cis,cis-Muconic acid (BioDeep_00000405605)
Main id: BioDeep_00000001306
PANOMIX_OTCML-2023 Volatile Flavor Compounds
代谢物信息卡片
cis,cis-Muconic acid
化学式: C6H6O4 (142.0266076)
中文名称: 顺,顺-粘康酸, 顺式，顺式-粘康酸
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C(=CC(=O)O)C=CC(=O)O
InChI: InChI=1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1-,4-2-
描述信息
The cis,cis-isomer of muconic acid. It is produced during the degradation of chlorobenzene by bacteria like Bacillus.
cis,cis-Muconic acid, a metabolic intermediate of Klebsiella pneumonia, can be converted to adipic acid and terephthalic acid, which are important monomers of synthetic polymers. cis,cis-Muconic acid is also a biochemical material that can be used for the production of various plastics and polymers and is particularly gaining attention as an adipic acid precursor for the synthesis of nylon-6,6[1][2].
同义名列表
数据库引用编号
17 个数据库交叉引用编号
- ChEBI: CHEBI:16508
- KEGG: C02480
- PubChem: 5280518
- CAS: 1119-72-8
- MoNA: HMDB0006331_ms_ms_2481
- MoNA: HMDB0006331_ms_ms_2483
- MoNA: HMDB0006331_ms_ms_2482
- MetaboLights: MTBLC16508
- PubChem: 5495
- LipidMAPS: LMFA01170077
- KNApSAcK: C00007490
- CAS: 505-70-4
- PDB-CCD: CCU
- 3DMET: B00448
- NIKKAJI: J73.682A
- medchemexpress: HY-W000800
- KNApSAcK: 16508
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)
2 个相关的物种来源信息
- 252963 - Plakortis simplex: 10.1021/NP000413D
- 303 - Pseudomonas putida: 10.1021/BI036205C
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
- Sepideh Abbaszadeh, Saeed Yousefinejad, Saeed Jafari, Esmaeel Soleimani. In-syringe ionic liquid-dispersive liquid-liquid microextraction coupled with HPLC for the determination of trans,trans-muconic acid in human urine sample.
Journal of separation science.
2021 Aug; 44(16):3126-3136. doi:
10.1002/jssc.202100044. [PMID: 34114310] - Marcia Domínguez, Juan F Blandez, Beatriz Lozano-Torres, Cristina de la Torre, Maurizio Licchelli, Carlo Mangano, Valeria Amendola, Félix Sancenón, Ramón Martínez-Máñez. A Nanoprobe Based on Gated Mesoporous Silica Nanoparticles for The Selective and Sensitive Detection of Benzene Metabolite t,t-Muconic Acid in Urine.
Chemistry (Weinheim an der Bergstrasse, Germany).
2021 Jan; 27(4):1306-1310. doi:
10.1002/chem.202004272. [PMID: 33064343] - Sunisa Chaiklieng, Pornnapa Suggaravetsiri, Herman Autrup. Biomatrix of health risk assessment of benzene-exposed workers at Thai gasoline stations.
Journal of occupational health.
2021 Jan; 63(1):e12307. doi:
10.1002/1348-9585.12307. [PMID: 34957641] - Barbara Rodrigues Geraldino, Rafaella Ferreira Nascimento Nunes, Juliana Barroso Gomes, Isabela Giardini, Paula Vieira Baptista da Silva, Élida Campos, Katia Soares da Poça, Rocio Hassan, Ubirani Barros Otero, Marcia Sarpa. Analysis of Benzene Exposure in Gas Station Workers Using Trans,Trans-Muconic Acid.
International journal of environmental research and public health.
2020 07; 17(15):. doi:
10.3390/ijerph17155295. [PMID: 32717818] - Luigi De Maria, Caterina Ledda, Antonio Caputi, Francesca Mansi, Enza Sabrina Silvana Cannone, Stefania Sponselli, Domenica Cavone, Francesco Birtolo, Emanuele Cannizzaro, Giovanni Maria Ferri, Venerando Rapisarda, Luigi Vimercati. Biological Monitoring of Exposure to Benzene in Port Workers.
Frontiers in public health.
