(R)-Citronellal (BioDeep_00000000622)

 

Secondary id: BioDeep_00000863888

human metabolite PANOMIX_OTCML-2023 Endogenous Volatile Flavor Compounds


代谢物信息卡片


(R)-(+)-Citronellal, technical grade, 90\\%

化学式: C10H18O (154.1357578)
中文名称: (R)-(+)-香茅醛, (R)-(+)-香茅, -(+)-香茅醛, （R） -（+）-香茅醛
谱图信息: 最多检出来源 Macaca mulatta(otcml) 0.12%

分子结构信息

SMILES: C/C(C)=C\CC[C@@H](C)CC=O
InChI: InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3/t10-/m1/s1

描述信息

(R)-(+)-citronellal is the (3R)-stereoisomer of 3,7-dimethyloct-6-enal (citronellal). It is an enantiomer of a (S)-(-)-citronellal.
(R)-(+)-Citronellal is a natural product found in Litsea cubeba, Backhousia citriodora, and other organisms with data available.
(R)-Citronellal is found in citrus. (R)-Citronellal is a constituent of citronella oil. Also in citrus, lavender, eucalyptus oils and others. (R)-Citronellal is a flavouring agent
Constituent of citronella oiland is) also in citrus, lavender, eucalyptus oils and others. Flavouring agent. (R)-Citronellal is found in lemon balm, citrus, and herbs and spices.
The (3R)-stereoisomer of 3,7-dimethyloct-6-enal (citronellal).
(R)-(+)-Citronellal, isolated from citrus, lavender and eucalyptus oils, is a monoterpenoid and main component of citronellal oil with a distinct lemon scent. A flavouring agent. Used for insect repellent and antifungal properties[1][2].
(R)-(+)-Citronellal, isolated from citrus, lavender and eucalyptus oils, is a monoterpenoid and main component of citronellal oil with a distinct lemon scent. A flavouring agent. Used for insect repellent and antifungal properties[1][2].

同义名列表

27 个代谢物同义名

(R)-(+)-Citronellal, technical grade, 90\\%; 2,6-Dimethylhept-5-enecarboxaldehyde; 6-Octenal, 3,7-dimethyl-, (theta)-; 6-Octenal, 3,7-dimethyl-, (3R)-; 6-Octenal, 3,7-dimethyl-, (R)-; 3,7-Dimethyl-6-octenal, (3R)-; (3R)-3,7-dimethyloct-6-enal; 3,7-Dimethyl-(3R)-6-Octenal; (3R)-3,7-Dimethyl-6-octenal; (R)-3,7-Dimethyloct-6-enal; (R)-3,7-dimethyl-6-octenal; 3,7-dimethyloct-6-en-1-al; 3,7-Dimethyl-6-octenal; (3R)-(+)-citronellal; (R)-(+)-Citronellal; 2,3-Dihydrocitral; beta-Citronellal; (+)-Citronellal; (±)-Citronellal; (R)-citronellal; dl-Citronellal; d-Citronellal; β-Citronellal; Rhodinal; Citronellal; (R)-(+)-Citronellal; (R)-(+)-Citronellal



数据库引用编号

23 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(0)

