PHTHALATES

(Redirected from Phthalate)

General chemical structure of phthalates. R and R' = CnH2n+1; n = 4-15

'Phthalates', or 'phthalate esters', are a group of chemical compounds that are mainly used as plasticizers (substances added to plastics to increase their flexibility). They are chiefly used to turn polyvinyl chloride from a hard plastic into a flexible plastic.
Phthalate esters are the dialkyl or alkyl aryl esters of 1,2-benzenedicarboxylic acid; the name ''phthalate'' derives from phthalic acid. When added to plastics, phthalates allow the long polyvinyl molecules to slide against one another. The phthalates show low water solubility, high oil solubility, and low volatility. The polar carboxyl group contributes little to the physical properties of the phthalates, except when R and R' are very small (such as ethyl or methyl groups). They are colorless, odorless liquids produced by reacting phthalic anhydride with an appropriate alcohol (usually 6 to 13 carbon).
As of 2004, manufacturers produce about 400,000 tons (800 million pounds or 363 million kilograms) of phthalates each year. They were first produced during the 1920s, and have been produced in large quantities since the 1950s, when PVC was introduced. The most widely used phthalates are di-2-ethyl hexyl phthalate (DEHP), diisodecyl phthalate (DIDP) and diisononyl phthalate (DINP). DEHP is the dominant plasticizer used in PVC, due to its low cost. Benzylbutylphthalate (BBzP) is used in the manufacture of foamed PVC, which is mostly used as a flooring material. Phthalates with small R and R' groups are used as solvents in perfumes and pesticides.
Phthalates are also frequently used in nail polish, fishing lures, adhesives, caulk, paint pigments, and sex toys made of so-called "jelly rubber." Some vendors of jelly rubber sex toys advise covering them in condoms when used internally, due to the possible health risks. Other vendors do not carry jelly rubber sex toys, in favor of phthalate-free varieties.[1] The Dutch office of Greenpeace UK sought to encourage the European Union to ban sex toys that contained phthalates.[2]

Contents
Table of more common phthalates
Health effects
See also
References

Table of more common phthalates


Name Acronym Structural formula CAS No.
Dimethyl phthalate DMP C6H4(COOCH3)2 131-11-3
Diethyl phthalate DEP C6H4(COOC2H5)2 84-66-2
Diallyl phthalate DAP C6H4(COOCH2CH=CH2)2 131-17-9
Di-n-propyl phthalate DPP C6H4[COO(CH2)2CH3]2 131-16-8
Di-n-butyl phthalate DBP C6H4[COO(CH2)3CH3]2 84-74-2
Diisobutyl phthalate DIBP C6H4[COOCH2CH(CH3)2]2 84-69-5
Butyl cyclohexyl phthalate BCP CH3(CH2)3OOCC6H4COOC6H11 84-64-0
Di-n-pentyl phthalate DNPP C6H4[COO(CH2)4CH3]2 131-18-0
Dicyclohexyl phthalate DCP C6H4[COOC6H11]2 84-61-7
Butyl benzyl phthalate BBP CH3(CH2)3OOCC6H4COOCH2C6H5 85-68-7
Di-n-hexyl phthalate DNHP C6H4[COO(CH2)5CH3]2 84-75-3
Diisohexyl phthalate DIHxP C6H4[COO(CH2)3CH(CH3)2]2 146-50-9
Diisoheptyl phthalate DIHpP C6H4[COO(CH2)4CH(CH3)2]2 41451-28-9
Butyl decyl phthalate BDP CH3(CH2)3OOCC6H4COO(CH2)9CH3 89-19-0
Di(2-ethylhexyl) phthalate DEHP, DOP C6H4[COOCH2CH(C2H5)(CH2)3CH3]2 117-81-7
Di(n-octyl) phthalate DNOP C6H4[COO(CH2)7CH3]2 117-84-0
Diisooctyl phthalate DIOP C6H4[COO(CH2)5CH(CH3)2]2 27554-26-3
n-Octyl n-decyl phthalate ODP CH3(CH2)7OOCC6H4COO(CH2)9CH3 119-07-3
Diisononyl phthalate DINP C6H4[COO(CH2)6CH(CH3)2]2 28553-12-0
Diisodecyl phthalate DIDP C6H4[COO(CH2)7CH(CH3)2]2 26761-40-0
Diundecyl phthalate DUP C6H4[COO(CH2)10CH3]2 3648-20-2
Diisoundecyl phthalate DIUP C6H4[COO(CH2)8CH(CH3)2]2 85507-79-5
Ditridecyl phthalate DTDP C6H4[COO(CH2)12CH3]2 119-06-2
Diisotridecyl phthalate DIUP C6H4[COO(CH2)10CH(CH3)2]2 68515-47-9

