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{{chembox {{chembox
| Verifiedfields = changed | Watchedfields = changed
| verifiedrevid = 407469120 | verifiedrevid = 429387478
| Reference=<ref> at chemicalland21.com</ref> | Reference =<ref> at chemicalland21.com</ref><ref name=PGCH/>
| ImageFile = dmp.png | ImageFile = Dimethyl phthalate V.1.svg
| ImageSize = 120px | ImageSize = 220px
| ImageFile2 = Dimethyl phthalate 3D BS.png
| IUPACName = dimethyl benzene-1,2-dicarboxylate
| OtherNames = | ImageSize2 = 220px
| PIN = Dimethyl benzene-1,2-dicarboxylate
| Section1 = {{Chembox Identifiers
| OtherNames = Dimethyl phthalate
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 131-11-3
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13837329 | ChemSpiderID = 13837329
| ChEBI = 4609
| DrugBank = DB13336
| EC_number = 205-011-6
| PubChem = 8554
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 08X7F5UDJM | UNII = 08X7F5UDJM
| UNNumber = 3082
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C11233 | KEGG = C11233
| InChI = 1/C10H10O4/c1-13-9(11)7-5-3-4-6-8(7)10(12)14-2/h3-6H,1-2H3 | InChI = 1/C10H10O4/c1-13-9(11)7-5-3-4-6-8(7)10(12)14-2/h3-6H,1-2H3
Line 22: Line 31:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NIQCNGHVCWTJSM-UHFFFAOYSA-N | StdInChIKey = NIQCNGHVCWTJSM-UHFFFAOYSA-N
| SMILES = O=C(OC)c1ccccc1C(=O)OC
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 131-11-3
| PubChem = 8554
| SMILES = O=C(OC)c1ccccc1C(=O)OC
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>10</sub>H<sub>10</sub>O<sub>4</sub> | Formula = C<sub>10</sub>H<sub>10</sub>O<sub>4</sub>
| MolarMass = 194.184 g/mol | MolarMass = 194.184 g/mol
| Appearance = Clear oily liquid | Appearance = Colorless oily liquid
| Odor = slight aromatic odor<ref name=PGCH/>
| Density = 1.19 g/cm<sup>3</sup>
| Density = 1.19 g/cm<sup>3</sup>
| MeltingPtC = 2
| MeltingPtC = 2
| BoilingPt = 283 - 284 °C
| BoilingPtC = 283 to 284
| Solubility = Slightly soluble
| BoilingPt_notes =
| Solubility = 0.4% (20°C)<ref name=PGCH/>
| VaporPressure = 0.01 mmHg (20°C)<ref name=PGCH/>
}} }}
| Section3 = {{Chembox Hazards |Section6={{Chembox Pharmacology
| MainHazards = | ATCCode_prefix = P03
| ATCCode_suffix = BX02
| FlashPt = 146 °C
| ATC_Supplemental = {{ATCvet|P53|GX02}}
| Autoignition = 460 °C
}}
| LD50 = 6800 mg/kg (oral, rat)
|Section7={{Chembox Hazards
| MainHazards =
| FlashPtC = 146
| AutoignitionPtC = 460
| LD50 = 6900 mg/kg (rat, oral)<br/>1000 mg/kg (rabbit, oral)<br/>2400 mg/kg (guinea pig, oral)<br/>6800 mg/kg (rat, oral)<br/>6800 mg/kg (mouse, oral)<br/>4400 mg/kg (rabbit, oral)<br/>2400 mg/kg (guinea pig, oral)<ref name=IDLH/>
| PEL = TWA 5 mg/m<sup>3</sup><ref name=PGCH>{{PGCH|0228}}</ref>
| ExploLimits = 0.9%-?<ref name=PGCH/>
| IDLH = 2000 mg/m<sup>3</sup><ref name=PGCH/>
| REL = TWA 5 mg/m<sup>3</sup><ref name=PGCH/>
| LCLo = 9630 mg/m<sup>3</sup><ref name=IDLH>{{IDLH|131113|Dimethylphthalate}}</ref>
| NFPA-H = 1
| NFPA-F = 1
| NFPA-I = 0
}} }}
}} }}


'''Dimethyl phthalate''' ('''DMP''') is an ] and ]. it is a colourless and oily liquid that is soluble in organic solvents,<ref name=":0">{{Cite report | vauthors = Carlson KR, Patton LE |title= Toxicity Review for Dimethyl Phthalate (DMP, CASRN 131-11-3) |url=https://www.cpsc.gov/s3fs-public/ToxicityReviewOfDMP.pdf | publisher = U.S Consumer Product Safety Commission}}</ref> but which is only poorly soluble in water (~4 g/L).
'''Dimethyl phthalate''' is a ] with molecular formula (CH<sub>3</sub>)<sub>2</sub>(C<sub>6</sub>H<sub>4</sub>(COO)<sub>2</sub>). It is the ] ] of ].