代谢反应

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

71 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

  • Akshay Kumar, Tanya Singh Raghuvanshi, Surya Pratap, Horesh Kumar, Bhanu Prakash. Nanofabrication of citronellal with chitosan biopolymer to boost its efficacy against aflatoxin B1 and Aspergillus flavus mediated biodeterioration of active ingredient of Piper longum. Food chemistry. 2024 Aug; 449(?):139240. doi: 10.1016/j.foodchem.2024.139240. [PMID: 38599109]
  • Yue Qiu, Xue Zhang, Shan-Shan Li, Yin-Lan Li, Bing-Yan Mao, Jia-Xin Fan, Shuang-Guo, Ya-Ling Yin, Peng Li. Citronellal can alleviate vascular endothelial dysfunction by reducing ectopic miR-133a expression. Life sciences. 2024 Feb; 339(?):122382. doi: 10.1016/j.lfs.2023.122382. [PMID: 38154610]
  • Thomas Vanegas-Estévez, Fanny Melina Duque, Diana L Urbina, Luis C Vesga, Stelia C Mendez-Sanchez, Jonny E Duque. Design and elucidation of an insecticide from natural compounds targeting mitochondrial proteins of Aedes aegypti. Pesticide biochemistry and physiology. 2024 Jan; 198(?):105721. doi: 10.1016/j.pestbp.2023.105721. [PMID: 38225076]
  • Laure Martinelli, Camille Bihanic, Aurélie Bony, Florence Gros, Corentin Conart, Sébastien Fiorucci, Hervé Casabianca, Frédéric Schiets, Giorgiana Chietera, Benoît Boachon, Bernard Blerot, Sylvie Baudino, Frédéric Jullien, Denis Saint-Marcoux. Citronellol biosynthesis in pelargonium is a multi-step pathway involving PRISE enzymes. Plant physiology. 2023 Oct; ?(?):. doi: 10.1093/plphys/kiad550. [PMID: 37831417]
  • Nikola M Stojanović, Marko Z Mladenović, Pavle J Randjelović, Niko S Radulović. The potential of lemon balm (Melissa officinalis L.) essential oil as an anti-anxiety agent - is the citronellal the activity carrier?. Journal of ethnopharmacology. 2023 Oct; 314(?):116661. doi: 10.1016/j.jep.2023.116661. [PMID: 37207879]
  • Caroline Deweer, Karin Sahmer, Jérôme Muchembled. Anti-oomycete activities from essential oils and their major compounds on Phytophthora infestans. Environmental science and pollution research international. 2023 Oct; ?(?):. doi: 10.1007/s11356-023-29270-6. [PMID: 37779122]
  • Xi Yang, Chunzhe Jin, Ziwei Wu, Hui Han, Zhilin Zhang, Yongjian Xie, Dayu Zhang. Toxicity and Physiological Effects of Nine Lamiaceae Essential Oils and Their Major Compounds on Reticulitermes dabieshanensis. Molecules (Basel, Switzerland). 2023 Feb; 28(5):. doi: 10.3390/molecules28052007. [PMID: 36903258]
  • Haneen Ibrahim Al Othman, Atiqah Zaid, Francesco Cacciola, Zhijun Zhao, Xiaosheng Guan, Jalal T Althakafy, Yong Foo Wong. Evaluation of Cryogen-Free Thermal Modulation-Based Enantioselective Comprehensive Two-Dimensional Gas Chromatography for Stereo-Differentiation of Monoterpenes in Citrus spp. Leaf Oils. Molecules (Basel, Switzerland). 2023 Feb; 28(3):. doi: 10.3390/molecules28031381. [PMID: 36771047]
  • A O C Costa, R I A Rego, H H N Andrade, T K V L Costa, M G S S Salvadori, R N Almeida, R D Castro. Evaluation of the antinociceptive effect generated by citronellal monoterpene isomers. Brazilian journal of biology = Revista brasleira de biologia. 2023; 83(?):e271781. doi: 10.1590/1519-6984.271781. [PMID: 37255202]
  • Desmond O Agwunobi, Min Wang, Zihao Wang, Ruwei Bai, Ruotong Wang, Qiuyu Hu, Zhijun Yu, Jingze Liu. The toxicity of the monoterpenes from lemongrass is mitigated by the detoxifying symbiosis of bacteria and fungi in the tick Haemaphysalis longicornis. Ecotoxicology and environmental safety. 2022 Dec; 247(?):114261. doi: 10.1016/j.ecoenv.2022.114261. [PMID: 36332404]
