Caprylic acid (BioDeep_00000002187)

 

Secondary id: BioDeep_00000229608, BioDeep_00000405283, BioDeep_00000419546, BioDeep_00000859546

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


代谢物信息卡片


octanoic acid

化学式: C8H16O2 (144.1150236)
中文名称: 辛酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.11%

Reviewed

Last reviewed on 2024-07-01.

Cite this Page

Caprylic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/caprylic_acid (retrieved 2024-11-22) (BioDeep RN: BioDeep_00000002187). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(=O)(O)CCCCCCC
InChI: InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)

描述信息

Caprylic acid is the common name for the eight-carbon straight-chain fatty acid known by the systematic name octanoic acid. It is found naturally in coconuts and breast milk. It is an oily liquid with a slightly unpleasant rancid taste that is minimally soluble in water. Caprylic acid is used commercially in the production of esters used in perfumery and also in the manufacture of dyes (Wikipedia). Caprylic acid can be found in numerous foods such as Prunus (Cherry, Plum), pineapple sages, black raspberries, and shallots. Caprylic acid is found to be associated with medium-chain acyl-CoA dehydrogenase deficiency, which is an inborn error of metabolism.
Widespread in plant oils, free and as glyceridesand is also present in apple, banana, orange juice and peel, pineapple, cognac, calamus, blue cheeses, cheddar cheese, Swiss cheese, feta cheese and other cheeses. Flavouring agent, defoamer, lubricant, binder and antimicrobial preservative in cheese wraps
KEIO_ID C037
Octanoic acid (Caprylic acid) is an oily liquid with a slightly unpleasant rancid taste and used commercially in the production of esters used in perfumery and also in the manufacture of dyes.
Octanoic acid (Caprylic acid) is an oily liquid with a slightly unpleasant rancid taste and used commercially in the production of esters used in perfumery and also in the manufacture of dyes.

同义名列表

72 个代谢物同义名

Caprylic acid, sodium salt, 11C-labeled; Caprylic acid, lanthanum(+3) salt; Caprylic acid, ruthenium(+3) salt; Caprylic acid, zirconium(+4) salt; Caprylic acid, chromium(+2) salt; Caprylic acid, nickel(+2) salt; Caprylic acid, iridum(+3) salt; Caprylic acid, copper(+2) salt; Caprylic acid, manganese salt; Caprylic acid, zirconium salt; Caprylic acid, potassium salt; OCTANOIC ACID (caprylIC ACID); Caprylic acid, aluminum salt; Caprylic acid, iron(+3) salt; Caprylic acid, lead(+2) salt; Caprylic acid, lithium salt; Caprylic acid, calcium salt; Caprylic acid, cadmium salt; Caprylic acid, ammonia salt; Caprylic acid, tin(+2) salt; Caprylic acid, cesium salt; Caprylic acid, barium salt; Caprylic acid, copper salt; Caprylic acid, 14C-labeled; Caprylic acid, cobalt salt; Caprylic acid, sodium salt; Caprylic acid, zinc salt; 1-Heptanecarboxylic acid; Caprylic acid, tin salt; OCTANOate (caprylate); 1-Heptanecarboxylate; Octanoic acid-8-13C; Octanoic acid-2-13C; Acidum octanoicum; Acidum octanocium; Lithium octanoate; Acide octanoique; Sodium caprylate; Sodium octanoate; Acido octanoico; n-Octanoic acid; CH3-[CH2]6-COOH; N-Caprylic acid; N-Octylic acid; Kortacid 0899; Caprylic acid; N-Octoic acid; octanoic acid; Kaprylsaeure; Octylic acid; Octansaeure; Octoic acid; Prifac 2901; N-Octanoate; N-Caprylate; N-Octylate; Neo-fat 8S; Lunac 8-95; Lunac 8-98; Octanoate; Emery 657; Neo-fat 8; Caprylate; N-Octoate; Octylate; Octoate; FA(8:0); C8:0; 8:0; Octanoic acid; Octanoic acid; Octanoic acid



