4-Methoxycinnamic acid (BioDeep_00000017732)

Main id: BioDeep_00000398293

 

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product


代谢物信息卡片


InChI=1/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-4+

化学式: C10H10O3 (178.063)
中文名称: 反-4-甲氧基肉桂酸, 4-甲氧基肉桂酸, (E)-3-(4-甲氧基苯基)丙烯酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: COC1=CC=C(C=C1)C=CC(=O)O
InChI: InChI=1S/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)

描述信息

4-Methoxycinnamic acid, also known as para-methoxycinnamate or O-methyl-p-coumarate, belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. Outside of the human body, 4-Methoxycinnamic acid is found, on average, in the highest concentration within turmerics. 4-Methoxycinnamic acid has also been detected, but not quantified in cow milk and wild celeries. This could make 4-methoxycinnamic acid a potential biomarker for the consumption of these foods.
4-methoxycinnamic acid is a methoxycinnamic acid having a single methoxy substituent at the 4-position on the phenyl ring. It is functionally related to a cinnamic acid.
4-Methoxycinnamic acid is a natural product found in Balanophora tobiracola, Murraya euchrestifolia, and other organisms with data available.
Esters of p-methoxycinnamic acid are among the popular UV-B screening compounds used in various cosmetic formulations in sunscreen products. trans-p-Methoxycinnamic acid is found in wild celery and turmeric.
(E)-3-(4-Methoxyphenyl)acrylic acid (compound 3) is isolated from Arachis hypogaea, Scrophularia buergeriana Miquel, Aquilegia vulgaris, Anigozanthos preissii and so on. (E)-3-(4-Methoxyphenyl)acrylic acid shows significant hepatoprotective activity, anti-amnesic, cognition-enhancing activity, antihyperglycemic, and neuroprotective activities[1].
(E)-3-(4-Methoxyphenyl)acrylic acid (compound 3) is isolated from Arachis hypogaea, Scrophularia buergeriana Miquel, Aquilegia vulgaris, Anigozanthos preissii and so on. (E)-3-(4-Methoxyphenyl)acrylic acid shows significant hepatoprotective activity, anti-amnesic, cognition-enhancing activity, antihyperglycemic, and neuroprotective activities[1].
4-Methoxycinnamic acid is detected as natural phenylpropanoid in A. preissii.
4-Methoxycinnamic acid is detected as natural phenylpropanoid in A. preissii.

同义名列表

84 个代谢物同义名

InChI=1/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-4+; 4-Methoxycinnamic acid;3-(4-Methoxyphenyl)acrylic acid; 4-Methoxycinnamic acid, predominantly trans, 99\\%; 2-Propenoic acid, 3-(4-methoxyphenyl)-, (2E)-; 2-Propenoic acid, 3-(4-methoxyphenyl)-, (E)-; trans-2-Propenoic acid, 3-(4-methoxyphenyl)-; (2E)-3-(4-Methoxyphenyl)-2-propenoic acid #; 4-Methoxycinnamic acid, predominantly trans; p-Methoxycinnamic acid, predominantly trans; TRANS-3-(4-METHOXYPHENYL)-2-PROPENOIC ACID; (2E)-3-(4-methoxyphenyl)prop-2-enoic acid; (2E)-3-(4-Methoxyphenyl)-2-propenoic acid; (E)-3-(4-methoxyphenyl)prop-2-enoic acid; (E)-3-(4-methoxyphenyl)-2-propenoic acid; 2-Propenoic acid, 3-(4-methoxyphenyl)-; (E)-3-(4-Methoxy-phenyl)-acrylic acid; 4-Methoxycinnamic acid, >=98.0\\% (GC); (2E)-3-(4-Methoxyphenyl)prop-2-enoate; (E)-3-(4-methoxyphenyl)-acrylic acid; 0C546A89-9721-4B4E-89EE-7EC28A9A3391; (2E)-3-(4-METHOXYPHENYL)ACRYLIC ACID; 3-(4-Methoxyphenyl)-2-propenoic acid; (E)-3-(4-Methoxyphenyl)acrylic acid; 4-methoxycinnamate, magnesium salt; 4-methoxycinnamate, zirconium salt; 4-methoxycinnamate, potassium salt; 4-methoxycinnamate, aluminum salt; 3-(4-Methoxy-phenyl)-acrylic acid; 3-(4-Methoxyphenyl)propenoic acid; 3-(4-methoxyphenyl)-2-Propenoate; 4-methoxycinnamate, calcium salt; 4-methoxycinnamate, sodium salt; (E)-3-(4-Methoxyphenyl)acrylate; 3-(4-methoxyphenyl)acrylic acid; 4-methoxycinnamate, (E)-isomer; 4-methoxycinnamate, (Z)-isomer; 3-(4-Methoxy-phenyl)-acrylate; 4-methoxycinnamate, zinc salt; trans-4-methoxy-cinnamic acid; 4-Methoxy-(2E)-cinnamic acid; 4-methoxycinnamic acid, (Z)-; trans-p-Methoxycinnamic acid; trans-4-methoxycinnamic-acid; trans-4-Methoxycinnamic acid; (E)-p-Methoxy-cinnamic acid; 3-(4-Methoxyphenyl)acrylate; (E)-4-METHOXYCINNAMIC ACID; AFDXODALSZRGIH-QPJJXVBHSA-; P-Hydroxy methyl cinnamate; METHOXYCINNAMIC ACID, PARA; (E)-p-Methoxycinnamic acid; para-methoxycinnamic acid; Cinnamic acid, p-methoxy-; Cinnamic acid, 4-methoxy-; trans-4-Methoxycinnamate; O-Methyl-p-coumaric acid; P-Methoxy ciannamic acid; E-p-methoxycinnamic acid; trans-p-Methoxycinnamate; 4-Methoxy cinnamic acid; p-methoxy-cinnamic acid; 4-Methyoxycinnamic acid; O-Methyl-p-cumaric Acid; 4’-Methoxycinnamic acid; 4-Methoxycinnamic acid; 4-methoxycinnamic acid; P-METHOXYCINNAMIC ACID; para-methoxycinnamate; 4-Methoxycinnamicacid; O-Methyl-p-coumarate; P-Methoxy ciannamate; 4-Methoxy cinnamate; 4-methoxycinnamate; p-methoxycinnamate; p-MeOCinnamicAcid; UNII-6G4ML8401A; Tox21_111674; Bernel hydro; 6G4ML8401A; AI3-23399; p-MCA; PMCA; K3Z; 4-Methoxycinnamic acid



