trans-Cinnamyl alcohol (BioDeep_00000000853)

 

Secondary id: BioDeep_00000018125, BioDeep_00000418820, BioDeep_00000861248, BioDeep_00001890883

human metabolite PANOMIX_OTCML-2023 Endogenous Volatile Flavor Compounds


代谢物信息卡片


CINNAMYL ALCOHOL (CONSTITUENT OF CINNAMOMUM CASSIA BARK) [DSC]

化学式: C9H10O (134.073161)
中文名称: 肉桂醇, 反式-肉桂醇, 苯乙烯基甲醇
谱图信息: 最多检出来源 Viridiplantae(plant) 3.22%

分子结构信息

SMILES: C1=CC=C(C=C1)C=CCO
InChI: InChI=1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2

描述信息

Cinnamyl alcohol is a primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C=C bond unspecified). It has a role as a plant metabolite.
Cinnamyl alcohol is a naturally occurring compound that is found within cinnamon. Due to the low levels found in cinnamon, cinnamyl alcohol is usually supplied as [DB14184] within commercial products. Cinnamyl alcohol has been shown to be a skin sensitizer, with a NOEL (No Effect Level) of ~4\\\\%. Sensitivity to cinnamyl alcohol may be identified with a clinical patch test.
Cinnamyl alcohol is a Standardized Chemical Allergen. The physiologic effect of cinnamyl alcohol is by means of Increased Histamine Release, and Cell-mediated Immunity.
Cinnamyl alcohol is a natural product found in Nicotiana bonariensis, Cinnamomum burmanni, and other organisms with data available.
See also: Cinnamon (part of); Chinese Cinnamon (part of); Cinnamomum cassia twig (part of).
Constituent of storax and Peruvian balsam, mainly as ester of Cinnamic acid. Flavouring. Stabiliser. trans-Cinnamyl alcohol is found in many foods, some of which are chinese mustard, italian sweet red pepper, alfalfa, and canada blueberry.
trans-Cinnamyl alcohol is found in bilberry. trans-Cinnamyl alcohol is a constituent of storax and Peruvian balsam, mainly as ester of Cinnamic acid. trans-Cinnamyl alcohol is a flavouring. trans-Cinnamyl alcohol is a stabiliser
A primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C=C bond unspecified).
Cinnamyl Alcohol is an active component from chestnut flower, inhibits increased PPARγ expression, with anti-obesity activity[1].
Cinnamyl Alcohol is an active component from chestnut flower, inhibits increased PPARγ expression, with anti-obesity activity[1].

