski, Steven C Huber. Calcium/calmodulin inhibition of the Arabidopsis BRASSINOSTEROID-INSENSITIVE 1 receptor kinase provides a possible link between calcium and brassinosteroid signalling. The Biochemical journal. 2012 Apr; 443(2):515-23. doi: 10.1042/bj20111871. [PMID: 22309147]
  • Emily B Merewitz, Hongmei Du, Wenjuan Yu, Yimin Liu, Thomas Gianfagna, Bingru Huang. Elevated cytokinin content in ipt transgenic creeping bentgrass promotes drought tolerance through regulating metabolite accumulation. Journal of experimental botany. 2012 Feb; 63(3):1315-28. doi: 10.1093/jxb/err372. [PMID: 22131157]
  • Chao Huang, Hong Wu, Zong-Jun Liu, Jun Cai, Wen-Yong Lou, Min-Hua Zong. Effect of organic acids on the growth and lipid accumulation of oleaginous yeast Trichosporon fermentans. Biotechnology for biofuels. 2012 Jan; 5(?):4. doi: 10.1186/1754-6834-5-4. [PMID: 22260291]
  • Georg Dierkes, Annette Bongartz, Helmut Guth, Heiko Hayen. Quality evaluation of olive oil by statistical analysis of multicomponent stable isotope dilution assay data of aroma active compounds. Journal of agricultural and food chemistry. 2012 Jan; 60(1):394-401. doi: 10.1021/jf203406s. [PMID: 22117816]
  • Janick Mathys, Kaat De Cremer, Pieter Timmermans, Stefan Van Kerckhove, Bart Lievens, Mieke Vanhaecke, Bruno P A Cammue, Barbara De Coninck. Genome-Wide Characterization of ISR Induced in Arabidopsis thaliana by Trichoderma hamatum T382 Against Botrytis cinerea Infection. Frontiers in plant science. 2012; 3(?):108. doi: 10.3389/fpls.2012.00108. [PMID: 22661981]
  • 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]
  • 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]
  • Harm van Bakel, Jake M Stout, Atina G Cote, Carling M Tallon, Andrew G Sharpe, Timothy R Hughes, Jonathan E Page. The draft genome and transcriptome of Cannabis sativa. Genome biology. 2011 Oct; 12(10):R102. doi: 10.1186/gb-2011-12-10-r102. [PMID: 22014239]
  • 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]
  • Diego L García-González, Jorge Vivancos, Ramón Aparicio. Mapping brain activity induced by olfaction of virgin olive oil aroma. Journal of agricultural and food chemistry. 2011 Sep; 59(18):10200-10. doi: 10.1021/jf202106b. [PMID: 21838262]
  • Heidi Najbjerg, Jette Feveile Young, Hanne Christine Bertram. NMR-based metabolomics reveals that conjugated double bond content and lipid storage efficiency in HepG2 cells are affected by fatty acid cis/trans configuration and chain length. Journal of agricultural and food chemistry. 2011 Aug; 59(16):8994-9000. doi: 10.1021/jf201489b. [PMID: 21786785]
  • Fuyuan Jing, David C Cantu, Jarmila Tvaruzkova, Jay P Chipman, Basil J Nikolau, Marna D Yandeau-Nelson, Peter J Reilly. Phylogenetic and experimental characterization of an acyl-ACP thioesterase family reveals significant diversity in enzymatic specificity and activity. BMC biochemistry. 2011 Aug; 12(?):44. doi: 10.1186/1471-2091-12-44. [PMID: 21831316]
  • Su Li, Peichi C Hu, Noah Malmstadt. Imaging molecular transport across lipid bilayers. Biophysical journal. 2011 Aug; 101(3):700-8. doi: 10.1016/j.bpj.2011.06.044. [PMID: 21806938]
  • Neta Shlezinger, Anna Minz, Yonatan Gur, Ido Hatam, Yasin F Dagdas, Nicholas J Talbot, Amir Sharon. Anti-apoptotic machinery protects the necrotrophic fungus Botrytis cinerea from host-induced apoptotic-like cell death during plant infection. PLoS pathogens. 2011 Aug; 7(8):e1002185. doi: 10.1371/journal.ppat.1002185. [PMID: 21876671]
  • Arnaldo Glogauer, Viviane P Martini, Helisson Faoro, Gustavo H Couto, Marcelo Müller-Santos, Rose A Monteiro, David A Mitchell, Emanuel M de Souza, Fabio O Pedrosa, Nadia Krieger. Identification and characterization of a new true lipase isolated through metagenomic approach. Microbial cell factories. 2011 Jul; 10(?):54. doi: 10.1186/1475-2859-10-54. [PMID: 21762508]