Health effects


Phthalates are controversial because high doses of many phthalates have shown hormonal activity in rodent studies. Studies on rodents involving large amounts of phthalates have shown damage to the liver, the kidneys, the lungs, and the developing testes. On the other hand, one Japanese study involving juvenile primates (marmosets) did not observe testicular effects (Tomonari et al, The Toxicologist, 2003). Research published in 2006 by Joint Research Centre, Institute for Health and Consumer Protection, and European Chemicals Bureau has found that two of the suspected dangerous phthalates banned by EU legislation - diisononyl phthalate (DINP) and diisodecyl phthalate (DIDP) - show no risks to human health or the environment for any current use.
2004 - a joint Swedish-Danish research team found a very strong link between allergies in children and the phthalates DEHP and BBzP.[3]
2004 - On the other hand, a study by Children's National Medical Center and George Washington University found no adverse effects in adolescents who had been exposed to phthalates as neonates. The study measured both physical characteristics and chemical characteristics of the subjects.[4]
2005 - study reported that phthalates may mimic the female hormone oestrogen (see xenoestrogens), and cause "feminisation" of baby boys. Phthalates and Baby Boys: Potential Disruption of Human Genital Development.
Barrett JR.
Environ Health Perspect. 2005 Aug; 113(8): A542.
In the study by the University of Missouri in Columbia, urine samples were collected from pregnant women in four United States cities. All were found to have levels of phthalate residues in their urine.
Upon birth of the children whose mother's urine had been previously measured, the genital features and anogenital distance were measured and correlated with the residue levels in the mother's urine. In boys, the highest levels of residue were seven times more likely to have a shortened anogenital distance.[5]There was also a correlation between heightened residue levels and smaller penis sizes. Boys with smaller penises were more likely to have testes that didn't descend properly into the scrotum.
The reaction of the public to the results study has been criticized[6]by STATS, a non-profit research organization affiliated with George Mason University. Critics claim that the methodology used, including a small, homogeneous study group that was not pulled from a wide variety of regions, cannot be used to definitively claim widespread problems related to phthalates. The criticism also states that the media overstated the findings in the report.
2006 - Two of the most commonly used phthalates (DINP and DIDP) are declared "safe" at current levels of use by EU research scientists.[7][8] Environmental impact, chronic and acute health effects in consumers (both adults and infants) and in chemical workers, have all been assessed and found to pose no risk. The rigorous EU risk assessments, which include a high degree of conservatism and built-in safety factors, have been carried out under the strict supervision of the European Commission and provide a clear scientific evaluation on which to judge whether a particular substance can be safely used. The research is the culmination of ten years of study into the suspect phthalates and goes against the previous conclusions and precautionary measures adopted by the EU government.
The authors of a study of Finnish boys with undescended testis hypothesized, based on their findings, that exposure to a combination of phthalates and anti-androgenic pesticides may have contributed to their condition.[9]
2007 - a cross-sectional study of U.S. males conducted by researchers at Rochester School of Medicine and Dentistry concluded that urine concentrations of four phthalate metabolites correlate with waist size and three phthalate metabolites correlate with the cellular resistance to insulin, a precursor to Type II diabetes. The authors note the need for follow-up longitudinal studies.[10]

See also



Xenoestrogen

References


1. Sustainable Kink. A local couple explores the last eco-frontier: sex toys. by Ethan Smith, "Willamette Week" 18 April 2007.
2. http://www.news24.com/News24/World/News/0,,2-10-1462_1995778,00.html
3. The Association between Asthma and Allergic Symptoms in Children and Phthalates in House Dust: A Nested Case–Control Study, C.-G. Bornehag, J. Sundell, C. J. Weschler, T. Sigsgaard, B. Lundgren, M. Hasselgren, L. Hägerhed-Engman, , , Environ Health Perspect., 2004

4. Follow-Up Study of Adolescents Exposed to Di(2-Ethylhexyl) Phthalate (DEHP) as Neonates on Extracorporeal Membrane Oxygenation (ECMO) Support, Khodayar Rais-Bahrami,1 Susan Nunez,2 Mary E. Revenis,1 Naomi L.C. Luban,3 and Billie L. Short, , , Environ Health Perspect, 2004

5. Follow-Up Study of Adolescents Exposed to Di(2-Ethylhexyl) Phthalate (DEHP) as Neonates on Extracorporeal Membrane Oxygenation (ECMO) Support Khodayar Rais-Bahram
6. Toy Tantrums - The Debate Over the Safety of Phthalates Rebecca Goldin Ph.D
7. 1,2-benzenedicarboxylic acid, di-c9-11 branched alkyl esthers, c10 rich, and Di-"isodectyl phthalate (DIDP) summary assesment report
8. 1,2-benzenedicarboxylic acid, di-c8-10 branched alkyl esthers, c10 rich, and Di-"isodectyl phthalate (DIDP) summary assesment report
9. Environmental effects on hormonal regulation of testicular descent, Toppari J, Virtanen H, Skakkebaek NE, Main KM, , , J Steroid Biochem Mol Biol, 2006
10. Concentrations of urinary phthalate metabolites are associated with increased waist circumference and insulin resistance in adult u.s. Males, Stahlhut RW, van Wijngaarden E, Dye TD, Cook S, Swan SH., , , Environ Health Perspect, 2007


