Dimethyl phthalate

Last updated
Dimethyl phthalate [1] [2]
Dimethyl phthalate V.1.svg
Dimethyl phthalate 3D BS.png
Names
Preferred IUPAC name
Dimethyl benzene-1,2-dicarboxylate
Other names
Dimethyl phthalate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.557 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C10H10O4/c1-13-9(11)7-5-3-4-6-8(7)10(12)14-2/h3-6H,1-2H3 Yes check.svgY
    Key: NIQCNGHVCWTJSM-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H10O4/c1-13-9(11)7-5-3-4-6-8(7)10(12)14-2/h3-6H,1-2H3
    Key: NIQCNGHVCWTJSM-UHFFFAOYAF
  • O=C(OC)c1ccccc1C(=O)OC
Properties
C10H10O4
Molar mass 194.184 g/mol
AppearanceColorless oily liquid
Odor slight aromatic odor [2]
Density 1.19 g/cm3
Melting point 2 °C (36 °F; 275 K)
Boiling point 283 to 284 °C (541 to 543 °F; 556 to 557 K)
0.4% (20°C) [2]
Vapor pressure 0.01 mmHg (20°C) [2]
Pharmacology
P03BX02 ( WHO ) QP53GX02 ( WHO )
Hazards
Flash point 146 °C (295 °F; 419 K)
460 °C (860 °F; 733 K)
Explosive limits 0.9%-? [2]
Lethal dose or concentration (LD, LC):
6900 mg/kg (rat, oral)
1000 mg/kg (rabbit, oral)
2400 mg/kg (guinea pig, oral)
6800 mg/kg (rat, oral)
6800 mg/kg (mouse, oral)
4400 mg/kg (rabbit, oral)
2400 mg/kg (guinea pig, oral) [3]
9630 mg/m3 [3]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 5 mg/m3 [2]
REL (Recommended)
TWA 5 mg/m3 [2]
IDLH (Immediate danger)
2000 mg/m3 [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Dimethyl phthalate (DMP) is an organic compound and phthalate ester. it is a colourless and oily liquid that is soluble in organic solvents, [4] but which is only poorly soluble in water (~4 g/L).

Contents

It is used in a variety of products and is most commonly used as insect repellent such as ectoparasiticide for mosquitoes and flies for animal livestock. [4] The short-chain or low molecular weight phthalate is also frequently used in consumer products such as cosmetics, ink, soap, household cleaning supplies, etc. [5] Other uses of DMP include solid rocket propellants (as a stabilizer) and plastics. [4] [5]

The U.S Environmental Protection Agency has classified Dimethyl phthalate as not classifiable for human carcinogenicity. [6] [7] Its oral LD50 is 4390 to 8200 mg/kg bw/d in rats and the dermal LD50 is 38000 mg/kg bw in rats and more than 4800 mg/kg bw in guinea pigs. [8]

Synthesis

Dimethyl phthalate is manufactured commercially via the esterification of phthalic anhydride with methanol. The reaction can be catalysed by a strong acid, such as sulfuric acid; various lewis acids may be used as an alterative, including complexes of titanium, zirconium or tin. Excess methanol is used to ensure complete conversion, with the remainder removed by distillation at the end. [4] [9]

Dimethyl phthalate synthesis EN.svg

Applications

Unlike most other phthalate esters, dimethyl phthalate is rarely used as a plasticizer for PVC. It is considered too volatile and causes excessive fuming during PVC processing. [10] It is a good plasticizer for cellulose-esters, including cellulose acetate, cellulose acetate butyrate and cellulose propionate compositions. Historically, this led to it being present in nail polish and some artificial nails but it is not commonly used today. [11] It is used as a plasticizer for cellulose acetate phthalate, which is used to make enteric coatings for medicines. [12] Other cosmetic uses include as a fixative for perfumes, although it is not as commonly used as DEP. [13] Dimethyl phthalate is able to dissolve nitrocellulose which made it historically important in some automotive coatings and vanishes.

