Methyl cinnamate (BioDeep_00000018209)

 

Secondary id: BioDeep_00000001094, BioDeep_00000017721, BioDeep_00000268351, BioDeep_00000408681, BioDeep_00000410396, BioDeep_00000859501

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


3-Phenyl-methyl ester(2E)-2-propenoic acid

化学式: C10H10O2 (162.06807600000002)
中文名称: 肉桂酸甲酯
谱图信息: 最多检出来源 Viridiplantae(plant) 0.25%

分子结构信息

SMILES: COC(=O)/C=C/c1ccccc1
InChI: InChI=1S/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7+

描述信息

Methyl cinnamate is found in ceylan cinnamon. Methyl cinnamate occurs in essential oils e.g. from Ocimum and Alpinia species Also present in various fruits, e.g. guava, feijoa, strawberry. Methyl cinnamate is a flavouring agent.Methyl cinnamate is the methyl ester of cinnamic acid and is a white or transparent solid with a strong, aromatic odor. It is found naturally in a variety of plants, including in fruits, like strawberry, and some culinary spices, such as Sichuan pepper and some varieties of basil. Eucalyptus olida has the highest known concentrations of methyl cinnamate (98\\\\\%) with a 2-6\\\\\% fresh weight yield in the leaf and twigs.
Occurs in essential oils e.g. from Ocimum and Alpinia subspecies Also present in various fruits, e.g. guava, feijoa, strawberry. Flavouring agent
Methyl cinnamate (Methyl 3-phenylpropenoate), an active component of Zanthoxylum armatum, is a widely used natural flavor compound. Methyl cinnamate (Methyl 3-phenylpropenoate) possesses antimicrobial activity and is a tyrosinase inhibitor that can prevent food browning. Methyl cinnamate (Methyl 3-phenylpropenoate) has antiadipogenic activity through mechanisms mediated, in part, by the CaMKK2-AMPK signaling pathway[1].
Methyl cinnamate (Methyl 3-phenylpropenoate), an active component of Zanthoxylum armatum, is a widely used natural flavor compound. Methyl cinnamate (Methyl 3-phenylpropenoate) possesses antimicrobial activity and is a tyrosinase inhibitor that can prevent food browning. Methyl cinnamate (Methyl 3-phenylpropenoate) has antiadipogenic activity through mechanisms mediated, in part, by the CaMKK2-AMPK signaling pathway[1].
Methyl cinnamate (Methyl 3-phenylpropenoate), an active component of Zanthoxylum armatum, is a widely used natural flavor compound. Methyl cinnamate (Methyl 3-phenylpropenoate) possesses antimicrobial activity and is a tyrosinase inhibitor that can prevent food browning. Methyl cinnamate (Methyl 3-phenylpropenoate) has antiadipogenic activity through mechanisms mediated, in part, by the CaMKK2-AMPK signaling pathway[1].

同义名列表

18 个代谢物同义名

3-Phenyl-methyl ester(2E)-2-propenoic acid; 3-Phenyl-methyl ester(e)-2-propenoic acid; 2-Propenoic acid, 3-phenyl-, methyl ester; Methyl (2Z)-3-phenylprop-2-enoic acid; Cinnamic acid,methyl ester (trans); Methyl (2E)-3-phenyl-2-propenoate; methyl (2Z)-3-phenylprop-2-enoate; Methyl ester(e)-cinnamic acid; Methyl (2E)-3-phenylacrylate; methyl trans-cinnamate; trans-Methyl cinnamate; Methyl cinnamate, (E); Methyl (E)-cinnamate; Methyl cinnamic acid; Methyl cinnamate; Methyl cubebin; FEMA 2698; Methyl 3-phenylpropenoate



数据库引用编号

20 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

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)

