4-Methylcatechol (BioDeep_00000002894)

 

Secondary id: BioDeep_00000018337, BioDeep_00000869414

human metabolite PANOMIX_OTCML-2023 BioNovoGene_Lab2019


代谢物信息卡片


1,2-Dihydroxy-4-methylbenzene

化学式: C7H8O2 (124.0524)
中文名称: 4-甲基儿茶酚, 3,4-二羟基甲苯
谱图信息: 最多检出来源 Homo sapiens(plant) 21.43%

分子结构信息

SMILES: CC1=CC(=C(C=C1)O)O
InChI: InChI=1S/C7H8O2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3

描述信息

A methylcatechol having a single methyl substituent at the 4-position. It has been isolated from Picea abies.
D002491 - Central Nervous System Agents > D018696 - Neuroprotective Agents
D020011 - Protective Agents > D000975 - Antioxidants
D009676 - Noxae > D002273 - Carcinogens
4-Methylcatechol, a metabolite of p-toluate, is a substrate as well as a suicide inhibitor of Catechol 2,3-Dioxygenase.
4-Methylcatechol, a metabolite of p-toluate, is a substrate as well as a suicide inhibitor of Catechol 2,3-Dioxygenase.

同义名列表

7 个代谢物同义名

4-Methylcatechol; 1,2-Dihydroxy-4-methylbenzene; 4-methylbenzene-1,2-diol; 4-Methyl-1,2-benzenediol; 3,4-Dihydroxytoluene; 4-Methylcatechol; 4-Methylcatechol



数据库引用编号

22 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

9 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(8)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(1)

  • Thiazole Biosynthesis I: L-Tyrosine + NADPH + S-Adenosylmethionine ⟶ 4-Methylcatechol + 5'-Deoxyadenosine + Dehydroglycine + Hydrogen Ion + L-Methionine + NADP

PharmGKB(0)