Insect repellent

DMP can be used as an insect repellent and is especially useful against ixodid ticks responsible for Lyme disease. [14] DMP has been shown to deter species of mosquitoes such as Anopheles stephensi, Culex pipeins and Ades aegypti . [15] [16] [17]

Metabolism/Biotransformation

DMP administered orally in rats largely undergoes phase I biotransformation to monomethyl phthalate (MMP) via hydrolysis in the liver and intestinal mucosa. MMP may also be further hydrolysed to phthalic acid. [18] However, low molecular weight phthalates such as MMP are primarily excreted as monoesters and do not undergo phase II biotransformation processes such as hydroxylation and oxidation unlike the well-known banned molecule DEHP. [19]

Human safety

Acute exposure to DMP via inhalation in humans and animals have shown to result in irritation to the eyes, nose and throat. [20] Although some research has shown the association between the susceptibility of the reproductive system and phthalates esters, most phthalates demonstrate low acute toxicity. [4] [21]

The chronic (long term) effects, reproductive effects, and carcinogenicity of DMP on humans and animals have yet to be fully established as compared to some other phthalate esters. [6] [7] [22] 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. [4] [21]

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 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 mg/kg in females and 5,12 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 ''acute toxic'' under FHSA via oral exposure. [23]

Hematoxicity

At high doses (1000 mg/kg), DMP may cause red blood cells (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 hemoglobin, 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 oxidative stress-induced on RBCs by DMP. [24]

A separate study found that the oxidative stress induced by DMP also decreased the immune functions of erythrocytes. The oxidative stress damages the structure and function of erythrocytes, in particular RBC-complement 3b (C3b) receptors. [25]

Hepatotoxicity

Animal studies on oral exposure of DMP in rats have established hepatotoxic effects including increased liver weight, elevated alkaline phosphatase activity and reduced cholesterol and lipid levels. [4] Increased liver weight was identified in rats exposed to DMP concentrations of approximately 1,860 mg/kg-day; heightened alkaline phosphatase activity (indicating liver damage) followed prolonged dosage of 500 mg/kg–day; lowered cholesterol and lipid levels were observed after exposure to 107 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. [26]

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. [27] 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. [27] 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 Pseudomonas fluorescens , a species that can cause bacteremia in humans. [28] Most specifically, cell membrane deformation and membrane channels misopening were observed, as well as altered gene expression responsible of energy metabolism. [29]

Aquatic toxicity

The toxicity of DMP on adult zebrafish (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. [30] The LC50 after 96h of exposure was 45.8 mg/L, with 100% of mortality in the 200 mg/L exposure group. After 96h of exposure at high concentrations the activity levels of the primary antioxidant enzymes catalase, superoxide dismutase, and glutathione transferase 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 free radicals that can cause enzyme inactivation, DNA and cholesterol damage and peroxidation of unsaturated fats in the cell membrane. The degree of lipid peroxidation in animals can be measured by following the trend in concentration of malondialdehyde, that is a product of lipid peroxidation. That is an indicator of DMP exposure. [30]

Related Research Articles

In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a given substance. The value of LD50 for a substance is the dose required to kill half the members of a tested population after a specified test duration. LD50 figures are frequently used as a general indicator of a substance's acute toxicity. A lower LD50 is indicative of higher toxicity.

<span class="mw-page-title-main">Xylene</span> Organic compounds with the formula (CH3)2C6H4

In organic chemistry, xylene or xylol are any of three organic compounds with the formula (CH3)2C6H4. They are derived from the substitution of two hydrogen atoms with methyl groups in a benzene ring; which hydrogens are substituted determines which of three structural isomers results. It is a colorless, flammable, slightly greasy liquid of great industrial value.

<span class="mw-page-title-main">Phthalates</span> Any ester derived from phthalic acid

Phthalates, or phthalate esters, are esters of phthalic acid. They are mainly used as plasticizers, i.e., substances added to plastics to increase their flexibility, transparency, durability, and longevity. They are used primarily to soften polyvinyl chloride (PVC). Note that while phthalates are usually plasticizers, not all plasticizers are phthalates. The two terms are specific and unique and cannot be used interchangeably.

