Hexanal (BioDeep_00000004908)

 

Secondary id: BioDeep_00000019511, BioDeep_00000405600, BioDeep_00000629951, BioDeep_00000859851, BioDeep_00001868245

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Toxin


代谢物信息卡片


N-Caproic aldehyde

化学式: C6H12O (100.0888102)
中文名称: 4-甲基戊醛, 正己醛, 正己醛
谱图信息: 最多检出来源 Homo sapiens(blood) 0.6%

分子结构信息

SMILES: CC(C)CCC=O
InChI: InChI=1S/C6H12O/c1-2-3-4-5-6-7/h6H,2-5H2,1H3

描述信息

Hexanal is an alkyl aldehyde found in human biofluids. Human milk samples collected from women contains hexanal. Among mediators of oxidative stress, highly reactive secondary aldehydic lipid peroxidation products can initiate the processes of spontaneous mutagenesis and carcinogenesis and can also act as a growth-regulating factors and signaling molecules. In specimens obtained from adult patients with brain astrocytomas, lower levels of n-hexanal are associated with poorer patient prognosis. Hexanal has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821). Hexanal is a volatile compound that has been associated with the development of undesirable flavours. The content of hexanal, which is a major breakdown product of linoleic acid (LA, n - 6 PUFA) oxidation, has been used to follow the course of lipid oxidation and off-flavour development in foods, and have been proposed as one potential marker of milk quality. A "cardboard-like" off-flavour is frequently associated with dehydrated milk products. This effect is highly correlated with the headspace concentration of hexanal. (Food Chemistry. Volume 107, Issue 1, 1 March 2008, Pages 558-569, PMID:17934948, 17487452).
Constituent of many foodstuffs. A production of aerobic enzymatic transformations of plant constits. It is used in fruit flavours and in perfumery
D000890 - Anti-Infective Agents > D000935 - Antifungal Agents
D010575 - Pesticides > D007306 - Insecticides
D016573 - Agrochemicals

同义名列表

19 个代谢物同义名

N-Caproic aldehyde; n-Capronaldehyde; Caproic aldehyde; 4-methylpentanal; Hexoic aldehyde; N-Caproaldehyde; N-Hexylaldehyde; Capronaldehyde; Hexylaldehyde; Caproaldehyde; Hexanaldehyde; Aldehyde C-6; Hexaldehyde; C6 Aldehyde; Hexan-1-al; N-C5H11CHO; 1-Hexanal; N-Hexanal; HEXANAL



数据库引用编号

21 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(9)

BioCyc(1)

PlantCyc(0)

代谢反应

270 个相关的代谢反应过程信息。

Reactome(122)

BioCyc(4)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(110)

COVID-19 Disease Map(0)

PathBank(34)

PharmGKB(0)