5 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
Cytoplasm 7 AXIN2, BDNF, CAT, KEAP1, MPI, NTRK2, TYR
Peripheral membrane protein 2 GORASP1, HSD17B6
Endosome membrane 2 NTRK1, NTRK2
Endoplasmic reticulum membrane 1 HMOX1
Nucleus 6 ATF3, AXIN2, FOS, HMOX1, JUN, KEAP1
cytosol 9 AXIN2, CAT, FOS, HMOX1, KEAP1, MPI, NGF, NTRK2, PRKCQ
dendrite 4 BDNF, NGF, NTRK1, NTRK2
centrosome 1 AXIN2
nucleoplasm 5 ATF3, FOS, HMOX1, JUN, KEAP1
RNA polymerase II transcription regulator complex 3 ATF3, FOS, JUN
Cell membrane 3 NTRK1, NTRK2, TNF
Cytoplasmic side 2 GORASP1, HMOX1
Cell projection, axon 1 NTRK2
Early endosome membrane 3 HSD17B6, NTRK1, NTRK2
Golgi apparatus membrane 1 GORASP1
Synapse 1 TAC1
cell surface 2 NTRK1, TNF
Golgi apparatus 2 GDNF, GORASP1
Golgi membrane 1 GORASP1
neuronal cell body 3 NTRK1, TAC1, TNF
synaptic vesicle 2 BDNF, NGF
Lysosome 1 TYR
plasma membrane 5 AXIN2, NTRK1, NTRK2, PRKCQ, TNF
terminal bouton 1 NTRK2
Membrane 5 BDNF, CAT, HMOX1, NTRK1, NTRK2
axon 5 BDNF, NGF, NTRK1, NTRK2, TAC1
extracellular exosome 2 CAT, MPI
Lumenal side 1 HSD17B6
endoplasmic reticulum 4 FOS, HMOX1, HSD17B6, KEAP1
extracellular space 7 ARTN, BDNF, GDNF, HMOX1, NGF, TAC1, TNF
perinuclear region of cytoplasm 4 BDNF, HMOX1, NTRK2, TYR
mitochondrion 2 CAT, NTRK1
protein-containing complex 2 CAT, NTRK1
intracellular membrane-bounded organelle 3 CAT, HSD17B6, TYR
Microsome membrane 1 HSD17B6
postsynaptic density 1 NTRK2
Single-pass type I membrane protein 3 NTRK1, NTRK2, TYR
Secreted 4 ARTN, BDNF, GDNF, NGF
extracellular region 7 ARTN, BDNF, CAT, GDNF, NGF, TAC1, TNF
mitochondrial outer membrane 1 HMOX1
mitochondrial matrix 1 CAT
transcription regulator complex 1 JUN
centriolar satellite 2 KEAP1, PRKCQ
external side of plasma membrane 1 TNF
dendritic spine 1 NTRK2
beta-catenin destruction complex 1 AXIN2
nucleolus 1 ATF3
Melanosome membrane 1 TYR
midbody 1 KEAP1
Early endosome 2 NTRK1, NTRK2
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cytoplasm, perinuclear region 1 NTRK2
Membrane raft 1 TNF
focal adhesion 1 CAT
cis-Golgi network 1 GORASP1
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Late endosome 1 NTRK1
receptor complex 2 NTRK1, NTRK2
chromatin 3 ATF3, FOS, JUN
Late endosome membrane 1 NTRK1
phagocytic cup 1 TNF
nuclear chromosome 1 JUN
actin filament 1 KEAP1
Cul3-RING ubiquitin ligase complex 1 KEAP1
Recycling endosome membrane 1 NTRK1
endosome lumen 1 NGF
Cell projection, dendrite 1 NTRK2
Melanosome 1 TYR
euchromatin 1 JUN
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
Golgi lumen 1 NGF
endoplasmic reticulum lumen 1 BDNF
nuclear matrix 1 FOS
axon terminus 1 NTRK2
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
immunological synapse 1 PRKCQ
aggresome 1 PRKCQ
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
Single-pass type IV membrane protein 1 HMOX1
protein-DNA complex 1 FOS
transcription factor AP-1 complex 2 FOS, JUN
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
inclusion body 1 KEAP1
CHOP-ATF3 complex 1 ATF3
[Neurotrophic factor BDNF precursor form]: Secreted 1 BDNF
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Lukáš Konečný, Marcel Hrubša, Jana Karlíčková, Alejandro Carazo, Lenka Javorská, Kateřina Matoušová, Lenka Kujovská Krčmová, Alena Šmahelová, Vladimír Blaha, Milan Bláha, Přemysl Mladěnka. The Effect of 4-Methylcatechol on Platelets in Familial Hypercholesterolemic Patients Treated with Lipid Apheresis and/or Proprotein Convertase Subtilisin Kexin 9 Monoclonal Antibodies. Nutrients. 2023 Apr; 15(8):. doi: 10.3390/nu15081842. [PMID: 37111061]