35 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

  • Lilin E, Wenjie Li, Yuanjia Hu, Lijuan Deng, Jianping Yao, Xingwang Zhou. Methyl cinnamate protects against dextran sulfate sodium-induced colitis in mice by inhibiting the MAPK signaling pathway. Acta biochimica et biophysica Sinica. 2023 Aug; ?(?):. doi: 10.3724/abbs.2023124. [PMID: 37654075]
  • Paco Noriega, Lissette Calderón, Andrea Ojeda, Erika Paredes. Chemical Composition, Antimicrobial and Antioxidant Bioautography Activity of Essential Oil from Leaves of Amazon Plant Clinopodium brownei (Sw.). Molecules (Basel, Switzerland). 2023 Feb; 28(4):. doi: 10.3390/molecules28041741. [PMID: 36838728]
  • Li Zhang, Hu-Qiang Jiang, Fan Wu, Ping Wen, Jing Qing, Xin-Mi Song, Hong-Liang Li. Eastern honeybee Apis cerana sense cold flowering plants by increasing the static binding affinity of odorant-binding protein to cold floral volatiles from loquats. International journal of biological macromolecules. 2023 Jan; 232(?):123227. doi: 10.1016/j.ijbiomac.2023.123227. [PMID: 36646342]
  • Nagwa A Shoeib, Lamiaa A Al-Madboly, Amany E Ragab. In vitro and in silico β-lactamase inhibitory properties and phytochemical profile of Ocimum basilicum cultivated in central delta of Egypt. Pharmaceutical biology. 2022 Dec; 60(1):1969-1980. doi: 10.1080/13880209.2022.2127791. [PMID: 36226757]
  • Gabriela Rabeschini, Pedro Joaquim Bergamo, Carlos E P Nunes. Meaningful Words in Crowd Noise: Searching for Volatiles Relevant to Carpenter Bees among the Diverse Scent Blends of Bee Flowers. Journal of chemical ecology. 2021 May; 47(4-5):444-454. doi: 10.1007/s10886-021-01257-y. [PMID: 33683547]
  • Chi Zhang, Xinlu Chen, Barbara Crandall-Stotler, Ping Qian, Tobias G Köllner, Hong Guo, Feng Chen. Biosynthesis of methyl (E)-cinnamate in the liverwort Conocephalum salebrosum and evolution of cinnamic acid methyltransferase. Phytochemistry. 2019 Aug; 164(?):50-59. doi: 10.1016/j.phytochem.2019.04.013. [PMID: 31078779]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • 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]
  • Natália Moreira Nunes, Ana Flávia Coelho Pacheco, Álvaro Javier Patiño Agudelo, Luis Henrique Mendes da Silva, Maximiliano Soares Pinto, Maria do Carmo Hespanhol, Ana Clarissa Dos Santos Pires. Interaction of cinnamic acid and methyl cinnamate with bovine serum albumin: A thermodynamic approach. Food chemistry. 2017 Dec; 237(?):525-531. doi: 10.1016/j.foodchem.2017.05.131. [PMID: 28764029]
  • Gislene M Fujiwara, Vinícius Annies, Camila F de Oliveira, Ricardo A Lara, Maria M Gabriel, Fernando C M Betim, Jéssica M Nadal, Paulo V Farago, Josiane F G Dias, Obdulio G Miguel, Marilis D Miguel, Francisco A Marques, Sandra M W Zanin. Evaluation of larvicidal activity and ecotoxicity of linalool, methyl cinnamate and methyl cinnamate/linalool in combination against Aedes aegypti. Ecotoxicology and environmental safety. 2017 May; 139(?):238-244. doi: 10.1016/j.ecoenv.2017.01.046. [PMID: 28152405]
  • 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]
  • Atul Anand, Ramesha H Jayaramaiah, Supriya D Beedkar, Priyanka A Singh, Rakesh S Joshi, Fayaj A Mulani, Bhushan B Dholakia, Sachin A Punekar, Wasudeo N Gade, Hirekodathakallu V Thulasiram, Ashok P Giri. Comparative functional characterization of eugenol synthase from four different Ocimum species: Implications on eugenol accumulation. Biochimica et biophysica acta. 2016 11; 1864(11):1539-47. doi: 10.1016/j.bbapap.2016.08.004. [PMID: 27519164]
