Acetonylacetone (BioDeep_00000358148)
Volatile Flavor Compounds
代谢物信息卡片
Acetonylacetone
化学式: C6H10O2 (114.068076)
中文名称: 2,5-己二酮
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(=O)CCC(=O)C
InChI: InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3
描述信息
A diketone that is hexane substituted by oxo groups at positions 2 and 5. It is a toxic metabolite of hexane and of 2-hexanone
D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D002800 - Cholinesterase Inhibitors
D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D003432 - Cross-Linking Reagents
D009676 - Noxae > D009498 - Neurotoxins
D004791 - Enzyme Inhibitors
同义名列表
3 个代谢物同义名
数据库引用编号
8 个数据库交叉引用编号
- ChEBI: CHEBI:85014
- PubChem: 8035
- Metlin: METLIN98116
- ChEMBL: CHEMBL1564795
- LipidMAPS: LMFA12000081
- CAS: 110-13-4
- PMhub: MS000170688
- MetaboLights: MTBLC85014
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)
0 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
- Aliyu Muhammad, David Ebuka Arthur, Sanusi Babangida, Ochuko L Erukainure, Ibrahim Malami, Hadiza Sani, Aliyu Waziri Abdulhamid, Idayat Omoyemi Ajiboye, Ahmed Ariyo Saka, Nafisa Muhammed Hamza, Suleiman Asema, Zaharaddeen Muhammad Ado, Taibat Ishaq Musa. Modulatory role of rutin on 2,5-hexanedione-induced chromosomal and DNA damage in rats: validation of computational predictions.
Drug and chemical toxicology.
2020 Mar; 43(2):113-126. doi:
10.1080/01480545.2018.1465948. [PMID: 29745774] - Xianjie Li, Qiong Wang, Ming Li, Shuo Wang, Cuiqin Zhang, Keqin Xie. Hair pyrrole adducts serve as biomarkers for peripheral nerve impairment induced by 2,5-hexanedione and n-hexane in rats.
PloS one.
2018; 13(12):e0209939. doi:
10.1371/journal.pone.0209939. [PMID: 30596762] - Z Ruan, H F Tang, H Wang. [Quality control methods of gas chromatography⁃ion trap mass determine for the 2, 5⁃hexanedione in normal population urinary].
Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases.
2017 Apr; 35(4):319-320. doi:
10.3760/cma.j.issn.1001-9391.2017.04.027. [PMID: 28614944] - Isaac A Adedara, Amos O Abolaji, Blessing E Odion, Abiola A Omoloja, Isioma J Okwudi, Ebenezer O Farombi. Redox status of the testes and sperm of rats following exposure to 2,5-hexanedione.
Redox report : communications in free radical research.
2016 Nov; 21(6):239-47. doi:
10.1080/13510002.2015.1107312. [PMID: 26818104] - Edward Dere, Shelby K Wilson, Linnea M Anderson, Kim Boekelheide. From the Cover: Sperm Molecular Biomarkers Are Sensitive Indicators of Testicular Injury following Subchronic Model Toxicant Exposure.
Toxicological sciences : an official journal of the Society of Toxicology.
2016 10; 153(2):327-40. doi:
10.1093/toxsci/kfw137. [PMID: 27466211] - Pan Xing-Fu, Qian Ya-Ling, Zhao Wei, Tang Hong-Fang, Ruan Zheng, Wu Bang-Hua, Huang Han-Lin, Zheng Yu-Xin, Yan Hui-Fang. Determination of total urinary 2,5-hexanedione in the Chinese general population.
Environmental research.
2016 10; 150(?):645-650. doi:
10.1016/j.envres.2016.05.030. [PMID: 27237929] - Wei Zou, Mengping Zhang, Haiyan Wei. [Readspace solid-phase microextraction-gas chromatography for determination of 2,5-hexanedione in urine].
Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases.
2015 Apr; 33(4):297-8. doi:
NULL. [PMID: 26506784] - M Edite Torres, A P Marreilha dos Santos, Luísa L Gonçalves, Vanda Andrade, M Camila Batoréu, M Luísa Mateus. Role of N-acetylcysteine in protecting against 2,5-hexanedione neurotoxicity in a rat model: changes in urinary pyrroles levels and motor activity performance.
Environmental toxicology and pharmacology.
2014 Nov; 38(3):807-13. doi:
10.1016/j.etap.2014.09.008. [PMID: 25305742] - Hong-Yin Yin, Ying Guo, Fu-Yong Song, Tao Zeng, Ke-Qin Xie. Toxicokinetic study of pyrrole adducts and its potential application for biological monitoring of 2,5-hexanedione subacute exposure.