  • Jangho Lee, Ji-Hye Song, Min-Yu Chung, Jin-Hyuk Lee, Tae-Gyu Nam, Jae Ho Park, Jin-Taek Hwang, Hyo-Kyoung Choi. 3,4-dihydroxytoluene, a metabolite of rutin, suppresses the progression of nonalcoholic fatty liver disease in mice by inhibiting p300 histone acetyltransferase activity. Acta pharmacologica Sinica. 2021 Sep; 42(9):1449-1460. doi: 10.1038/s41401-020-00571-7. [PMID: 33303988]
  • Mohd Asraf Mohd Zainudin, Sisse Jongberg, Marianne N Lund. Combination of light and oxygen accelerates formation of covalent protein-polyphenol bonding during chill storage of meat added 4-methyl catechol. Food chemistry. 2021 Jan; 334(?):127611. doi: 10.1016/j.foodchem.2020.127611. [PMID: 32712493]
  • Qian-Yun Han, Fang Liu, Mo Li, Kun-Li Wang, Yuan-Ying Ni. Comparison of biochemical properties of membrane-bound and soluble polyphenol oxidase from Granny Smith apple (Malus × domestica Borkh.). Food chemistry. 2019 Aug; 289(?):657-663. doi: 10.1016/j.foodchem.2019.02.064. [PMID: 30955661]
  • Lenka Applová, Jana Karlíčková, Paul Warncke, Kateřina Macáková, Marcel Hrubša, Miloslav Macháček, Václav Tvrdý, Dagmar Fischer, Přemysl Mladěnka. 4-Methylcatechol, a Flavonoid Metabolite with Potent Antiplatelet Effects. Molecular nutrition & food research. 2019 08; 63(20):e1900261. doi: 10.1002/mnfr.201900261. [PMID: 31343835]
  • Selda Gezginci-Oktayoglu, Ediz Coskun, Merve Ercin, Sehnaz Bolkent. 4-Methylcatechol prevents streptozotocin-induced acute kidney injury through modulating NGF/TrkA and ROS-related Akt/GSK3β/β-catenin pathways. International immunopharmacology. 2018 Nov; 64(?):52-59. doi: 10.1016/j.intimp.2018.08.017. [PMID: 30145470]
  • Donald R Senger, Mien V Hoang, Ki Hyun Kim, Chunshun Li, Shugeng Cao. Anti-inflammatory activity of Barleria lupulina: Identification of active compounds that activate the Nrf2 cell defense pathway, organize cortical actin, reduce stress fibers, and improve cell junctions in microvascular endothelial cells. Journal of ethnopharmacology. 2016 Dec; 193(?):397-407. doi: 10.1016/j.jep.2016.09.017. [PMID: 27660013]
  • R Gul Guven, N Aslan, K Guven, F Matpan Bekler, O Acer. Purification and characterization of polyphenol oxidase from corn tassel. Cellular and molecular biology (Noisy-le-Grand, France). 2016 Nov; 62(13):6-11. doi: 10.14715/cmb/2016.62.13.2. [PMID: 28040055]
  • F Gadeyne, G Van Ranst, B Vlaeminck, E Vossen, P Van der Meeren, V Fievez. Protection of polyunsaturated oils against ruminal biohydrogenation and oxidation during storage using a polyphenol oxidase containing extract from red clover. Food chemistry. 2015 Mar; 171(?):241-50. doi: 10.1016/j.foodchem.2014.08.109. [PMID: 25308665]
  • Esteban F Durán-Lara, Xaviera A López-Cortés, Ricardo I Castro, Fabián Avila-Salas, Fernando D González-Nilo, V Felipe Laurie, Leonardo S Santos. Experimental and theoretical binding affinity between polyvinylpolypyrrolidone and selected phenolic compounds from food matrices. Food chemistry. 2015 Feb; 168(?):464-70. doi: 10.1016/j.foodchem.2014.07.048. [PMID: 25172736]
  • Gisela Palma-Orozco, Norma A Marrufo-Hernández, José G Sampedro, Hugo Nájera. Purification and partial biochemical characterization of polyphenol oxidase from mango (Mangifera indica cv. Manila). Journal of agricultural and food chemistry. 2014 Oct; 62(40):9832-40. doi: 10.1021/jf5029784. [PMID: 25211397]
