1-Methoxy-4-(2-propenyl)benzene (BioDeep_00000003765)

Main id: BioDeep_00000396723

 

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


BENZENE,1-ALLYL,4-METHOXY METHYLCHAVICOL

化学式: C10H12O (148.08881019999998)
中文名称: 草蒿脑
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c1c(ccc(c1)CC=C)OC
InChI: InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H3

描述信息

1-Methoxy-4-(2-propenyl)benzene, also known as methylchavicol or estragol, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. 1-Methoxy-4-(2-propenyl)benzene is a sweet, alcohol, and anise tasting compound. 1-Methoxy-4-(2-propenyl)benzene is found, on average, in the highest concentration within a few different foods, such as anises, fennels, and sweet basils and in a lower concentration in cumins, tarragons, and parsley. 1-Methoxy-4-(2-propenyl)benzene has also been detected, but not quantified, in several different foods, such as citrus, chinese cinnamons, caraway, fats and oils, and cloves. This could make 1-methoxy-4-(2-propenyl)benzene a potential biomarker for the consumption of these foods. 1-Methoxy-4-(2-propenyl)benzene, with regard to humans, has been linked to the inborn metabolic disorder celiac disease.
Constituent of many essential oils. Found in apple, bilberry and orange fruits and juices. Flavouring agent.
Estragole (4-Allylanisole), a relatively nontoxic volatile terpenoid ether, is a major component of the essential oil of many plants. Estragole dose-dependently blocks nerve excitability[1]. Estragole displays anti-toxoplasma activity[2].
Estragole (4-Allylanisole), a relatively nontoxic volatile terpenoid ether, is a major component of the essential oil of many plants. Estragole dose-dependently blocks nerve excitability[1]. Estragole displays anti-toxoplasma activity[2].

同义名列表

47 个代谢物同义名

BENZENE,1-ALLYL,4-METHOXY METHYLCHAVICOL; 1-Methoxy-4-(2-propenyl)benzene, 9CI; 1-methoxy-4-(prop-2-en-1-yl)benzene; 1-Methoxy-4-(2-propen-1-yl)-Benzene; 1-Methoxy-4-(2-propen-1-yl)benzene; Benzene, 1-methoxy, 4-prop-2-enyl; 1-methoxy-4-(2-propenyl)-benzene; 1-METHOXY-4-(2-PROPENYL)BENZENE; 1-methoxy-4-prop-2-enylbenzene; 3-(4-Methoxyphenyl)-1-propene; 3-(p-Methoxyphenyl)-1-propene; Para-allylanisole (estragole); Methyl chavicole (estragole); Ether, p-allylphenyl methyl; 3-(p-Methoxyphenyl)propene; 3-(4-Methoxyphenyl)propene; p-Allylphenyl methyl ether; Estragol (methylchavicol); 4-Allyl-1-methoxybenzene; 1-Allyl-4-methoxybenzene; Chavicol methyl ether; p-Allylmethoxybenzene; 4-Methoxyallylbenzene; 4-Allylmethoxybenzene; Chavicyl methyl ether; p-Methoxyallylbenzene; O-Methyl-Chavicol; O-Methylchavicol; Methyl chavicole; methyl chavicol; p-Allyl-Anisole; Methyl-Chavicol; p-allylanisole; Methylchavicol; 4-allylanisole; Isoanthethole; Estragenole; Isoanethole; Estragole; Esdragole; Esteragol; FEMA 2411; Esdragon; Estragol; Esdragol; Terragon; Tarragon



数据库引用编号

19 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(1)

代谢反应

30 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(29)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