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

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代谢反应

0 个相关的代谢反应过程信息。

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106 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。

亚细胞结构定位 关联基因列表


文献列表

  • Yongwoo Jeong, Ho Jung Bae, Keontae Park, Hyo Jeoung Bae, Xingquan Yang, Young-Jin Cho, Seo Yun Jung, Dae Sik Jang, Jong Hoon Ryu. 4-Methoxycinnamic acid attenuates schizophrenia-like behaviors induced by MK-801 in mice. Journal of ethnopharmacology. 2022 Mar; 285(?):114864. doi: 10.1016/j.jep.2021.114864. [PMID: 34822958]
  • Wei-Jia Cheng, Jin-Wei Zhou, Ping-Ping Zhang, Huai-Zhi Luo, Shi Tang, Jun-Jian Li, Shi-Ming Deng, Ai-Qun Jia. Quorum sensing inhibition and tobramycin acceleration in Chromobacterium violaceum by two natural cinnamic acid derivatives. Applied microbiology and biotechnology. 2020 Jun; 104(11):5025-5037. doi: 10.1007/s00253-020-10593-0. [PMID: 32248442]
  • Yanran Huang, Japhet Cheuk-Fung Law, Yingya Zhao, Huijing Shi, Yunhui Zhang, Kelvin Sze-Yin Leung. Fate of UV filter Ethylhexyl methoxycinnamate in rat model and human urine: Metabolism, exposure and demographic associations. The Science of the total environment. 2019 Oct; 686(?):729-736. doi: 10.1016/j.scitotenv.2019.05.440. [PMID: 31195281]
  • William Hidalgo, Marco Kai, Bernd Schneider. 4-Methoxycinnamic acid--An unusual phenylpropanoid involved in phenylphenalenone biosynthesis in Anigozanthos preissii. Phytochemistry. 2015 Sep; 117(?):476-481. doi: 10.1016/j.phytochem.2015.07.017. [PMID: 26218676]
  • Sivagami Gunasekaran, Karthikkumar Venkatachalam, Kabalimoorthy Jeyavel, Nalini Namasivayam. Protective effect of p-methoxycinnamic acid, an active phenolic acid against 1,2-dimethylhydrazine-induced colon carcinogenesis: modulating biotransforming bacterial enzymes and xenobiotic metabolizing enzymes. Molecular and cellular biochemistry. 2014 Sep; 394(1-2):187-98. doi: 10.1007/s11010-014-2094-3. [PMID: 24908112]
  • Zhang-wei Wang, Xiang-hong Xu, Xiao-tian Chen, Shi-shan Yu, Hong-dong Liu, Toshimitsu Hayashi, Bin Li. [Chemical constituents from the aerial part of Sibiraea angustata]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Jan; 37(1):57-60. doi: ". [PMID: 25090704]
  • M Krause, A Klit, M Blomberg Jensen, T Søeborg, H Frederiksen, M Schlumpf, W Lichtensteiger, N E Skakkebaek, K T Drzewiecki. Sunscreens: are they beneficial for health? An overview of endocrine disrupting properties of UV-filters. International journal of andrology. 2012 Jun; 35(3):424-36. doi: 10.1111/j.1365-2605.2012.01280.x. [PMID: 22612478]
  • You-Sheng Liu, Guang-Guo Ying, Ali Shareef, Rai S Kookana. Occurrence and removal of benzotriazoles and ultraviolet filters in a municipal wastewater treatment plant. Environmental pollution (Barking, Essex : 1987). 2012 Jun; 165(?):225-32. doi: 10.1016/j.envpol.2011.10.009. [PMID: 22019204]
  • Gunasekaran Sivagami, Venkatachalam Karthikkumar, Thangavel Balasubramanian, Namashivayam Nalini. The modulatory influence of p-methoxycinnamic acid, an active rice bran phenolic acid, against 1,2-dimethylhydrazine-induced lipid peroxidation, antioxidant status and aberrant crypt foci in rat colon carcinogenesis. Chemico-biological interactions. 2012 Mar; 196(1-2):11-22. doi: 10.1016/j.cbi.2012.01.008. [PMID: 22326950]