It is used in a variety of products and is most commonly used as ] such as ] for mosquitoes and flies for animal livestock.<ref name=":0" /> The short-chain or low molecular weight phthalate is also frequently used in consumer products such as cosmetics, ink, soap, household cleaning supplies, etc.<ref name=":2">{{cite journal | vauthors = Schettler T | title = Human exposure to phthalates via consumer products | journal = International Journal of Andrology | volume = 29 | issue = 1 | pages = 134–139; discussion 181–185 | date = February 2006 | pmid = 16466533 | doi = 10.1111/j.1365-2605.2005.00567.x | doi-access = free }}</ref> Other uses of DMP include solid rocket propellants (as a stabilizer) and plastics.<ref name=":0" /><ref name=":2" />
Dimethyl phthalate is an ] and has many other uses, including in solid rocket propellants, plastics, and insect repellants.


The ] has classified Dimethyl phthalate as not classifiable for human ]icity.<ref name=":3">{{Cite journal | vauthors = Phillips L |date= June 2015 |title=EPA's Exposure Assessment Toolbox (EPA-Expo-Box) |journal=Journal of Environmental Informatics |volume=25 |issue=2 |pages=81–84 |doi=10.3808/jei.201400269 |s2cid= 113872276 |issn=1726-2135|doi-access=free }}</ref><ref name=":4">{{Cite journal | vauthors = Newburg-Rinn SD |date= November 1982 |title=Commentary: Activities of the Environmental Protection Agency concerning Phthalate Esters |journal=Environmental Health Perspectives |volume=45 |pages=137–139 |doi=10.2307/3429398 |jstor= 3429398 |issn=0091-6765|doi-access=free |pmid= 7140687 |pmc=1568984 }}</ref> Its oral ] is 4390 to 8200&nbsp;mg/kg bw/d in rats and the dermal LD50 is 38000&nbsp;mg/kg bw in rats and more than 4800&nbsp;mg/kg bw in guinea pigs.<ref>{{Cite journal | author1 = National Industrial Chemicals Notification and Assessment Scheme (NICNAS) | author2 = Australia Government |date=June 2008 |title=Dimethyl Phthalate |url=https://www.industrialchemicals.gov.au/sites/default/files/Dimethyl%20phthalate%20DMP.pdf |journal=Existing Chemical Hazard Assessment Report}}</ref>
==References==
{{reflist}}


== Synthesis ==
Dimethyl phthalate is manufactured commercially via the ] of ] with ]. The reaction can be ] by a strong acid, such as ]; various ]s may be used as an alterative, including ] of titanium, zirconium or tin. Excess methanol is used to ensure complete conversion, with the remainder removed by distillation at the end.<ref name=":0" /><ref>{{Cite patent| country = US | number = 5534652 |title=Preparation of plasticizer esters from phthalic anhydride residue|gdate=1996-07-09|inventor= Jones L, Daniels PH, Krauskopf LG, Rigopoulos KR |url= https://patents.google.com/patent/US5534652A/en }}</ref>


