Heptanal (BioDeep_00000004183)

 

Secondary id: BioDeep_00000629894

human metabolite Endogenous blood metabolite natural product Volatile Flavor Compounds


代谢物信息卡片


Oenanthic aldehyde

化学式: C7H14O (114.10445940000001)
中文名称: 正庚醛, 庚醛
谱图信息: 最多检出来源 Homo sapiens(feces) 81.82%

分子结构信息

SMILES: CCCCCCC=O
InChI: InChI=1S/C7H14O/c1-2-3-4-5-6-7-8/h7H,2-6H2,1H3

描述信息

Heptanal, also known as enanthal or N-heptaldehyde, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, heptanal is considered to be a fatty aldehyde lipid molecule. It is a colourless liquid with a strong fruity odor, which is used as precursor to components in perfumes and lubricants. Heptanal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Heptanal exists in all eukaryotes, ranging from yeast to humans. Heptanal is an aldehydic, citrus, and fat tasting compound. heptanal is found, on average, in the highest concentration in a few different foods, such as corns, tea, and sweet oranges and in a lower concentration in lemons, wild carrots, and carrots. heptanal has also been detected, but not quantified, in several different foods, such as horned melons, common beets, dills, red bell peppers, and malus (crab apple). This could make heptanal a potential biomarker for the consumption of these foods. The formation of heptanal in the fractional distillation of castor oil was already described in 1878. The large-scale production is based on the pyrolytic cleavage of ricinoleic acid ester (Arkema method) and on the hydroformylation of 1-hexene with rhodium 2-ethylhexanoate as a catalyst upon addition of some 2-ethylhexanoic acid (Oxea method):Heptanal naturally occurs in the essential oils of ylang-ylang (Cananga odorata), clary sage (Salvia sclarea), lemon (Citrus x limon), bitter orange (Citrus x aurantium), rose (Rosa) and hyacinth (Hyacinthus). Heptanal is a potentially toxic compound. Heptanal has been found to be associated with several diseases such as ulcerative colitis, crohns disease, uremia, and nonalcoholic fatty liver disease; also heptanal has been linked to the inborn metabolic disorders including celiac disease. The compound has a flash point of 39.5 °C. The explosion range is between 1.1\\% by volume as the lower explosion limit (LEL) and 5.2\\% by volume as the upper explosion limit. Heptanal or heptanaldehyde is an alkyl aldehyde. Full hydrogenation provides the branched primary alcohol 2-pentylnonan-1-ol, also accessible from the Guerbet reaction from heptanol. A by-product of the given reaction is the unpleasant rancid smelling (Z)-2-pentyl-2-nonenal. Heptanal forms flammable vapor-air mixtures. Heptanal is a flammable, slightly volatile colorless liquid of pervasive fruity to oily-greasy odor, which is miscible with alcohols and practically insoluble in water. Heptanal reacts with benzaldehyde in a Knoevenagel reaction under basic catalysis with high yield and selectivity (> 90\\%) to alpha-pentylcinnamaldehyde (also called jasmine aldehyde because of the typical jasmine odor), which is mostly used in many fragrances as a cis/trans isomer mixture.
Found in essential oils of ylang-ylang, clary sage, California orange, bitter orange and others. Flavouring agent

同义名列表

26 个代谢物同义名

Oenanthic aldehyde; Enanthic aldehyde; N-Heptylaldehyde; Heptyl aldehyde; Oenanthaldehyde; N-Heptaldehyde; Enanthaldehyde; Heptanaldehyde; 1-Heptaldehyde; Heptylaldehyde; Aldehyde C-7; Heptaldehyde; Heptan-1-al; Aldehyde C7; N-C6H13CHO; Oenanthole; N-Heptanal; 1-Heptanal; Enanthole; FEMA 2540; Oenanthal; Oenanthol; Heptanal; Enanthal; Heptanal; Heptanal