110 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

  • Arlene Sobrinho Ventura, Ruy Alberto Caetano Corrêa Filho, Claudia Andrea Lima Cardoso, Giovanna Rodrigues Stringhetta, Lucas de Oliveira Brasileiro, Juliana Silva Ribeiro, Scheila Anelise Pereira, Gabriela Tomas Jerônimo, Jayme Aparecido Povh. Ocimum basilicum essential oil in pacu Piaractus mesopotamicus: anesthetic efficacy, distribution, and depletion in different tissues. Veterinary research communications. 2023 Oct; ?(?):. doi: 10.1007/s11259-023-10225-8. [PMID: 37851315]
  • Zhengyu Bao, Mingcong Fan, Kanza Hannachi, Tingting Li, Jiajia Zhao, Yan Li, Haifeng Qian, Li Wang. Antifungal activity of star anise extract against Penicillium roqueforti and Aspergillus niger for bread shelf life. Food research international (Ottawa, Ont.). 2023 10; 172(?):113225. doi: 10.1016/j.foodres.2023.113225. [PMID: 37689961]
  • Tae-Kyun Hong, Seung-Hwan Lee, Jeong-Seop Shin, Kyoung-Hwa Jang, Eun-Shik Na, Chol-Soo Park, Chung-Hwan Kim, Jun-Ran Kim, Sri Renukadevi Balusamy, Haribalan Perumalsamy. Toxicological and molecular adverse effect of Illicium verum fruit constituents toward Bradysia procera. Pest management science. 2023 Mar; 79(3):1131-1139. doi: 10.1002/ps.7283. [PMID: 36358028]
  • Gholamreza Gohari, Sima Panahirad, Asghar Mohammadi, Muhittin Kulak, Mohamad Reza Dadpour, Zohreh Mehri Lighvan, Sina Sharifi, Bagher Eftekhari-Sis, Sławomir Szafert, Vasileios Fotopoulos, Ali Akbari. Characterization of Octa-aminopropyl polyhedral oligomeric silsesquioxanes (OA-POSS) nanoparticles and their effect on sweet basil (Ocimum basilicum L.) response to salinity stress. Plant physiology and biochemistry : PPB. 2023 Mar; 196(?):89-102. doi: 10.1016/j.plaphy.2023.01.019. [PMID: 36706695]
  • Subhash Shivaramu, Saravan Kumar Parepally, Varun Yennurukadirenahalli Byregowda, Kamala Jayanthi Pagadala Damodaram, Anuj Bhatnagar, Kailash Chandra Naga, Sanjeev Sharma, Manoj Kumar, Vivek Kempraj. Estragole, a potential attractant of the winged melon aphid, Aphis gossypii. Pest management science. 2023 Feb; ?(?):. doi: 10.1002/ps.7413. [PMID: 36797594]
  • Ugur Avcibasi, Mouhaman Toukour Dewa, Kadriye Busra Karatay, Ayfer Yurt Kilcar, Fazilet Zumrut Biber Muftuler. Investigation Of Bioactivity Of Estragole Isolated From Basil Plant On Brain Cancer Cell Lines Using Nuclear Method. Current radiopharmaceuticals. 2023 Jan; ?(?):. doi: 10.2174/1874471016666230110144021. [PMID: 36627786]
  • Elaheh Sadat Hosseini, Mohammad Mahdi Majidi, Mohammad Hossein Ehtemam, N Hughes. Characterization of fennel germplasm for physiological persistence and drought recovery: Association with biochemical properties. Plant physiology and biochemistry : PPB. 2023 Jan; 194(?):499-512. doi: 10.1016/j.plaphy.2022.11.037. [PMID: 36516537]
  • Daniela-Simina Stefan, Mariana Popescu, Cristina-Mihaela Luntraru, Alexandru Suciu, Mihai Belcu, Lucia-Elena Ionescu, Mihaela Popescu, Petrica Iancu, Mircea Stefan. Comparative Study of Useful Compounds Extracted from Lophanthus anisatus by Green Extraction. Molecules (Basel, Switzerland). 2022 Nov; 27(22):. doi: 10.3390/molecules27227737. [PMID: 36431837]
  • Dhouha Alimi, Azhar Hajri, Selim Jallouli, Hichem Sebai. Acaricidal and anthelmintic efficacy of Ocimum basilicum essential oil and its major constituents estragole and linalool, with insights on acetylcholinesterase inhibition. Veterinary parasitology. 2022 Sep; 309(?):109743. doi: 10.1016/j.vetpar.2022.109743. [PMID: 35714433]
  • Fatemeh Najafi, Gholamreza Kavoosi, Roghayeh Siahbalaei, Amina Kariminia. Anti-oxidative and anti-hyperglycemic properties of Agastache foeniculum essential oil and oily fraction in hyperglycemia-stimulated and lipopolysaccharide-stimulated macrophage cells: In vitro and in silico studies. Journal of ethnopharmacology. 2022 Feb; 284(?):114814. doi: 10.1016/j.jep.2021.114814. [PMID: 34775034]
  • Rajendran Senthoorraja, Kesavan Subaharan, Sowmya Manjunath, Vppalayam Shanmugam Pragadheesh, Nandagopal Bakthavatsalam, Muthu Gounder Mohan, Sengottayan Senthil-Nathan, Sekarappa Basavarajappa. Electrophysiological, behavioural and biochemical effect of Ocimum basilicum oil and its constituents methyl chavicol and linalool on Musca domestica L. Environmental science and pollution research international. 2021 Sep; 28(36):50565-50578. doi: 10.1007/s11356-021-14282-x. [PMID: 33963471]