The relationship between environmental exposures to phthalates and DNA damage in human sperm using the neutral comet assay, Susan M. Duty, Narendra P. Singh, Manori J. Silva, Dana B. Barr, John W. Brock, Louise Ryan, Robert F. Herrick, David C. Christiani, and Russ Hauser, , , Environmental Health Perspectives, 2003

Decrease in anogenital distance among male infants with prenatal phthalate exposure, Shanna H. Swan, Katharina M. Main, Fan Liu, Sara L. Stewart, Robin L. Kruse, Antonia M. Calafat, Catherine S. Mao, J. Bruce Redmon, Christine L. Ternand, Shannon Sullivan, J. Lynn Teague, and the Study for Future Families Research Team, , , Environmental Health Perspectives, 2005

★ Swan, S.H. 2004. Phthalates in pregnant women and children. e.hormone 2004 conference. October 27-30. New Orleans.

★ Swan, S.H. ''et al.'' 2005. Decrease in anogenital distance among male infants with prenatal phthalate exposure. ''Environmental Health Perspectives'' '113':1056--1061.

Mechanisms of Phthalate Ester Toxicity in the Female Reproductive System, Barbara J. Davis, Tara Lovekamp-Swant, , , Environmental Health Perspectives, 2003

★ {{cite journal
| author = L. Earl Gray, Jr.
★ ,1, Joseph Ostby
★ , Johnathan Furr
★ , Matthew Price
★ , D. N. Rao Veeramachaneni{dagger} and Louise Parks
| title = Perinatal Exposure to the Phthalates DEHP, BBP, and DINP, but Not DEP, DMP, or DOTP, Alters Sexual Differentiation of the Male Rat
| journal = Toxicological Sciences
| year = 2000
| volume = 58
| issue =
| pages = 350-365
| url = http://171.66.120.171/cgi/reprint/58/2/350
}}

Health risks posed by use of Di-2-ethylhexyl phthalate (DEHP) in PVC medical devices: A critical review, Joel A. Tickner, ScD 1
★ , Ted Schettler, MD, MPH 2, Tee Guidotti, MD, MPH 3, Michael McCally, MD, MPH 4, Mark Rossi, MA 5, , , American Journal of Industrial Medicine,


Decrease in Anogenital Distance among Male Infants with Prenatal Phthalate Exposure, Shanna H. Swan,1 Katharina M. Main,2 Fan Liu,3 Sara L. Stewart,3 Robin L. Kruse,3 Antonia M. Calafat,4 Catherine S. Mao,5 J. Bruce Redmon,6 Christine L. Ternand,7 Shannon Sullivan,8 and J. Lynn Teague9, , , Environmental Health Perspectives, 2005

Human Exposure Estimates for Phthalates, Michael C. Kohn; Frederick Parham; Scott A. Masten; Christopher J. Portier; Michael D. Shelby; John W. Brock; Larry L. Needham, , , Environmental Health Perspectives, 2000

The Association between Asthma and Allergic Symptoms in Children and Phthalates in House Dust: A Nested Case–Control Study, Carl-Gustaf Bornehag,1,2,3 Jan Sundell,2 Charles J. Weschler,2,4 Torben Sigsgaard,5 Björn Lundgren,1 Mikael Hasselgren,3 and Linda Hägerhed-Engman1, , , Environmental Health Perspectives, 2004

Concentrations of Urinary Phthalate Metabolites are Associated with Increased Waist Circumference and Insulin Resistance in Adult U.S. Males, Richard W Stahlhut, Edwin van Wijngaarden, Timothy D Dye, Stephen Cook and Shanna H Swan, , , Environmental Health Perspectives, 2007


Sustainable Kink by Ethan Smith, "Willamette Week," 18 April 2007

"Phthalates Information Centre"

phthalates.org

Phthalates and Human Health

A mass spectral guide for quick identification of phthalate esters (pdf)

The Association between Asthma and Allergic Symptoms in Children and Phthalates in House Dust: A Nested Case-Control Study

Unsafe Sex Toys with Violet Blue

'Gender-bending' chemicals found to 'feminise' boys, ''New Scientist'', 27 May 2005.

Ubiquitous Chemical Associated with Abnormal Human Reproductive Development, ''Scientific American'', May 27 2005.

Toy Tantrums - The Debate Over the Safety of Phthalates, Dr. Rebecca Goldin, Jan 2006

DIDP, DINP, and DBP - Risk Assessment Reports by the European Chemicals Bureau (ECB).

Naughty by Nature: Ever thought about the toxins in your sex toys? by Emily Gertz, "Grist magazine", 6 December 2005

List of funding sources for stats.org

Phthalates now linked to fat, related health risks

Phthalates linked to obesity in men, University of Rochester Medical Center, March 14 2007.

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