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

176 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]
  • Yipeng Liu, Sai Zhang, Song Cao, Emmanuelle Jacquin-Joly, Qiong Zhou, Yang Liu, Guirong Wang. An odorant receptor mediates the avoidance of Plutella xylostella against parasitoid. BMC biology. 2024 Mar; 22(1):61. doi: 10.1186/s12915-024-01862-9. [PMID: 38475722]
  • F Farahbakhsh, A Massah, H Hamzehzarghani, M Yassaie, Z Amjadi, H El-Zaeddi, A A Carbonell-Barrachina. Comparative profiling of volatile organic compounds associated to temperature sensitive resistance to wheat streak mosaic virus (WSMV) in resistant and susceptible wheat cultivars at normal and elevated temperatures. Journal of plant physiology. 2023 Feb; 281(?):153903. doi: 10.1016/j.jplph.2022.153903. [PMID: 36608365]
  • Sheng-Fa Li, Shuai-Bing Zhang, Yang-Yong Lv, Huan-Chen Zhai, Yuan-Sen Hu, Jing-Ping Cai. Transcriptome analysis reveals the underlying mechanism of heptanal against Aspergillus flavus spore germination. Applied microbiology and biotechnology. 2022 Feb; 106(3):1241-1255. doi: 10.1007/s00253-022-11783-8. [PMID: 35075519]
  • Anthony Zhu, Xuan Luo. Detection of Covid-19 through a Heptanal Biomarker Using Transition Metal Doped Graphene. The journal of physical chemistry. B. 2022 01; 126(1):151-160. doi: 10.1021/acs.jpcb.1c09580. [PMID: 34982559]
  • 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]
  • 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]
  • Antoine Hoffmann, Thomas Bourgeois, Alicia Munoz, Sylvia Anton, Jeremy Gevar, Matthieu Dacher, Michel Renou. A plant volatile alters the perception of sex pheromone blend ratios in a moth. Journal of comparative physiology. A, Neuroethology, sensory, neural, and behavioral physiology. 2020 07; 206(4):553-570. doi: 10.1007/s00359-020-01420-y. [PMID: 32335729]
  • Francesca Bennato, Denise Innosa, Andrea Ianni, Camillo Martino, Lisa Grotta, Giuseppe Martino. Volatile Profile in Yogurt Obtained from Saanen Goats Fed with Olive Leaves. Molecules (Basel, Switzerland). 2020 May; 25(10):. doi: 10.3390/molecules25102311. [PMID: 32423117]
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  • Anderson Luiz Oenning, Lucas Morés, Adriana Neves Dias, Eduardo Carasek. A new configuration for bar adsorptive microextraction (BAμE) for the quantification of biomarkers (hexanal and heptanal) in human urine by HPLC providing an alternative for early lung cancer diagnosis. Analytica chimica acta. 2017 May; 965(?):54-62. doi: 10.1016/j.aca.2017.02.034. [PMID: 28366212]
  • Di Chen, Jun Ding, Ming-Ke Wu, Tian-Yi Zhang, Chu-Bo Qi, Yu-Qi Feng. A liquid chromatography-mass spectrometry method based on post column derivatization for automated analysis of urinary hexanal and heptanal. Journal of chromatography. A. 2017 Apr; 1493(?):57-63. doi: 10.1016/j.chroma.2017.02.071. [PMID: 28292517]
  • Xiaowei Xin, Qingshen Liu, Yingying Zhang, Demin Gao. Chemical composition and antibacterial activity of the essential oil from Pyrrosia tonkinensis (Giesenhagen) Ching. Natural product research. 2016; 30(7):853-6. doi: 10.1080/14786419.2015.1062759. [PMID: 26214127]
  • Jiu-Feng Liu, Bi-Feng Yuan, Yu-Qi Feng. Determination of hexanal and heptanal in human urine using magnetic solid phase extraction coupled with in-situ derivatization by high performance liquid chromatography. Talanta. 2015 May; 136(?):54-9. doi: 10.1016/j.talanta.2015.01.003. [PMID: 25702985]