International archives of occupational and environmental health.
2014 Aug; 87(6):655-62. doi:
10.1007/s00420-013-0907-4. [PMID: 24078145] - M Edite Torres, Luísa L Gonçalves, M Rosário Bronze, A P Marreilha dos Santos, M Camila Batoréu, M Luísa Mateus. Alternative biomarkers of n-hexane exposure: characterization of aminoderived pyrroles and thiol-pyrrole conjugates in urine of rats exposed to 2,5-hexanedione.
Toxicology letters.
2014 Jan; 224(1):54-63. doi:
. [PMID: 24459702] - Ming-xing Zhu, Hong-yin Yin, Ke-qin Xie. [Formation of pyrrole adducts in 2,5-hexanedione-containing human serum cultured in vitro].
Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases.
2013 Aug; 31(8):611-4. doi:
NULL. [PMID: 24053965] - Zoltan Erdos, Kara Pearson, Michael Goedken, Karsten Menzel, Frank D Sistare, Warren E Glaab, Louise Parks Saldutti. Inhibin B response to testicular toxicants hexachlorophene, ethane dimethane sulfonate, di-(n-butyl)-phthalate, nitrofurazone, DL-ethionine, 17-alpha ethinylestradiol, 2,5-hexanedione, or carbendazim following short-term dosing in male rats.
Birth defects research. Part B, Developmental and reproductive toxicology.
2013 Feb; 98(1):41-53. doi:
10.1002/bdrb.21035. [PMID: 23348767] - Hongyin Yin, Ying Guo, Tao Zeng, Xiulan Zhao, Keqin Xie. Correlation between levels of 2, 5-hexanedione and pyrrole adducts in tissues of rats exposure to n-hexane for 5-days.
PloS one.
2013; 8(9):e76011. doi:
10.1371/journal.pone.0076011. [PMID: 24098756] - Hai-fang Liu, Ying Chen, Gang Zhou, Xin Cheng, Ba-xiong Wei. [Studying the damages of mouse retina induced by 2,5-hexanedione].
Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases.
2012 May; 30(5):331-4. doi:
". [PMID: 22804983] - Yosuke Hanai, Ken Shimono, Hiroaki Oka, Yoshinobu Baba, Kunio Yamazaki, Gary K Beauchamp. Analysis of volatile organic compounds released from human lung cancer cells and from the urine of tumor-bearing mice.
Cancer cell international.
2012 Feb; 12(1):7. doi:
10.1186/1475-2867-12-7. [PMID: 22364569] - Imed Gargouri, Moncef Khadhraoui, Catherine Nisse, Ariane Leroyer, Mohamed L Masmoudi, Paul Frimat, Daniel Marzin, Boubaker Elleuch, Denis Zmirou-Navier. A case study on co-exposure to a mixture of organic solvents in a Tunisian adhesive-producing company.
Journal of occupational medicine and toxicology (London, England).
2011 Nov; 6(?):28. doi:
10.1186/1745-6673-6-28. [PMID: 22082240] - Mi-Young Lee, Jeong Sun Yang, Seong-Kyu Kang. External quality assessment scheme for biological monitoring of occupational exposure to toxic chemicals.
Safety and health at work.
2011 Sep; 2(3):229-35. doi:
10.5491/shaw.2011.2.3.229. [PMID: 22953206] - Lei Zhao, QingJun Liu, Hong Chen, HuaWei Duan, Ping Bin, Qing Liu, Yong Niu, YuFei Dai, YuXin Zheng. The effect of 2,5-hexanedione on myelin protein zero expression, and its mitigation using Ginkgo biloba extract.
Biomedical and environmental sciences : BES.
2011 Aug; 24(4):374-82. doi:
10.3967/0895-3988.2011.04.008. [PMID: 22108326] - Wei Zhou, Juan Yi, Hui-Ping Huang, Ying-Ping Xiang, Jia-Xi He, Qing-Jun Liu, Xian-Qing Huang. [Effects of n-hexane exposure on human serum myelin basic proteins].
Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases.
2011 Jun; 29(6):421-3. doi:
NULL. [PMID: 22096852] - Juan Yi, Wei Zhou, Jia-xi He, Qing-jun Liu, Xian-qing Huang. [Effects on serum myelin proteins of n-hexane exposure].
Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases.