  • Eduardo Valarezo, Vladimir Morocho, Luis Cartuche, Fernanda Chamba-Granda, Magdaly Correa-Conza, Ximena Jaramillo-Fierro, Miguel Angel Meneses. Variability of the Chemical Composition and Bioactivity between the Essential Oils Isolated from Male and Female Specimens of Hedyosmum racemosum (Ruiz & Pav.) G. Don. Molecules (Basel, Switzerland). 2021 Jul; 26(15):. doi: 10.3390/molecules26154613. [PMID: 34361766]
  • Nigel J Gooderham, Samuel M Cohen, Gerhard Eisenbrand, Shoji Fukushima, F Peter Guengerich, Stephen S Hecht, Ivonne M C M Rietjens, Thomas J Rosol, Jeanne M Davidsen, Christie L Harman, Ian J Murray, Sean V Taylor. FEMA GRAS assessment of natural flavor complexes: Clove, cinnamon leaf and West Indian bay leaf-derived flavoring ingredients. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2020 Nov; 145(?):111585. doi: 10.1016/j.fct.2020.111585. [PMID: 32702506]
  • Edvaldo Balbino Alves Júnior, Rodrigo de Oliveira Formiga, Catarina Alves de Lima Serafim, Maria Elaine Cristina Araruna, Michele Liz de Souza Pessoa, Roseane Carvalho Vasconcelos, Thais Gomes de Carvalho, Tamires Gonçalves de Jesus, Aurigena Antunes Araújo, Raimundo Fernandes de Araujo Junior, Giciane Carvalho Vieira, Marianna Vieira Sobral, Leônia Maria Batista. Estragole prevents gastric ulcers via cytoprotective, antioxidant and immunoregulatory mechanisms in animal models. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2020 Oct; 130(?):110578. doi: 10.1016/j.biopha.2020.110578. [PMID: 32750650]
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  • Bernhard H Monien, Benjamin Sachse, Bela Niederwieser, Klaus Abraham. Detection of N-Acetyl-S-[3'-(4-methoxyphenyl)allyl]-l-Cys (AMPAC) in Human Urine Samples after Controlled Exposure to Fennel Tea: A New Metabolite of Estragole and trans-Anethole. Chemical research in toxicology. 2019 11; 32(11):2260-2267. doi: 10.1021/acs.chemrestox.9b00287. [PMID: 31565931]
  • Laura Marabini, Corrado L Galli, Pierpaolo La Fauci, Marina Marinovich. Effect of plant extracts on the genotoxicity of 1'-hydroxy alkenylbenzenes. Regulatory toxicology and pharmacology : RTP. 2019 Jul; 105(?):36-41. doi: 10.1016/j.yrtph.2019.03.017. [PMID: 30935955]
  • Domenico Cautela, Filomena Monica Vella, Domenico Castaldo, Bruna Laratta. Characterization of essential oil recovered from fennel horticultural wastes. Natural product research. 2019 Jul; 33(13):1964-1968. doi: 10.1080/14786419.2018.1478827. [PMID: 29846092]
  • Nurhayat Tabanca, Marco Masi, Nancy D Epsky, Paola Nocera, Alessio Cimmino, Paul E Kendra, Jerome Niogret, Antonio Evidente. Laboratory Evaluation of Natural and Synthetic Aromatic Compounds as Potential Attractants for Male Mediterranean fruit Fly, Ceratitis capitata. Molecules (Basel, Switzerland). 2019 Jun; 24(13):. doi: 10.3390/molecules24132409. [PMID: 31261896]
  • Alexander V Samet, Oksana G Shevchenko, Vyacheslav V Rusak, Eduard M Chartov, Andrey B Myshlyavtsev, Daniil A Rusanov, Marina N Semenova, Victor V Semenov. Antioxidant Activity of Natural Allylpolyalkoxybenzene Plant Essential Oil Constituents. Journal of natural products. 2019 Jun; ?(?):. doi: 10.1021/acs.jnatprod.8b00878. [PMID: 31244145]
  • Maryam Akhbari, Reza Kord, Saeedeh Jafari Nodooshan, Sepideh Hamedi. Analysis and evaluation of the antimicrobial and anticancer activities of the essential oil isolated from Foeniculum vulgare from Hamedan, Iran. Natural product research. 2019 Jun; 33(11):1629-1632. doi: 10.1080/14786419.2017.1423310. [PMID: 29308661]
  • Mina Arbabi, Hassanali Naghdi Badi, Mohammadreza Labbafi, Ali Mehrafarin, Ebrahim Saboki. Morphophysiological and Phytochemical Variability in Some Wild Populations of Ducrosia anethifolia from Iran. Chemistry & biodiversity. 2018 Dec; 15(12):e1800301. doi: 10.1002/cbdv.201800301. [PMID: 30240144]