  • Immacolata Iovinella, Beniamino Caputo, Pietro Cobre, Mattia Manica, Alessandro Mandoli, Francesca Romana Dani. Advances in mosquito repellents: effectiveness of citronellal derivatives in laboratory and field trials. Pest management science. 2022 Dec; 78(12):5106-5112. doi: 10.1002/ps.7127. [PMID: 36102335]
  • Seyyed Morteza Hoseini, Ali Taheri Mirghaed, Esmail Pagheh, Seyed Hossein Hoseinifar, Hien Van Doan. Anesthesia of rainbow trout with citronellal: Efficacy and biochemical effects. Journal of experimental zoology. Part A, Ecological and integrative physiology. 2022 03; 337(3):227-237. doi: 10.1002/jez.2560. [PMID: 34826206]
  • Nikola M Stojanović, Marko Z Mladenović, Aleksandra Maslovarić, Nenad I Stojiljković, Pavle J Randjelović, Niko S Radulović. Lemon balm (Melissa officinalis L.) essential oil and citronellal modulate anxiety-related symptoms - In vitro and in vivo studies. Journal of ethnopharmacology. 2022 Feb; 284(?):114788. doi: 10.1016/j.jep.2021.114788. [PMID: 34718102]
  • Xu Liu, Yue Qiu, Yanhua Liu, Ning Huang, Cai Hua, Qianqian Wang, Zeqing Wu, Junxiu Lu, Ping Song, Jian Xu, Peng Li, Yaling Yin. Citronellal ameliorates doxorubicin-induced hepatotoxicity via antioxidative stress, antiapoptosis, and proangiogenesis in rats. Journal of biochemical and molecular toxicology. 2021 Feb; 35(2):e22639. doi: 10.1002/jbt.22639. [PMID: 33051984]
  • Bagora Bayala, Ahmed Y Coulibaly, Florencia W Djigma, Bolni Marius Nagalo, Silvère Baron, Gilles Figueredo, Jean-Marc A Lobaccaro, Jacques Simpore. Chemical composition, antioxidant, anti-inflammatory and antiproliferative activities of the essential oil of Cymbopogon nardus, a plant used in traditional medicine. Biomolecular concepts. 2020 Apr; 11(1):86-96. doi: 10.1515/bmc-2020-0007. [PMID: 32304294]
  • J Joe Hull, Yu-Wen Yang, Katelyn Miyasaki, Colin S Brent. TRPA1 modulates noxious odor responses in Lygus hesperus. Journal of insect physiology. 2020 04; 122(?):104038. doi: 10.1016/j.jinsphys.2020.104038. [PMID: 32113955]
  • Khan Bilal Mukhtar Ahmed, M Masroor A Khan, Ajmat Jahan, Husna Siddiqui, Moin Uddin. Gamma rays induced acquisition of structural modification in chitosan boosts photosynthetic machinery, enzymatic activities and essential oil production in citronella grass (Cymbopogon winterianus Jowitt). International journal of biological macromolecules. 2020 Feb; 145(?):372-389. doi: 10.1016/j.ijbiomac.2019.12.130. [PMID: 31862372]
  • Abeer A Mohamed, Said I Behiry, Hosny A Younes, Nader A Ashmawy, Mohamed Z M Salem, Ofelia Márquez-Molina, Alberto Barbabosa-Pilego. Antibacterial activity of three essential oils and some monoterpenes against Ralstonia solanacearum phylotype II isolated from potato. Microbial pathogenesis. 2019 Oct; 135(?):103604. doi: 10.1016/j.micpath.2019.103604. [PMID: 31247257]
  • Laurence Lins, Simon Dal Maso, Berenice Foncoux, Anouar Kamili, Yoann Laurin, Manon Genva, M Haissam Jijakli, Caroline De Clerck, Marie Laure Fauconnier, Magali Deleu. Insights into the Relationships Between Herbicide Activities, Molecular Structure and Membrane Interaction of Cinnamon and Citronella Essential Oils Components. International journal of molecular sciences. 2019 Aug; 20(16):. doi: 10.3390/ijms20164007. [PMID: 31426453]