  • Surapan Jitviriyanon, Phanida Phanthong, Pattamapan Lomarat, Nuntavan Bunyapraphatsara, Sarthorn Porntrakulpipat, Nuanchan Paraksa. In vitro study of anti-coccidial activity of essential oils from indigenous plants against Eimeria tenella. Veterinary parasitology. 2016 Sep; 228(?):96-102. doi: 10.1016/j.vetpar.2016.08.020. [PMID: 27692340]
  • Gianluca Amadei, Brian M Ross. Quantification of character-impacting compounds in Ocimum basilicum and 'Pesto alla Genovese' with selected ion flow tube mass spectrometry. Rapid communications in mass spectrometry : RCM. 2012 Feb; 26(3):219-25. doi: 10.1002/rcm.5293. [PMID: 22223305]
  • Bhanu Prakash, Priyanka Singh, Prashant Kumar Mishra, N K Dubey. Safety assessment of Zanthoxylum alatum Roxb. essential oil, its antifungal, antiaflatoxin, antioxidant activity and efficacy as antimicrobial in preservation of Piper nigrum L. fruits. International journal of food microbiology. 2012 Feb; 153(1-2):183-91. doi: 10.1016/j.ijfoodmicro.2011.11.007. [PMID: 22137251]
  • Poonkodi Kathirvel, Subban Ravi. Chemical composition of the essential oil from basil (Ocimum basilicum Linn.) and its in vitro cytotoxicity against HeLa and HEp-2 human cancer cell lines and NIH 3T3 mouse embryonic fibroblasts. Natural product research. 2012; 26(12):1112-8. doi: 10.1080/14786419.2010.545357. [PMID: 21939371]
  • Teun Dekker, Rickard Ignell, Maedot Ghebru, Robert Glinwood, Richard Hopkins. Identification of mosquito repellent odours from Ocimum forskolei. Parasites & vectors. 2011 Sep; 4(?):183. doi: 10.1186/1756-3305-4-183. [PMID: 21936953]
  • Mashitah M Yusoff, Halijah Ibrahim, Nurulhusna A Hamid. Chemical characterization and antimicrobial activity of rhizome essential oils of very closely allied Zingiberaceae species endemic to Borneo: Alpinia ligulata K. Schum. and Alpinia nieuwenhuizii Val. Chemistry & biodiversity. 2011 May; 8(5):916-23. doi: 10.1002/cbdv.201000270. [PMID: 21560240]
  • Xiaona Fan, Sheng Lin, Chenggen Zhu, Yang Liu, Jinfeng Hu, Xiaoguang Chen, Wenjie Wang, Naihong Chen, Jiangong Shi. [Aromatic constituents of Heteroplexis micocephal and their bioactivities]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Jan; 36(1):48-56. doi: . [PMID: 21473152]
  • Tran Trung Hieu, Soon-Il Kim, Hyung Wook Kwon, Young-Joon Ahn. Enhanced repellency of binary mixtures of Zanthoxylum piperitum pericarp steam distillate or Zanthoxylum armatum seed oil constituents and Calophyllum inophyllum nut oil and their aerosols to Stomoxys calcitrans. Pest management science. 2010 Nov; 66(11):1191-8. doi: 10.1002/ps.1993. [PMID: 20628994]
  • Rajendra C Padalia, Ram S Verma, Velusamy Sundaresan, Chandan S Chanotiya. Chemical diversity in the genus Alpinia (Zingiberaceae): comparative composition of four Alpinia species grown in Northern India. Chemistry & biodiversity. 2010 Aug; 7(8):2076-87. doi: 10.1002/cbdv.201000013. [PMID: 20730971]
  • S B Jaju, N H Indurwade, D M Sakarkar, N K Fuloria, M D Ali, S P Basu. Isolation of β-sitosterol diglucosyl caprate from Alpinia galanga. Pharmacognosy research. 2010 Jul; 2(4):264-6. doi: 10.4103/0974-8490.69129. [PMID: 21808579]
  • Vigilio Ballabeni, Massimiliano Tognolini, Carmine Giorgio, Simona Bertoni, Renato Bruni, Elisabetta Barocelli. Ocotea quixos Lam. essential oil: in vitro and in vivo investigation on its anti-inflammatory properties. Fitoterapia. 2010 Jun; 81(4):289-95. doi: 10.1016/j.fitote.2009.10.002. [PMID: 19825398]