2011 Feb; 29(2):131-3. doi:
NULL. [PMID: 21619844] - Jie Yan, Hong-yin Yin, Zhong Liu, De-feng Chi, Yang Li, Qiang-qiang Fu, Ke-qin Xie. [Effects of garlic oil, age and sex on n-hexane metabolism in rats].
Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases.
2011 Jan; 29(1):49-52. doi:
NULL. [PMID: 21619798] - Qingjun Liu, Lei Zhao, Huawei Duan, Yufei Dai, Yong Niu, Hong Chen, Qing Liu, Ping Bin, Yuxin Zheng. [Effect of 2,5-hexanedione on myelin protein zero in sciatic nerve and its antibody in serum of rats at different time points].
Wei sheng yan jiu = Journal of hygiene research.
2010 May; 39(3):275-8. doi:
NULL. [PMID: 20568451] - Eun-Hee Lee, Jaisoo Kim, Kyung-Suk Cho, Yun Gyong Ahn, Geum-Sook Hwang. Degradation of hexane and other recalcitrant hydrocarbons by a novel isolate, Rhodococcus sp. EH831.
Environmental science and pollution research international.
2010 Jan; 17(1):64-77. doi:
10.1007/s11356-009-0238-x. [PMID: 19756804] - Irène Sari-Minodier, Ginette Truchon, Ginette Charest-Tardif, Anick Bérubé, Robert Tardif. The effect of workload on biological monitoring of occupational exposure to toluene and n-Hexane: contribution of physiologically based toxicokinetic modeling.
Journal of occupational and environmental hygiene.
2009 Jul; 6(7):415-32. doi:
10.1080/15459620902928141. [PMID: 19384711] - Xu-cong Gao, Hong-yin Yin, Cui-li Zhang, Zhen-ping Zhu, Li-hua Yu, Ke-qin Xie. [Effects of garlic oil on n-hexane metabolized to 2, 5-hexanedione in mice serum].
Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases.
2009 May; 27(5):262-5. doi:
NULL. [PMID: 19538836] - Antônio Felipe F Oliveira, Patrícia P Maia, Maria José N Paiva, Maria Elisa P B Siqueira. Determination of 2,5-hexanedione in urine by headspace solid-phase microextraction and gas chromatography.
Journal of analytical toxicology.
2009 May; 33(4):223-8. doi:
10.1093/jat/33.4.223. [PMID: 19470226] - Anthony P DeCaprio, Elizabeth A Kinney, Richard M LoPachin. Comparative covalent protein binding of 2,5-hexanedione and 3-acetyl-2,5-hexanedione in the rat.
Journal of toxicology and environmental health. Part A.
2009; 72(14):861-9. doi:
10.1080/15287390902959508. [PMID: 19557614] - Xu-Cong Gao, Tao Zeng, Qian Wang, Qing-Shan Wang, Ke-Qin Xie. [Effects of garlic oil on 2, 5-HD induced lipid peroxidation damage in rat nerve tissues].
Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases.
2008 Nov; 26(11):649-53. doi:
". [PMID: 19467181] - Yue Qian, Fuqing Zeng. Re-establishment of spermatogenesis by diethylstilbestrol after 2,5-hexanedione-induced irreversible testicular atrophy in rats.
Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban.
2008 Apr; 28(2):179-81. doi:
10.1007/s11596-008-0216-4. [PMID: 18480992] - Qing-Shan Wang, Li-Yan Hou, Cui-Li Zhang, Fu-Yong Song, Ke-Qin Xie. Changes of cytoskeletal proteins in nerve tissues and serum of rats treated with 2,5-hexanedione.
Toxicology.
2008 Feb; 244(2-3):166-78. doi:
10.1016/j.tox.2007.11.009. [PMID: 18177991] - 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] - Satoshi Endo, Toshiyuki Matsunaga, Kenji Horie, Kazuo Tajima, Yasuo Bunai, Vincenzo Carbone, Ossama El-Kabbani, Akira Hara. Enzymatic characteristics of an aldo-keto reductase family protein (AKR1C15) and its localization in rat tissues.
Archives of biochemistry and biophysics.
2007 Sep; 465(1):136-47. doi:
10.1016/j.abb.2007.05.008. [PMID: 17574202] - Robert Tardif, Véronique Nadeau, Ginette Truchon, Martin Brochu. Effect of physical exertion on the biological monitoring of exposure to various solvents following exposure by inhalation in human volunteers: II. n-Hexane.
Journal of occupational and environmental hygiene.