]
{{ester-stub}}
{{pharmacology-stub}}


== Applications ==
]
Unlike most other phthalate esters, dimethyl phthalate is rarely used as a ] for ]. It is considered too volatile and causes excessive fuming during PVC processing.<ref>{{cite book |last1=Verlag |first1=Carl Hanser |title=Plastics additives handbook |date=2009 |location=Munich |isbn=978-3-446-40801-2 |page=490 |edition=6.}}</ref> It is a good plasticizer for cellulose-esters, including ], ] and cellulose propionate compositions. Historically, this led to it being present in ] and some ] but it is not commonly used today.<ref>{{cite journal |last1=Young |first1=AS |last2=Allen |first2=JG |last3=Kim |first3=UJ |last4=Seller |first4=S |last5=Webster |first5=TF |last6=Kannan |first6=K |last7=Ceballos |first7=DM |title=Phthalate and Organophosphate Plasticizers in Nail Polish: Evaluation of Labels and Ingredients. |journal=Environmental Science & Technology |date=6 November 2018 |volume=52 |issue=21 |pages=12841–12850 |doi=10.1021/acs.est.8b04495 |pmid=30302996|pmc=6222550 |bibcode=2018EnST...5212841Y }}</ref> It is used as a plasticizer for ], which is used to make ]s for medicines.<ref>{{Cite web |date=September 2001 |title=Committee for veterinary medicinal products: Dimethyl and Diethyl phthalates summary report |url=https://www.ema.europa.eu/en/documents/mrl-report/dimethyl-diethyl-phthalates-summary-report-committee-veterinary-medicinal-products_en.pdf |access-date=March 15, 2022 |website=ema.europa.eu}}</ref> Other cosmetic uses include as a fixative for perfumes, although it is not as commonly used as ].<ref>{{cite journal |last1=Al-Saleh |first1=Iman |last2=Elkhatib |first2=Rola |title=Screening of phthalate esters in 47 branded perfumes |journal=Environmental Science and Pollution Research |date=January 2016 |volume=23 |issue=1 |pages=455–468 |doi=10.1007/s11356-015-5267-z|pmid=26310707 |bibcode=2016ESPR...23..455A |s2cid=22840018 }}</ref> Dimethyl phthalate is able to dissolve ] which made it historically important in some automotive coatings and vanishes.
]


=== Insect repellent ===
]
DMP can be used as an ] and is especially useful against ] responsible for ].<ref>{{Cite journal |last1=Brown |first1=Margaret |last2=Hebert |first2=Adelaide A. |date=1997-02-01 |title=Insect repellents: An overview |url=https://www.sciencedirect.com/science/article/pii/S0190962297702895 |journal=Journal of the American Academy of Dermatology |language=en |volume=36 |issue=2 |pages=243–249 |doi=10.1016/S0190-9622(97)70289-5 |pmid=9039177 |issn=0190-9622}}</ref> DMP has been shown to deter species of mosquitoes such as ''], ] and ]''.<ref name=":6">{{cite journal | vauthors = Karunamoorthi K, Sabesan S | title = Laboratory evaluation of dimethyl phthalate treated wristbands against three predominant mosquito (Diptera: Culicidae) vectors of disease | journal = European Review for Medical and Pharmacological Sciences | volume = 14 | issue = 5 | pages = 443–448 | date = May 2010 | pmid = 20556923 }}</ref><ref name=":7">{{Cite journal |last1=Nathan |first1=Sengottayan Senthil |last2=Kalaivani |first2=Kandaswamy |last3=Murugan |first3=Kadarkarai |date=October 2005 |title=Effects of neem limonoids on the malaria vector Anopheles stephensi Liston (Diptera: Culicidae) |url=http://dx.doi.org/10.1016/j.actatropica.2005.07.002 |journal=Acta Tropica |volume=96 |issue=1 |pages=47–55 |doi=10.1016/j.actatropica.2005.07.002 |pmid=16112073 |issn=0001-706X}}</ref><ref>{{Cite journal |last1=Kalyanasundaram |first1=Muthuswami |last2=Mathew |first2=Nisha |date=2006-05-01 |title=N,N-Diethyl Phenylacetamide (DEPA): A Safe and Effective Repellent for Personal Protection Against Hematophagous Arthropods |url=http://openurl.ingenta.com/content/xref?genre=article&issn=0022-2585&volume=43&issue=3&spage=518 |journal=Journal of Medical Entomology |language=en |volume=43 |issue=3 |pages=518–525 |doi=10.1603/0022-2585(2006)432.0.CO;2 |pmid=16739410 |s2cid=22623121 }}{{Dead link|date=April 2023 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>
]

]
== Metabolism/Biotransformation ==
DMP administered orally in rats largely undergoes phase I ] to monomethyl phthalate (MMP) via hydrolysis in the liver and intestinal mucosa. MMP may also be further hydrolysed to ].<ref>{{cite journal | doi=10.3389/fpubh.2020.00366 | doi-access=free | title=The Endocrine Disruption of Prenatal Phthalate Exposure in Mother and Offspring | year=2020 | last1=Qian | first1=Yiyu | last2=Shao | first2=Hailing | last3=Ying | first3=Xinxin | last4=Huang | first4=Wenle | last5=Hua | first5=Ying | journal=Frontiers in Public Health | volume=8 | page=366 | pmid=32984231 | pmc=7483495 }}</ref> However, low molecular weight phthalates such as MMP are primarily excreted as monoesters and do not undergo phase II biotransformation processes such as ] and ] unlike the well-known banned molecule DEHP.<ref>{{Cite journal |last1=Hauser |first1=R. |last2=Calafat |first2=A. M. |date=2005-11-01 |title=Phthalates and Human Health |journal=Occupational and Environmental Medicine |language=en |volume=62 |issue=11 |pages=806–818 |doi=10.1136/oem.2004.017590 |issn=1351-0711 |pmid=16234408|pmc=1740925 }}</ref>