97 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

  • Qiwei Wang, Jialing Xie, Lilei Wang, Yongwen Jiang, Yuliang Deng, Jiayi Zhu, Haibo Yuan, Yanqin Yang. Comprehensive investigation on the dynamic changes of volatile metabolites in fresh scent green tea during processing by GC-E-Nose, GC-MS, and GC × GC-TOFMS. Food research international (Ottawa, Ont.). 2024 Jul; 187(?):114330. doi: 10.1016/j.foodres.2024.114330. [PMID: 38763633]
  • Xiao-Min Li, Lie-Hua Che, Wen-di Zhang, Qian-Li Huang, Cong Li, Bao-Cai Xu. Insight into the autochthonous bacterial strains as starter cultures for improving the flavor profiles of dry-cured duck: Changes in microbial diversity and metabolic profiles. Food chemistry. 2024 Jun; 443(?):138446. doi: 10.1016/j.foodchem.2024.138446. [PMID: 38281415]
  • Rachel Irankunda, Mads Bjørlie, Betül Yesiltas, Laurence Muhr, Laetitia Canabady-Rochelle, Charlotte Jacobsen. Evaluation of primary and secondary oxidation products in fish oil-in-water emulsions: Effect of metal-complexing peptides and protein hydrolysates. Food chemistry. 2024 May; 439(?):138042. doi: 10.1016/j.foodchem.2023.138042. [PMID: 38100881]
  • Yanqun Xu, Jieqiong Wang, Ziqing Wu, Jing Huang, Zhenbiao Li, Jiayi Xu, Dan Long, Tian Ye, Gennv Wang, Junfeng Yin, Zisheng Luo, Yongquan Xu. The role of glutathione in stabilizing aromatic volatile organic compounds in Rougui Oolong tea: A comprehensive study from content to mechanisms. Food chemistry. 2023 Oct; 437(Pt 1):137802. doi: 10.1016/j.foodchem.2023.137802. [PMID: 37866345]
  • Zelong Zhang, Minghong Liu, Xiaoyan Wang, Jianyu Gou, Tianliang Li, Te Zhao, Lin Zhou, Fulong Zhang, Fujia Cheng. Plant volatiles mediated the orientation preference of slugs to different plant species. Pest management science. 2023 Sep; ?(?):. doi: 10.1002/ps.7757. [PMID: 37672502]
  • Djalma Vitorino Costa Filho, Thayse Cavalcante da Rocha, Jéssica Moreira de Carvalho, Leila Moreira de Carvalho, Mércia de Sousa Galvão, Mayka Reghiany Pedrao, Mario Estévez, Marta Suely Madruga. Oxidative stability of white striping chicken breasts: effect of cold storage and heat treatments. Poultry science. 2023 May; 102(8):102826. doi: 10.1016/j.psj.2023.102826. [PMID: 37343347]
  • Haining Yin, Lin Wang, Hanmei Su, Yanying Liang, Ping Ji, Xuefei Wang, Zhumei Xi. Effects of ultraviolet and infrared radiation absence or presence on the aroma volatile compounds in winegrape during veraison. Food research international (Ottawa, Ont.). 2023 05; 167(?):112662. doi: 10.1016/j.foodres.2023.112662. [PMID: 37087251]
  • Yaozheng Liu, Dylan C Cadwallader, MaryAnne Drake. Identification of predominant aroma components of dried pea protein concentrates and isolates. Food chemistry. 2023 Apr; 406(?):134998. doi: 10.1016/j.foodchem.2022.134998. [PMID: 36450193]
  • Zhijie Liu, Yiqun Huang, Shanshan Kong, Junjian Miao, Keqiang Lai. Selection and quantification of volatile indicators for quality deterioration of reheated pork based on simultaneously extracting volatiles and reheating precooked pork. Food chemistry. 2023 Mar; 419(?):135962. doi: 10.1016/j.foodchem.2023.135962. [PMID: 37004364]
  • Anna Coenen, Manuel Ferrer, Karl-Erich Jaeger, Ulrich Schörken. Synthesis of 12-aminododecenoic acid by coupling transaminase to oxylipin pathway enzymes. Applied microbiology and biotechnology. 2023 Feb; ?(?):. doi: 10.1007/s00253-023-12422-6. [PMID: 36807735]