  • S Scott Bowersox, Luke K Lightning, Satish Rao, Monica Palme, Dave Ellis, Renee Coleman, Adrian M Davies, Padmapriya Kumaraswamy, Pascal Druzgala. Metabolism and pharmacokinetics of naronapride (ATI-7505), a serotonin 5-HT(4) receptor agonist for gastrointestinal motility disorders. Drug metabolism and disposition: the biological fate of chemicals. 2011 Jul; 39(7):1170-80. doi: 10.1124/dmd.110.037564. [PMID: 21447732]
  • R Huang, G Q Li, J Zhang, L Yang, H J Che, D H Jiang, H C Huang. Control of postharvest Botrytis fruit rot of strawberry by volatile organic compounds of Candida intermedia. Phytopathology. 2011 Jul; 101(7):859-69. doi: 10.1094/phyto-09-10-0255. [PMID: 21323467]
  • Xiuzhu Yu, F R van de Voort, Jacqueline Sedman, Jin-ming Gao. A new direct Fourier transform infrared analysis of free fatty acids in edible oils using spectral reconstitution. Analytical and bioanalytical chemistry. 2011 Jul; 401(1):315-24. doi: 10.1007/s00216-011-5036-x. [PMID: 21556753]
  • John J Beck, Noreen E Mahoney, Daniel Cook, Wai S Gee. Volatile analysis of ground almonds contaminated with naturally occurring fungi. Journal of agricultural and food chemistry. 2011 Jun; 59(11):6180-7. doi: 10.1021/jf200739a. [PMID: 21528918]
  • Sibao Wang, Weiguo Fang, Chengshu Wang, Raymond J St Leger. Insertion of an esterase gene into a specific locust pathogen (Metarhizium acridum) enables it to infect caterpillars. PLoS pathogens. 2011 Jun; 7(6):e1002097. doi: 10.1371/journal.ppat.1002097. [PMID: 21731492]
  • Jhon Castañeda-Gómez, Rogelio Pereda-Miranda. Resin glycosides from the herbal drug jalap (Ipomoea purga). Journal of natural products. 2011 May; 74(5):1148-53. doi: 10.1021/np200080k. [PMID: 21446661]
  • Alicia Olivares, Kseniya Dryahina, José Luis Navarro, David Smith, Patrik Spanĕl, Mónica Flores. SPME-GC-MS versus Selected Ion Flow Tube Mass Spectrometry (SIFT-MS) analyses for the study of volatile compound generation and oxidation status during dry fermented sausage processing. Journal of agricultural and food chemistry. 2011 Mar; 59(5):1931-8. doi: 10.1021/jf104281a. [PMID: 21294565]
  • Zhana Kravchuk, Begonya Vicedo, Víctor Flors, Gemma Camañes, Carmen González-Bosch, Pilar García-Agustín. Priming for JA-dependent defenses using hexanoic acid is an effective mechanism to protect Arabidopsis against B. cinerea. Journal of plant physiology. 2011 Mar; 168(4):359-66. doi: 10.1016/j.jplph.2010.07.028. [PMID: 20950893]
  • P Martínez-Lozano, L Zingaro, A Finiguerra, S Cristoni. Secondary electrospray ionization-mass spectrometry: breath study on a control group. Journal of breath research. 2011 Mar; 5(1):016002. doi: 10.1088/1752-7155/5/1/016002. [PMID: 21383424]
  • Nadav Sorek, Orit Gutman, Einat Bar, Mohamad Abu-Abied, Xuehui Feng, Mark P Running, Efraim Lewinsohn, Naomi Ori, Einat Sadot, Yoav I Henis, Shaul Yalovsky. Differential effects of prenylation and s-acylation on type I and II ROPS membrane interaction and function. Plant physiology. 2011 Feb; 155(2):706-20. doi: 10.1104/pp.110.166850. [PMID: 21139084]
  • Sharareh Eskandari, Jaleh Varshosaz, Mohsen Minaiyan, Majid Tabbakhian. Brain delivery of valproic acid via intranasal administration of nanostructured lipid carriers: in vivo pharmacodynamic studies using rat electroshock model. International journal of nanomedicine. 2011; 6(?):363-71. doi: 10.2147/ijn.s15881. [PMID: 21499426]
  • Diana M Lee, Kenneth W Jackson, Nicholas Knowlton, Joshua Wages, Petar Alaupovic, Ola Samuelsson, Aso Saeed, Michael Centola, Per-Ola Attman. Oxidative stress and inflammation in renal patients and healthy subjects. PloS one. 2011; 6(7):e22360. doi: 10.1371/journal.pone.0022360. [PMID: 21829457]
