Glycerol alpha-monochlorohydrin (BioDeep_00000012367)

 

Secondary id: BioDeep_00001867742

human metabolite Endogenous Volatile Flavor Compounds


代谢物信息卡片


beta,Beta-dihydroxyisopropyl chloride

化学式: C3H7ClO2 (110.0134552)
中文名称: 3-氯-1,2-丙二醇, 3-氯-1,2-丙二醇标准溶液
谱图信息: 最多检出来源 Mentha canadensis(plant) 87.5%

分子结构信息

SMILES: C(C(CCl)O)O
InChI: InChI=1S/C3H7ClO2/c4-1-3(6)2-5/h3,5-6H,1-2H2

描述信息

Glycerol alpha-monochlorohydrin is found in herbs and spices. By-product of vegetable protein hydrolysed by HCl. Identified in some soy sauce product
D010575 - Pesticides > D002629 - Chemosterilants
D016573 - Agrochemicals

同义名列表

61 个代谢物同义名

beta,Beta-dihydroxyisopropyl chloride; alpha-Monochlorohydrin, glycerol; Glycerine alpha-monochlorohydrin; Glycerol-alpha -monochlorohydrin; (+-)-2,3-Dihydroxychloropropane; Glycerin alpha -monochlorhydrin; Glycerol alpha-monochlorohydrin; Glycerol alpha monochlorohydrin; Glycerin alpha-monochlorhydrin; (+/-)-3-chloro-1,2-propanediol; 3-Chloro-1,2-dihydroxypropane; 3-Chloro-1,2-propylene glycol; 1,2-Dihydroxy-3-chloropropane; (RS)-3-Chloro-1,2-propanediol; 1-Chloro-2,3-dihydroxypropane; 2,3-Dihydroxypropyl chloride; 3 Monochloropropane 1,2 diol; 3-Monochloropropane-1,2-diol; 3-Monochloro-1,2-propanediol; Glyceryl alpha -chlorohydrin; Glycerol alpha -chlorohydrin; Glycerol a-monochlorohydrin; Glyceryl-alpha-chlorohydrin; Chloro-1,2-dihydroxypropane; Glycerol α-monochlorohydrin; alpha-Glycerol chlorohydrin; Glyceryl alpha-chlorohydrin; 3-Dichloro-1,2-propanediol; 3-Chloro-1,2-propanediol; 1-Chloro-1-deoxyglycerol; 3 Chloro 1,2 propanediol; 3-Chloropropylene glycol; 1-Chloropropane-2,3-diol; 1-Chloro-2,3-propanediol; 3-Chloropropane-1,2-diol; Glycerin epichlorohydrin; a-Glycerol chlorohydrin; Glycerol 3-chlorohydrin; 3-Chloro-1,2-propandiol; Chloropropylene glycol; Chloro-1,2-propanediol; alpha-Monochlorohydrin; Glycerol chlorohydrin; alpha-Chlorohydrine; 3-Chloropropanediol; Chlorodeoxyglycerol; 3 Chloropropanediol; a-Monochlorohydrin; alpha Chlorohydrin; alpha-Chlorohydrin; alpha Chlorhydrin; Chloropropanediol; Glyceryl chloride; alpha-Chlorhydrin; α chlorohydrin; a-Chlorohydrin; Α-chlorohydrin; Epibloc; 3-MCPD; alpha-Chlorohydrin; 3-Chloro-1,2-propanediol



数据库引用编号

17 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)