2007 Jul; 4(7):502-8; quiz D68. doi:
10.1080/15459620701401936. [PMID: 17503295] - Yanshu Zhang, Qingjun Liu, Qiang Liu, Hong Chen. [Effect of nerve growth factor on mitochondrion dysfunction of motor neuron induced by 2,5-hexanedione].
Wei sheng yan jiu = Journal of hygiene research.
2007 May; 36(3):263-5. doi:
NULL. [PMID: 17712933] - M J Prieto-Castelló, M L Hernández-Viadel, A Cardona, D Marhuenda, V Felipo. Activation of soluble guanylate cyclase by nitric oxide is increased in lymphocytes from both rats chronically exposed to 2,5-hexanedione and workers chronically exposed to n-hexane.
Toxicology.
2007 Jan; 229(1-2):73-8. doi:
10.1016/j.tox.2006.10.002. [PMID: 17125898] - Ying-yu Huang, Wei-ping Xie, Hui-rong Fu, Gui-lian Hu. [Combined application of gas and mass chromatography for determination of 2, 5-hexanedione].
Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases.
2006 May; 24(5):299-300. doi:
NULL. [PMID: 16737598] - Toshinori Yamamoto, Tamio Fukushima, Rie Kikkawa, Hiroshi Yamada, Ikuo Horii. Protein expression analysis of rat testes induced testicular toxicity with several reproductive toxicants.
The Journal of toxicological sciences.
2005 May; 30(2):111-26. doi:
10.2131/jts.30.111. [PMID: 15928459] - G Hamelin, G Charest-Tardif, G Truchon, R Tardif. Physiologically based modeling of n-hexane kinetics in humans following inhalation exposure at rest and under physical exertion: impact on free 2,5-hexanedione in urine and on n-hexane in alveolar air.
Journal of occupational and environmental hygiene.
2005 Feb; 2(2):86-97; quiz D6. doi:
10.1080/15459620590909673. [PMID: 15764529] - Steffen Strassnig, Marion Gfrerer, Ernst P Lankmayr. Microwave-assisted derivatization of 2,5-hexanedione in urine: evaluation using GC-MS and GC-ECD.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2004 Dec; 813(1-2):151-8. doi:
10.1016/j.jchromb.2004.09.025. [PMID: 15556528] - G Hamelin, G Truchon, R Tardif. Comparison of unchanged n-hexane in alveolar air and 2,5-hexanedione in urine for the biological monitoring of n-hexane exposure in human volunteers.
International archives of occupational and environmental health.
2004 May; 77(4):264-70. doi:
10.1007/s00420-004-0506-5. [PMID: 15024572] - M J Prieto, D Marhuenda, J Roel, A Cardona. Free and total 2,5-hexanedione in biological monitoring of workers exposed to n-hexane in the shoe industry.
Toxicology letters.
2003 Dec; 145(3):249-60. doi:
10.1016/s0378-4274(03)00302-3. [PMID: 14580896] - A Baldasseroni, P Bavazzano, V Li Donni, E Buiatti, E Lanciotti, C Lorini, S Toti, A Biggeri. Occupational exposure to n-hexane in Italy--analysis of a registry of biological monitoring.
International archives of occupational and environmental health.
2003 May; 76(4):260-6. doi:
10.1007/s00420-002-0411-8. [PMID: 12768281] - M Canesi, L Perbellini, L Maestri, A Silvani, L Zecca, L Bet, G Pezzoli. Poor metabolization of n-hexane in Parkinson's disease.
Journal of neurology.
2003 May; 250(5):556-60. doi:
10.1007/s00415-003-1035-y. [PMID: 12736734] - M Luisa Mateus, Ana P M dos Santos, M Camila C Batoréu. Evidence of zinc protection against 2,5-hexanedione neurotoxicity: correlation of neurobehavioral testing with biomarkers of excretion.
Neurotoxicology.
2002 Dec; 23(6):747-54. doi:
10.1016/s0161-813x(02)00011-6. [PMID: 12520764] - Baoyu Han, Zongmao Chen. Behavioral and electrophysiological responses of natural enemies to synomones from tea shoots and kairomones from tea aphids, Toxoptera aurantii.
Journal of chemical ecology.