  • Andreea Pușcaș, Andruța Mureșan, Sonia Socaci, Francisc Dulf, Sevastița Muste, Florinela Fetea, Cristina Anamaria Semeniuc, Andrea Bunea, Vlad Mureșan, Adela Pintea. Cold pressed pumpkin seed oil fatty acids, carotenoids, volatile compounds profiles and infrared fingerprints as affected by storage time and wax-based oleogelation. Journal of the science of food and agriculture. 2023 Jan; 103(2):680-691. doi: 10.1002/jsfa.12180. [PMID: 36053837]
  • Mengyi Lin, Songbai Liu. Naphthalimide-Based Fluorescent Probe for Profiling of Aldehydes during Oxidation of Unsaturated Lipids. Journal of agricultural and food chemistry. 2022 Nov; 70(44):14304-14311. doi: 10.1021/acs.jafc.2c05659. [PMID: 36286393]
  • Ge-Ge Yuan, Lin-Chao Zhao, Yuan-Wen Du, Huan Yu, Xiao-Bin Shi, Wen-Chao Chen, Gong Chen. Repellence or attraction: secondary metabolites in pepper mediate attraction and defense against Spodoptera litura. Pest management science. 2022 Nov; 78(11):4859-4870. doi: 10.1002/ps.7107. [PMID: 36181416]
  • Mitchell D Culler, Ipek Bayram, Eric A Decker. Enzymatic Modification of Lecithin for Improved Antioxidant Activity in Combination with Tocopherol in Emulsions and Bulk Oil. Journal of agricultural and food chemistry. 2022 Oct; 70(41):13404-13412. doi: 10.1021/acs.jafc.2c05182. [PMID: 36215731]
  • Karthika Sriskantharajah, Walid El Kayal, Davoud Torkamaneh, Murali M Ayyanath, Praveen K Saxena, Alan J Sullivan, Gopinadhan Paliyath, Jayasankar Subramanian. Transcriptomics of Improved Fruit Retention by Hexanal in 'Honeycrisp' Reveals Hormonal Crosstalk and Reduced Cell Wall Degradation in the Fruit Abscission Zone. International journal of molecular sciences. 2021 Aug; 22(16):. doi: 10.3390/ijms22168830. [PMID: 34445535]
  • Ping Yang, Huanlu Song, Yanping Lin, Tianyang Guo, Lijin Wang, Michael Granvogl, Yongquan Xu. Differences of characteristic aroma compounds in Rougui tea leaves with different roasting temperatures analyzed by switchable GC-O-MS and GC × GC-O-MS and sensory evaluation. Food & function. 2021 Jun; 12(11):4797-4807. doi: 10.1039/d1fo00165e. [PMID: 33861271]
  • Deepa Agarwal, Lim Mui, Emma Aldridge, James McKinney, Louise Hewson, Ian Denis Fisk. The progression of lipid oxidation, β-carotenes degradation and sensory perception of batch-fried sliced sweet potato crisps during storage. Food & function. 2021 May; 12(10):4535-4543. doi: 10.1039/d0fo03100c. [PMID: 33903860]
  • Lukas M Müller-Wirtz, Daniel Kiefer, Joschua Knauf, Maximilian A Floss, Jonas Doneit, Beate Wolf, Felix Maurer, Daniel I Sessler, Thomas Volk, Sascha Kreuer, Tobias Fink. Differential Response of Pentanal and Hexanal Exhalation to Supplemental Oxygen and Mechanical Ventilation in Rats. Molecules (Basel, Switzerland). 2021 May; 26(9):. doi: 10.3390/molecules26092752. [PMID: 34067078]
  • Caimeng Zhang, Yufei Hua, Xingfei Li, Xiangzhen Kong, Yeming Chen. Key volatile off-flavor compounds in peas (Pisum sativum L.) and their relations with the endogenous precursors and enzymes using soybean (Glycine max) as a reference. Food chemistry. 2020 Dec; 333(?):127469. doi: 10.1016/j.foodchem.2020.127469. [PMID: 32673955]
  • W S Harwood, B G Carter, D C Cadwallader, M A Drake. The role of heat treatment in light oxidation of fluid milk. Journal of dairy science. 2020 Dec; 103(12):11244-11256. doi: 10.3168/jds.2020-18933. [PMID: 33010920]