2 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

  • Chen Liu, Shang-Ta Wang, Choon-Hui Tan, Zih-Ee Lin, Wei-Ju Lee. Occurrence and risk assessment of glycidyl and 3-monochloropropanediol esters in infant formulas marketed in Taiwan. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2024 Apr; 41(4):352-364. doi: 10.1080/19440049.2024.2319271. [PMID: 38422382]
  • Yu-Hsuan Chang, Kai-Wei Liao, Zih-Ee Lin, Wei-Ju Lee. Preliminary assessments of population exposure to glycidyl esters and 3-monochloropropane-1,2-diol esters from miscellaneous oil-containing packaged foods in Taiwan. Food chemistry. 2024 Jan; 430(?):137055. doi: 10.1016/j.foodchem.2023.137055. [PMID: 37536070]
  • Yen Li Yung, Shyam Lakshmanan, Sivakumar Kumaresan, Chi Ming Chu, Heng Jin Tham. Mitigation of 3-monochloropropane 1,2 diol ester and glycidyl ester in refined oil - A review. Food chemistry. 2023 Dec; 429(?):136913. doi: 10.1016/j.foodchem.2023.136913. [PMID: 37506659]
  • Yen Li Yung, Shyam Lakshmanan, Chi Ming Chu, Heng Jin Tham, Sivakumar Kumaresan. Optimization of water washing for mitigation of 3-monochloropropane 1,2 diol ester in palm oil physical refining process. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2023 Dec; 40(12):1541-1550. doi: 10.1080/19440049.2023.2283873. [PMID: 38011619]
  • Wei Jia, Xixuan Wu, Jing Shu, Lin Shi. 3-Monochloropropane-1,2-diol reduced bioaccessibility of sn-2 palmitate via bounding with pancreatic lipase in infant formula during gastrointestinal digestion. Journal of dairy science. 2023 Sep; ?(?):. doi: 10.3168/jds.2023-23730. [PMID: 37690726]
  • Nur Aainaa Syahirah Ramli, Nur Azmina Roslan, Fadzlina Abdullah, Bahriah Bilal, Razmah Ghazali, Raznim Arni Abd Razak, Azmil Haizam Ahmad Tarmizi. Determination of process contaminants 2- and 3-MCPD esters and glycidyl esters in palm-based glycerol by indirect analysis using GC-MS. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2023 Sep; ?(?):1-15. doi: 10.1080/19440049.2023.2255290. [PMID: 37682685]
  • Yen Li Yung, Shyam Lakshmanan, Chi Ming Chu, Sivakumar Kumaresan, Heng Jin Tham. Simultaneous mitigation of 3-monochloropropane 1,2 diol ester and glycidyl ester in edible oils: a review. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2023 Sep; 40(9):1164-1182. doi: 10.1080/19440049.2023.2235608. [PMID: 37549246]
  • Luqiu Peng, Chen Yang, Chengming Wang, Qihui Xie, Yu Gao, Shilin Liu, Guobin Fang, Yang Zhou. Effects of deodorization on the content of polycyclic aromatic hydrocarbons (PAHs), 3-monochloropropane-1,2-diol esters (3-MCPDE) and glycidyl esters (GE) in rapeseed oil using ethanol steam distillation at low temperature. Food chemistry. 2023 Jul; 413(?):135616. doi: 10.1016/j.foodchem.2023.135616. [PMID: 36758391]
  • Liqun Zhang, Pinggu Wu, Xiaoling Xiang, Dajin Yang, Liyuan Wang, Zhengyan Hu. Optimization of Physical Refining Process of Camellia Oil for Reduction of 3-Monochloropropane-1,2-Diol (3-MCPD) Ester Formation Using Response Surface Methodology on a Laboratory Scale. Molecules (Basel, Switzerland). 2023 Apr; 28(8):. doi: 10.3390/molecules28083616. [PMID: 37110851]
  • Jorge Antonio Custodio-Mendoza, Andrea Ramos, Rosa Antonia Lorenzo, Antonia M Carro. Ultrasound-assisted enzymatic indirect determination of total 3-monochloropropane-1,2-diol esters in canned fish oil fraction. Food chemistry. 2023 Mar; 403(?):134423. doi: 10.1016/j.foodchem.2022.134423. [PMID: 36183472]
  • Xin Yi, Xiao Long, Canzhang Liu. Activating autophagy and ferroptosis of 3‑Chloropropane‑1,2‑diol induces injury of human umbilical vein endothelial cells via AMPK/mTOR/ULK1. Molecular medicine reports. 2023 Mar; 27(3):. doi: 10.3892/mmr.2023.12963. [PMID: 36799162]
  • Nik Nur Ashirah Nik Azmi, Thuan-Chew Tan, May Yen Ang, Yin-Hui Leong. Occurrence and risk assessment of 3-monochloropropanediols esters (3-MCPDE), 2-monochloropropanediol esters (2-MCPDE), and glycidyl esters (GE) in commercial infant formula samples from Malaysia. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2023 Feb; 40(2):212-221. doi: 10.1080/19440049.2022.2163054. [PMID: 36602442]
  • Liqun Zhang, Pinggu Wu, Xiaoling Xiang, Huali He, Sha Yu. Risk assessment of 3-monochloropropane-1,2-diol esters through dietary exposure from edible oils for the Zhejiang population in China by Monte Carlo simulation. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2023 Feb; 40(2):202-211. doi: 10.1080/19440049.2022.2155709. [PMID: 36512554]
  • Jorge A Custodio-Mendoza, Raquel Sendón, Ana Rodríguez-Bernaldo de Quirós, Rosa A Lorenzo, Antonia M Carro. Development of a QuEChERS method for simultaneous analysis of 3-Monochloropropane-1,2-diol monoesters and Glycidyl esters in edible oils and margarine by LC-APCI-MS/MS. Analytica chimica acta. 2023 Jan; 1239(?):340712. doi: 10.1016/j.aca.2022.340712. [PMID: 36628717]