2002 Nov; 28(11):2203-19. doi:
10.1023/a:1021045231501. [PMID: 12523563] - Claudia Regina dos Santos, Miriam Meyer Meyer Passarelli, Elizabeth de Souza Nascimento. Evaluation of 2,5-hexanedione in urine of workers exposed to n-hexane in Brazilian shoe factories.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2002 Oct; 778(1-2):237-44. doi:
10.1016/s1570-0232(02)00036-3. [PMID: 12376131] - Sinikka Valkonen, Arja Kallio. Finnish quality assurance programme for biological monitoring of organic solvents.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2002 Oct; 778(1-2):419-27. doi:
10.1016/s0378-4347(01)00464-9. [PMID: 12376146] - Eiji Shibata, Gunnar Johanson, Agneta Löf, Lena Ernstgård, Elisabeth Gullstrand, Karl Sigvardsson. Changes in n-hexane toxicokinetics in short-term single exposure due to co-exposure to methyl ethyl ketone in volunteers.
International archives of occupational and environmental health.
2002 Aug; 75(6):399-405. doi:
10.1007/s00420-002-0325-5. [PMID: 12070636] - Olga Mayan, Joao Paulo Teixeira, Sandra Alves, Conceição Azevedo. Urinary 2,5 hexanedione as a biomarker of n-hexane exposure.
Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals.
2002 Jul; 7(4):299-305. doi:
10.1080/13547500210136796. [PMID: 12171757] - Carlos Pastore, Virginia Izura, Dolores Marhuenda, María-José Prieto, José Roel, Antonio Cardona. Partial conduction blocks in N-hexane neuropathy.
Muscle & nerve.
2002 Jul; 26(1):132-5. doi:
10.1002/mus.10183. [PMID: 12115958] - Sema Burgaz, Onur Erdem, Gonca Cakmak, Nurten Erdem, Asuman Karakaya, Ali Esat Karakaya. Cytogenetic analysis of buccal cells from shoe-workers and pathology and anatomy laboratory workers exposed to n-hexane, toluene, methyl ethyl ketone and formaldehyde.
Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals.
2002 Mar; 7(2):151-61. doi:
10.1080/13547500110113242. [PMID: 12101634] - Kazuhito Yokoyama, Shunichi Araki, Mariko Nishikitani, Hajime Sato. Computerized posturography with sway frequency analysis: application in occupational and environmental health.
Industrial health.
2002 Jan; 40(1):14-22. doi:
10.2486/indhealth.40.14. [PMID: 11926510] - O Mayan, J P Teixeira, A F Pires. Biological monitoring of n-hexane exposure in Portuguese shoe manufacturing workers.
Applied occupational and environmental hygiene.
2001 Jul; 16(7):736-41. doi:
10.1080/10473220116711. [PMID: 11458920] - M L Mateus, A P dos Santos, M C Batoréu. Interaction of zinc on biomarker responses in rats exposed to 2,5-hexanedione by two routes of exposure.
Toxicology letters.
2001 Feb; 119(1):39-47. doi:
10.1016/s0378-4274(00)00298-8. [PMID: 11275420] - M M Iba, J Fung, F J Gonzalez. Functional Cyp2e1 is required for substantial in vivo formation of 2,5-hexanedione from n-hexane in the mouse.
Archives of toxicology.
2000 Dec; 74(10):582-6. doi:
10.1007/s002040000182. [PMID: 11201664] - T Kawai, Y Miyama, S Horiguchi, K Sakamoto, Z W Zhang, K Higashikawa, M Ikeda. Possible metabolic interaction between hexane and other solvents co-exposed at sub-occupational exposure limit levels.
International archives of occupational and environmental health.
2000 Sep; 73(7):449-56. doi:
10.1007/s004200000165. [PMID: 11057413] - M L Mateus, A P Santos, M C Batoreu. Evidence for zinc protection against 2,5-hexanedione toxicity by co-exposure of rats to zinc chloride.
Journal of applied toxicology : JAT.
2000 May; 20(3):211-4. doi:
10.1002/(sici)1099-1263(200005/06)20:3<211::aid-jat636>3.0.co;2-o. [PMID: 10797474] - P Manini, R Andreoli, A Mutti, E Bergamaschi, I Franchini. Determination of free and glucuronated hexane metabolites without prior hydrolysis by liquid- and gas-chromatography coupled with mass spectrometry.
Toxicology letters.
1999 Sep; 108(2-3):225-31. doi:
10.1016/s0378-4274(99)00093-4. [PMID: 10511266] - G Xu, Y Liu, M M Kansal, L M Sayre. Rapid cross-linking of proteins by 4-ketoaldehydes and 4-hydroxy-2-alkenals does not arise from the lysine-derived monoalkylpyrroles.