  • Wirginia Kukula-Koch, Wojciech Koch, Lidia Czernicka, Kazimierz Głowniak, Yoshinori Asakawa, Akemi Umeyama, Zbigniew Marzec, Takashi Kuzuhara. MAO-A Inhibitory Potential of Terpene Constituents from Ginger Rhizomes-A Bioactivity Guided Fractionation. Molecules (Basel, Switzerland). 2018 May; 23(6):. doi: 10.3390/molecules23061301. [PMID: 29844252]
  • Raiane S Lemes, Cassia C F Alves, Elisângela B B Estevam, Mariana B Santiago, Carlos H G Martins, Tainá C L Dos Santos, Antônio E M Crotti, Mayker L D Miranda. Chemical composition and antibacterial activity of essential oils from Citrus aurantifolia leaves and fruit peel against oral pathogenic bacteria. Anais da Academia Brasileira de Ciencias. 2018 Apr; 90(2):1285-1292. doi: 10.1590/0001-3765201820170847. [PMID: 29898096]
  • Jhones L de Oliveira, Estefânia V R Campos, Anderson E S Pereira, Tatiane Pasquoto, Renata Lima, Renato Grillo, Daniel Junior de Andrade, Fabiano Aparecido Dos Santos, Leonardo Fernandes Fraceto. Zein Nanoparticles as Eco-Friendly Carrier Systems for Botanical Repellents Aiming Sustainable Agriculture. Journal of agricultural and food chemistry. 2018 Feb; 66(6):1330-1340. doi: 10.1021/acs.jafc.7b05552. [PMID: 29345934]
  • Akanksha Singh, Rupali Gupta, Sudeep Tandon, Prateeksha, Rakesh Pandey. Anti-biofilm and anti-virulence potential of 3,7-dimethyloct-6-enal derived from Citrus hystrix against bacterial blight of rice caused by Xanthomonas oryzae pv. oryzae. Microbial pathogenesis. 2018 Feb; 115(?):264-271. doi: 10.1016/j.micpath.2017.12.051. [PMID: 29273511]
  • Remigius Chizzola, Ulrike Lohwasser, Chlodwig Franz. Biodiversity within Melissa officinalis: Variability of Bioactive Compounds in a Cultivated Collection. Molecules (Basel, Switzerland). 2018 Jan; 23(2):. doi: 10.3390/molecules23020294. [PMID: 29385035]
  • Mei-Lin Tsai, Cai-Di Lin, Keh Ai Khoo, Mei-Ying Wang, Tsang-Kuei Kuan, Wei-Chao Lin, Ya-Nan Zhang, Ya-Ying Wang. Composition and Bioactivity of Essential Oil from Citrus grandis (L.) Osbeck 'Mato Peiyu' Leaf. Molecules (Basel, Switzerland). 2017 Dec; 22(12):. doi: 10.3390/molecules22122154. [PMID: 29206180]
  • Ki-Suk Kim, In-Seung Lee, Kang-Hoon Kim, Jiyoung Park, Yumi Kim, Jeong-Hee Choi, Jin-Sung Choi, Hyeung-Jin Jang. Activation of intestinal olfactory receptor stimulates glucagon-like peptide-1 secretion in enteroendocrine cells and attenuates hyperglycemia in type 2 diabetic mice. Scientific reports. 2017 10; 7(1):13978. doi: 10.1038/s41598-017-14086-5. [PMID: 29070885]
  • Miyeon Jang, Junheon Kim, Kyungjae Andrew Yoon, Si Hyeock Lee, Chung Gyoo Park. Biological activity of Myrtaceae plant essential oils and their major components against Drosophila suzukii (Diptera: Drosophilidae). Pest management science. 2017 Feb; 73(2):404-409. doi: 10.1002/ps.4430. [PMID: 27607409]
  • T Fu, J J Hull, T Yang, G Wang. Identification and functional characterization of four transient receptor potential ankyrin 1 variants in Apolygus lucorum (Meyer-Dür). Insect molecular biology. 2016 08; 25(4):370-84. doi: 10.1111/imb.12231. [PMID: 27038267]
  • Leopoldina de Fátima Dantas de Almeida, Jacqueline Felipe de Paula, Rossana Vanessa Dantas de Almeida, David Wynne Williams, Josimeri Hebling, Yuri Wanderley Cavalcanti. Efficacy of citronella and cinnamon essential oils on Candida albicans biofilms. Acta odontologica Scandinavica. 2016 Jul; 74(5):393-8. doi: 10.3109/00016357.2016.1166261. [PMID: 27098375]