  • Jakob F Schneider, Adam Becalski, Tony Zhao, Yihui Liu, Fuqi Chen, Dorothea F K Rawn. Occurrence of glycidyl esters in infant formula products on the Canadian market between 2015 and 2019. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2023 Jan; 40(1):43-55. doi: 10.1080/19440049.2022.2141468. [PMID: 36369749]
  • Quan-Kuo He, Yan-Ping Li, Zhi-Ran Xu, Wen-Bo Wei, Feng-Xin Qiao, Ming-Xin Sun, Yue-Cen Liu, Yan-Zhu Chen, Hai-Long Wang, Zhong-Quan Qi, Yu Liu. 3-MCPD exposure enhances ovarian fibrosis and reduces oocyte quality in mice. Environmental pollution (Barking, Essex : 1987). 2023 Jan; 316(Pt 2):120662. doi: 10.1016/j.envpol.2022.120662. [PMID: 36395906]
  • Kazuaki Yoshinaga, Kaori Yamazaki, Toshiharu Nagai, Seiya Tanaka, Naohiro Gotoh. Stable Isotope Tracer to Reveal the Interconversion between 3-Monochloro-1,2-propanediol Ester and Glycidyl Ester during the Deodorization Process. Journal of agricultural and food chemistry. 2022 Dec; 70(50):15955-15961. doi: 10.1021/acs.jafc.2c06706. [PMID: 36480579]
  • Shuang Guan, Ranran Zhang, Yanan Zhao, Zhuoqun Meng, Jing Lu. 1,3-Dichloro-2-propanol induced ferroptosis through Nrf2/ARE signaling pathway in hepatocytes. Environmental toxicology. 2022 Oct; 37(10):2515-2528. doi: 10.1002/tox.23615. [PMID: 35870111]
  • Sabrina S Andrade, Klícia A Sampaio, Mariana C Costa, Pedro P Corbi, Antonio J A Meirelles, Guilherme J Maximo. Solid-liquid equilibrium of free form of oil contaminants (3-MCPD and glycidol) in lipidic systems. Food research international (Ottawa, Ont.). 2022 10; 160(?):111740. doi: 10.1016/j.foodres.2022.111740. [PMID: 36076422]
  • Atefeh Tavakoli, Mohammad Ali Sahari, Mohsen Barzegar, Hassan Ahmadi Gavlighi, Silvia Marzocchi, Sara Marziali, Maria Caboni. Deodorization of sunflower oil by high voltage electric field as a nonthermal method sunflower oil refining by electric field. Journal of food science. 2022 Oct; 87(10):4363-4378. doi: 10.1111/1750-3841.16312. [PMID: 36102045]
  • Jakob F Schneider, Adam Becalski, Tony Zhao, Fuqi Chen, Yifu Liao, Dorothea F K Rawn. Occurrence of 2- and 3-monochloropropanediol esters (MCPDE) in infant formula products on the Canadian market between 2015 and 2019. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2022 Oct; 39(10):1663-1673. doi: 10.1080/19440049.2022.2104934. [PMID: 35921604]
  • Bernhard H Monien, Klaus Abraham. Levels of 2,3-dihydroxypropyl mercapturic acid (DHPMA) in human urine do not reflect the exposure to 3-chloro-1,2-propanediol (3-MCPD) or glycidol. Environmental research. 2022 08; 211(?):112977. doi: 10.1016/j.envres.2022.112977. [PMID: 35248561]
  • Hao An, Yuxiang Ma, Xuede Wang, Yongzhan Zheng. Effects of Deodorization on the Formation of Processing Contaminants and Chemical Quality of Sunflower Oil. Journal of oleo science. 2022 Jul; 71(7):975-984. doi: 10.5650/jos.ess22050. [PMID: 35691841]
  • Di Chen, Man-Yu Zhang, Xin-Miao Bu, Bin Wang, Xin-Li Xu, Sen Yang, Zhi Sun, Xia Xu. In-syringe cotton fiber-supported liquid extraction coupled with gas chromatography-tandem mass spectrometry for the determination of free 3-mono-chloropropane-1,2-diol in edible oils. Journal of chromatography. A. 2022 Jun; 1673(?):463081. doi: 10.1016/j.chroma.2022.463081. [PMID: 35489242]
  • Sergio B Oey, H J van der Fels-Klerx, Vincenzo Fogliano, Stefan P J van Leeuwen. Chemical refining methods effectively mitigate 2-MCPD esters, 3-MCPD esters, and glycidyl esters formation in refined vegetable oils. Food research international (Ottawa, Ont.). 2022 06; 156(?):111137. doi: 10.1016/j.foodres.2022.111137. [PMID: 35651009]
  • Yujie Zhong, Dianjun Sun, Yanpeng Yao, Qi Liu, Tianmin Guo, Xin Wang, Xiaoli Peng. Autophagy and mitochondrial dynamics contribute to the protective effect of diosgenin against 3-MCPD induced kidney injury. Chemico-biological interactions. 2022 Mar; 355(?):109850. doi: 10.1016/j.cbi.2022.109850. [PMID: 35149085]
  • Pan Gao, Yuling Zheng, Hui Liu, Wei Yang, Chuanrong Hu, Dongping He. Effects of roasting and deodorisation on 3-monochloropropane-1, 2-diol esters, 3, 4-benzopyrene and trans fatty acids in peanut oil. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2022 Mar; 39(3):451-461. doi: 10.1080/19440049.2021.2022772. [PMID: 35061578]
  • Chengni Jin, Fenyi Min, Yujie Zhong, Dianjun Sun, Ruilin Luo, Qi Liu, Xiaoli Peng. Nephrotoxicity evaluation of 3-monochloropropane-1,2-diol exposure in Sprague-Dawley rats using data-independent acquisition-based quantitative proteomics analysis. Toxicology letters. 2022 Mar; 356(?):110-120. doi: 10.1016/j.toxlet.2021.12.008. [PMID: 34915118]
  • Xueting Wang, Jingjing Li, Shan Jiang, Weijian Shen, Yiqian Wang, Qiang Gu. [Simultaneous determination of monochloropropanediol esters and glycidyl esters in vegetable oils by acidic transesterification-gas chromatography-mass spectrometry]. Se pu = Chinese journal of chromatography. 2022 Feb; 40(2):198-205. doi: 10.3724/sp.j.1123.2021.05009. [PMID: 35080167]