数据库引用编号

28 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(1)

BioCyc(0)

PlantCyc(0)

代谢反应

34 个相关的代谢反应过程信息。

Reactome(24)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(10)

PharmGKB(0)

297 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

  • Huiquan Zhu, Pu Zhao, Xiaodan Wang, Yunna Wang, Shuwen Zhang, Xiaoyang Pang, Jiaping Lv. Fabrication of Human Milk Fat Substitute: Based on the Similarity Evaluation Model and Computer Software. Molecules (Basel, Switzerland). 2024 May; 29(9):. doi: 10.3390/molecules29092096. [PMID: 38731587]
  • Marta N Mota, Madalena Matos, Nada Bahri, Isabel Sá-Correia. Shared and more specific genetic determinants and pathways underlying yeast tolerance to acetic, butyric, and octanoic acids. Microbial cell factories. 2024 Feb; 23(1):71. doi: 10.1186/s12934-024-02309-0. [PMID: 38419072]
  • Reham I El Shazly, Huda S El-Sheshtawy, Nehal S Ahmed, Amal M Nassar. Synthesis and biodegradation testing of some synthetic oils based on ester. Scientific reports. 2024 02; 14(1):3416. doi: 10.1038/s41598-024-53331-6. [PMID: 38341447]
  • Joshua M Lyte, Komala Arsi, Valentina Caputi, Rohana Liyanage, Anna L Facchetti V Assumpcao, Palmy R R Jesudhasan, Annie M Donoghue. Inclusion of trans-cinnamaldehyde and caprylic acid in feed results in detectable concentrations in the chicken gut and reduces foodborne pathogen carriage. Poultry science. 2023 Dec; 103(2):103368. doi: 10.1016/j.psj.2023.103368. [PMID: 38157787]
  • Xiang Gao, Haonan Li, Siyu Wang, Xiaokang Long, Xuehai Guo, Huiming Hua, Dahong Li. Discovery of sinomenine/8-Bis(benzylthio)octanoic acid hybrids as potential anti-leukemia drug candidate via mitochondrial pathway. Bioorganic & medicinal chemistry letters. 2023 Nov; 97(?):129545. doi: 10.1016/j.bmcl.2023.129545. [PMID: 37939862]
  • Paula V Gaete, Luz D Nieves-Barreto, Valentina Guatibonza-García, Mónica Losada-Barragán, Karina Vargas-Sánchez, Carlos O Mendivil. Medium-chain fatty acids modify macrophage expression of metabolic and inflammatory genes in a PPAR β/δ-dependent manner. Scientific reports. 2023 07; 13(1):11573. doi: 10.1038/s41598-023-38700-x. [PMID: 37463952]
  • Douglas Burdette, Lei Ci, Barclay Shilliday, Richard Slauter, Andrew Auerbach, Matthew Kenney, Örn Almarsson, Eugene Cheung, Tracy Hendrick. Systemic Exposure, Metabolism, and Elimination of [14C]-Labeled Amino Lipid, Lipid 5, after a Single Administration of mRNA Encapsulating Lipid Nanoparticles to Sprague-Dawley Rats. Drug metabolism and disposition: the biological fate of chemicals. 2023 Jul; 51(7):804-812. doi: 10.1124/dmd.122.001194. [PMID: 37208185]
  • Jian-Yu Wang, Qiu-Yue Li, Li Ren, Cheng Guo, Jian-Ping Qu, Zheng Gao, Hui-Fang Wang, Qian Zhang, Bo Zhou. Transcriptomic and physiological analysis of the effect of octanoic acid on Meloidogyne incognita. Pesticide biochemistry and physiology. 2023 Jun; 193(?):105432. doi: 10.1016/j.pestbp.2023.105432. [PMID: 37247998]
  • 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]