Chemical research in toxicology.
1999 Sep; 12(9):855-61. doi:
10.1021/tx990056a. [PMID: 10490508] - B Bäckström, E Shibata, P Nylén, V P Collins. 2,5-Hexanedione concentrations and morphological changes within the eye of albino rat.
Archives of toxicology.
1998 Sep; 72(9):597-600. doi:
10.1007/s002040050548. [PMID: 9806432] - W Zhao, J Misumi, T Yasui, K Aoki, T Kimura. Effects of methyl ethyl ketone, acetone, or toluene coadministration on 2,5-hexanedione concentration in the sciatic nerve, serum, and urine of rats.
International archives of occupational and environmental health.
1998 Jun; 71(4):236-44. doi:
10.1007/s004200050275. [PMID: 9638479] - W Zhao, J Misumi, T Yasui, K Aoki, T Kimura. Relationship between 2,5-hexanedione concentrations in nerve, serum, and urine alone or under co-treatment with different doses of methyl ethyl ketone, acetone, and toluene.
Neurochemical research.
1998 Jun; 23(6):837-43. doi:
10.1023/a:1022402810695. [PMID: 9572672] - P Bavazzano, P Apostoli, C Balducci, G B Bartolucci, M Buratti, P Duca, G Gori, V Li Donni, L Perbellini, A Perico, C Minoia. Determination of urinary 2,5-hexanedione in the general Italian population.
International archives of occupational and environmental health.
1998 Jun; 71(4):284-8. doi:
10.1007/s004200050282. [PMID: 9638486] - G Ichihara, I Saito, M Kamijima, X Yu, E Shibata, M Toida, Y Takeuchi. Urinary 2,5-hexanedione increases with potentiation of neurotoxicity in chronic coexposure to n-hexane and methyl ethyl ketone.
International archives of occupational and environmental health.
1998 Mar; 71(2):100-4. doi:
10.1007/s004200050255. [PMID: 9553785] - R Andreoli, P Manini, A Mutti, E Bergamaschi, W M Niessen. Determination of n-hexane metabolites by liquid chromatography/mass spectrometry. 1. 2,5-hexanedione and other phase I metabolites in untreated and hydrolyzed urine samples by atmospheric pressure chemical ionization.
Rapid communications in mass spectrometry : RCM.
1998; 12(19):1410-6. doi:
10.1002/(sici)1097-0231(19981015)12:19<1410::aid-rcm339>3.0.co;2-m. [PMID: 9773526] - M Ogata, T Numano, M Hosokawa, H Michitsuji. Large-scale biological monitoring in Japan.
The Science of the total environment.
1997 Jun; 199(1-2):197-204. doi:
10.1016/s0048-9697(97)05496-x. [PMID: 9200864] - J R Jackson, G de Kechove, A Karakay. Changes in immunoglobulin concentrations and urinary 2,5-hexanedione concentrations.
Human & experimental toxicology.
1997 May; 16(5):284-5. doi:
10.1177/096032719701600511. [PMID: 9192211] - J Misumi, M Nagano, M Futatsuka, W Zhao, M Kudo. Different administration schedules of the same dose of 2,5-hexanedione influence the development of neuropathy and the toxicokinetics.
Neurochemical research.
1997 Jan; 22(1):27-32. doi:
10.1023/a:1027317002386. [PMID: 9021758] - B Yan, A P DeCaprio, M Zhu, S Bank. Solid-state 13C-NMR spectroscopy of adduction products of 2,5-hexanedione with ribonuclease, albumin, and rat neurofilament protein.
Chemico-biological interactions.
1996 Oct; 102(2):101-16. doi:
10.1016/s0009-2797(96)03738-6. [PMID: 8950225] - A Cardona, D Marhuenda, M J Prieto, J Martí, J F Periago, J M Sánchez. Behaviour of urinary 2,5-hexanedione in occupational co-exposure to n-hexane and acetone.
International archives of occupational and environmental health.
1996; 68(2):88-93. doi:
10.1007/bf00381240. [PMID: 8720278] - S Valkonen, K Engström, I Ahonen, P Mutanen, A Aitio. FIOH external quality assurance scheme for organic solvent metabolites.
Annali dell'Istituto superiore di sanita.
1996; 32(2):225-31. doi:
NULL. [PMID: 8913040] - J G Filser, G A Csanády, W Dietz, W Kessler, P E Kreuzer, M Richter, A Störmer. Comparative estimation of the neurotoxic risks of N-hexane and N-heptane in rats and humans based on the formation of the metabolites 2,5-hexanedione and 2,5-heptanedione.