  • Wei Jia, Pan Zhuang, Qiao Wang, Xuzhi Wan, Lei Mao, Xinyu Chen, Hong Miao, Dawei Chen, Yiping Ren, Yu Zhang. Urinary non-targeted toxicokinetics and metabolic fingerprinting of exposure to 3-monochloropropane-1,2-diol and glycidol from refined edible oils. Food research international (Ottawa, Ont.). 2022 02; 152(?):110898. doi: 10.1016/j.foodres.2021.110898. [PMID: 35181075]
  • Azmil Haizam Ahmad Tarmizi, Ainie Kuntom. The occurrence of 3-monochloropropane-1,2-diol esters and glycidyl esters in vegetable oils during frying. Critical reviews in food science and nutrition. 2022; 62(12):3403-3419. doi: 10.1080/10408398.2020.1865264. [PMID: 33397128]
  • Jianing Lu, Jing Lu, Xiujuan Bu, Yazhuo Li, Guangcai Ge, Shuang Guan. Ginsenoside Rb1 alleviates liver injury induced by 3-chloro-1,2-propanediol by stimulating autophagic flux. Journal of food science. 2021 Dec; 86(12):5503-5515. doi: 10.1111/1750-3841.15968. [PMID: 34812491]
  • Yong Fan, Jing Lu, Jinhua Liu, Ranran Zhang, Zelin Yu, Shuang Guan. 1,3-dichloro-2-propanol induced hepatic lipid accumulation by inhibiting autophagy via AKT/mTOR/FOXO1 pathway in mice. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2021 Nov; 157(?):112578. doi: 10.1016/j.fct.2021.112578. [PMID: 34560177]
  • Hsuan Chen, Chieh-Hsi Tsao, Yu-Hsuan Chang, Wei-Ju Lee. Occurrence of thermally induced glycidyl esters and 3-monochloropropane-1,2-diol esters in refined oils and pressed oils manufactured by different processes and associated with human health risks in Taiwan. Food chemistry. 2021 Oct; 360(?):130053. doi: 10.1016/j.foodchem.2021.130053. [PMID: 34022517]
  • Mahboob Nemati, Nail Altunay, Mustafa Tuzen, Mir Ali Farajzadeh, Ali Akbar Alizadeh Nabil, Farzaneh Lotfipour, Mohammad Reza Afshar Mogaddam. Air-assisted liquid-liquid microextraction of total 3-monochloropropane-1,2-diol from refined edible oils based on a natural deep eutectic solvent and its determination by gas chromatography-mass spectrometry. Journal of chromatography. A. 2021 Oct; 1656(?):462559. doi: 10.1016/j.chroma.2021.462559. [PMID: 34571280]
  • Yujie Zhong, Chengni Jin, Jiahui Han, Jiachang Zhu, Qi Liu, Dianjun Sun, Xiaodong Xia, Xiaoli Peng. Inhibition of ER stress attenuates kidney injury and apoptosis induced by 3-MCPD via regulating mitochondrial fission/fusion and Ca2+ homeostasis. Cell biology and toxicology. 2021 10; 37(5):795-809. doi: 10.1007/s10565-021-09589-x. [PMID: 33651226]
  • Kohei Matsushita, Shinji Takasu, Yuji Ishii, Takeshi Toyoda, Takanori Yamada, Tomomi Morikawa, Kumiko Ogawa. In vivo mutagenicity and tumor-promoting activity of 1,3-dichloro-2-propanol in the liver and kidneys of gpt delta rats. Archives of toxicology. 2021 09; 95(9):3117-3131. doi: 10.1007/s00204-021-03120-1. [PMID: 34269859]
  • Chengni Jin, Wei Xue, Qi Liu, Jiahui Han, Ruilin Luo, Jiayu Feng, Jiayu Liu, Tianmin Guo, Xiaoli Peng, Tianming Hu. LKB1/AMPKα signaling pathway and mitochondrial fission/fusion dynamics regulate apoptosis induced by 3-chlorpropane-1,2-diol in HEK293 cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2021 Aug; 154(?):112350. doi: 10.1016/j.fct.2021.112350. [PMID: 34139305]
  • Yujie Zhong, Chengni Jin, Jiahui Han, Jiachang Zhu, Qi Liu, Dianjun Sun, Xiaodong Xia, Yu Zhang, Xiaoli Peng. Diosgenin Protects Against Kidney Injury and Mitochondrial Apoptosis Induced by 3-MCPD Through the Regulation of ER Stress, Ca2+ Homeostasis, and Bcl2 Expression. Molecular nutrition & food research. 2021 08; 65(15):e2001202. doi: 10.1002/mnfr.202001202. [PMID: 34075698]
  • Roya Khosrokhavar, Rana Dizaji, Firouzeh Nazari, Ali Sharafi, Javad Tajkey, Mir-Jamal Hosseini. The role of PGC-1α and metabolic signaling pathway in kidney injury following chronic administration with 3-MCPD as a food processing contaminant. Journal of food biochemistry. 2021 06; 45(6):e13744. doi: 10.1111/jfbc.13744. [PMID: 33913518]
  • Jing Lu, Yong Fan, Meitong Liu, Qian Zhang, Shuang Guan. 1,3-dichloro-2-propanol induced lipid accumulation by blocking autophagy flux in HepG2 cells. Toxicology. 2021 04; 454(?):152716. doi: 10.1016/j.tox.2021.152716. [PMID: 33581215]
  • Puyu Yang, Yaqiong Zhang, Yanfang Li, Michael Granvogl, Boyan Gao, Liangli Lucy Yu. Proteomic Analyses of 3-Monochloropropanediol 1-Monooleate and 1-Monostearate Induced Testicular Toxicity in a 90 Day Sprague-Dawley Rats' Study. Journal of agricultural and food chemistry. 2021 Apr; 69(15):4542-4549. doi: 10.1021/acs.jafc.0c07242. [PMID: 33843233]
  • Hsin-Ya Tsai, Jhih-Ning Hsu, Chun-Jen Fang, Nan-Wei Su. Determination of glycidyl esters and 3-MCPD esters in edible oils by sample pretreatment with the combination of lipase hydrolysis and modified QuEChERS for GC-MS analysis. Journal of food and drug analysis. 2021 03; 29(1):153-167. doi: 10.38212/2224-6614.3202. [PMID: 35696223]