同义名列表

75 个代谢物同义名

CINNAMYL ALCOHOL (CONSTITUENT OF CINNAMOMUM CASSIA BARK) [DSC]; CINNAMYL ALCOHOL (CONSTITUENT OF CINNAMOMUM VERUM BARK) [DSC]; InChI=1/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4; CINNAMYL ALCOHOL (CONSTITUENT OF CINNAMOMUM CASSIA BARK); CINNAMYL ALCOHOL (CONSTITUENT OF CINNAMOMUM VERUM BARK); Cinnamyl alcohol, Vetec(TM) reagent grade, 98\\%; (E)-3-phenyl-2-propen-1-ol(E)-cinnamyl alcohol; 1-06-00-00281 (Beilstein Handbook Reference); Cinnamyl alcohol, purum, >=97.0\\% (GC); Cinnamyl alcohol, analytical standard; cinnamyl alcohol, titanium (4+) salt; Cinnamyl alcohol, natural, 96\\%, FG; Propenoic acid, 3-phenyl-, (trans)-; PROPENOIC ACID, 3-PHENYL-(TRANS); 2-Propen-1-ol, 3-phenyl-, (2E)-; 2-Propen-1-ol, 3-phenyl-, (E)-; trans-3-phenyl-prop-2-en-1-ol; 3-Fenyl-2-propen-1-ol [Czech]; 3-HYDROXY-1-PHENYLPROP-1-ENE; cinnamyl alcohol, (E)-isomer; Cinnamyl alcohol, >=98\\%, FG; 1-PHENYL-3-HYDROXY-1-PROPENE; Trans-3-phenylprop-2-en-1-ol; (2E)-3-Phenyl-2-propen-1-ol; .gamma.-Phenylallyl alcohol; (E)-3-phenyl-prop-2-en-1-ol; (2E)-3-phenylprop-2-en-1-ol; (E)-3-Phenyl-2-propen-1-ol; Cinnamic alcohol (natural); (E)-3-phenylprop-2-en-1-ol; gamma-Phenylallyl alcohol; 2-Propen-y1-ol, 3-phenyl-; Alkohol skoricovy [Czech]; CINNAMYL ALCOHOL [WHO-DD]; 2-Propen-1-ol, 3-phenyl-; CINNAMYL ALCOHOL [INCI]; 3-phenyl-2-propene-1-ol; CINNAMYL ALCOHOL [FHFI]; trans-Cinnamyl-alcohol; trans-Cinnamyl alcohol; 3-phenylprop-2-en-1-ol; CINNAMYL ALCOHOL [FCC]; Cinnamyl alcohol, 98\\%; trans cinnamyl alcohol; trans-cinnamic alcohol; 1-Phenylprop-1-en-3-ol; 3-PHENYL-2-PROPEN-1-OL; Cinnamyl alcohol purum; 3-Phenylallyl alcohol; 3-Fenyl-2-propen-1-ol; CINNAMYL ALCOHOL [MI]; Phenyl-2-propen-1-ol; (E)-cinnamyl alcohol; 3-Phenyl-2-propenol; (E)-Cinnam Alcohol; E-cinnamyl alcohol; E-Cinnamic alcohol; Alkohol skoricovy; cinnamyl-alcohol; cinnamic alcohol; Cinnamyl alcohol; UNII-SS8YOP444F; Cinnamylalcohol; Styryl carbinol; Styryl alcohol; Styrylcarbinol; Tox21_112313; Tox21_300847; Zimtalcohol; SS8YOP444F; WLN: Q2U1R; AI3-00949; Styrone; Cinnamyl alcohol; Styryl carbinol



数据库引用编号

28 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)