2020; 8(?):271. doi:
10.3389/fpubh.2020.00271. [PMID: 32766192] - Sunisa Chaiklieng, Pornnapa Suggaravetsiri, Norbert Kaminski, Herman Autrup. Factors Affecting Urinary tt-Muconic Acid Detection among Benzene Exposed Workers at Gasoline Stations.
International journal of environmental research and public health.
2019 10; 16(21):. doi:
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Annals of work exposures and health.
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Annals of global health.
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PloS one.
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Mutation research. Genetic toxicology and environmental mutagenesis.
2014 Aug; 770(?):61-5. doi:
10.1016/j.mrgentox.2014.05.008. [PMID: 25344165] - Piero Lovreglio, Francesca Maffei, Mariella Carrieri, Maria N D'Errico, Ignazio Drago, Patrizia Hrelia, Giovanni B Bartolucci, Leonardo Soleo. Evaluation of chromosome aberration and micronucleus frequencies in blood lymphocytes of workers exposed to low concentrations of benzene.
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2013 May; 27(5):664-8. doi:
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Analytical and bioanalytical chemistry.
2013 Jan; 405(1):341-9. doi:
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The international journal of occupational and environmental medicine.
2013 Jan; 4(1):45-9. doi:
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The Science of the total environment.
2012 Oct; 435-436(?):115-23. doi:
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La Medicina del lavoro.
2012 Sep; 103(5):324-37. doi:
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Toxicology letters.
2012 Aug; 213(1):57-62. doi:
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The Analyst.
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Toxicology letters.
2010 Jan; 192(1):29-33. doi:
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Toxicology letters.
2010 Jan; 192(1):17-21. doi:
10.1016/j.toxlet.2009.07.015. [PMID: 19628029] - P Lovreglio, G Cancanelli, A Barbieri, L Sabatini, M N D'Errico, L Scicolone, R Ghitti, F S Violante, P Apostoli, L Soleo. [Influence of non-occupational sources on the levels of biomarkers of internal dose for use in biological monitoring of occupational exposure to extremely low concentrations of benzene].
Giornale italiano di medicina del lavoro ed ergonomia.
2010 Jan; 32(1):49-58. doi:
NULL. [PMID: 20464977] - Perrine Hoet, Erika De Smedt, Massimo Ferrari, Marcello Imbriani, Luciano Maestri, Sara Negri, Peter De Wilde, Dominique Lison, Vincent Haufroid. Evaluation of urinary biomarkers of exposure to benzene: correlation with blood benzene and influence of confounding factors.
International archives of occupational and environmental health.
2009 Aug; 82(8):985-95. doi:
10.1007/s00420-008-0381-6. [PMID: 19009306] - R Chakroun, F Faidi, A Hedhili, M Kolsi, S Fehri, H Nouaigui. Determination of urinary trans, trans-muconic acid reference values in general Tunisian population.
Annales de biologie clinique.
2009 Mar; 67(2):163-9. doi:
10.1684/abc.2009.0310. [PMID: 19297291] - Zhen Wang, Lina Zhang. [Study advances on carcinogens and their metabolites in urine of smokers].
Wei sheng yan jiu = Journal of hygiene research.
2008 Nov; 37(6):757-9. doi:
NULL. [PMID: 19239020] - Paola Manini, Giuseppe De Palma, Roberta Andreoli, Diana Poli, Marta Petyx, Massimo Corradi, Antonio Mutti, Pietro Apostoli. Biological monitoring of low benzene exposure in Italian traffic policemen.
Toxicology letters.
2008 Sep; 181(1):25-30. doi:
10.1016/j.toxlet.2008.06.865. [PMID: 18640250] - C Aprea, G Sciarra, N Bozzi, M Pagliantini, A Perico, P Bavazzano, A Leandri, M Carrieri, M L Scapellato, M Bettinelli, G B Bartolucci. Reference values of urinary trans,trans-muconic acid: Italian Multicentric Study.
Archives of environmental contamination and toxicology.