Advances in experimental medicine and biology.
1996; 387(?):411-27. doi:
10.1007/978-1-4757-9480-9_50. [PMID: 8794236] - G Gori, G B Bartolucci, A Sturaro, G Parvoli, L Doretti, R Troiano, B Casetta. High-performance liquid chromatographic determination of urinary 2,5-hexanedione as mono-2,4-dinitrophenylhydrazone using ultraviolet detection.
Journal of chromatography. B, Biomedical applications.
1995 Nov; 673(2):165-72. doi:
10.1016/0378-4347(95)00257-x. [PMID: 8611949] - D J Johnson, L Lack, S Ibrahim, S M Abdel-Rahman, M B Abou-Donia. Protein-bound pyrroles in rat hair following subchronic intraperitoneal injections of 2,5-hexanedione.
Journal of toxicology and environmental health.
1995 Jul; 45(3):313-24. doi:
10.1080/15287399509531998. [PMID: 7609005] - M P Serve, D D Bombick, T M Baughman, B M Jarnot, M Ketcha, D R Mattie. The metabolism of n-nonane in male Fischer 344 rats.
Chemosphere.
1995 Jul; 31(2):2661-8. doi:
10.1016/0045-6535(95)00137-w. [PMID: 7663950] - J G van Engelen, S Kezić, W de Haan, J J Opdam, F A de Wolff. Determination of 2,5-hexanedione, a metabolite of n-hexane, in urine: evaluation and application of three analytical methods.
Journal of chromatography. B, Biomedical applications.
1995 May; 667(2):233-40. doi:
10.1016/0378-4347(95)00029-i. [PMID: 7663695] - T Kawamoto, Y Kodama, K Kohno. Interlaboratory quality control and status of n-hexane biological monitoring in Japan.
Archives of environmental contamination and toxicology.
1995 May; 28(4):529-36. doi:
10.1007/bf00211638. [PMID: 7755406] - G Rosiepen, R E Chapin, G F Weinbauer. The duration of the cycle of the seminiferous epithelium is altered by administration of 2,5-hexanedione in the adult Sprague-Dawley rat.
Journal of andrology.
1995 Mar; 16(2):127-35. doi:
NULL. [PMID: 7559142] - M Governa, M Valentino, I Visonà, F Monaco. Human polymorphonuclear leukocyte chemotaxis as a tool in detecting biological early effects in workers occupationally exposed to low levels of n-hexane.
Human & experimental toxicology.
1994 Oct; 13(10):663-70. doi:
10.1177/096032719401301003. [PMID: 7826683] - C Pastore, D Marhuenda, J Marti, A Cardona. Early diagnosis of n-hexane-caused neuropathy.
Muscle & nerve.
1994 Sep; 17(9):981-6. doi:
10.1002/mus.880170904. [PMID: 8065400] - L Maestri, S Ghittori, M Imbriani, E Capodaglio. Determination of 2,5-hexandione by high-performance liquid chromatography after derivatization with dansylhydrazine.
Journal of chromatography. B, Biomedical applications.
1994 Jul; 657(1):111-7. doi:
10.1016/0378-4347(94)80076-6. [PMID: 7952056] - Y Takeuchi. n-hexane polyneuropathy in Japan: a review of n-hexane poisoning and its preventive measures.
Environmental research.
1993 Jul; 62(1):76-80. doi:
10.1006/enrs.1993.1091. [PMID: 8325270] - K Aoki, J Misumi, T Yasui, M Kudo, T Goto, A Shimaoka. [Effect of hyperglycemia on the excretion levels of urinary 2,5-hexanedione in persons not exposed to n-hexane].
Sangyo igaku. Japanese journal of industrial health.
1993 Jul; 35(4):292-3. doi:
10.1539/joh1959.35.292. [PMID: 8377267] - P Bavazzano, V Li Donni, A Baldasseroni. [Quality control in a system for the biological surveillance of exposure to n-hexane].
La Medicina del lavoro.
1993 Mar; 84(2):115-20. doi:
NULL. [PMID: 8316142] - A Sturaro, G Parvoli, L Doretti. High-performance liquid chromatographic determination of urinary 2,5-hexanedione.
Journal of chromatography.
1993 Jan; 628(2):316-8. doi:
10.1016/0021-9673(93)80014-y. [PMID: 8425924] - L Perbellini, G Pezzoli, F Brugnone, M Canesi. Biochemical and physiological aspects of 2,5-hexanedione: endogenous or exogenous product?.