27 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

  • Yae Rim Choi, Young-Suk Kim, Min Jung Kim. Cinnamyl Alcohol Attenuates Adipogenesis in 3T3-L1 Cells by Arresting the Cell Cycle. International journal of molecular sciences. 2024 Jan; 25(2):. doi: 10.3390/ijms25020693. [PMID: 38255766]
  • Yu Dai, Xuemin Zhang, Yao Xu, Ya Wu, Liqi Yang. The Protective Effects of Cinnamyl Alcohol Against Hepatic Steatosis, Oxidative and Inflammatory Stress in Nonalcoholic Fatty Liver Disease Induced by Childhood Obesity. Immunological investigations. 2023 Nov; ?(?):1-15. doi: 10.1080/08820139.2023.2280248. [PMID: 37962037]
  • Yueshan Pang, Yali Zheng, Ni Yang, Meng Zan, Lu Zhang, WeiJun Ding. Potential novel biomarkers in small intestine for obesity/obesity resistance revealed by multi-omics analysis. Lipids in health and disease. 2022 Oct; 21(1):98. doi: 10.1186/s12944-022-01711-0. [PMID: 36209126]
  • Meng Zhang, Menglan Dou, Yingying Xia, Zhan Hu, Beijing Zhang, Yongxia Bai, Jia Xie, Qifeng Liu, Changping Xie, Dadong Lu, Shuai Hou, Jianguo He, Jun Tao, Ranfeng Sun. Photostable 1-Trifluoromethyl Cinnamyl Alcohol Derivatives Designed as Potential Fungicides and Bactericides. Journal of agricultural and food chemistry. 2021 May; 69(19):5435-5445. doi: 10.1021/acs.jafc.1c00272. [PMID: 33945271]
  • Hui Jiang, Jian Liu, Yanling Wang, Leijing Chen, Hui Liu, Zhen Wang, Bin Wang. Screening the Q-markers of TCMs from RA rat plasma using UHPLC-QTOF/MS technique for the comprehensive evaluation of Wu-Wei-Wen-Tong Capsule. Journal of mass spectrometry : JMS. 2021 May; 56(5):e4711. doi: 10.1002/jms.4711. [PMID: 33764633]
  • Chen Zhang, Qian Xu, Hongliang Hou, Jiawei Wu, Zhaojuan Zheng, Jia Ouyang. Efficient biosynthesis of cinnamyl alcohol by engineered Escherichia coli overexpressing carboxylic acid reductase in a biphasic system. Microbial cell factories. 2020 Aug; 19(1):163. doi: 10.1186/s12934-020-01419-9. [PMID: 32787860]
  • Alexander N Shikov, Vera M Kosman, Elena V Flissyuk, Irina E Smekhova, Abdelhameed Elameen, Olga N Pozharitskaya. Natural Deep Eutectic Solvents for the Extraction of Phenyletanes and Phenylpropanoids of Rhodiola rosea L. Molecules (Basel, Switzerland). 2020 Apr; 25(8):. doi: 10.3390/molecules25081826. [PMID: 32316279]
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  • Julia K Hoi, Barbara Lieder, Marc Pignitter, Joachim Hans, Jakob P Ley, Jory Lietard, Kathrin Hoelz, Mark Somoza, Veronika Somoza. Identification of Cinnamaldehyde as Most Effective Fatty Acid Uptake Reducing Cinnamon-Derived Compound in Differentiated Caco-2 Cells Compared to Its Structural Analogues Cinnamyl Alcohol, Cinnamic Acid, and Cinnamyl Isobutyrate. Journal of agricultural and food chemistry. 2019 Oct; 67(42):11638-11649. doi: 10.1021/acs.jafc.9b04274. [PMID: 31532204]
  • Yan-Mei Wu, Yan-Yu Wang, Yang-Fei Zhou, Xin Meng, Zeng-Rong Huang, Li-Song Chen, Lin-Tong Yang. Analysis of Interacting Proteins of Aluminum Toxicity Response Factor ALS3 and CAD in Citrus. International journal of molecular sciences. 2019 Sep; 20(19):. doi: 10.3390/ijms20194846. [PMID: 31569546]
  • Chen Zhang, Ying Zang, Peng Liu, Zhaojuan Zheng, Jia Ouyang. Characterization, functional analysis and application of 4-Coumarate: CoA ligase genes from Populus trichocarpa. Journal of biotechnology. 2019 Aug; 302(?):92-100. doi: 10.1016/j.jbiotec.2019.06.300. [PMID: 31233773]
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  • Tatsuru Hayashi, Hiroshi Tsuchikawa, Yuichi Umegawa, Michio Murata. Small structural alterations greatly influence the membrane affinity of lipophilic ligands: Membrane interactions of bafilomycin A1 and its desmethyl derivative bearing 19F-labeling. Bioorganic & medicinal chemistry. 2019 04; 27(8):1677-1682. doi: 10.1016/j.bmc.2019.03.017. [PMID: 30878192]
  • Steffen N Lindner, Liliana Calzadiaz Ramirez, Jan L Krüsemann, Oren Yishai, Sophia Belkhelfa, Hai He, Madeleine Bouzon, Volker Döring, Arren Bar-Even. NADPH-Auxotrophic E. coli: A Sensor Strain for Testing in Vivo Regeneration of NADPH. ACS synthetic biology. 2018 12; 7(12):2742-2749. doi: 10.1021/acssynbio.8b00313. [PMID: 30475588]