  • Ryota Motooka, Atsushi Usami, Hiroshi Nakahashi, Satoshi Koutari, Satoshi Nakaya, Ryoyu Shimizu, Kaoru Tsuji, Shinsuke Marumoto, Mitsuo Miyazawa. Characteristic odor components of essential oils from Eurya japonica. Journal of oleo science. 2015; 64(5):577-84. doi: 10.5650/jos.ess14225. [PMID: 25843279]
  • Raymond T Marsili, Charles R Laskonis. Odorant synergy effects as the cause of fishy malodors in algal marine oils. Journal of agricultural and food chemistry. 2014 Oct; 62(40):9676-82. doi: 10.1021/jf502252q. [PMID: 25232667]
  • Antoine Chaffiol, Fabienne Dupuy, Romina B Barrozo, Jan Kropf, Michel Renou, Jean-Pierre Rospars, Sylvia Anton. Pheromone modulates plant odor responses in the antennal lobe of a moth. Chemical senses. 2014 Jun; 39(5):451-63. doi: 10.1093/chemse/bju017. [PMID: 24798893]
  • Jong Hyun Lim, Juhun Park, Eun Hae Oh, Hwi Jin Ko, Seunghun Hong, Tai Hyun Park. Nanovesicle-based bioelectronic nose for the diagnosis of lung cancer from human blood. Advanced healthcare materials. 2014 Mar; 3(3):360-6. doi: 10.1002/adhm.201300174. [PMID: 23868879]
  • Fang Chen, Chunqiu Wang, Meijiang Zhang, Xiaoli Zhang, Yan Liu, Jiannong Ye, Qingcui Chu. Sensitive determination of endogenous hexanal and heptanal in urine by hollow-fiber liquid-phase microextraction prior to capillary electrophoresis with amperometric detection. Talanta. 2014 Feb; 119(?):83-9. doi: 10.1016/j.talanta.2013.10.052. [PMID: 24401388]
  • A J Fox, T J Smith, P D Gerard, M A Drake. The influence of bleaching agent and temperature on bleaching efficacy and volatile components of fluid whey and whey retentate. Journal of food science. 2013 Oct; 78(10):C1535-C1542. doi: 10.1111/1750-3841.12251. [PMID: 24102418]
  • Ingrid Kohl, Jonathan Beauchamp, Ferguel Cakar-Beck, Jens Herbig, J Dunkl, Olaf Tietje, Martin Tiefenthaler, Claudia Boesmueller, Armin Wisthaler, Martin Breitenlechner, Stephan Langebner, August Zabernigg, Florian Reinstaller, Klaus Winkler, Rene Gutmann, Armin Hansel. First observation of a potential non-invasive breath gas biomarker for kidney function. Journal of breath research. 2013 Mar; 7(1):017110. doi: 10.1088/1752-7155/7/1/017110. [PMID: 23446042]
  • Nicholas P L Tuckey, Jacqueline R Day, Matthew R Miller. Determination of volatile compounds in New Zealand Greenshell™ mussels (Perna canaliculus) during chilled storage using solid phase microextraction gas chromatography-mass spectrometry. Food chemistry. 2013 Jan; 136(1):218-23. doi: 10.1016/j.foodchem.2012.07.118. [PMID: 23017416]
  • Y F Ma, C Xiao. Push-pull effects of three plant secondary metabolites on oviposition of the potato tuber moth, Phthorimaea operculella. Journal of insect science (Online). 2013; 13(?):128. doi: 10.1673/031.013.12801. [PMID: 24786822]
  • In Hee Cho, Hyun Jeong Lee, Young-Suk Kim. Differences in the volatile compositions of ginseng species (Panax sp.). Journal of agricultural and food chemistry. 2012 Aug; 60(31):7616-22. doi: 10.1021/jf301835v. [PMID: 22804575]
  • Hiroshi M Ueno, Makoto Shiota, Noriko Ueda, Tomoyuki Isogai, Toshiya Kobayashi. Iron-lactoferrin complex reduces iron-catalyzed off-flavor formation in powdered milk with added fish oil. Journal of food science. 2012 Aug; 77(8):C853-8. doi: 10.1111/j.1750-3841.2012.02809.x. [PMID: 22860577]
