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Nonylphenol information


Nonylphenol
Names
IUPAC name
4-(2,4-dimethylheptan-3-yl)phenol
Other names
Phenol, nonyl-
Identifiers
CAS Number
  • 25154-52-3 (general class) checkY
  • 104-40-5 (4-n-Nonyl phenol) checkY
  • 84852-15-3 (branched 4-Nonyl phenols) checkY
  • 11066-49-2 (isononylphenols) ☒N
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL153062 ☒N
ChemSpider
  • 60628 checkY
PubChem CID
  • 67296
UNII
  • 79F6A2ILP5 (general class) checkY
  • I03GBV4WEL (4-n-Nonyl phenol) checkY
  • JRW3Q994VG (branched 4-Nonyl phenols) checkY
InChI
  • InChI=1S/C15H24O/c1-2-3-4-5-6-7-8-11-14-12-9-10-13-15(14)16/h9-10,12-13,16H,2-8,11H2,1H3 checkY
    Key: SNQQPOLDUKLAAF-UHFFFAOYSA-N checkY
  • InChI=1/C15H24O/c1-2-3-4-5-6-7-8-11-14-12-9-10-13-15(14)16/h9-10,12-13,16H,2-8,11H2,1H3
    Key: SNQQPOLDUKLAAF-UHFFFAOYAP
SMILES
  • Oc1ccccc1CCCCCCCCC
Properties
Chemical formula
C15H24O
Molar mass 220.35 g/mol
Appearance Light yellow viscous liquid with phenolic smell [1]
Density 0.953
Melting point −8 to 2 °C (18 to 36 °F; 265 to 275 K)
Boiling point 293 to 297 °C (559 to 567 °F; 566 to 570 K)
Solubility in water
6 mg/L (pH 7)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
low level endrocrine disruptor
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Nonylphenols are a family of closely related organic compounds composed of phenol bearing a 9 carbon-tail. Nonylphenols can come in numerous structures, all of which may be considered alkylphenols. They are used in manufacturing antioxidants, lubricating oil additives, laundry and dish detergents, emulsifiers, and solubilizers.[2] They are used extensively in epoxy formulation in North America[3][4] but its use has been phased out in Europe.[5] These compounds are also precursors to the commercially important non-ionic surfactants alkylphenol ethoxylates and nonylphenol ethoxylates, which are used in detergents, paints, pesticides, personal care products, and plastics. Nonylphenol has attracted attention due to its prevalence in the environment and its potential role as an endocrine disruptor and xenoestrogen, due to its ability to act with estrogen-like activity.[6] The estrogenicity and biodegradation heavily depends on the branching of the nonyl sidechain.[7][8][9] Nonylphenol has been found to act as an agonist of the GPER (GPR30).[10]

  1. ^ Record of Nonylphenol, mixed isomers in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 6 April 2011.
  2. ^ Cite error: The named reference Soares was invoked but never defined (see the help page).
  3. ^ "Epoxy Nonyl Phenol Alert is it in your epoxy?". www.epoxyproducts.com. Retrieved 2021-03-18.
  4. ^ "para nonyl phenol" (PDF). squarespace.
  5. ^ "No, no, nonyl(phenol)". Healthy Building Network. Retrieved 2021-03-18.
  6. ^ Cite error: The named reference maria was invoked but never defined (see the help page).
  7. ^ Guenther, Klaus; Kleist, Einhard; Thiele, Bjoern (2005-12-10). "Estrogen-active nonylphenols from an isomer-specific viewpoint: a systematic numbering system and future trends". Analytical and Bioanalytical Chemistry. 384 (2): 542–546. doi:10.1007/s00216-005-0181-8. ISSN 1618-2642. PMID 16341851. S2CID 39833642.
  8. ^ Gabriel FL, Routledge EJ, Heidelberger A, Rentsch D, Guenther K, Giger W, et al. (2008). "Isomer-specific degradation and endocrine disrupting activity of nonylphenols" (PDF). Environ Sci Technol. 42 (17): 6399–408. Bibcode:2008EnST...42.6399G. doi:10.1021/es800577a. PMID 18800507.
  9. ^ Lu, Zhijiang; Gan, Jay (2014-01-21). "Isomer-Specific Biodegradation of Nonylphenol in River Sediments and Structure-Biodegradability Relationship". Environmental Science & Technology. 48 (2): 1008–1014. Bibcode:2014EnST...48.1008L. doi:10.1021/es403950y. ISSN 0013-936X. PMID 24345275.
  10. ^ Prossnitz, Eric R.; Barton, Matthias (2014). "Estrogen biology: New insights into GPER function and clinical opportunities". Molecular and Cellular Endocrinology. 389 (1–2): 71–83. doi:10.1016/j.mce.2014.02.002. ISSN 0303-7207. PMC 4040308. PMID 24530924.

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