<span class="mw-page-title-main">Chlorfenvinphos</span> Chemical compound

Chlorfenvinphos is an organophosphorus compound that was widely used as an insecticide and an acaricide. The molecule itself can be described as an enol ester derived from dichloroacetophenone and diethylphosphonic acid. Chlorfenvinphos has been included in many products since its first use in 1963. However, because of its toxic effect as a cholinesterase inhibitor it has been banned in several countries, including the United States and the European Union. Its use in the United States was cancelled in 1991.

<span class="mw-page-title-main">Ethion</span> Chemical compound

Ethion (C9H22O4P2S4) is an organophosphate insecticide. Ethion is known to affect a neural enzyme called acetylcholinesterase and prevent it from working.

Demeton-S-methyl is an organic compound with the molecular formula C6H15O3PS2. It was used as an organothiophosphate acaricide and organothiophosphate insecticide. It is flammable. With prolonged storage, Demeton-S-methyl becomes more toxic due to formation of a sulfonium derivative which has greater affinity to the human form of the acetylcholinesterase enzyme, and this may present a hazard in agricultural use.

<span class="mw-page-title-main">Bis(2-ethylhexyl) phthalate</span> Organic compound used as a plasticizer to soften polymer matrix

Bis(2-ethylhexyl) phthalate (di-2-ethylhexyl phthalate, diethylhexyl phthalate, diisooctyl phthalate, DEHP; incorrectly — dioctyl phthalate, DIOP) is an organic compound with the formula C6H4(CO2C8H17)2. DEHP is the most common member of the class of phthalates, which are used as plasticizers. It is the diester of phthalic acid and the branched-chain 2-ethylhexanol. This colorless viscous liquid is soluble in oil, but not in water.

<span class="mw-page-title-main">Benzyl butyl phthalate</span> Chemical compound

Benzyl butyl phthalate (BBP) is an organic compound historically used a plasticizer, but which has now been largely phased out due to health concerns. It is a phthalate ester of containing benzyl alcohol, and n-butanol tail groups. Like most phthalates, BBP is non-volatile and remains liquid over a wide range of temperatures. It was mostly used as a plasticizer for PVC, but was also a common plasticizer for PVCA and PVB.

<span class="mw-page-title-main">2-Ethylhexanol</span> Chemical compound

2-Ethylhexanol is an organic compound with the chemical formula CH3CH2CH2CH2CH(CH2CH3)CH2OH. It is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is produced on a large scale (>2,000,000,000 kg/y) for use in numerous applications such as solvents, flavors, and fragrances and especially as a precursor for production of other chemicals such as emollients and plasticizers. It is encountered in plants, fruits, and wines. The odor has been reported as "heavy, earthy, and slightly floral" for the R enantiomer and "a light, sweet floral fragrance" for the S enantiomer.

<span class="mw-page-title-main">Diisobutyl phthalate</span> Chemical compound

Diisobutyl phthalate (DIBP) is a phthalate ester having the structural formula C6H4(COOCH2CH 2)2. It is formed by the esterification of isobutanol and phthalic anhydride. This and other phthalates are used as plasticizers due to their flexibility and durability. They are found in many industrial and personal products, such as lacquers, nail polish and cosmetics. DIBP can be absorbed via oral ingestion and dermal exposure. When it comes to excretion, DIBP is first converted into the hydrolytic monoester monoisobutyl phthalate (MIBP). The primary excretory route is urine, with biliary excretion being noted in minor amounts. DIBP has lower density and freezing point than the related compound dibutyl phthalate (DBP).

<span class="mw-page-title-main">Phosmet</span> Organophosphate non-systemic insecticide

Phosmet is a phthalimide-derived, non-systemic, organophosphate insecticide used on plants and animals. It is mainly used on apple trees for control of codling moth, though it is also used on a wide range of fruit crops, ornamentals, and vines for the control of aphids, suckers, mites, and fruit flies.

<span class="mw-page-title-main">Dibutyl phthalate</span> Chemical compound

Dibutyl phthalate (DBP) is an organic compound which is commonly used as a plasticizer because of its low toxicity and wide liquid range. With the chemical formula C6H4(CO2C4H9)2, it is a colorless oil, although impurities often render commercial samples yellow.