  • Susanna Roeder, Katharina Dreschler, Markus Wirtz, Simona M Cristescu, Frans J M van Harren, Rüdiger Hell, Birgit Piechulla. SAM levels, gene expression of SAM synthetase, methionine synthase and ACC oxidase, and ethylene emission from N. suaveolens flowers. Plant molecular biology. 2009 Jul; 70(5):535-46. doi: 10.1007/s11103-009-9490-1. [PMID: 19396585]
  • Shio Murakami, Wei Li, Mariko Matsuura, Tadaaki Satou, Shinichiro Hayashi, Kazuo Koike. Composition and seasonal variation of essential oil in Alpinia zerumbet from Okinawa Island. Journal of natural medicines. 2009 Apr; 63(2):204-8. doi: 10.1007/s11418-008-0306-4. [PMID: 19067113]
  • Ji-Wen Zhang, Sheng-Kun Li, Wen-Jun Wu. The main chemical composition and in vitro antifungal activity of the essential oils of Ocimum basilicum Linn. var. pilosum (Willd.) Benth. Molecules (Basel, Switzerland). 2009 Jan; 14(1):273-8. doi: 10.3390/molecules14010273. [PMID: 19136915]
  • Valtcho D Zheljazkov, Amber Callahan, Charles L Cantrell. Yield and oil composition of 38 basil (Ocimum basilicum L.) accessions grown in Mississippi. Journal of agricultural and food chemistry. 2008 Jan; 56(1):241-5. doi: 10.1021/jf072447y. [PMID: 18072735]
  • Vigilio Ballabeni, Massimiliano Tognolini, Simona Bertoni, Renato Bruni, Alessandra Guerrini, Gabriela Moreno Rueda, Elisabetta Barocelli. Antiplatelet and antithrombotic activities of essential oil from wild Ocotea quixos (Lam.) Kosterm. (Lauraceae) calices from Amazonian Ecuador. Pharmacological research. 2007 Jan; 55(1):23-30. doi: 10.1016/j.phrs.2006.09.009. [PMID: 17079160]
  • Stefan Lunkenbein, Mariluz Bellido, Asaph Aharoni, Elma M J Salentijn, Ralf Kaldenhoff, Heather A Coiner, Juan Muñoz-Blanco, Wilfried Schwab. Cinnamate metabolism in ripening fruit. Characterization of a UDP-glucose:cinnamate glucosyltransferase from strawberry. Plant physiology. 2006 Mar; 140(3):1047-58. doi: 10.1104/pp.105.074955. [PMID: 16443693]
  • Ian A Southwell. 25 years of natural product R&D with New South Wales agriculture. Molecules (Basel, Switzerland). 2005 Oct; 10(10):1232-41. doi: 10.3390/10101232. [PMID: 18007515]
  • Björn M Hausen. Evaluation of the main contact allergens in propolis (1995 to 2005). Dermatitis : contact, atopic, occupational, drug. 2005 Sep; 16(3):127-9. doi: . [PMID: 16242084]
  • Kathrin Fink, Elke Richling, Frank Heckel, Peter Schreier. Determination of 2H/1H and 13C/12C isotope ratios of (E)-methyl cinnamate from different sources using isotope ratio mass spectrometry. Journal of agricultural and food chemistry. 2004 May; 52(10):3065-8. doi: 10.1021/jf040018j. [PMID: 15137854]
  • Leopold Jirovetz, Gerhard Buchbauer, Mohamed Pottachola Shafi, Neettiyath Kalathil Leela. Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from southern India. Acta pharmaceutica (Zagreb, Croatia). 2003 Jun; 53(2):73-81. doi: . [PMID: 14764241]
  • S Tawata, S Taira, N Kobamoto, J Zhu, M Ishihara, S Toyama. Synthesis and antifungal activity of cinnamic acid esters. Bioscience, biotechnology, and biochemistry. 1996 May; 60(5):909-10. doi: 10.1271/bbb.60.909. [PMID: 8704323]
  • L P Delbressin, H C van Balen, F Seutter-Berlage. Isolation and identification of mercapturic acid metabolites of phenyl substituted acrylate esters from urine of female rats. Archives of toxicology. 1982 Mar; 49(3-4):321-30. doi: 10.1007/bf00347880. [PMID: 7092571]
  • L Giuliani, G Carmignani, E Belgrano, P Puppo. Transcatheter arterial embolization in urological tumors: the use of isobutyl-2-cyanoacrylate. The Journal of urology. 1979 May; 121(5):630-4. doi: 10.1016/s0022-5347(17)56913-x. [PMID: 439260]