  • Xinsheng Zhang, Peng Zhang, Yinghua Liu, Zhao Liu, Qing Xu, Yong Zhang, Lu Liu, Xueyan Yang, Liya Li, Changyong Xue. Effects of Caprylic Acid and Eicosapentaenoic Acid on Lipids, Inflammatory Levels, and the JAK2/STAT3 Pathway in ABCA1-Deficient Mice and ABCA1 Knock-Down RAW264.7 Cells. Nutrients. 2023 Mar; 15(5):. doi: 10.3390/nu15051296. [PMID: 36904298]
  • Jingyuan Yang, Pan Wang, Xiangkang Jiang, Jiefeng Xu, Minhai Zhang, Fei Liu, Yao Lin, Jiawei Tao, Jiantao He, Xing Zhou, Mao Zhang. A Nanotherapy of Octanoic Acid Ameliorates Cardiac Arrest/Cardiopulmonary Resuscitation-Induced Brain Injury via RVG29- and Neutrophil Membrane-Mediated Injury Relay Targeting. ACS nano. 2023 Feb; ?(?):. doi: 10.1021/acsnano.2c09931. [PMID: 36758159]
  • Manxi Zhao, Zhou Zhang, Yongtao Liu, Wencong Zhang, Ye Gong, Yuhang Tang, Fan Chen, Jianmin Zhang, Guobin Liu, Haitao Zhang, Yueru Li, Kangsen Mai, Qinghui Ai. Effects of supplemental octanoate on hepatic lipid metabolism, serum biochemical indexes, antioxidant capacity and inflammation-related genes expression of large yellow croaker (Larimichthys crocea) fed with high soybean oil diet. Frontiers in immunology. 2023; 14(?):1162633. doi: 10.3389/fimmu.2023.1162633. [PMID: 37051230]
  • Jordi G López-Velázquez, Lidia E Ayón-Reyna, Misael O Vega-García, Gabriela López-Angulo, Martha E López-López, Blanca A López-Zazueta, Francisco Delgado-Vargas. Caprylic acid in Vitex mollis fruit and its inhibitory activity against a thiabendazole-resistant Colletotrichum gloeosporioides strain. Pest management science. 2022 Dec; 78(12):5271-5280. doi: 10.1002/ps.7149. [PMID: 36054649]
  • Christin Koch, Steffen Nordzieke, Jessica Grieger, Peter Mayser. Medium-chain fatty acid esters are effective even in azole-resistant Malassezia pachydermatis. Mycoses. 2022 Dec; 65(12):1188-1193. doi: 10.1111/myc.13512. [PMID: 35923130]
  • Mateus S Dalcin, Bruna L Dias, Luis O Viteri Jumbo, Ana C S S Oliveira, Sabrina H C Araújo, Wellington S Moura, Dalmarcia S C Mourão, Talita P S Ferreira, Fabricio S Campos, Alex Sander R Cangussu, Marcos V G Alves, Bruno S Andrade, Javier G Mantilla-Afanador, Raimundo W A Aguiar, Eugênio E Oliveira, Gil R Santos. Potential Action Mechanism and Inhibition Efficacy of Morinda citrifolia Essential Oil and Octanoic Acid against Stagonosporopsis cucurbitacearum Infestations. Molecules (Basel, Switzerland). 2022 Aug; 27(16):. doi: 10.3390/molecules27165173. [PMID: 36014413]
  • Adela Štimac, Tihana Kurtović, Nediljko Pavlović, Beata Halassy. Development of Improved High-Performance Liquid Chromatography Method for the Determination of Residual Caprylic Acid in Formulations of Human Immunoglobulins. Molecules (Basel, Switzerland). 2022 Mar; 27(5):. doi: 10.3390/molecules27051665. [PMID: 35268765]
  • Patrick-Pascal Strunz, Raphael N Vuille-Dit-Bille, Mark R Fox, Andreas Geier, Marco Maggiorini, Max Gassmann, Heiko Fruehauf, Thomas A Lutz, Oliver Goetze. Effect of high altitude on human postprandial 13 C-octanoate metabolism, intermediary metabolites, gastrointestinal peptides, and visceral perception. Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society. 2022 03; 34(3):e14225. doi: 10.1111/nmo.14225. [PMID: 34342373]