  • Mahmoud Tabibpour, Yadollah Yamini, Seyyed Hamid Ahmadi, Ali Esrafili, Kourosh Tabar Heydar, Seyed Ali Javad Mousavi, Mahroo Baharfar. Microextraction on a screw for determination of trace amounts of hexanal and heptanal as lung cancer biomarkers. Journal of pharmaceutical and biomedical analysis. 2020 Nov; 191(?):113528. doi: 10.1016/j.jpba.2020.113528. [PMID: 32916561]
  • Hiroshi Ueno, Atsumi Shimada, Shunsuke Suemitsu, Shinji Murakami, Naoya Kitamura, Kenta Wani, Yu Takahashi, Yosuke Matsumoto, Motoi Okamoto, Takeshi Ishihara. Hexanal inhalation affects cognition and anxiety-like behavior in mice. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2020 Nov; 75(11-12):409-415. doi: 10.1515/znc-2019-0215. [PMID: 32589610]
  • Angelique Vandemoortele, Marie Simon, Arnaud Claes, Bruno De Meulenaer. Behavior of Hexanal, (E)-Hex-2-enal, 4-Hydroxyhex-2-enal, and 4-Hydroxynon-2-enal in Oil-in-Water Emulsions. Journal of agricultural and food chemistry. 2020 Oct; 68(41):11568-11577. doi: 10.1021/acs.jafc.0c04060. [PMID: 32924473]
  • Riska Rian Fauziah, Shinjiro Ogita, Tomoyuki Yoshino, Yukihiro Yamamoto. Effect of Molecular Form of Conjugated Linoleic Acid on Oxidative Stability : Comparison of Triacylglycerol and Phosphatidylcholine Form. Journal of oleo science. 2020 Aug; 69(8):801-807. doi: 10.5650/jos.ess20028. [PMID: 32641609]
  • Xiao Wang, Shang Wang, Jiankun Yi, Yunshuo Li, Jianan Liu, Jun Wang, Jinghui Xi. Three Host Plant Volatiles, Hexanal, Lauric Acid, and Tetradecane, are Detected by an Antenna-Biased Expressed Odorant Receptor 27 in the Dark Black Chafer Holotrichia parallela. Journal of agricultural and food chemistry. 2020 Jul; 68(28):7316-7323. doi: 10.1021/acs.jafc.0c00333. [PMID: 32551589]
  • Jana Goritschnig, Klaudia Tadus, Jürgen König, Marc Pignitter. Free Radical Scavenging Activity of Carbonyl-Amine Adducts Formed in Soybean Oil Fortified with Phosphatidylethanolamine. Molecules (Basel, Switzerland). 2020 Jan; 25(2):. doi: 10.3390/molecules25020373. [PMID: 31963288]
  • Jianqiu Chen, Jiahong Lü, Zishun He, Feng Zhang, Shaoling Zhang, Huping Zhang. Investigations into the production of volatile compounds in Korla fragrant pears (Pyrus sinkiangensis Yu). Food chemistry. 2020 Jan; 302(?):125337. doi: 10.1016/j.foodchem.2019.125337. [PMID: 31419770]
  • Renata Zawirska-Wojtasiak, Beata Jankowska, Paulina Piechowska, Sylwia Mildner-Szkudlarz. Vitamin C and aroma composition of fresh leaves from Kalanchoe pinnata and Kalanchoe daigremontiana. Scientific reports. 2019 12; 9(1):19786. doi: 10.1038/s41598-019-56359-1. [PMID: 31875020]
  • Lilia Zago, Giacomo Squeo, Edna Ivani Bertoncini, Graziana Difonzo, Francesco Caponio. Chemical and sensory characterization of Brazilian virgin olive oils. Food research international (Ottawa, Ont.). 2019 12; 126(?):108588. doi: 10.1016/j.foodres.2019.108588. [PMID: 31732048]
  • Ricard Bou, Mar Llauger, Rachel Joosse, José Antonio García-Regueiro. Effect of high hydrostatic pressure on the oxidation of washed muscle with added chicken hemoglobin. Food chemistry. 2019 Sep; 292(?):227-236. doi: 10.1016/j.foodchem.2019.04.067. [PMID: 31054669]
  • L G Dias, G H B Duarte, L R B Mariutti, N Bragagnolo. Aroma profile of rice varieties by a novel SPME method able to maximize 2-acetyl-1-pyrroline and minimize hexanal extraction. Food research international (Ottawa, Ont.). 2019 09; 123(?):550-558. doi: 10.1016/j.foodres.2019.05.025. [PMID: 31285004]