  • Namki Cho, Jungmoo Huh, Heejung Yang, Eun Ju Jeong, Young Choong Kim, Jinwoong Kim, Sang Hyun Sung. Chemical constituents of Polygala tenuifolia roots and their inhibitory activity on lipopolysaccharide-induced nitric oxide production in BV2 microglia. Journal of enzyme inhibition and medicinal chemistry. 2012 Feb; 27(1):1-4. doi: 10.3109/14756366.2011.562203. [PMID: 21740104]
  • Wei Peng, Ting Han, Qingchun Liu, Luping Qin. [Chemical constituents from aerial part of Atractylodes macrocephala]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Mar; 36(5):578-81. doi: 10.4268/cjcmm20110513. [PMID: 21657075]
  • Shu Ping Xu, Yan Yan Yang, Dan Xue, Jin Xiu Liu, Xin Min Liu, Tai-Ping Fan, Rui le Pan, Pengtao Li. Cognitive-enhancing effects of polygalasaponin hydrolysate in aβ(25-35)-induced amnesic mice. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):839720. doi: 10.1155/2011/839720. [PMID: 21423642]
  • Sung-Hwa Sohn, Eunjung Ko, Sung-Bae Jeon, Beom-Joon Lee, Sung-Hoon Kim, Mi-Sook Dong, Dong-Ung Lee, Jong-Hwan Kwak, Yangseok Kim, Minkyu Shin, Moochang Hong, Hyunsu Bae. The genome-wide expression profile of Scrophularia ningpoensis-treated thapsigargin-stimulated U-87MG cells. Neurotoxicology. 2009 May; 30(3):368-76. doi: 10.1016/j.neuro.2009.02.006. [PMID: 19442820]
  • Peng Zhang, Xiu-Wei Yang. [Studies on chemical constituents in roots and rhizomes of Notopterygium incisum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Dec; 33(24):2918-21. doi: . [PMID: 19294850]
  • Sirichai Adisakwattana, Preecha Moonsan, Sirintorn Yibchok-Anun. Insulin-releasing properties of a series of cinnamic acid derivatives in vitro and in vivo. Journal of agricultural and food chemistry. 2008 Sep; 56(17):7838-44. doi: 10.1021/jf801208t. [PMID: 18651742]
  • Sirintorn Yibchok-anun, Sirichai Adisakwattana, Preecha Moonsan, Walter H Hsu. Insulin-secretagogue activity of p-methoxycinnamic acid in rats, perfused rat pancreas and pancreatic beta-cell line. Basic & clinical pharmacology & toxicology. 2008 May; 102(5):476-82. doi: 10.1111/j.1742-7843.2008.00218.x. [PMID: 18346054]
  • Han-Shen Zhen, Jing Ge, Jie Liang, Qin Qiu, Zhi-Hua Song, Zhen-Guo Zhong, Wen-Hui Wang, Jian-Ping Jiang. [Analysis of the volatile oils chemical constituents of roots of Actinidia deliciosa]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2008 May; 31(5):677-8. doi: ". [PMID: 18826142]
  • Jeongsu Nam, Hyunju Choi. Effect of butanol fraction from Cassia tora L. seeds on glycemic control and insulin secretion in diabetic rats. Nutrition research and practice. 2008; 2(4):240-6. doi: 10.4162/nrp.2008.2.4.240. [PMID: 20016725]
  • Aziz Abdur Rahman, Surk-Sik Moon. Antimicrobial phenolic derivatives from Dendranthema zawadskii var. latilobum Kitamura (Asteraceae). Archives of pharmacal research. 2007 Nov; 30(11):1374-9. doi: 10.1007/bf02977359. [PMID: 18087803]
  • Mi Kyeong Lee, Ok-Gyung Choi, Jin-Ho Park, Hi-Jae Cho, Mi-Jeong Ahn, Seung Hyun Kim, Young Choong Kim, Sang Hyun Sung. Simultaneous determination of four active constituents in the roots of Scrophularia buergeriana by HPLC-DAD and LC-ESI-MS. Journal of separation science. 2007 Oct; 30(15):2345-50. doi: 10.1002/jssc.200700117. [PMID: 17628873]