  • Pei-Wen Liu, Chung-I Li, Kuo-Ching Huang, Chiang-Shin Liu, Hsiu-Lin Chen, Ching-Chang Lee, Yuan-Yow Chiou, Rong-Jane Chen. 3-MCPD and glycidol coexposure induces systemic toxicity and synergistic nephrotoxicity via NLRP3 inflammasome activation, necroptosis, and autophagic cell death. Journal of hazardous materials. 2021 03; 405(?):124241. doi: 10.1016/j.jhazmat.2020.124241. [PMID: 33187795]
  • Shyam Lakshmanan, Yen Li Yung. Chloride reduction by water washing of crude palm oil to assist in 3-monochloropropane-1, 2 diol ester (3-MCPDE) mitigation. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2021 Mar; 38(3):371-387. doi: 10.1080/19440049.2020.1842516. [PMID: 33596165]
  • Hee-Seok Lee, Jaewook Lee, Seok-Hee Lee, Hyeyeong Seo, Kwang-Geun Lee, Yooheon Park. 3-MCPD (3-monochloro-1,2-propanediol) inhibit myogenic differentiation in murine skeletal myoblasts. Chemico-biological interactions. 2021 Feb; 336(?):109311. doi: 10.1016/j.cbi.2020.109311. [PMID: 33171136]
  • Nick Bergau, Zhiyong Zhao, Klaus Abraham, Bernhard H Monien. Metabolites of 2- and 3-Monochloropropanediol (2- and 3-MCPD) in Humans: Urinary Excretion of 2-Chlorohydracrylic Acid and 3-Chlorolactic Acid after Controlled Exposure to a Single High Dose of Fatty Acid Esters of 2- and 3-MCPD. Molecular nutrition & food research. 2021 02; 65(4):e2000736. doi: 10.1002/mnfr.202000736. [PMID: 33112049]
  • Katharina Schultrich, Fulya Oez, Nick Bergau, Thorsten Buhrke, Albert Braeuning. Absorption and metabolism of 3-MCPD in hepatic and renal cell lines. Toxicology in vitro : an international journal published in association with BIBRA. 2021 Feb; 70(?):105042. doi: 10.1016/j.tiv.2020.105042. [PMID: 33129984]
  • Klaus Abraham, Jan Hielscher, Jan Kuhlmann, Bernhard H Monien. Urinary Excretion of 2/3-Monochloropropanediol (2/3-MCPD) and 2,3-Dihydroxypropylmercapturic Acid (DHPMA) after a Single High dose of Fatty Acid Esters of 2/3-MCPD and Glycidol: A Controlled Exposure Study in Humans. Molecular nutrition & food research. 2021 02; 65(4):e2000735. doi: 10.1002/mnfr.202000735. [PMID: 33079463]
  • Noor Asma Shaari, Azmil Haizam Ahmad Tarmizi, Adi Md Sikin. In-house validation of accelerated solvent extraction-gas chromatography-mass spectrometry for the determination of bound 3- and 2-monochloropropanediols (MCPD) and glycidol in food products. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2021 Feb; 38(2):223-236. doi: 10.1080/19440049.2020.1845400. [PMID: 33332229]
  • Jéssika Karolline Santiago, Willian Cruzeiro Silva, Maisa Freitas Capristo, Marcela Cravo Ferreira, Roseli Aparecida Ferrari, Eduardo Vicente, Antônio José A Meirelles, Adriana Pavesi Arisseto, Klicia Araujo Sampaio. Organic, conventional and sustainable palm oil (RSPO): Formation of 2- and 3-MCPD esters and glycidyl esters and influence of aqueous washing on their reduction. Food research international (Ottawa, Ont.). 2021 02; 140(?):109998. doi: 10.1016/j.foodres.2020.109998. [PMID: 33648232]
  • Xia Cui, Lei Zhang, Pingping Zhou, Zhaoping Liu, Sai Fan, Dajin Yang, Jianwen Li, Qing Liu. Dietary exposure of general Chinese population to fatty acid esters of 3-monochloropropane-1, 2-diol (3-MCPD) from edible oils and oil-containing foods. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2021 Jan; 38(1):60-69. doi: 10.1080/19440049.2020.1834151. [PMID: 33232634]
  • Guangyong Yang, Cangting Guo, Guang Xue, Jinxi Guo. [Determination of 15 3-chloro-1,2-propanediol fatty acid esters in vegetable oils and fritters by ultra performance convergence chromatography-tandem mass spectrometry]. Se pu = Chinese journal of chromatography. 2020 Dec; 38(12):1388-1395. doi: 10.3724/sp.j.1123.2020.03020. [PMID: 34213253]
  • Anna Sadowska-Rociek. Monochloropropanediol esters and glycidyl esters in dietary supplements based on fish oils. Food additives & contaminants. Part B, Surveillance. 2020 Dec; 13(4):305-312. doi: 10.1080/19393210.2020.1803419. [PMID: 32772639]
  • Firouzeh Nazari, Parvaneh Naserzadeh, Rana Dizaji, Hamidreza Kheiri Manjili, Hadis Bahrami, Mina Soleimani, Ali Sharafi, Mir-Jamal Hosseini. Toxicological assessment of 3-monochloropropane-1,2-diol (3-MCPD) as a main contaminant of foodstuff in three different in vitro models: Involvement of oxidative stress and cell death signaling pathway. Journal of food science. 2020 Nov; 85(11):4061-4069. doi: 10.1111/1750-3841.15471. [PMID: 33037666]
  • Chengni Jin, Yujie Zhong, Jiahui Han, Jiachang Zhu, Qi Liu, Dianjun Sun, Xiaodong Xia, Xiaoli Peng. Drp1-mediated mitochondrial fission induced autophagy attenuates cell apoptosis caused by 3-chlorpropane-1,2-diol in HEK293 cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2020 Nov; 145(?):111740. doi: 10.1016/j.fct.2020.111740. [PMID: 32910998]