2008 Aug; 55(2):329-40. doi:
10.1007/s00244-007-9119-9. [PMID: 18214577] - Sam De Coster, Gudrun Koppen, Marc Bracke, Carmen Schroijen, Elly Den Hond, Vera Nelen, Els Van de Mieroop, Liesbeth Bruckers, Maaike Bilau, Willy Baeyens, Greet Schoeters, Nik van Larebeke. Pollutant effects on genotoxic parameters and tumor-associated protein levels in adults: a cross sectional study.
Environmental health : a global access science source.
2008 Jun; 7(?):26. doi:
10.1186/1476-069x-7-26. [PMID: 18522717] - Lung-Cheng Lin, Wan-Jou Chen, Yin-Mei Chiung, Tung-Sheng Shih, Pao-Chi Liao. Association between GST genetic polymorphism and dose-related production of urinary benzene metabolite markers, trans, trans-muconic acid and S-phenylmercapturic acid.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2008 Jun; 17(6):1460-9. doi:
10.1158/1055-9965.epi-08-0160. [PMID: 18559562] - Giovanna Tranfo, Enrico Paci, Renata Sisto, Daniela Pigini. Validation of an HPLC/MS/MS method with isotopic dilution for quantitative determination of trans,trans-muconic acid in urine samples of workers exposed to low benzene concentrations.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2008 May; 867(1):26-31. doi:
10.1016/j.jchromb.2008.03.004. [PMID: 18373962] - Nantaporn Buthbumrung, Chulabhorn Mahidol, Panida Navasumrit, Jeerawan Promvijit, Potchanee Hunsonti, Herman Autrup, Mathuros Ruchirawat. Oxidative DNA damage and influence of genetic polymorphisms among urban and rural schoolchildren exposed to benzene.
Chemico-biological interactions.
2008 Apr; 172(3):185-94. doi:
10.1016/j.cbi.2008.01.005. [PMID: 18282563] - Radhouane Chakroun, Fayçal Faidi, Abderrazek Hedhili, Kaouther Charbaji, Habib Nouaigui, Mohamed Ben Laiba. Inhalant abuse detection and evaluation in young Tunisians.
Journal of forensic sciences.
2008 Jan; 53(1):232-7. doi:
10.1111/j.1556-4029.2007.00623.x. [PMID: 18279264] - Ashraf M Emara, Hoda El-Bahrawy. Green tea attenuates benzene-induced oxidative stress in pump workers.
Journal of immunotoxicology.
2008 Jan; 5(1):69-80. doi:
10.1080/15476910802019029. [PMID: 18382860] - Dennis J Paustenbach, Shannon H Gaffney, Paul K Scott, Jay L Brown, Julie M Panko. High background levels of urinary benzene metabolites found in a volunteer study.
Journal of occupational and environmental hygiene.
2007 Aug; 4(8):71-7. doi:
10.1080/15459620701426016. [PMID: 17530536] - P De Marchis, E Tranchina, G Tranchina, S Schillaci, M G Verso, D Picciotto. [Benzene low dose exposure: comparison of different biologic markers among exposed workers and the general population].
Giornale italiano di medicina del lavoro ed ergonomia.
2007 Jul; 29(3 Suppl):528-9. doi:
NULL. [PMID: 18409813] - M Valentino, V Rapisarda, M Scorcelletti, M Caldaroni, F Mariani. [Biological monitoring in oil refinery workers].
Giornale italiano di medicina del lavoro ed ergonomia.
2007 Jul; 29(3 Suppl):555-6. doi:
NULL. [PMID: 18409828] - D Sapienza, A Asmundo, P Gualniera, G Sole, M Bambara, G Spatari. [Genetic polymorphisms (GSTT1 e GSTM1) and urinary excretion of t,t-muconic acid among refinery workers].
Giornale italiano di medicina del lavoro ed ergonomia.
2007 Jul; 29(3 Suppl):541-2. doi:
NULL. [PMID: 18409821] - S Abbate, C Alibrando, D De Pasquale, L Piscioneri, M Iachello, R Catanoso. [Trans-muconic (t,t-MA) and S-phenilmercapturic acid: two biologic markers of benzene low dose exposure].
Giornale italiano di medicina del lavoro ed ergonomia.
2007 Jul; 29(3 Suppl):538-9. doi:
NULL. [PMID: 18409819] - G Tranfo, E Paci, D Pigini. [Isotopic dilution HPLC/MS/MS urinary trans, trans-muconic quantitative analysis among refinery workers].