  • Kang-Yi Su, Chao Yuan Yu, Ya-Ping Chen, Kuo-Feng Hua, Yi-Lin Sophia Chen. 3,4-Dihydroxytoluene, a metabolite of rutin, inhibits inflammatory responses in lipopolysaccharide-activated macrophages by reducing the activation of NF-κB signaling. BMC complementary and alternative medicine. 2014 Jan; 14(?):21. doi: 10.1186/1472-6882-14-21. [PMID: 24417898]
  • Mareike E Dirks-Hofmeister, Stephan Kolkenbrock, Bruno M Moerschbacher. Parameters that enhance the bacterial expression of active plant polyphenol oxidases. PloS one. 2013; 8(10):e77291. doi: 10.1371/journal.pone.0077291. [PMID: 24204791]
  • Sisse Jongberg, Marianne N Lund, Henrik Østdal, Leif H Skibsted. Phenolic antioxidant scavenging of myosin radicals generated by hypervalent myoglobin. Journal of agricultural and food chemistry. 2012 Dec; 60(48):12020-8. doi: 10.1021/jf304227t. [PMID: 23163579]
  • Masoumeh Hasani, Masoumeh Mohammadi, Masoud Shariati-Rad, Hamid Abdollahi. H-point curve isolation method for determination of catechol in complex unknown mixtures. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2012 Oct; 96(?):563-8. doi: 10.1016/j.saa.2012.07.024. [PMID: 22864391]
  • Hanna Richter, Reinhard Lieberei, Miroslav Strnad, Ondrej Novák, Jiri Gruz, Stefan A Rensing, Klaus von Schwartzenberg. Polyphenol oxidases in Physcomitrella: functional PPO1 knockout modulates cytokinin-dependent development in the moss Physcomitrella patens. Journal of experimental botany. 2012 Sep; 63(14):5121-35. doi: 10.1093/jxb/ers169. [PMID: 22865913]
  • Selda Gezginci-Oktayoglu, Sehnaz Bolkent. Ras signaling in NGF reduction and TNF-α-related pancreatic β cell apoptosis in hyperglycemic rats. Apoptosis : an international journal on programmed cell death. 2012 Jan; 17(1):14-24. doi: 10.1007/s10495-011-0657-2. [PMID: 21938476]
  • Rahele Ghanbari, Farooq Anwar, Khalid M Alkharfy, Anwarul-Hassan Gilani, Nazamid Saari. Valuable nutrients and functional bioactives in different parts of olive (Olea europaea L.)-a review. International journal of molecular sciences. 2012; 13(3):3291-3340. doi: 10.3390/ijms13033291. [PMID: 22489153]
  • Selda Gezginci-Oktayoglu, Sehnaz Bolkent. 4-Methlycatechol prevents NGF/p75(NTR)-mediated apoptosis via NGF/TrkA system in pancreatic β cells. Neuropeptides. 2011 Apr; 45(2):143-50. doi: 10.1016/j.npep.2011.01.001. [PMID: 21295348]
  • Vinita Verma, Sajan C Raju, Atya Kapley, Vipin Chandra Kalia, Gajanan S Kanade, Hatim F Daginawala, Hemant J Purohit. Degradative potential of Stenotrophomonas strain HPC383 having genes homologous to dmp operon. Bioresource technology. 2011 Feb; 102(3):3227-33. doi: 10.1016/j.biortech.2010.11.016. [PMID: 21123060]
  • Sanjeev Kumar Diwakar, Sarad Kumar Mishra. Purification and biochemical characterization of ionically unbound polyphenol oxidase from Musa paradisiaca leaf. Preparative biochemistry & biotechnology. 2011; 41(2):187-200. doi: 10.1080/10826068.2011.547377. [PMID: 21442554]
  • Prontipa Nokthai, Vannajan Sanghiran Lee, Lalida Shank. Molecular modeling of peroxidase and polyphenol oxidase: substrate specificity and active site comparison. International journal of molecular sciences. 2010 Sep; 11(9):3266-76. doi: 10.3390/ijms11093266. [PMID: 20957092]
  • Srinath Pashikanti, David R de Alba, Gilbert A Boissonneault, Daniel Cervantes-Laurean. Rutin metabolites: novel inhibitors of nonoxidative advanced glycation end products. Free radical biology & medicine. 2010 Mar; 48(5):656-63. doi: 10.1016/j.freeradbiomed.2009.11.019. [PMID: 19969069]