  • Xin Sheng Zhang, Peng Zhang, Ying Hua Liu, Qing Xu, Yong Zhang, Hui Zi Li, Lu Liu, Yu Meng Liu, Xue Yan Yang, Chang Yong Xue. Caprylic Acid Improves Lipid Metabolism, Suppresses the Inflammatory Response and Activates the ABCA1/p-JAK2/p-STAT3 Signaling Pathway in C57BL/6J Mice and RAW264.7 Cells. Biomedical and environmental sciences : BES. 2022 Feb; 35(2):95-106. doi: 10.3967/bes2022.014. [PMID: 35197174]
  • 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]
  • Laxmi Shanthi Chede, Brett A Wagner, Garry R Buettner, Maureen D Donovan. Electron Spin Resonance Evaluation of Buccal Membrane Fluidity Alterations by Sodium Caprylate and L-Menthol. International journal of molecular sciences. 2021 Oct; 22(19):. doi: 10.3390/ijms221910708. [PMID: 34639049]
  • Khaled I Alatibi, Stefan Tholen, Zeinab Wehbe, Judith Hagenbuchner, Daniela Karall, Michael J Ausserlechner, Oliver Schilling, Sarah C Grünert, Jerry Vockley, Sara Tucci. Lipidomic and Proteomic Alterations Induced by Even and Odd Medium-Chain Fatty Acids on Fibroblasts of Long-Chain Fatty Acid Oxidation Disorders. International journal of molecular sciences. 2021 Sep; 22(19):. doi: 10.3390/ijms221910556. [PMID: 34638902]
  • John P Kowalski, Robert D Pelletier, Matthew G McDonald, Edward J Kelly, Allan E Rettie. Pharmacokinetics, metabolism and off-target effects in the rat of 8-[(1H- benzotriazol-1-yl)amino]octanoic acid, a selective inhibitor of human cytochrome P450 4Z1: β-oxidation as a potential augmenting pathway for inhibition. Xenobiotica; the fate of foreign compounds in biological systems. 2021 Aug; 51(8):901-915. doi: 10.1080/00498254.2021.1930281. [PMID: 33993844]
  • Derya Cansız, İsmail Ünal, Ünsal Veli Üstündağ, Ahmet Ata Alturfan, Meriç A Altinoz, İlhan Elmacı, Ebru Emekli-Alturfan. Caprylic acid ameliorates rotenone induced inflammation and oxidative stress in the gut-brain axis in Zebrafish. Molecular biology reports. 2021 Jun; 48(6):5259-5273. doi: 10.1007/s11033-021-06532-5. [PMID: 34228274]
  • Yankai Liu, Yajie Wang, Jingming Zhou, Yumei Chen, Hongliang Liu, Yanhua Qi, Luhui Zhao, Yuanyuan Zhang, Aiping Wang. Establishment of an immunological detection method of fleroxacin by fluorescence-linked immunosorbent assay. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2021 Apr; 38(4):594-601. doi: 10.1080/19440049.2021.1876251. [PMID: 33667148]
  • Jing Guo, Jinhui Zhao, Rui Liu, Jiaying Yu, Mingjia Zhang, Hanming Wang, Liyan Liu. Metabolomics analysis of serum in pediatric nephrotic syndrome based on targeted and non-targeted platforms. Metabolomics : Official journal of the Metabolomic Society. 2021 03; 17(4):38. doi: 10.1007/s11306-021-01788-1. [PMID: 33788045]
  • Shreshta Jain, Reena Rai, Divya Singh, Divya Vohora. Octanoic acid a major component of widely consumed medium-chain triglyceride ketogenic diet is detrimental to bone. Scientific reports. 2021 03; 11(1):7003. doi: 10.1038/s41598-021-86468-9. [PMID: 33772066]
  • Joscha Brinkmann, Isabel Becker, Peter Kroll, Christian Luebbert, Gabriele Sadowski. Predicting the API partitioning between lipid-based drug delivery systems and water. International journal of pharmaceutics. 2021 Feb; 595(?):120266. doi: 10.1016/j.ijpharm.2021.120266. [PMID: 33486017]