Giornale italiano di medicina del lavoro ed ergonomia.
2007 Jul; 29(3 Suppl):522-3. doi:
NULL. [PMID: 18409810] - Abdul Rahman Bahrami, Ahmad Joneidi Jafari, Hassan Ahmadi, Hossein Mahjub. Comparison of benzene exposure in drivers and petrol stations workers by urinary trans,trans-muconic acid in west of Iran.
Industrial health.
2007 Jun; 45(3):396-401. doi:
10.2486/indhealth.45.396. [PMID: 17634688] - G Koppen, G Verheyen, A Maes, U Van Gorp, G Schoeters, E Den Hond, J Staessen, T Nawrot, H A Roels, R Vlietinck, L Verschaeve. A battery of DNA effect biomarkers to evaluate environmental exposure of Flemish adolescents.
Journal of applied toxicology : JAT.
2007 May; 27(3):238-46. doi:
10.1002/jat.1174. [PMID: 17226746] - M R Ray, S Roychoudhury, S Mukherjee, T Lahiri. Occupational benzene exposure from vehicular sources in India and its effect on hematology, lymphocyte subsets and platelet P-selectin expression.
Toxicology and industrial health.
2007 Apr; 23(3):167-75. doi:
10.1177/0748233707080907. [PMID: 18220159] - Mathuros Ruchirawat, Daam Settachan, Panida Navasumrit, Jantamas Tuntawiroon, Herman Autrup. Assessment of potential cancer risk in children exposed to urban air pollution in Bangkok, Thailand.
Toxicology letters.
2007 Feb; 168(3):200-9. doi:
10.1016/j.toxlet.2006.09.013. [PMID: 17157453] - Viroj Wiwanitkit, Suphan Soogarun, Jamsai Suwansaksri. A correlative study on red blood cell parameters and urine trans, trans-muconic acid in subjects with occupational benzene exposure.
Toxicologic pathology.
2007 Feb; 35(2):268-9. doi:
10.1080/01926230601156278. [PMID: 17366320] - Paola Manini, Giuseppe De Palma, Roberta Andreoli, Diana Poli, Paola Mozzoni, Giuseppina Folesani, Antonio Mutti, Pietro Apostoli. Environmental and biological monitoring of benzene exposure in a cohort of Italian taxi drivers.
Toxicology letters.
2006 Dec; 167(2):142-51. doi:
10.1016/j.toxlet.2006.08.016. [PMID: 17056211] - Shi-Zhen Song, Xia-Min Hu, Li-Wen Liu, Cheng-Hong Fu, Fang-Li Ye. [Determination of urine muconic acid and biological limit in workers occupationally exposed to benzene].
Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases.
2006 Nov; 24(11):676-9. doi:
NULL. [PMID: 17181949] - Sungkyoon Kim, Roel Vermeulen, Suramya Waidyanatha, Brent A Johnson, Qing Lan, Martyn T Smith, Luoping Zhang, Guilan Li, Min Shen, Songnian Yin, Nathaniel Rothman, Stephen M Rappaport. Modeling human metabolism of benzene following occupational and environmental exposures.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2006 Nov; 15(11):2246-52. doi:
10.1158/1055-9965.epi-06-0262. [PMID: 17119053] - Xia-Min Hu, Shi-Zhen Song, Fang-Li Ye, Li-Wen Liu. High-performance liquid chromatographic determination of urinary trans, trans-muconic acid excreted by workers occupationally exposed to benzene.
Biomedical and environmental sciences : BES.
2006 Aug; 19(4):292-6. doi:
NULL. [PMID: 17044647] - Liwen Liu, Shizhen Song, Xiamin Hu, Fangli Ye. [Determination of urinary trans, trans-muconic acid by high performance liquid chromatography].
Se pu = Chinese journal of chromatography.
2006 May; 24(3):260-2. doi:
NULL. [PMID: 16929844] - Valentina Olmos, Silvia C Lenzken, Clara M López, Edda C Villaamil. High-performance liquid chromatography method for urinary trans,trans-muconic acid. Application to environmental exposure to benzene.