Patulin is an organic compound classified as a polyketide. It is named after the fungus from which it was isolated, Penicillium patulum. It is a white powder soluble in acidic water and in organic solvents. It is a lactone that is heat-stable, so it is not destroyed by pasteurization or thermal denaturation. However, stability following fermentation is lessened. It is a mycotoxin produced by a variety of molds, in particular, Aspergillus and Penicillium and Byssochlamys. Most commonly found in rotting apples, the amount of patulin in apple products is generally viewed as a measure of the quality of the apples used in production. In addition, patulin has been found in other foods such as grains, fruits, and vegetables. Its presence is highly regulated.

<span class="mw-page-title-main">Benzotrichloride</span> Chemical compound

Benzotrichloride (BTC), also known as α,α,α-trichlorotoluene, phenyl chloroform or (trichloromethyl)benzene, is an organic compound with the formula C6H5CCl3. Benzotrichloride is an unstable, colorless or somewhat yellowish, viscous, chlorinated hydrocarbon with a penetrating odor. Benzotrichloride is used extensively as a chemical intermediate for products of various classes, i.e. dyes and antimicrobial agents.

<span class="mw-page-title-main">Diisononyl phthalate</span> Chemical compound

Diisononyl phthalate (DINP) is a phthalate used as a plasticizer. DINP is typically a mixture of chemical compounds consisting of various isononyl esters of phthalic acid, and is commonly used in a large variety of plastic items.

<span class="mw-page-title-main">Diethyl phthalate</span> Chemical compound

Diethyl phthalate (DEP) is a phthalate ester. It occurs as a colourless liquid without significant odour but has a bitter, disagreeable taste. It is more dense than water and insoluble in water; hence, it sinks in water.

Bis(2-ethylhexyl) terephthalate commonly abbreviated DEHT (Dioctyl terephthalate or DOTP), is an organic compound with the formula C6H4(CO2C8H17)2. It is a non-phthalate plasticizer, being the diester of terephthalic acid and the branched-chain 2-ethylhexanol, which is often generically referred to as octyl. This colorless viscous liquid is used for softening PVC plastics and is known for chemical similarity to general purpose phthalates such as DEHP and DINP, but without any negative regulatory pressure. It possesses very good plasticizing properties and may be used as a direct replacement for DEHP and DINP in many applications.

<span class="mw-page-title-main">Ethoprophos</span> Chemical compound

Ethoprophos (or ethoprop) is an organophosphate ester with the formula C8H19O2PS2. It is a clear yellow to colourless liquid that has a characteristic mercaptan-like odour. It is used as an insecticide and nematicide and it is an acetylcholinesterase inhibitor.

<span class="mw-page-title-main">Tebufenpyrad</span> Chemical compound

Tebufenpyrad is an insecticide and acaricide widely used in greenhouses. It is a white solid chemical with a slight aromatic smell. It is soluble in water and also in organic solvents.

Antiandrogens in the environment have become a topic of concern. Many industrial chemicals, including phthalates and pesticides, exhibit antiandrogen activity in animal experiments. Certain plant species have also been found to produce antiandrogens. In animal studies, environmental antiandrogens can harm reproductive organ development in fetuses exposed in utero as well as their offspring.