  • João Vito B Freitas, Elenilson G Alves Filho, Lorena Mara A Silva, Guilherme J Zocolo, Edy S de Brito, Nilce V Gramosa. Chemometric analysis of NMR and GC datasets for chemotype characterization of essential oils from different species of Ocimum. Talanta. 2018 Apr; 180(?):329-336. doi: 10.1016/j.talanta.2017.12.053. [PMID: 29332819]
  • Sara Levorato, Luca Dominici, Cristina Fatigoni, Claudia Zadra, Rita Pagiotti, Massimo Moretti, Milena Villarini. In vitro toxicity evaluation of estragole-containing preparations derived from Foeniculum vulgare Mill. (fennel) on HepG2 cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2018 Jan; 111(?):616-622. doi: 10.1016/j.fct.2017.12.014. [PMID: 29233689]
  • Iveta Bartoňková, Zdeněk Dvořák. Essential oils of culinary herbs and spices display agonist and antagonist activities at human aryl hydrocarbon receptor AhR. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2018 Jan; 111(?):374-384. doi: 10.1016/j.fct.2017.11.049. [PMID: 29191726]
  • Bruna Celeida Silva Santos, Andressa Soares Pires, Célia Hitomi Yamamoto, Mara Rubia Costa Couri, Alex Gutterres Taranto, Maria Silvana Alves, Ana Lúcia Dos Santos de Matos Araújo, Orlando Vieira de Sousa. Methyl Chavicol and Its Synthetic Analogue as Possible Antioxidant and Antilipase Agents Based on the In Vitro and In Silico Assays. Oxidative medicine and cellular longevity. 2018; 2018(?):2189348. doi: 10.1155/2018/2189348. [PMID: 29849872]
  • Ran Li, Vaishnavi Amarr Reddy, Jingjing Jin, Chakaravarthy Rajan, Qian Wang, Genhua Yue, Chin Huat Lim, Nam-Hai Chua, Jian Ye, Rajani Sarojam. Comparative transcriptome analysis of oil palm flowers reveals an EAR-motif-containing R2R3-MYB that modulates phenylpropene biosynthesis. BMC plant biology. 2017 Nov; 17(1):219. doi: 10.1186/s12870-017-1174-4. [PMID: 29169327]
  • Andrea Muráriková, Anton Ťažký, Jarmila Neugebauerová, Alexandra Planková, Josef Jampílek, Pavel Mučaji, Peter Mikuš. Characterization of Essential Oil Composition in Different Basil Species and Pot Cultures by a GC-MS Method. Molecules (Basel, Switzerland). 2017 Jul; 22(7):. doi: 10.3390/molecules22071221. [PMID: 28726757]
  • Babak Abdollahi Mandoulakani, Elham Eyvazpour, Morteza Ghadimzadeh. The effect of drought stress on the expression of key genes involved in the biosynthesis of phenylpropanoids and essential oil components in basil (Ocimum basilicum L.). Phytochemistry. 2017 Jul; 139(?):1-7. doi: 10.1016/j.phytochem.2017.03.006. [PMID: 28366608]
  • Yar-Khing Yauk, Edwige J F Souleyre, Adam J Matich, Xiuyin Chen, Mindy Y Wang, Blue Plunkett, Andrew P Dare, Richard V Espley, Sumathi Tomes, David Chagné, Ross G Atkinson. Alcohol acyl transferase 1 links two distinct volatile pathways that produce esters and phenylpropenes in apple fruit. The Plant journal : for cell and molecular biology. 2017 Jul; 91(2):292-305. doi: 10.1111/tpj.13564. [PMID: 28380280]
  • Elasyed A Omer, Saber F Hendawy, Rasha F Ismail, Giacomo L Petretto, Jonathan P Rourke, Giorgio Pintore. Acclimatization study of Tagetes lucida L. in Egypt and the chemical characterization of its essential oils. Natural product research. 2017 Jul; 31(13):1509-1517. doi: 10.1080/14786419.2017.1278594. [PMID: 28152613]
  • María J Jordán, María Quílez, María C Luna, Farzaneh Bekhradi, José A Sotomayor, Pedro Sánchez-Gómez, María I Gil. Influence of water stress and storage time on preservation of the fresh volatile profile of three basil genotypes. Food chemistry. 2017 Apr; 221(?):169-177. doi: 10.1016/j.foodchem.2016.10.059. [PMID: 27979148]
  • Santosh Shiwakoti, Osama Saleh, Shital Poudyal, Abdulssamad Barka, Yanping Qian, Valtcho D Zheljazkov. Yield, Composition and Antioxidant Capacity of the Essential Oil of Sweet Basil and Holy Basil as Influenced by Distillation Methods. Chemistry & biodiversity. 2017 Apr; 14(4):. doi: 10.1002/cbdv.201600417. [PMID: 28028933]
  • Juan Carlos Romero-Benavides, Ana Lucía Ruano, Ronal Silva-Rivas, Paola Castillo-Veintimilla, Sara Vivanco-Jaramillo, Natalia Bailon-Moscoso. Medicinal plants used as anthelmintics: Ethnomedical, pharmacological, and phytochemical studies. European journal of medicinal chemistry. 2017 Mar; 129(?):209-217. doi: 10.1016/j.ejmech.2017.02.005. [PMID: 28231520]
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