== Human safety ==
Acute exposure to DMP via inhalation in humans and animals have shown to result in ] to the eyes, nose and throat.<ref>{{cite journal | vauthors = Fonger GC, Hakkinen P, Jordan S, Publicker S | title = The National Library of Medicine's (NLM) Hazardous Substances Data Bank (HSDB): background, recent enhancements and future plans | journal = Toxicology | volume = 325 | pages = 209–216 | date = November 2014 | pmid = 25223694 | doi = 10.1016/j.tox.2014.09.003 | pmc = 4195797 | bibcode = 2014Toxgy.325..209F }}</ref> Although some research has shown the association between the susceptibility of the reproductive system and phthalates esters, most phthalates demonstrate low acute toxicity.<ref name=":0" /><ref name=":5">{{Cite book | author = National Research Council (US) Committee on the Health Risks of Phthalates |url=https://www.ncbi.nlm.nih.gov/books/NBK215030/ |title=Toxicity Assessment |date=2008 |publisher=National Academies Press (US) |language=en | isbn = 978-0-309-12841-4 }}</ref>

The chronic (long term) effects, reproductive effects, and ]icity of DMP on humans and animals have yet to be fully established as compared to some other ].<ref name=":3" /><ref name=":4" /><ref>{{Cite journal |last1=Gray |first1=L. E. |last2=Ostby |first2=J. |last3=Furr |first3=J. |last4=Price |first4=M. |last5=Veeramachaneni |first5=D. N. |last6=Parks |first6=L. |date=December 2000 |title=Perinatal exposure to the phthalates DEHP, BBP, and DINP, but not DEP, DMP, or DOTP, alters sexual differentiation of the male rat |url=https://pubmed.ncbi.nlm.nih.gov/11099647/ |journal=Toxicological Sciences|volume=58 |issue=2 |pages=350–365 |doi=10.1093/toxsci/58.2.350 |issn=1096-6080 |pmid=11099647}}</ref> This is due to insufficient animal evidence and inadequate lifetime-exposure carcinogenicity studies available. However, DMP does appear to have less potential towards inducing health hazards than other phthalates, such as DEHP and BBP.<ref name=":0" /><ref name=":5" />

== Animal toxicity ==
Studies have shown that DMP is readily absorbed in the gastrointestinal tract of rats. After an orally administered dose of 0.1mL of DMP, about 77% of monomethyl phthalate and 8% of DMP have been detected in urine collected for 24 hours from male rats. Acute oral toxicity results in an LD50 of 8,2, 5,2, 2,9, 10,1 and 8,6&nbsp;mg/kg for rats, rabbits, guinea pigs, chicks, and mice respectively. Another study on Sprague-Dawley albino rats resulted in a lower LD50 of 4,39&nbsp;mg/kg in females and 5,12&nbsp;mg/kg in males. Treatment was applied and for dead subjects, necropsy revealed toxic effects in the lungs, stomach and intestines of rats. Based on this animal data, DMP does not fit the definition of <nowiki>''</nowiki>acute toxic<nowiki>''</nowiki> under FHSA via oral exposure.<ref>{{Cite web |last=R. Carlson E. Patton |first=Kent Leslie |date=October 30, 2010 |title=Toxicity Review of Dimethyl phthalate |url=https://www.cpsc.gov/s3fs-public/ToxicityReviewOfDMP.pdf |url-status=live |access-date=March 17, 2022 |website=United states consumer product safety commission|archive-url=https://web.archive.org/web/20170131194030/https://www.cpsc.gov/s3fs-public/ToxicityReviewOfDMP.pdf |archive-date=2017-01-31 }}</ref>