References

  1. ↑ Dimethyl phthlate at chemicalland21.com
  2. 1 2 3 4 5 6 7 8 NIOSH Pocket Guide to Chemical Hazards. "#0228". National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 "Dimethylphthalate". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. 1 2 3 4 5 6 7 Carlson KR, Patton LE. Toxicity Review for Dimethyl Phthalate (DMP, CASRN 131-11-3) (PDF) (Report). U.S Consumer Product Safety Commission.
  5. 1 2 Schettler T (February 2006). "Human exposure to phthalates via consumer products". International Journal of Andrology. 29 (1): 134–139, discussion 181–185. doi: 10.1111/j.1365-2605.2005.00567.x . PMID   16466533.
  6. 1 2 Phillips L (June 2015). "EPA's Exposure Assessment Toolbox (EPA-Expo-Box)". Journal of Environmental Informatics. 25 (2): 81–84. doi: 10.3808/jei.201400269 . ISSN   1726-2135. S2CID   113872276.
  7. 1 2 Newburg-Rinn SD (November 1982). "Commentary: Activities of the Environmental Protection Agency concerning Phthalate Esters". Environmental Health Perspectives. 45: 137–139. doi: 10.2307/3429398 . ISSN   0091-6765. JSTOR   3429398. PMC   1568984 .
  8. ↑ National Industrial Chemicals Notification and Assessment Scheme (NICNAS); Australia Government (June 2008). "Dimethyl Phthalate" (PDF). Existing Chemical Hazard Assessment Report.
  9. ↑ US 5534652,Jones L, Daniels PH, Krauskopf LG, Rigopoulos KR,"Preparation of plasticizer esters from phthalic anhydride residue",issued 1996-07-09
  10. ↑ Verlag, Carl Hanser (2009). Plastics additives handbook (6. ed.). Munich. p. 490. ISBN   978-3-446-40801-2.{{cite book}}: CS1 maint: location missing publisher (link)
  11. ↑ Young, AS; Allen, JG; Kim, UJ; Seller, S; Webster, TF; Kannan, K; Ceballos, DM (6 November 2018). "Phthalate and Organophosphate Plasticizers in Nail Polish: Evaluation of Labels and Ingredients". Environmental Science & Technology. 52 (21): 12841–12850. Bibcode:2018EnST...5212841Y. doi:10.1021/acs.est.8b04495. PMC   6222550 . PMID   30302996.
  12. ↑ "Committee for veterinary medicinal products: Dimethyl and Diethyl phthalates summary report" (PDF). ema.europa.eu. September 2001. Retrieved March 15, 2022.
  13. ↑ Al-Saleh, Iman; Elkhatib, Rola (January 2016). "Screening of phthalate esters in 47 branded perfumes". Environmental Science and Pollution Research. 23 (1): 455–468. doi:10.1007/s11356-015-5267-z. PMID   26310707. S2CID   22840018.
  14. ↑ Brown, Margaret; Hebert, Adelaide A. (1997-02-01). "Insect repellents: An overview". Journal of the American Academy of Dermatology. 36 (2): 243–249. doi:10.1016/S0190-9622(97)70289-5. ISSN   0190-9622. PMID   9039177.
  15. ↑ Karunamoorthi K, Sabesan S (May 2010). "Laboratory evaluation of dimethyl phthalate treated wristbands against three predominant mosquito (Diptera: Culicidae) vectors of disease". European Review for Medical and Pharmacological Sciences. 14 (5): 443–448. PMID   20556923.
  16. ↑ Nathan, Sengottayan Senthil; Kalaivani, Kandaswamy; Murugan, Kadarkarai (October 2005). "Effects of neem limonoids on the malaria vector Anopheles stephensi Liston (Diptera: Culicidae)". Acta Tropica. 96 (1): 47–55. doi:10.1016/j.actatropica.2005.07.002. ISSN   0001-706X. PMID   16112073.
  17. ↑ Kalyanasundaram, Muthuswami; Mathew, Nisha (2006-05-01). "N,N-Diethyl Phenylacetamide (DEPA): A Safe and Effective Repellent for Personal Protection Against Hematophagous Arthropods". Journal of Medical Entomology. 43 (3): 518–525. doi:10.1603/0022-2585(2006)43[518:NPDASA]2.0.CO;2. PMID   16739410. S2CID   22623121.[ permanent dead link ]
  18. ↑ Qian, Yiyu; Shao, Hailing; Ying, Xinxin; Huang, Wenle; Hua, Ying (2020). "The Endocrine Disruption of Prenatal Phthalate Exposure in Mother and Offspring". Frontiers in Public Health. 8: 366. doi: 10.3389/fpubh.2020.00366 . PMC   7483495 . PMID   32984231.