  • H Tolba, H Moghrani, A Benelmouffok, D Kellou, R Maachi. Essential oil of Algerian Eucalyptus citriodora: Chemical composition, antifungal activity. Journal de mycologie medicale. 2015 Dec; 25(4):e128-33. doi: 10.1016/j.mycmed.2015.10.009. [PMID: 26597375]
  • Eun Jo Du, Tae Jung Ahn, Min Sung Choi, Ilmin Kwon, Hyung-Wook Kim, Jae Young Kwon, KyeongJin Kang. The Mosquito Repellent Citronellal Directly Potentiates Drosophila TRPA1, Facilitating Feeding Suppression. Molecules and cells. 2015 Oct; 38(10):911-7. doi: 10.14348/molcells.2015.0215. [PMID: 26447139]
  • J J Wei, T Fu, T Yang, Y Liu, G R Wang. A TRPA1 channel that senses thermal stimulus and irritating chemicals in Helicoverpa armigera. Insect molecular biology. 2015 Aug; 24(4):412-21. doi: 10.1111/imb.12168. [PMID: 25827167]
  • Irmanida Batubara, Irma H Suparto, Siti Sa'diah, Ryunosuke Matsuoka, Tohru Mitsunaga. Effects of inhaled citronella oil and related compounds on rat body weight and brown adipose tissue sympathetic nerve. Nutrients. 2015 Mar; 7(3):1859-70. doi: 10.3390/nu7031859. [PMID: 25774603]
  • Martin F Strube-Bloss, Austin Brown, Johannes Spaethe, Thomas Schmitt, Wolfgang Rössler. Extracting the Behaviorally Relevant Stimulus: Unique Neural Representation of Farnesol, a Component of the Recruitment Pheromone of Bombus terrestris. PloS one. 2015; 10(9):e0137413. doi: 10.1371/journal.pone.0137413. [PMID: 26340263]
  • Valéria de Mello, Márcia Cristina de Azevedo Prata, Márcio Roberto da Silva, Erik Daemon, Luciane Santos da Silva, Flávia del Gaudio Guimarães, Alessandra Esther de Mendonça, Evelize Folly, Fernanda Maria Pinto Vilela, Lilian Henriques do Amaral, Lucio Mendes Cabral, Maria da Penha Henriques do Amaral. Acaricidal properties of the formulations based on essential oils from Cymbopogon winterianus and Syzygium aromaticum plants. Parasitology research. 2014 Dec; 113(12):4431-7. doi: 10.1007/s00436-014-4121-4. [PMID: 25199555]
  • Francine Novack Victoria, Roberta Anversa, Filipe Penteado, Micheli Castro, Eder João Lenardão, Lucielli Savegnago. Antioxidant and antidepressant-like activities of semi-synthetic α-phenylseleno citronellal. European journal of pharmacology. 2014 Nov; 742(?):131-8. doi: 10.1016/j.ejphar.2014.09.005. [PMID: 25218989]
  • Akbar Ali, M Masroor A Khan, Moin Uddin, M Naeem, Mohd Idrees, Nadeem Hashmi, Tariq Ahmad Dar, Lalit Varshney. Radiolytically depolymerized sodium alginate improves physiological activities, yield attributes and composition of essential oil of Eucalyptus citriodora Hook. Carbohydrate polymers. 2014 Nov; 112(?):134-44. doi: 10.1016/j.carbpol.2014.05.070. [PMID: 25129727]
  • J C Ribeiro, W L C Ribeiro, A L F Camurça-Vasconcelos, I T F Macedo, J M L Santos, H C B Paula, J V Araújo Filho, R D Magalhães, C M L Bevilaqua. Efficacy of free and nanoencapsulated Eucalyptus citriodora essential oils on sheep gastrointestinal nematodes and toxicity for mice. Veterinary parasitology. 2014 Aug; 204(3-4):243-8. doi: 10.1016/j.vetpar.2014.05.026. [PMID: 24929446]
  • Andrea Cavalieri, Ravit Fischer, Olga Larkov, Nativ Dudai. Enantioselectivity of the bioconversion of chiral citronellal during the inhibition of wheat seeds germination. Chemistry & biodiversity. 2014 Mar; 11(3):419-26. doi: 10.1002/cbdv.201300131. [PMID: 24634071]
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