  • Biow Ing Sim, Yih Phing Khor, Oi Ming Lai, Chee Beng Yeoh, Yong Wang, Yuanfa Liu, Imededdine Arbi Nehdi, Chin Ping Tan. Mitigation of 3-MCPD esters and glycidyl esters during the physical refining process of palm oil by micro and macro laboratory scale refining. Food chemistry. 2020 Oct; 328(?):127147. doi: 10.1016/j.foodchem.2020.127147. [PMID: 32497897]
  • Yu Hua Wong, Kok Ming Goh, Kar Lin Nyam, Ling Zhi Cheong, Yong Wang, Imededdine Arbi Nehdi, Lamjed Mansour, Chin Ping Tan. Monitoring of heat-induced carcinogenic compounds (3-monochloropropane-1,2-diol esters and glycidyl esters) in fries. Scientific reports. 2020 09; 10(1):15110. doi: 10.1038/s41598-020-72118-z. [PMID: 32934328]
  • Guoren Huang, Yanbei Wu, Man Liu, Xiangjun Sun, Weiying Lu, Boyan Gao, Thomas T Y Wang, Liangli Yu. Potential Biomarkers for Early Detection of 3-MCPD Dipalmitate Exposure in Sprague-Dawley Rats. Journal of agricultural and food chemistry. 2020 Sep; 68(35):9594-9602. doi: 10.1021/acs.jafc.0c03474. [PMID: 32786827]
  • Renan Tivanello, Maisa Capristo, Eduardo Vicente, Roseli Ferrari, Klicia Sampaio, Adriana Arisseto. Effects of deodorization temperature and time on the formation of 3-MCPD, 2-MCPD, and glycidyl esters and physicochemical changes of palm oil. Journal of food science. 2020 Jul; 85(7):2255-2260. doi: 10.1111/1750-3841.15304. [PMID: 32579733]
  • Hexiang Zhang, Jiang Chen, Lichun Huang, Lili Chen, Jikai Wang, Xiaojuan Qi, Liang Sun, Ningbo Liao, Ronghua Zhang. Occurrence and risk assessment of 3- and 2-monochloropropanediol (MCPD) esters in vegetable oils and related products from Zhejiang market. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2020 Jun; 37(6):931-937. doi: 10.1080/19440049.2020.1745298. [PMID: 32240043]
  • Miriam E Mossoba, Mapa S T Mapa, Magali Araujo, Yang Zhao, Brenna Flannery, Thomas Flynn, Jessica Sprando, Paddy Wiesenfeld, Robert L Sprando. In vitro toxicological assessment of free 3-MCPD and select 3-MCPD esters on human proximal tubule HK-2 cells. Cell biology and toxicology. 2020 06; 36(3):209-221. doi: 10.1007/s10565-019-09498-0. [PMID: 31686351]
  • Puyu Yang, Jinyu Hu, Junchen Liu, Yaqiong Zhang, Boyan Gao, Thomas T Y Wang, Lianzhou Jiang, Michael Granvogl, Liangli Lucy Yu. Ninety-Day Nephrotoxicity Evaluation of 3-MCPD 1-Monooleate and 1-Monostearate Exposures in Male Sprague Dawley Rats Using Proteomic Analysis. Journal of agricultural and food chemistry. 2020 Mar; 68(9):2765-2772. doi: 10.1021/acs.jafc.0c00281. [PMID: 32045244]
  • Minwei Xu, Zhao Jin, Zhongyu Yang, Jiajia Rao, Bingcan Chen. Optimization and validation of in-situ derivatization and headspace solid-phase microextraction for gas chromatography-mass spectrometry analysis of 3-MCPD esters, 2-MCPD esters and glycidyl esters in edible oils via central composite design. Food chemistry. 2020 Mar; 307(?):125542. doi: 10.1016/j.foodchem.2019.125542. [PMID: 31639573]
  • Katharina Schultrich, Colin J Henderson, Albert Braeuning, Thorsten Buhrke. Correlation between 3-MCPD-induced organ toxicity and oxidative stress response in male mice. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2020 Feb; 136(?):110957. doi: 10.1016/j.fct.2019.110957. [PMID: 31712104]
  • M A Makarenko, A D Malinkin, V V Bessonov, D O Bokov. [Alkaline transesterification CG-MS/MS method of monochlorpropanediol and glycidyl esters' determination in some edible fats, oils and fat blends on Russian market]. Voprosy pitaniia. 2020 ; 89(6):113-122. doi: 10.24411/0042-8833-2020-10084. [PMID: 33476504]
  • Miriam E Mossoba, Mapa S T Mapa, Magali Araujo, Yang Zhao, Brenna Flannery, Thomas Flynn, Jessica Sprando, Paddy Wiesenfeld, Robert L Sprando. Long-term in vitro effects of exposing the human HK-2 proximal tubule cell line to 3-monochloropropane-1,2-diol. The Journal of toxicological sciences. 2020; 45(1):45-56. doi: 10.2131/jts.45.45. [PMID: 31932557]
  • Wei Jia, Di Wu, Xinyu Chen, Lei Mao, Hong Miao, Dawei Chen, Yiping Ren, Yu Zhang. Metabolomics-based biomarker analysis of dihydroxypropyl mercapturic acid isomers from 3-monochloropropane-1,2-diol and glycidol for evaluation of toxicokinetics in rats and daily internal exposure in humans. Talanta. 2019 Nov; 204(?):329-336. doi: 10.1016/j.talanta.2019.06.009. [PMID: 31357301]
  • Adriana Pavesi Arisseto, Willian Cruzeiro Silva, Priscila Francisca Corrêa Marcolino, Gabriela Ramiro Scaranelo, Shirley Aparecida Garcia Berbari, Ana Maria Rauen de Oliveira Miguel, Eduardo Vicente. Influence of potato cultivar, frying oil and sample pre-treatments on the contamination of French fries by 3-monochloropropane-1,2-diol fatty acid esters. Food research international (Ottawa, Ont.). 2019 10; 124(?):43-48. doi: 10.1016/j.foodres.2018.10.070. [PMID: 31466649]
  • T O Ajiboye, R A Ajala-Lawal, A B Adeyiga. Caffeic acid abrogates 1,3-dichloro-2-propanol-induced hepatotoxicity by upregulating nuclear erythroid-related factor 2 and downregulating nuclear factor-kappa B. Human & experimental toxicology. 2019 Sep; 38(9):1092-1101. doi: 10.1177/0960327119851257. [PMID: 31142131]