  19. ↑ Hauser, R.; Calafat, A. M. (2005-11-01). "Phthalates and Human Health". Occupational and Environmental Medicine. 62 (11): 806–818. doi:10.1136/oem.2004.017590. ISSN   1351-0711. PMC   1740925 . PMID   16234408.
  20. ↑ Fonger GC, Hakkinen P, Jordan S, Publicker S (November 2014). "The National Library of Medicine's (NLM) Hazardous Substances Data Bank (HSDB): background, recent enhancements and future plans". Toxicology. 325: 209–216. doi:10.1016/j.tox.2014.09.003. PMC   4195797 . PMID   25223694.
  21. 1 2 National Research Council (US) Committee on the Health Risks of Phthalates (2008). Toxicity Assessment. National Academies Press (US). ISBN   978-0-309-12841-4.
  22. ↑ Gray, L. E.; Ostby, J.; Furr, J.; Price, M.; Veeramachaneni, D. N.; Parks, L. (December 2000). "Perinatal exposure to the phthalates DEHP, BBP, and DINP, but not DEP, DMP, or DOTP, alters sexual differentiation of the male rat". Toxicological Sciences. 58 (2): 350–365. doi:10.1093/toxsci/58.2.350. ISSN   1096-6080. PMID   11099647.
  23. ↑ R. Carlson E. Patton, Kent Leslie (October 30, 2010). "Toxicity Review of Dimethyl phthalate" (PDF). United states consumer product safety commission. Archived (PDF) from the original on 2017-01-31. Retrieved March 17, 2022.
  24. ↑ Chi, Zhenxing; Liu, Jia; Tan, Songwen; Lin, Hongwei; Wu, Weilin; Li, Weiguo (2021-01-01). "Revealing the toxicity of dimethyl phthalate (DMP) to the oxygen-carrying function of red blood cells (RBCs): The iron release mechanism". Chemosphere. 263: 128017. Bibcode:2021Chmsp.263l8017C. doi:10.1016/j.chemosphere.2020.128017. ISSN   0045-6535. PMID   32841881. S2CID   221325980.
  25. ↑ Li, Shixuan; Chi, Zhenxing; Li, Weiguo (2019-10-01). "Invitro toxicity of dimethyl phthalate to human erythrocytes: From the aspects of antioxidant and immune functions". Environmental Pollution. 253: 239–245. doi:10.1016/j.envpol.2019.07.014. ISSN   0269-7491. PMID   31319240. S2CID   197664449.
  26. ↑ Prasad, Bablu (2021-04-01). "Phthalate pollution: environmental fate and cumulative human exposure index using the multivariate analysis approach". Environmental Science: Processes & Impacts. 23 (3): 389–399. doi:10.1039/D0EM00396D. ISSN   2050-7895. PMID   33566875. S2CID   231883186.
  27. 1 2 Wang, Zhigang; Wang, Chunlong; You, Yimin; Xu, Weihui; Lv, Zhihang; Liu, Zeping; Chen, Wenjing; Shi, Yiran; Wang, Junhe (2019-01-15). "Response of Pseudomonas fluorescens to dimethyl phthalate". Ecotoxicology and Environmental Safety. 167: 36–43. doi:10.1016/j.ecoenv.2018.09.078. ISSN   0147-6513. PMID   30292974. S2CID   52947405.
  28. ↑ Scales, Brittan S.; Dickson, Robert P.; LiPuma, John J.; Huffnagle, Gary B. (October 2014). "Microbiology, Genomics, and Clinical Significance of the Pseudomonas fluorescens Species Complex, an Unappreciated Colonizer of Humans". Clinical Microbiology Reviews. 27 (4): 927–948. doi:10.1128/CMR.00044-14. ISSN   0893-8512. PMC   4187640 . PMID   25278578.
  29. ↑ Huang, Ling; Zhu, Xunzhi; Zhou, Shixing; Cheng, Zhenrui; Shi, Kai; Zhang, Chi; Shao, Hua (July 2021). "Phthalic Acid Esters: Natural Sources and Biological Activities". Toxins. 13 (7): 495. doi: 10.3390/toxins13070495 . ISSN   2072-6651. PMC   8310026 . PMID   34357967.
  30. 1 2 Cong, Bailin; Liu, Cong; Wang, Lujie; Chai, Yingmei (April 2020). "The Impact on Antioxidant Enzyme Activity and Related Gene Expression Following Adult Zebrafish (Danio rerio) Exposure to Dimethyl Phthalate". Animals. 10 (4): 717. doi: 10.3390/ani10040717 . ISSN   2076-2615. PMC   7222705 . PMID   32325949.
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