  • S Jervis, R Campbell, K L Wojciechowski, E A Foegeding, M A Drake, D M Barbano. Effect of bleaching whey on sensory and functional properties of 80\% whey protein concentrate. Journal of dairy science. 2012 Jun; 95(6):2848-62. doi: 10.3168/jds.2011-4967. [PMID: 22612922]
  • Antoine Chaffiol, Jan Kropf, Romina B Barrozo, Christophe Gadenne, Jean-Pierre Rospars, Sylvia Anton. Plant odour stimuli reshape pheromonal representation in neurons of the antennal lobe macroglomerular complex of a male moth. The Journal of experimental biology. 2012 May; 215(Pt 10):1670-80. doi: 10.1242/jeb.066662. [PMID: 22539734]
  • Hisashi Omura, Nanako Yanai, Keiichi Honda. Sexual dimorphism in scent substances and cuticular lipids of adult Papilio protenor butterflies. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2012 May; 67(5-6):331-41. doi: 10.1515/znc-2012-5-614. [PMID: 22888540]
  • Hui Xu, Shuyu Wang. A novel sorptive extraction method based on polydimethylsiloxane frit for determination of lung cancer biomarkers in human serum. Analytica chimica acta. 2012 Apr; 724(?):61-6. doi: 10.1016/j.aca.2012.02.046. [PMID: 22483210]
  • Hui Xu, Zhihua Yan, Dandan Song. Development of a novel monolith frit-based solid-phase microextraction method for determination of hexanal and heptanal in human serum samples. Journal of separation science. 2012 Mar; 35(5-6):713-20. doi: 10.1002/jssc.201100908. [PMID: 22271665]
  • Pierluigi Caboni, Nikoletta G Ntalli, Nadhem Aissani, Ivana Cavoski, Alberto Angioni. Nematicidal activity of (E,E)-2,4-decadienal and (E)-2-decenal from Ailanthus altissima against Meloidogyne javanica. Journal of agricultural and food chemistry. 2012 Feb; 60(4):1146-51. doi: 10.1021/jf2044586. [PMID: 22224661]
  • Nina Deisig, Jan Kropf, Simon Vitecek, Delphine Pevergne, Angela Rouyar, Jean-Christophe Sandoz, Philippe Lucas, Christophe Gadenne, Sylvia Anton, Romina Barrozo. Differential interactions of sex pheromone and plant odour in the olfactory pathway of a male moth. PloS one. 2012; 7(3):e33159. doi: 10.1371/journal.pone.0033159. [PMID: 22427979]
  • Mengyao Liu, Hui Zhu, Jinquan Li, Cristiana C Garcia, Wenchao Feng, Liliya N Kirpotina, Jonathan Hilmer, Luciana P Tavares, Arthur W Layton, Mark T Quinn, Brian Bothner, Mauro M Teixeira, Benfang Lei. Group A Streptococcus secreted esterase hydrolyzes platelet-activating factor to impede neutrophil recruitment and facilitate innate immune evasion. PLoS pathogens. 2012; 8(4):e1002624. doi: 10.1371/journal.ppat.1002624. [PMID: 22496650]
  • 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]
  • 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]
  • Rossella Guadagni, Nadia Miraglia, Angela Simonelli, Angela Silvestre, Monica Lamberti, Daniela Feola, Antonio Acampora, Nicola Sannolo. Solid-phase microextraction-gas chromatography-mass spectrometry method validation for the determination of endogenous substances: urinary hexanal and heptanal as lung tumor biomarkers. Analytica chimica acta. 2011 Sep; 701(1):29-36. doi: 10.1016/j.aca.2011.05.035. [PMID: 21763805]
  • Yongxia Xu, Qingchan Chen, Shengjiao Lei, Peng Wu, Gang Fan, Xiaoyun Xu, Siyi Pan. Effects of lard on the formation of volatiles from the Maillard reaction of cysteine with xylose. Journal of the science of food and agriculture. 2011 Sep; 91(12):2241-6. doi: 10.1002/jsfa.4445. [PMID: 21618545]
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