=== Hematoxicity ===
At high doses (1000&nbsp;mg/kg), DMP may cause ]s (RBCs) to lose their oxygen-carrying function. In both in vitro and in vivo rat studies, DMP-incubated red blood cells released iron. Iron is the site of oxygen binding for ], without it, hemoglobin is unable to bind to oxygen and transport it to the rest of the body. Release of iron from RBCs was not found in RBCs not incubated with DMP, nor at low and medium doses of DMP. One mechanism of iron release is the ]-induced on RBCs by DMP.<ref>{{Cite journal |last1=Chi |first1=Zhenxing |last2=Liu |first2=Jia |last3=Tan |first3=Songwen |last4=Lin |first4=Hongwei |last5=Wu |first5=Weilin |last6=Li |first6=Weiguo |date=2021-01-01 |title=Revealing the toxicity of dimethyl phthalate (DMP) to the oxygen-carrying function of red blood cells (RBCs): The iron release mechanism |url=https://www.sciencedirect.com/science/article/pii/S0045653520322128 |journal=Chemosphere |language=en |volume=263 |pages=128017 |doi=10.1016/j.chemosphere.2020.128017 |pmid=32841881 |bibcode=2021Chmsp.26328017C |s2cid=221325980 |issn=0045-6535}}</ref>

A separate study found that the ] induced by DMP also decreased the immune functions of erythrocytes. The ] damages the structure and function of erythrocytes, in particular RBC-complement 3b (C3b) receptors.<ref>{{Cite journal |last1=Li |first1=Shixuan |last2=Chi |first2=Zhenxing |last3=Li |first3=Weiguo |date=2019-10-01 |title=Invitro toxicity of dimethyl phthalate to human erythrocytes: From the aspects of antioxidant and immune functions |url=https://www.sciencedirect.com/science/article/pii/S026974911932233X |journal=Environmental Pollution |language=en |volume=253 |pages=239–245 |doi=10.1016/j.envpol.2019.07.014 |pmid=31319240 |bibcode=2019EPoll.253..239L |s2cid=197664449 |issn=0269-7491}}</ref>

=== Hepatotoxicity ===
Animal studies on oral exposure of DMP in rats have established ] effects including increased liver weight, elevated ] activity and reduced ] and lipid levels.<ref name=":0" /> Increased liver weight was identified in rats exposed to DMP concentrations of approximately 1,860&nbsp;mg/kg-day; heightened ] activity (indicating liver damage) followed prolonged dosage of 500&nbsp;mg/kg–day; lowered cholesterol and lipid levels were observed after exposure to 107&nbsp;mg/kg-day.

== Environmental toxicity ==
Environmental contamination by phthalates, inclusive of DMP, has been a pressing issue for human and marine health. DMP is readily released to the environment could potentially pose harmful risks of exposure on humans. Additionally, pollution of DMP into the environment could also be harmful to micro-organisms and aquatic animals.<ref>{{Cite journal |last=Prasad |first=Bablu |date=2021-04-01 |title=Phthalate pollution: environmental fate and cumulative human exposure index using the multivariate analysis approach |url=https://pubs.rsc.org/en/content/articlelanding/2021/em/d0em00396d |journal=Environmental Science: Processes & Impacts |language=en |volume=23 |issue=3 |pages=389–399 |doi=10.1039/D0EM00396D |pmid=33566875 |s2cid=231883186 |issn=2050-7895}}</ref>

=== Toxic effects on bacteria ===
A study on the environmental contamination of DMP has a direct influence on the cell function of Pseudomonas fluroescens (P. fluorescens), such as inhibition of growth, reduced glucose utilisation, etc. Results from the study suggest the presence of alterations in gene expressions that are involved in energy metabolism such as ATP-binding cassette transporters.<ref name=":8">{{Cite journal |last1=Wang |first1=Zhigang |last2=Wang |first2=Chunlong |last3=You |first3=Yimin |last4=Xu |first4=Weihui |last5=Lv |first5=Zhihang |last6=Liu |first6=Zeping |last7=Chen |first7=Wenjing |last8=Shi |first8=Yiran |last9=Wang |first9=Junhe |date=2019-01-15 |title=Response of Pseudomonas fluorescens to dimethyl phthalate |url=https://www.sciencedirect.com/science/article/pii/S0147651318309394 |journal=Ecotoxicology and Environmental Safety |language=en |volume=167 |pages=36–43 |doi=10.1016/j.ecoenv.2018.09.078 |pmid=30292974 |bibcode=2019EcoES.167...36W |s2cid=52947405 |issn=0147-6513}}</ref> Additionally, inhibition of the Cori cycle and glycolysis pathway by DMP were also observed in the bacteria. P. fluorescens, a Plant Growth Promoting Rhizobacterium (PGPR), is an important bacteria found in soil, leaves and water that produces metabolites that allow plants to resist biotic and abiotic stresses.<ref name=":8" /> Hence, the release of DMP as waste into the environment should be more carefully considered.