  • Vladimir Krasikov, Henk L Dekker, Martijn Rep, Frank L W Takken. The tomato xylem sap protein XSP10 is required for full susceptibility to Fusarium wilt disease. Journal of experimental botany. 2011 Jan; 62(3):963-73. doi: 10.1093/jxb/erq327. [PMID: 20974736]
  • Xiangdong Zheng, Jiubiao Guo, Lipeng Xu, Honglei Li, Dongwei Zhang, Kai Zhang, Fei Sun, Tingyi Wen, Siguo Liu, Hai Pang. Crystal structure of a novel esterase Rv0045c from Mycobacterium tuberculosis. PloS one. 2011; 6(5):e20506. doi: 10.1371/journal.pone.0020506. [PMID: 21637775]
  • Jaeduk Goh, Junhyun Jeon, Kyoung Su Kim, Jongsun Park, Sook-Young Park, Yong-Hwan Lee. The PEX7-mediated peroxisomal import system is required for fungal development and pathogenicity in Magnaporthe oryzae. PloS one. 2011; 6(12):e28220. doi: 10.1371/journal.pone.0028220. [PMID: 22194815]
  • Mikael A Carlsson, Sonja Bisch-Knaden, Alexander Schäpers, Raimondas Mozuraitis, Bill S Hansson, Niklas Janz. Odour maps in the brain of butterflies with divergent host-plant preferences. PloS one. 2011; 6(8):e24025. doi: 10.1371/journal.pone.0024025. [PMID: 21901154]
  • Danilo C Centeno, Sonia Osorio, Adriano Nunes-Nesi, Ana L F Bertolo, Raphael T Carneiro, Wagner L Araújo, Marie-Caroline Steinhauser, Justyna Michalska, Johannes Rohrmann, Peter Geigenberger, Sandra N Oliver, Mark Stitt, Fernando Carrari, Jocelyn K C Rose, Alisdair R Fernie. Malate plays a crucial role in starch metabolism, ripening, and soluble solid content of tomato fruit and affects postharvest softening. The Plant cell. 2011 Jan; 23(1):162-84. doi: 10.1105/tpc.109.072231. [PMID: 21239646]
  • Dolores Pérez, Sara Martín, Gloria Fernández-Lorente, Marco Filice, José Manuel Guisán, Antonio Ventosa, María Teresa García, Encarnación Mellado. A novel halophilic lipase, LipBL, showing high efficiency in the production of eicosapentaenoic acid (EPA). PloS one. 2011; 6(8):e23325. doi: 10.1371/journal.pone.0023325. [PMID: 21853111]
  • Nikoletta G Ntalli, Simona Vargiu, Urania Menkissoglu-Spiroudi, Pierluigi Caboni. nematicidal carboxylic acids and aldehydes from Melia azedarach fruits. Journal of agricultural and food chemistry. 2010 Nov; 58(21):11390-4. doi: 10.1021/jf1025345. [PMID: 20925380]
  • T W Binsl, A A De Graaf, K Venema, J Heringa, A Maathuis, P De Waard, J H G M Van Beek. Measuring non-steady-state metabolic fluxes in starch-converting faecal microbiota in vitro. Beneficial microbes. 2010 Nov; 1(4):391-405. doi: 10.3920/bm2010.0038. [PMID: 21831778]
  • Jeremy Grojean, Brian Downes. Riboswitches as hormone receptors: hypothetical cytokinin-binding riboswitches in Arabidopsis thaliana. Biology direct. 2010 Oct; 5(?):60. doi: 10.1186/1745-6150-5-60. [PMID: 20961447]
  • Jiubiao Guo, Xiangdong Zheng, Lipeng Xu, Zhongyuan Liu, Kehui Xu, Shentao Li, Tingyi Wen, Siguo Liu, Hai Pang. Characterization of a novel esterase Rv0045c from Mycobacterium tuberculosis. PloS one. 2010 Oct; 5(10):. doi: 10.1371/journal.pone.0013143. [PMID: 20957207]
  • J Bruce German, Cora J Dillard. Saturated fats: a perspective from lactation and milk composition. Lipids. 2010 Oct; 45(10):915-23. doi: 10.1007/s11745-010-3445-9. [PMID: 20652757]
  • Takuya Kato, Hisamitsu Hayashi, Yuichi Sugiyama. Short- and medium-chain fatty acids enhance the cell surface expression and transport capacity of the bile salt export pump (BSEP/ABCB11). Biochimica et biophysica acta. 2010 Sep; 1801(9):1005-12. doi: 10.1016/j.bbalip.2010.04.002. [PMID: 20398791]
  • Lena Ohlsson. Dairy products and plasma cholesterol levels. Food & nutrition research. 2010 Aug; 54(?):. doi: 10.3402/fnr.v54i0.5124. [PMID: 20806084]
  • Baojun Shi, Wei Liu, Shao-Peng Wei, Wen-Jun Wu. Chemical composition, antibacterial and antioxidant activity of the essential oil of Bupleurum longiradiatum. Natural product communications. 2010 Jul; 5(7):1139-42. doi: ". [PMID: 20734959]