Journal of analytical toxicology.
2006 May; 30(4):258-61. doi:
10.1093/jat/30.4.258. [PMID: 16803664] - Mariella Carrieri, Enrico Bonfiglio, Maria Luisa Scapellato, Isabella Maccà, Giovanna Tranfo, Paolo Faranda, Enrico Paci, Giovanni Battista Bartolucci. Comparison of exposure assessment methods in occupational exposure to benzene in gasoline filling-station attendants.
Toxicology letters.
2006 Apr; 162(2-3):146-52. doi:
10.1016/j.toxlet.2005.09.036. [PMID: 16289653] - Sungkyoon Kim, Roel Vermeulen, Suramya Waidyanatha, Brent A Johnson, Qing Lan, Nathaniel Rothman, Martyn T Smith, Luoping Zhang, Guilan Li, Min Shen, Songnian Yin, Stephen M Rappaport. Using urinary biomarkers to elucidate dose-related patterns of human benzene metabolism.
Carcinogenesis.
2006 Apr; 27(4):772-81. doi:
10.1093/carcin/bgi297. [PMID: 16339183] - S Feng, H J Roethig, Q Liang, R Kinser, Y Jin, G Scherer, M Urban, J Engl, K Riedel. Evaluation of urinary 1-hydroxypyrene, S-phenylmercapturic acid, trans,trans-muconic acid, 3-methyladenine, 3-ethyladenine, 8-hydroxy-2'-deoxyguanosine and thioethers as biomarkers of exposure to cigarette smoke.
Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals.
2006 Jan; 11(1):28-52. doi:
10.1080/13547500500399730. [PMID: 16484135] - Viroj Wiwanitkit. Classification of risk occupation for benzene exposure by urine trans, trans-munconic acid level.
Asian Pacific journal of cancer prevention : APJCP.
2006 Jan; 7(1):149-50. doi:
NULL. [PMID: 16629534] - S Raghavan, K Basavaiah. Biological monitoring among benzene-exposed workers in Bangalore city, India.
Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals.
2005 Sep; 10(5):336-41. doi:
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Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2005 Sep; 14(9):2237-44. doi:
10.1158/1055-9965.epi-04-0798. [PMID: 16172237] - Nelia D Dimitrova, Ralitsa Y Kostadinova, Snejina N Marinova, Todor A Popov, Teodor I Panev. Specific immune responses in workers exposed to benzene.
International immunopharmacology.
2005 Sep; 5(10):1554-9. doi:
10.1016/j.intimp.2005.04.012. [PMID: 16023607] - A Gelormini, M Barbaro, D Cidaria, M Dall'Olio. [Integration of biological and workplace monitoring as an efficient control of chemical exposure].
Giornale italiano di medicina del lavoro ed ergonomia.
2005 Jul; 27(3):329-31. doi:
NULL. [PMID: 16240587] - Viroj Wiwanitkit, Jamsai Suwansaksri, Suphan Soogarun. Monitoring of urine trans, trans-muconic acid level among smokers and non-smokers.
Respiratory medicine.
2005 Jun; 99(6):788-91. doi:
10.1016/j.rmed.2004.10.017. [PMID: 15878497] - Qingshan Qu, Roy Shore, Guilan Li, Lin Su, Ximei Jin, Asseih A Melikian, Nirmal Roy, Lung Chi Chen, Isaac Wirgin, Beverly Cohen, Songnian Yin, Yuying Li, Ruidong Mu. Biomarkers of benzene: urinary metabolites in relation to individual genotype and personal exposure.
Chemico-biological interactions.
2005 May; 153-154(?):85-95. doi:
10.1016/j.cbi.2005.03.012. [PMID: 15935803] - Silvia Fustinoni, Marina Buratti, Laura Campo, Antonio Colombi, Dario Consonni, Angela C Pesatori, Matteo Bonzini, Peter Farmer, Seymour Garte, Federico Valerio, Domenico F Merlo, Pier A Bertazzi. Urinary t,t-muconic acid, S-phenylmercapturic acid and benzene as biomarkers of low benzene exposure.
Chemico-biological interactions.
2005 May; 153-154(?):253-6. doi:
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