Another study shows the ability of DMP to inhibit the growth and glucose utilization of '']'', a species that can cause ] in humans.<ref>{{Cite journal |last1=Scales |first1=Brittan S. |last2=Dickson |first2=Robert P. |last3=LiPuma |first3=John J. |last4=Huffnagle |first4=Gary B. |date=October 2014 |title=Microbiology, Genomics, and Clinical Significance of the Pseudomonas fluorescens Species Complex, an Unappreciated Colonizer of Humans |journal=Clinical Microbiology Reviews |volume=27 |issue=4 |pages=927–948 |doi=10.1128/CMR.00044-14 |issn=0893-8512 |pmc=4187640 |pmid=25278578}}</ref> Most specifically, cell membrane deformation and membrane channels misopening were observed, as well as altered gene expression responsible of energy metabolism.<ref>{{Cite journal |last1=Huang |first1=Ling |last2=Zhu |first2=Xunzhi |last3=Zhou |first3=Shixing |last4=Cheng |first4=Zhenrui |last5=Shi |first5=Kai |last6=Zhang |first6=Chi |last7=Shao |first7=Hua |date=July 2021 |title=Phthalic Acid Esters: Natural Sources and Biological Activities |journal=Toxins |language=en |volume=13 |issue=7 |pages=495 |doi=10.3390/toxins13070495 |pmid=34357967 |pmc=8310026 |issn=2072-6651|doi-access=free }}</ref>

=== Aquatic toxicity ===
The toxicity of DMP on adult ] (Danio rerio) was examined and showed oxidative damage after high concentrations of exposure. There was also found that antioxidant enzymes can be used as biochemical markers to identify the toxicant to be DMP.<ref name=":9">{{Cite journal |last1=Cong |first1=Bailin |last2=Liu |first2=Cong |last3=Wang |first3=Lujie |last4=Chai |first4=Yingmei |date=April 2020 |title=The Impact on Antioxidant Enzyme Activity and Related Gene Expression Following Adult Zebrafish (Danio rerio) Exposure to Dimethyl Phthalate |journal=Animals |language=en |volume=10 |issue=4 |pages=717 |doi=10.3390/ani10040717 |pmid=32325949 |pmc=7222705 |issn=2076-2615|doi-access=free }}</ref> The LC50 after 96h of exposure was 45.8&nbsp;mg/L, with 100% of mortality in the 200&nbsp;mg/L exposure group. After 96h of exposure at high concentrations the activity levels of the primary antioxidant enzymes ], ], and ] activities were significantly reduced. This resulted in reduction of gene expression of these enzymes. Antioxidant enzymes act as defenders of cells from oxidant damage from contaminants present as ] that can cause enzyme inactivation, DNA and cholesterol damage and ] of unsaturated fats in the cell membrane. The degree of lipid peroxidation in animals can be measured by following the trend in concentration of ], that is a product of lipid peroxidation. That is an indicator of DMP exposure.<ref name=":9" />

== Production and Business ==
Chittajit Mohan Dhar was a pioneer in the production of ] and ] in ].

Chittajit Mohan Dhar (C.M. Dhar) played a crucial role in pioneering the domestic production of ] at Perfect Chemical Industries Pvt. Ltd., located at 39 ], ], ]. This innovation was essential for defense applications, and by shifting production to Indian soil, the company saved the nation valuable foreign exchange, amounting to ₹1 crore annually. This move significantly reduced India's dependency on imports and demonstrated the company's ability to produce complex chemicals domestically.

In addition, under Dhar's leadership, the company manufactured basic dyes such as ], ], ], and ], using indigenous plants and equipment. This commitment to self-reliant industrial processes was further evidenced by their production of ], another critical chemical for defense applications.

The company's achievements in the chemical sector were recognized by ], then ] for Petroleum and Chemical Industries, who visited the factory to commend the rapid progress and the substantial contribution to saving foreign exchange. This visit highlighted the national importance of the company’s advancements and its role in supporting India's industrial and defense sectors.

<ref>{{Cite web |title=Bombay Times Newspaper- Chittajit Mohan Dhar and Professor Humayun Kabir |url=https://miro.medium.com/v2/resize:fit:640/format:webp/0*zu1eH1GNCecYhhoU.jpeg}}</ref>

== References ==
{{reflist}}

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