  • Saifudeen Ismael, R Renuka Nair. Reactivation of fatty acid oxidation by medium chain fatty acid prevents myocyte hypertrophy in H9c2 cell line. Molecular and cellular biochemistry. 2021 Jan; 476(1):483-491. doi: 10.1007/s11010-020-03925-1. [PMID: 33000353]
  • Naohisa Nosaka, Shougo Tsujino, Kazumitsu Honda, Hiromi Suemitsu, Kazuhiko Kato, Kazuo Kondo. Effect of Ingestion of Medium-Chain Triglycerides on Substrate Oxidation during Aerobic Exercise Could Depend on Sex Difference in Middle-Aged Sedentary Persons. Nutrients. 2020 Dec; 13(1):. doi: 10.3390/nu13010036. [PMID: 33374218]
  • Beatriz N Zurbano, Eugenia Tavarone, Belén González Viacava, José C Dokmetjian, Osvaldo Cascone, Matías Fingermann. Critical aspects on traditional antivenom production processes and their optimization by factorial analysis. Biologicals : journal of the International Association of Biological Standardization. 2020 Nov; 68(?):65-73. doi: 10.1016/j.biologicals.2020.08.005. [PMID: 32912811]
  • Zahra Nochi, Rune Isak Dupont Birkler, Paula Fernandez-Guerra, Jakob Hansen, Flemming Wibrand, Thomas Juhl Corydon, Niels Gregersen, Rikke Katrine Jentoft Olsen. Increased antioxidant response in medium-chain acyl-CoA dehydrogenase deficiency: does lipoic acid have a protective role?. Pediatric research. 2020 10; 88(4):556-564. doi: 10.1038/s41390-020-0801-1. [PMID: 32045933]
  • Yingxi Chen, Erin E Boggess, Efrain Rodriguez Ocasio, Aric Warner, Lucas Kerns, Victoria Drapal, Chloe Gossling, Wilma Ross, Richard L Gourse, Zengyi Shao, Julie Dickerson, Thomas J Mansell, Laura R Jarboe. Reverse engineering of fatty acid-tolerant Escherichia coli identifies design strategies for robust microbial cell factories. Metabolic engineering. 2020 09; 61(?):120-130. doi: 10.1016/j.ymben.2020.05.001. [PMID: 32474056]
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  • Harleen Kaur, Beverly S Muhlhausler, Pamela Su-Lin Sim, Amanda J Page, Hui Li, Maria Nunez-Salces, Georgia S Clarke, Lili Huang, Rebecca L Wilson, Johannes D Veldhuis, Chen Chen, Claire T Roberts, Kathryn L Gatford. Pregnancy, but not dietary octanoic acid supplementation, stimulates the ghrelin-pituitary growth hormone axis in mice. The Journal of endocrinology. 2020 05; 245(2):327-342. doi: 10.1530/joe-20-0072. [PMID: 32176867]
  • Karl B McCann, James Van Alstine, Jose Martinez, Jamil Shanagar, Joseph Bertolini. Polyacrylic acid based plasma fractionation for the production of albumin and IgG: Compatibility with existing commercial downstream processes. Biotechnology and bioengineering. 2020 04; 117(4):1072-1081. doi: 10.1002/bit.27265. [PMID: 31930475]
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  • Xiao-Pei Hu, Fa-Wen Yin, Da-Yong Zhou, Hong-Kai Xie, Bei-Wei Zhu, Xiao-Chi Ma, Xiang-Ge Tian, Chao Wang, Fereidoon Shahidi. Stability of resveratrol esters with caprylic acid during simulated in vitro gastrointestinal digestion. Food chemistry. 2019 Mar; 276(?):675-679. doi: 10.1016/j.foodchem.2018.10.062. [PMID: 30409647]
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