  • Enrico Cappellini, M Thomas P Gilbert, Filippo Geuna, Girolamo Fiorentino, Allan Hall, Jane Thomas-Oates, Peter D Ashton, David A Ashford, Paul Arthur, Paula F Campos, Johan Kool, Eske Willerslev, Matthew J Collins. A multidisciplinary study of archaeological grape seeds. Die Naturwissenschaften. 2010 Feb; 97(2):205-17. doi: 10.1007/s00114-009-0629-3. [PMID: 20033124]
  • Takumi Satoh, Sachie Saitoh, Manami Hosaka, Kunio Kosaka. Simple ortho- and para-hydroquinones as compounds neuroprotective against oxidative stress in a manner associated with specific transcriptional activation. Biochemical and biophysical research communications. 2009 Feb; 379(2):537-41. doi: 10.1016/j.bbrc.2008.12.106. [PMID: 19118528]
  • Márcio S T Pinto, Fabrício P Siqueira, Antônia E A Oliveira, Kátia V S Fernandes. A wounding-induced PPO from cowpea (Vigna unguiculata) seedlings. Phytochemistry. 2008 Sep; 69(12):2297-302. doi: 10.1016/j.phytochem.2008.06.003. [PMID: 18675435]
  • Yoshiki Yamasaki, Haruyoshi Konno, Kazuhiko Noda. Polyphenol oxidase from wheat bran is a serpin. Acta biochimica Polonica. 2008; 55(2):325-8. doi: . [PMID: 18506224]
  • Valdir Augusto Neves, Maraiza Aparecida da Silva. Polyphenol oxidase from yacon roots (Smallanthus sonchifolius). Journal of agricultural and food chemistry. 2007 Mar; 55(6):2424-30. doi: 10.1021/jf063148w. [PMID: 17316020]
  • Roman Lang, Christoph Mueller, Thomas Hofmann. Development of a stable isotope dilution analysis with liquid chromatography-tandem mass spectrometry detection for the quantitative analysis of di- and trihydroxybenzenes in foods and model systems. Journal of agricultural and food chemistry. 2006 Aug; 54(16):5755-62. doi: 10.1021/jf061118n. [PMID: 16881674]
  • M B Levanti, A Germanà, F de Carlos, E Ciriaco, J A Vega, G Germanà. Effects of increased nerve growth factor plasma levels on the expression of TrkA and p75 in rat testicles. Journal of anatomy. 2006 Mar; 208(3):373-9. doi: 10.1111/j.1469-7580.2006.00528.x. [PMID: 16533319]
  • Serap Dogan, Pinar Turan, Mehmet Dogan, Oktay Arslan, Mahir Alkan. Purification and characterization of Ocimum basilicum L. polyphenol oxidase. Journal of agricultural and food chemistry. 2005 Dec; 53(26):10224-30. doi: 10.1021/jf051646j. [PMID: 16366719]
  • Petr Galuszka, Jitka Frébortová, Lenka Luhová, Kristin D Bilyeu, James T English, Ivo Frébort. Tissue localization of cytokinin dehydrogenase in maize: possible involvement of quinone species generated from plant phenolics by other enzymatic systems in the catalytic reaction. Plant & cell physiology. 2005 May; 46(5):716-28. doi: 10.1093/pcp/pci074. [PMID: 15746157]
  • Serap Dogan, Yusuf Turan, Hatibe Ertürk, Oktay Arslan. Characterization and purification of polyphenol oxidase from artichoke (Cynara scolymus L.). Journal of agricultural and food chemistry. 2005 Feb; 53(3):776-85. doi: 10.1021/jf049053g. [PMID: 15686433]
  • Daisuke Miyazawa, Gouri Mukerjee-Dhar, Minoru Shimura, Takashi Hatta, Kazuhide Kimbara. Genes for Mn(II)-dependent NahC and Fe(II)-dependent NahH located in close proximity in the thermophilic naphthalene and PCB degrader, Bacillus sp. JF8: cloning and characterization. Microbiology (Reading, England). 2004 Apr; 150(Pt 4):993-1004. doi: 10.1099/mic.0.26858-0. [PMID: 15073308]