  • Leyla Alizadeh, Khadije Abdolmaleki, Kooshan Nayebzadeh, Reyhane Shahin. Effects of tocopherol, rosemary essential oil and Ferulago angulata extract on oxidative stability of mayonnaise during its shelf life: A comparative study. Food chemistry. 2019 Jul; 285(?):46-52. doi: 10.1016/j.foodchem.2019.01.028. [PMID: 30797371]
  • Yu Cao, Giovanni Benelli, Giacinto Salvatore Germinara, Filippo Maggi, Yuanjie Zhang, Shuangli Luo, Hong Yang, Can Li. Innate positive chemotaxis to paeonal from highly attractive Chinese medicinal herbs in the cigarette beetle, Lasioderma serricorne. Scientific reports. 2019 05; 9(1):6995. doi: 10.1038/s41598-019-43198-3. [PMID: 31061503]
  • Xin Yao, Mengxiang Gao, Zhidong Wei, Mingxia Chen, Wenfeng Shangguan. Removal of hexanal in cooking fume by combination of storage and plasma-catalytic oxidation on alkali-modified Co-Mn solid solution. Chemosphere. 2019 Apr; 220(?):738-747. doi: 10.1016/j.chemosphere.2018.12.201. [PMID: 30611072]
  • Juliana Villasante, Marina Girbal, Isidoro Metón, María Pilar Almajano. Effects of Pecan Nut (Carya illinoiensis) and Roselle Flower (Hibiscus sabdariffa) as Antioxidant and Antimicrobial Agents for Sardines (Sardina pilchardus). Molecules (Basel, Switzerland). 2018 Dec; 24(1):. doi: 10.3390/molecules24010085. [PMID: 30591660]
  • Giacomo Braschi, Diana I Serrazanetti, Lorenzo Siroli, Francesca Patrignani, Maria De Angelis, Rosalba Lanciotti. Gene expression responses of Listeria monocytogenes Scott A exposed to sub-lethal concentrations of natural antimicrobials. International journal of food microbiology. 2018 Dec; 286(?):170-178. doi: 10.1016/j.ijfoodmicro.2018.07.026. [PMID: 30172105]
  • L Siroli, G Braschi, A de Jong, J Kok, F Patrignani, R Lanciotti. Transcriptomic approach and membrane fatty acid analysis to study the response mechanisms of Escherichia coli to thyme essential oil, carvacrol, 2-(E)-hexanal and citral exposure. Journal of applied microbiology. 2018 Nov; 125(5):1308-1320. doi: 10.1111/jam.14048. [PMID: 30028070]
  • Ying Zhang, Jie Kong, Fei Huang, Yunfei Xie, Yahui Guo, Yuliang Cheng, He Qian, Weirong Yao. Hexanal as a QS inhibitor of extracellular enzyme activity of Erwinia carotovora and Pseudomonas fluorescens and its application in vegetables. Food chemistry. 2018 Jul; 255(?):1-7. doi: 10.1016/j.foodchem.2018.02.038. [PMID: 29571454]
  • Alessandro Genovese, Tiziana Rispoli, Raffaele Sacchi. Extra virgin olive oil aroma release after interaction with human saliva from individuals with different body mass index. Journal of the science of food and agriculture. 2018 Jul; 98(9):3376-3383. doi: 10.1002/jsfa.8848. [PMID: 29277918]
  • Cheng Chen, Qunli Yu, Ling Han, Jiaying Zhang, Zhaobin Guo. Effects of aldehyde products of lipid oxidation on the color stability and metmyoglobin reducing ability of bovine Longissimus muscle. Animal science journal = Nihon chikusan Gakkaiho. 2018 May; 89(5):810-816. doi: 10.1111/asj.12993. [PMID: 29460317]
  • Jill K Winkler-Moser, Erica L Bakota, Hong-Sik Hwang. Stability and Antioxidant Activity of Annatto (Bixa orellana L.) Tocotrienols During Frying and in Fried Tortilla Chips. Journal of food science. 2018 Feb; 83(2):266-274. doi: 10.1111/1750-3841.14037. [PMID: 29337368]
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