4-Methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene

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4-Methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene
MBP.svg
Names
IUPAC name
4,4’-(4-Methyl-1-pentene-2,4-diyl)diphenol
Identifiers
3D model (JSmol)
Abbreviations MBP
ChemSpider
Properties
C18H20O2
Molar mass 268.36 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

4-Methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene (MBP) is a metabolite of bisphenol A (BPA).[1] MBP has potent estrogenic activity in vitro and in vivo, about 1000 times more than BPA.[2] Computer modeling has shown that this greater potency is due to stronger binding to estrogen receptors.[3]

These results suggest that a greater health threat may result from the metabolism of BPA inside the body than from BPA itself.[4][5]

References[edit]

  1. ^ Yoshihara, Shin'ichi; Mizutare, Tohru; Makishima, Misako; Suzuki, Noriko; Fujimoto, Nariaki; Igarashi, Kazuo; Ohta, Shigeru (2004). "Potent Estrogenic Metabolites of Bisphenol A and Bisphenol B Formed by Rat Liver S9 Fraction: Their Structures and Estrogenic Potency". Toxicological Sciences. 78 (1): 50–59. PMID 14691209. doi:10.1093/toxsci/kfh047. 
  2. ^ Okuda, Katsuhiro; Takiguchi, Masufumi; Yoshihara, Shin'ichi (2010). "In vivo estrogenic potential of 4-methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene, an active metabolite of bisphenol A, in uterus of ovariectomized rat". Toxicology Letters. 197 (1): 7–11. PMID 20435109. doi:10.1016/j.toxlet.2010.04.017. 
  3. ^ Baker, Michael E.; Chandsawangbhuwana, Charlie (2012). Laudet, Vincent, ed. "3D Models of MBP, a Biologically Active Metabolite of Bisphenol A, in Human Estrogen Receptor α and Estrogen Receptor β". PLoS ONE. 7 (10): e46078. PMC 3464279Freely accessible. PMID 23056236. doi:10.1371/journal.pone.0046078. 
  4. ^ "BPA’s Real Threat May Be After It Has Metabolized". UC San Diego Health System. October 4, 2012. Retrieved 22 October 2012. 
  5. ^ "Red Flag Raised for BPA Metabolite". Chemical & Engineering News. American Chemical Society. 90 (41): 43. October 8, 2012.