  • Anna Sadowska-Rociek, Ewa Cieślik. Carbohydrate-Based Fat Mimetics Can Affect the Levels of 3-Monochloropropane-1,2-Diol Esters and Glycidyl Esters in Shortbread Biscuits. Plant foods for human nutrition (Dordrecht, Netherlands). 2019 Jun; 74(2):216-222. doi: 10.1007/s11130-019-00723-z. [PMID: 30838503]
  • Kornél Nagy, Karine Redeuil, Sabine Lahrichi, Marine Nicolas. Removal of organochlorines from vegetable oils and its benefits in preventing formation of monochloropropanediol diesters. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2019 May; 36(5):712-721. doi: 10.1080/19440049.2019.1588999. [PMID: 30945995]
  • Rong Guo, Wei Wang, Min Li, Guoxia Cheng, Cunwei Liu, Li Tian, Caixia Wang, Xiaocong Liang. [Contamination and dietary exposure assessment of fatty acid esters of chloropropanediols in vegetable oil and fat-rich food in Shaanxi Province]. Wei sheng yan jiu = Journal of hygiene research. 2019 May; 48(3):493-503. doi: ". [PMID: 31133141]
  • Ruijie Liu, Min Cheng, Kumar S D Kothapalli, Zhen Wang, Elizabeth Mendralla, Hui Gyu Park, Robert C Block, Xingguo Wang, J Thomas Brenna. Glycerol derived process contaminants in refined coconut oil induce cholesterol synthesis in HepG2 cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2019 May; 127(?):135-142. doi: 10.1016/j.fct.2019.03.005. [PMID: 30878531]
  • Y I Mahmoud, F S Abo-Zied, S T Salem. Effects of subacute 3-monochloropropane-1,2-diol treatment on the kidney of male albino rats. Biotechnic & histochemistry : official publication of the Biological Stain Commission. 2019 Apr; 94(3):199-203. doi: 10.1080/10520295.2018.1543894. [PMID: 30449186]
  • Yunping Yao, Ruizhi Cao, Wentao Liu, Hang Zhou, Changmo Li, Shuo Wang. Molecular Reaction Mechanism for the Formation of 3-Chloropropanediol Esters in Oils and Fats. Journal of agricultural and food chemistry. 2019 Mar; 67(9):2700-2708. doi: 10.1021/acs.jafc.8b06632. [PMID: 30722664]
  • Han-Zhu Xing, Bing Fang, Guo-Fang Pang, Fa-Zheng Ren. 3-Monochloropropane-1, 2-diol causes irreversible damage to reproductive ability independent of hormone changes in adult male rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2019 Feb; 124(?):10-16. doi: 10.1016/j.fct.2018.11.023. [PMID: 30453003]
  • J A Custodio-Mendoza, A M Carro, M A Lage-Yusty, A Herrero, I M Valente, J A Rodrigues, R A Lorenzo. Occurrence and exposure of 3-monochloropropanediol diesters in edible oils and oil-based foodstuffs from the Spanish market. Food chemistry. 2019 Jan; 270(?):214-222. doi: 10.1016/j.foodchem.2018.07.100. [PMID: 30174037]
  • Yujie Zhong, Chengni Jin, Xiaorui Wang, Xuan Li, Jiahui Han, Wei Xue, Peng Wu, Xiaoli Peng, Xiaodong Xia. Protective effects of apigenin against 3-MCPD-induced renal injury in rat. Chemico-biological interactions. 2018 Dec; 296(?):9-17. doi: 10.1016/j.cbi.2018.08.005. [PMID: 30107153]
  • Xinwei Jiang, Cuijuan Zhu, Xusheng Li, Jianxia Sun, Lingmin Tian, Weibin Bai. Cyanidin-3- O-glucoside at Low Doses Protected against 3-Chloro-1,2-propanediol Induced Testis Injury and Improved Spermatogenesis in Male Rats. Journal of agricultural and food chemistry. 2018 Dec; 66(48):12675-12684. doi: 10.1021/acs.jafc.8b04229. [PMID: 30376326]
  • Guoren Huang, Boyan Gao, Jinli Xue, Zhihong Cheng, Xiangjun Sun, Yaqiong Zhang, Liangli Lucy Yu. Toxicokinetics and Metabolism of 3-Monochloropropane 1,2-Diol Dipalmitate in Sprague Dawley Rats. Journal of agricultural and food chemistry. 2018 Nov; 66(44):11672-11680. doi: 10.1021/acs.jafc.8b05422. [PMID: 30303014]
  • Jing Lu, Baochen Fang, Yixuan Huang, Siyu Tao, Bo Sun, Shuang Guan, Yingli Jin. Epigallocatechin-3-gallate protects against 1,3-dichloro-2-propanol-induced lipid accumulation in C57BL/6J mice. Life sciences. 2018 Sep; 209(?):324-331. doi: 10.1016/j.lfs.2018.08.007. [PMID: 30092300]
  • Xiuzhen Qiu, Xian-Yan Xu, Yong Liang, Huishi Guo. The molecularly imprinted polymer supported by anodic alumina oxide nanotubes membrane for efficient recognition of chloropropanols in vegetable oils. Food chemistry. 2018 Aug; 258(?):295-300. doi: 10.1016/j.foodchem.2018.03.071. [PMID: 29655736]
  • Guoren Huang, Jinli Xue, Xiangjun Sun, Jing Wang, Liangli Lucy Yu. Necroptosis in 3-chloro-1, 2-propanediol (3-MCPD)-dipalmitate-induced acute kidney injury in vivo and its repression by miR-223-3p. Toxicology. 2018 08; 406-407(?):33-43. doi: 10.1016/j.tox.2018.05.015. [PMID: 29860048]
  • Jing Yan, Sergio B Oey, Stefan P J van Leeuwen, Saskia M van Ruth. Discrimination of processing grades of olive oil and other vegetable oils by monochloropropanediol esters and glycidyl esters. Food chemistry. 2018 May; 248(?):93-100. doi: 10.1016/j.foodchem.2017.12.025. [PMID: 29329876]