  • Jung-Hoon Kim. Extraction time and temperature affect the extraction efficiencies of coumarin and phenylpropanoids from Cinnamomum cassia bark using a microwave-assisted extraction method. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Sep; 1063(?):196-203. doi: 10.1016/j.jchromb.2017.08.008. [PMID: 28886578]
  • Shuxin Liu, Jiabin Liu, Jiayin Hou, Nan Chao, Ying Gai, Xiangning Jiang. Three steps in one pot: biosynthesis of 4-hydroxycinnamyl alcohols using immobilized whole cells of two genetically engineered Escherichia coli strains. Microbial cell factories. 2017 Jun; 16(1):104. doi: 10.1186/s12934-017-0722-9. [PMID: 28606145]
  • Manuela Gottardi, Jan Dines Knudsen, Lydie Prado, Mislav Oreb, Paola Branduardi, Eckhard Boles. De novo biosynthesis of trans-cinnamic acid derivatives in Saccharomyces cerevisiae. Applied microbiology and biotechnology. 2017 Jun; 101(12):4883-4893. doi: 10.1007/s00253-017-8220-x. [PMID: 28353001]
  • Dae Il Hwang, Kyung-Jong Won, Do-Yoon Kim, Bokyung Kim, Hwan Myung Lee. Cinnamyl Alcohol, the Bioactive Component of Chestnut Flower Absolute, Inhibits Adipocyte Differentiation in 3T3-L1 Cells by Downregulating Adipogenic Transcription Factors. The American journal of Chinese medicine. 2017; 45(4):833-846. doi: 10.1142/s0192415x17500446. [PMID: 28490236]
  • Panagiotis Theodosis-Nobelos, Malamati Kourti, Paraskevi Tziona, Panos N Kourounakis, Eleni A Rekka. Esters of some non-steroidal anti-inflammatory drugs with cinnamyl alcohol are potent lipoxygenase inhibitors with enhanced anti-inflammatory activity. Bioorganic & medicinal chemistry letters. 2015 Nov; 25(22):5028-31. doi: 10.1016/j.bmcl.2015.10.036. [PMID: 26494261]
  • Hang Zhao, Qian Yang, Yanhua Xie, Jiyuan Sun, Honghai Tu, Wei Cao, Siwang Wang. Simultaneous determination of cinnamaldehyde and its metabolite in rat tissues by gas chromatography-mass spectrometry. Biomedical chromatography : BMC. 2015 Feb; 29(2):182-7. doi: 10.1002/bmc.3254. [PMID: 24898181]
  • Marta Grech-Baran, Katarzyna Sykłowska-Baranek, Anna Krajewska-Patan, Anna Wyrwał, Agnieszka Pietrosiuk. Biotransformation of cinnamyl alcohol to rosavins by non-transformed wild type and hairy root cultures of Rhodiola kirilowii. Biotechnology letters. 2014 Mar; 36(3):649-56. doi: 10.1007/s10529-013-1401-5. [PMID: 24190481]
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  • Brijesh Pandey, Veda Prakash Pandey, Upendra Nath Dwivedi. Cloning, expression, functional validation and modeling of cinnamyl alcohol dehydrogenase isolated from xylem of Leucaena leucocephala. Protein expression and purification. 2011 Oct; 79(2):197-203. doi: 10.1016/j.pep.2011.06.003. [PMID: 21708267]
  • Cesar Rodriguez-Saona, Leonardo Parra, Andrés Quiroz, Rufus Isaacs. Variation in highbush blueberry floral volatile profiles as a function of pollination status, cultivar, time of day and flower part: implications for flower visitation by bees. Annals of botany. 2011 Jun; 107(8):1377-90. doi: 10.1093/aob/mcr077. [PMID: 21498566]
  • Ahmed M A Abd El-Mawla, Salwa F Farag, Till Beuerle. Cinnamyl alcohols and methyl esters of fatty acids from Wedelia prostrata callus cultures. Natural product research. 2011 Jan; 25(1):45-52. doi: 10.1080/14786419.2010.482937. [PMID: 21240761]
  • Friederike Woehrlin, Hildburg Fry, Klaus Abraham, Angelika Preiss-Weigert. Quantification of flavoring constituents in cinnamon: high variation of coumarin in cassia bark from the German retail market and in authentic samples from indonesia. Journal of agricultural and food chemistry. 2010 Oct; 58(19):10568-75. doi: 10.1021/jf102112p. [PMID: 20853872]
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  • Kentaro Tsuji-Naito. Aldehydic components of cinnamon bark extract suppresses RANKL-induced osteoclastogenesis through NFATc1 downregulation. Bioorganic & medicinal chemistry. 2008 Oct; 16(20):9176-83. doi: 10.1016/j.bmc.2008.09.036. [PMID: 18823786]
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