  • Kyoji Morita, Hideki Arimochi, Yoshinari Ohnishi. In vitro cytotoxicity of 4-methylcatechol in murine tumor cells: induction of apoptotic cell death by extracellular pro-oxidant action. The Journal of pharmacology and experimental therapeutics. 2003 Jul; 306(1):317-23. doi: 10.1124/jpet.103.050351. [PMID: 12676882]
  • Takashi Hatta, Gouri Mukerjee-Dhar, Jiri Damborsky, Hohzoh Kiyohara, Kazuhide Kimbara. Characterization of a novel thermostable Mn(II)-dependent 2,3-dihydroxybiphenyl 1,2-dioxygenase from a polychlorinated biphenyl- and naphthalene-degrading Bacillus sp. JF8. The Journal of biological chemistry. 2003 Jun; 278(24):21483-92. doi: 10.1074/jbc.m210240200. [PMID: 12672826]
  • Stuart McLean, Sue Brandon, Noel W Davies, Rebecca Boyle, William J Foley, Ben Moore, Georgia J Pass. Glucuronuria in the koala. Journal of chemical ecology. 2003 Jun; 29(6):1465-77. doi: 10.1023/a:1024273722192. [PMID: 12918928]
  • Agnes W Boots, Guido R M M Haenen, Gertjan J M den Hartog, Aalt Bast. Oxidative damage shifts from lipid peroxidation to thiol arylation by catechol-containing antioxidants. Biochimica et biophysica acta. 2002 Aug; 1583(3):279-84. doi: 10.1016/s1388-1981(02)00247-0. [PMID: 12176395]
  • G Glässer, E U Graefe, F Struck, M Veit, R Gebhardt. Comparison of antioxidative capacities and inhibitory effects on cholesterol biosynthesis of quercetin and potential metabolites. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2002 Jan; 9(1):33-40. doi: 10.1078/0944-7113-00080. [PMID: 11924762]
  • R Debowska, A Podstolski. Properties of diphenolase from Vanilla planifolia (Andr.) shoot primordia cultured in vitro. Journal of agricultural and food chemistry. 2001 Jul; 49(7):3432-7. doi: 10.1021/jf001180z. [PMID: 11453787]
  • O García-Suárez, A Germanà, J Hannestad, M Pérez-Pérez, I Esteban, F J Naves, J A Vega. Changes in the expression of the nerve growth factor receptors TrkA and p75LNGR in the rat thymus with ageing and increased nerve growth factor plasma levels. Cell and tissue research. 2000 Aug; 301(2):225-34. doi: 10.1007/s004419900133. [PMID: 10955718]
  • T Ishikawa, O Nakanishi, N Funatsu, H Kameyama. Nerve growth factor inducer, 4-methyl catechol, potentiates central sensitization associated with acceleration of spinal glutamate release after mustard oil paw injection in rats. Cellular and molecular neurobiology. 1999 Oct; 19(5):587-96. doi: 10.1023/a:1006928317312. [PMID: 10384257]
  • E Asakawa, M Hirose, A Hagiwara, S Takahashi, N Ito. Carcinogenicity of 4-methoxyphenol and 4-methylcatechol in F344 rats. International journal of cancer. 1994 Jan; 56(1):146-52. doi: 10.1002/ijc.2910560126. [PMID: 8262672]
  • A K Hubbard, C L Lohr, K Hastings, J B Clarke, A J Gandolfi. Immunogenicity studies of a synthetic antigen of alpha methyl dopa. Immunopharmacology and immunotoxicology. 1993 Nov; 15(5):621-37. doi: 10.3109/08923979309019734. [PMID: 8301021]
  • S Carswell, E K Hoffman, K Clopton-Hartpence, H M Wilcox, M E Lewis. Induction of NGF by isoproterenol, 4-methylcatechol and serum occurs by three distinct mechanisms. Brain research. Molecular brain research. 1992 Sep; 15(1-2):145-50. doi: 10.1016/0169-328x(92)90162-5. [PMID: 1331660]
  • S G Carmella, E J La Voie, S S Hecht. Quantitative analysis of catechol and 4-methylcatechol in human urine. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1982 Oct; 20(5):587-90. doi: 10.1016/s0278-6915(82)80068-9. [PMID: 6890513]