  • J A Custodio-Mendoza, R A Lorenzo, I M Valente, P J Almeida, M A Lage, J A Rodrigues, A M Carro. Development of a partitioned liquid-liquid extraction- dispersive solid phase extraction procedure followed by liquid chromatography-tandem mass spectrometry for analysis of 3-monochloropropane-1,2-diol diesters in edible oils. Journal of chromatography. A. 2018 May; 1548(?):19-26. doi: 10.1016/j.chroma.2018.03.017. [PMID: 29555360]
  • Jing Lu, Bijun Cheng, Zhuoqun Meng, Baochen Fang, Tianjiao Li, Maocheng Sun, Meitong Liu, Shuang Guan. Alliin attenuates 1, 3-dichloro-2-propanol-induced lipogenesis in HepG2 cells through activation of the AMP-activated protein kinase-dependent pathway. Life sciences. 2018 Feb; 195(?):19-24. doi: 10.1016/j.lfs.2017.12.040. [PMID: 29305303]
  • Soon Huat Tiong, Norliza Saparin, Huey Fang Teh, Theresa Lee Mei Ng, Mohd Zairey Bin Md Zain, Bee Keat Neoh, Ahmadilfitri Md Noor, Chin Ping Tan, Oi Ming Lai, David Ross Appleton. Natural Organochlorines as Precursors of 3-Monochloropropanediol Esters in Vegetable Oils. Journal of agricultural and food chemistry. 2018 Jan; 66(4):999-1007. doi: 10.1021/acs.jafc.7b04995. [PMID: 29260544]
  • Thorsten Buhrke, Linn Voss, Anja Briese, Heike Stephanowitz, Eberhard Krause, Albert Braeuning, Alfonso Lampen. Oxidative inactivation of the endogenous antioxidant protein DJ-1 by the food contaminants 3-MCPD and 2-MCPD. Archives of toxicology. 2018 Jan; 92(1):289-299. doi: 10.1007/s00204-017-2027-5. [PMID: 28707023]
  • Y I Mahmoud, A Taha, S Soliman. 3-Monochloropropane-1,2-diol (alpha-chlorohydrin) disrupts spermatogenesis and causes spermatotoxicity in males of the Egyptian fruit-bat (Rousettus aegyptiacus). Biotechnic & histochemistry : official publication of the Biological Stain Commission. 2018; 93(4):293-300. doi: 10.1080/10520295.2018.1437471. [PMID: 29595063]
  • Ivonne M C M Rietjens, P Dussort, Helmut Günther, Paul Hanlon, Hiroshi Honda, Angela Mally, Sue O'Hagan, Gabriele Scholz, Albrecht Seidel, James Swenberg, Justin Teeguarden, Gerhard Eisenbrand. Exposure assessment of process-related contaminants in food by biomarker monitoring. Archives of toxicology. 2018 Jan; 92(1):15-40. doi: 10.1007/s00204-017-2143-2. [PMID: 29302712]
  • Giulia Graziani, Anna Gaspari, Donato Chianese, Lanfranco Conte, Alberto Ritieni. Direct determination of 3-chloropropanol esters in edible vegetable oils using high resolution mass spectrometry (HRMS-Orbitrap). Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2017 Nov; 34(11):1893-1903. doi: 10.1080/19440049.2017.1368721. [PMID: 28820048]
  • Mine Senyildiz, Buket Alpertunga, Sibel Ozden. DNA methylation analysis in rat kidney epithelial cells exposed to 3-MCPD and glycidol. Drug and chemical toxicology. 2017 Oct; 40(4):432-439. doi: 10.1080/01480545.2016.1255951. [PMID: 27884059]
  • Jing Lu, Baochen Fang, Yiying Zheng, Xin Yu, Guoren Huang, Zhenning Wang, Xuming Deng, Shuang Guan. 1,3-dichloro-2-propanol induced lipid accumulation in HepG2 cells through cAMP/protein kinase A and AMP-activated protein kinase pathways via Gi/o-coupled receptors. Environmental toxicology and pharmacology. 2017 Oct; 55(?):118-126. doi: 10.1016/j.etap.2017.07.013. [PMID: 28843851]
  • Axel Oberemm, Monique Braun, Stefanie Sawada, Mario Pink, Falko Frenzel, Christel Rozycki, Christine Meckert, Elke Zabinsky, Albert Braeuning, Alfonso Lampen. Lanthanum chloride precipitation-based toxicoproteomic analysis of 3-monochloropropane-1,2-diol toxicity in rat kidney reveals involvement of extracellular signal-regulated kinase 2. Archives of toxicology. 2017 Oct; 91(10):3247-3260. doi: 10.1007/s00204-017-1959-0. [PMID: 28393304]
  • Katharina Schultrich, Falko Frenzel, Axel Oberemm, Thorsten Buhrke, Albert Braeuning, Alfonso Lampen. Comparative proteomic analysis of 2-MCPD- and 3-MCPD-induced heart toxicity in the rat. Archives of toxicology. 2017 Sep; 91(9):3145-3155. doi: 10.1007/s00204-016-1927-0. [PMID: 28133701]
  • Thorsten Buhrke, Katharina Schultrich, Albert Braeuning, Alfonso Lampen. Comparative analysis of transcriptomic responses to repeated-dose exposure to 2-MCPD and 3-MCPD in rat kidney, liver and testis. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2017 Aug; 106(Pt A):36-46. doi: 10.1016/j.fct.2017.05.028. [PMID: 28522335]
  • Renata Jędrkiewicz, Agnieszka Głowacz-Różyńska, Justyna Gromadzka, Piotr Konieczka, Jacek Namieśnik. Novel fast analytical method for indirect determination of MCPD fatty acid esters in edible oils and fats based on simultaneous extraction and derivatization. Analytical and bioanalytical chemistry. 2017 Jul; 409(17):4267-4278. doi: 10.1007/s00216-017-0381-z. [PMID: 28484809]
  • Boyan Gao, Man Liu, Guoren Huang, Zhongfei Zhang, Yue Zhao, Thomas T Y Wang, Yaqiong Zhang, Jie Liu, Liangli Yu. Absorption, Distribution, Metabolism and Excretion of 3-MCPD 1-Monopalmitate after Oral Administration in Rats. Journal of agricultural and food chemistry. 2017 Mar; 65(12):2609-2614. doi: 10.1021/acs.jafc.7b00639. [PMID: 28276235]