International archives of occupational and environmental health.
1993; 65(1):49-52. doi:
10.1007/bf00586058. [PMID: 8354575] - T Kawai, T Yasugi, K Mizunuma, S Horiguchi, M Ikeda. Comparative evaluation of blood and urine analysis as a tool for biological monitoring of n-hexane and toluene.
International archives of occupational and environmental health.
1993; 65(1 Suppl):S123-6. doi:
10.1007/bf00381322. [PMID: 8406907] - A Cardona, D Marhuenda, J Martí, F Brugnone, J Roel, L Perbellini. Biological monitoring of occupational exposure to n-hexane by measurement of urinary 2,5-hexanedione.
International archives of occupational and environmental health.
1993; 65(1):71-4. doi:
10.1007/bf00586062. [PMID: 8354578] - A Mutti, E Bergamaschi, S Ghittori, M Imbriani, I Franchini. On the need of a sampling strategy in biological monitoring: the example of hexane exposure.
International archives of occupational and environmental health.
1993; 65(1 Suppl):S171-5. doi:
10.1007/bf00381334. [PMID: 8406920] - J F Periago, A Cardona, D Marhuenda, J Roel, M Villanueva, J Marti, A Luna. Biological monitoring of occupational exposure to n-hexane by exhaled air analysis and urinalysis.
International archives of occupational and environmental health.
1993; 65(4):275-8. doi:
10.1007/bf00381203. [PMID: 8144240] - Y Takeuchi, N Hisanaga, Y Ono, E Shibata, I Saito, M Iwata. Modification of metabolism and neurotoxicity of hexane by co-exposure of toluene.
International archives of occupational and environmental health.
1993; 65(1 Suppl):S227-30. doi:
10.1007/bf00381347. [PMID: 8406932] - T Kawai, T Yasugi, K Mizunuma, S Horiguchi, M Ikeda. Urinalysis vs. blood analysis, as a tool for biological monitoring of solvent exposure.
Toxicology letters.
1992 Dec; 63(3):333-43. doi:
10.1016/0378-4274(92)90095-2. [PMID: 1488781] - T Sakai, T Araki, K Ushio, Y Takeuchi, Y Ikeya. [Effect of hydrolysis conditions on the determination of urinary 2,5-hexanedione in workers exposed or not exposed to N-hexane].
Sangyo igaku. Japanese journal of industrial health.
1992 Sep; 34(5):440-7. doi:
10.1539/joh1959.34.440. [PMID: 1405004] - K Vohra, V S Gaind. Gas chromatographic determination of 2,5-hexanedione in urine as an indicator of exposure to n-hexane.
Journal of analytical toxicology.
1992 May; 16(3):176-8. doi:
10.1093/jat/16.3.176. [PMID: 1522712] - M P Colombini, P Carrai, R Fuoco, C Abete. Rapid and sensitive determination of urinary 2,5-hexanedione by reversed-phase high-performance liquid chromatography.
Journal of chromatography.
1992 Feb; 592(1-2):255-60. doi:
10.1016/0021-9673(92)85092-8. [PMID: 1583096] - I Saito, E Shibata, J Huang, N Hisanaga, Y Ono, Y Takeuchi. Determination of urinary 2,5-hexanedione concentration by an improved analytical method as an index of exposure to n-hexane.
British journal of industrial medicine.
1991 Aug; 48(8):568-74. doi:
10.1136/oem.48.8.568. [PMID: 1878315] - S Kezić, A C Monster. Determination of 2,5-hexanedione in urine and serum by gas chromatography after derivatization with O-(pentafluorobenzyl)hydroxylamine and solid-phase extraction.
Journal of chromatography.
1991 Jan; 563(1):199-204. doi:
10.1016/0378-4347(91)80296-o. [PMID: 2061389] - K Boekelheide, S J Hall. 2,5-hexanedione exposure in the rat results in long-term testicular atrophy despite the presence of residual spermatogonia.
Journal of andrology.
1991 Jan; 12(1):18-26. doi:
NULL. [PMID: 2010348] - T Kawai, T Yasugi, K Mizunuma, S Horiguchi, Y Uchida, O Iwami, H Iguchi, M Ikeda. Dose-dependent increase in 2,5-hexanedione in the urine of workers exposed to n-hexane.
International archives of occupational and environmental health.
1991; 63(4):285-91. doi:
10.1007/bf00386379. [PMID: 1743771]