  • Daniela Rigano, Carmen Formisano, Adriana Basile, Alfredo Lavitola, Felice Senatore, Sergio Rosselli, Maurizio Bruno. Antibacterial activity of flavonoids and phenylpropanoids from Marrubium globosum ssp. libanoticum. Phytotherapy research : PTR. 2007 Apr; 21(4):395-7. doi: 10.1002/ptr.2061. [PMID: 17186490]
  • Dong-bao Zhao, Wei Zhang, Ming-jing Li, Xiu-hua Liu. [Studies on chemical constituents of Acroptilon repens]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 Nov; 31(22):1869-72. doi: . [PMID: 17285986]
  • Victor S Sobolev, Bruce W Horn, Thomas L Potter, Stephen T Deyrup, James B Gloer. Production of stilbenoids and phenolic acids by the peanut plant at early stages of growth. Journal of agricultural and food chemistry. 2006 May; 54(10):3505-11. doi: 10.1021/jf0602673. [PMID: 19127717]
  • Sirichai Adisakwattana, Sophon Roengsamran, Walter H Hsu, Sirintorn Yibchok-anun. Mechanisms of antihyperglycemic effect of p-methoxycinnamic acid in normal and streptozotocin-induced diabetic rats. Life sciences. 2005 Dec; 78(4):406-12. doi: 10.1016/j.lfs.2005.04.073. [PMID: 16139846]
  • Wiesława Bylka. E- and Z-p-methoxycinnamic acid from Aquilegia vulgaris. Acta poloniae pharmaceutica. 2004 Jul; 61(4):307-8. doi: ". [PMID: 15575598]
  • Hisashi Matsuda, Toshio Morikawa, Hiromi Managi, Masayuki Yoshikawa. Antiallergic principles from Alpinia galanga: structural requirements of phenylpropanoids for inhibition of degranulation and release of TNF-alpha and IL-4 in RBL-2H3 cells. Bioorganic & medicinal chemistry letters. 2003 Oct; 13(19):3197-202. doi: 10.1016/s0960-894x(03)00710-8. [PMID: 12951092]
  • So Ra Kim, So Young Kang, Ki Yong Lee, Seung Hyun Kim, George J Markelonis, Tae H Oh, Young Choong Kim. Anti-amnestic activity of E-p-methoxycinnamic acid from Scrophularia buergeriana. Brain research. Cognitive brain research. 2003 Jul; 17(2):454-61. doi: 10.1016/s0926-6410(03)00161-7. [PMID: 12880915]
  • M Ricking, J Schwarzbauer, S Franke. Molecular markers of anthropogenic activity in sediments of the Havel and Spree Rivers (Germany). Water research. 2003 Jun; 37(11):2607-17. doi: 10.1016/s0043-1354(03)00078-2. [PMID: 12753838]
  • Eun Ju Lee, So Ra Kim, Jinwoong Kim, Young Choong Kim. Hepatoprotective phenylpropanoids from Scrophularia buergeriana roots against CCl(4)-induced toxicity: action mechanism and structure-activity relationship. Planta medica. 2002 May; 68(5):407-11. doi: 10.1055/s-2002-32081. [PMID: 12058315]
  • Hoi-Seon Lee. Tyrosinase inhibitors of Pulsatilla cernua root-derived materials. Journal of agricultural and food chemistry. 2002 Mar; 50(6):1400-3. doi: 10.1021/jf011230f. [PMID: 11879010]
  • Ghezala Gaidi, Maria Correia, Bruno Chauffert, Jean-Luc Beltramo, Hildebert Wagner, Marie-Aleth Lacaille-Dubois. Saponins-mediated potentiation of cisplatin accumulation and cytotoxicity in human colon cancer cells. Planta medica. 2002 Jan; 68(1):70-2. doi: 10.1055/s-2002-19873. [PMID: 11842333]
  • H S Lee, M S Beon, M K Kim. Selective growth inhibitor toward human intestinal bacteria derived from Pulsatilla cernua root. Journal of agricultural and food chemistry. 2001 Oct; 49(10):4656-61. doi: 10.1021/jf010609z. [PMID: 11600003]