WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 591913
CAS#: 104-40-5 (4-n-Nonyl phenol)
Description: 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. They are used extensively in epoxy formulation in North America but its use has been phased out in Europe. 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. The estrogenicity and biodegradation heavily depends on the branching of the nonyl sidechain. Nonylphenol has been found to act as an agonist of the GPER (GPR30).
MedKoo Cat#: 591913
CAS#: 104-40-5 (4-n-Nonyl phenol)
Chemical Formula: C15H24O
Exact Mass: 220.1827
Molecular Weight: 220.36
Elemental Analysis: C, 81.76; H, 10.98; O, 7.26
Related CAS #: 25154-52-3 (general class) 104-40-5 (4-n-Nonyl phenol) 84852-15-3 (branched 4-Nonyl phenols) 11066-49-2 (isononylphenols)
Synonym: 4-Nonylphenol, n-Nonylphenol; NSC 71410; NSC-71410; NSC-71410
IUPAC/Chemical Name: 4-nonyl-Phenol
InChi Key: IGFHQQFPSIBGKE-UHFFFAOYSA-N
InChi Code: InChI=1S/C15H24O/c1-2-3-4-5-6-7-8-9-14-10-12-15(16)13-11-14/h10-13,16H,2-9H2,1H3
SMILES Code: OC1=CC=C(CCCCCCCCC)C=C1
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.03.00
|Biological target:||Nonylphenol has been found to act as an agonist of the GPER (GPR30).|
|In vitro activity:||In this study, the effects of NPEO, VAEO, 4-n-NP and Vanillin on the estrogen receptor α (ERα), androgen receptor (AR), thyroid hormone receptor (TR), retinoic X receptor β (RXRβ) and estrogen-related receptor γ (ERRγ) were determined and compared using a battery of recombined yeast strains expressing β-galactosidase. The results showed that NPEO and 4-n-NP acted as significant antagonists of ER, AR, TR and ERRγ. In addition, 4-n-NP also had antagonistic activity toward RXRβ. The in vitro data indicated that NPEO, 4-n-NP and VAEO have the potential to act as endocrine disruptors involving more than one nuclear hormone receptor. Reference: Ecotoxicol Environ Saf. 2019 Jul 15;175:208-214. https://pubmed.ncbi.nlm.nih.gov/30901638/|
|In vivo activity:||After a 20-week 4-n-NP treatment orally at the dosage of 10 and 50 muM in the drinking water, phenylephrine- and potassium chloride-induced concentration-dependent responsiveness assessed by wire myograph were both significantly higher in aorta isolated from 4-n-NP-treated rats compared with control rats, but acetylcholine-induced vasorelaxation was similar between these two groups. In addition, systemic oxidative stress and vascular, but not intestinal, oxidant enzyme activities assessed by lucigenin-amplified chemiluminescence were all markedly higher in 4-n-NP-treated rats. In conclusion, the results suggested that chronic in vivo 4-n-NP exposure augments vascular contractile responsiveness through enhanced vascular oxidant enzyme activity. Reference: Arch Toxicol. 2009 Oct;83(10):941-6. https://pubmed.ncbi.nlm.nih.gov/19533100/|
The following data is based on the product molecular weight 220.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
|Formulation protocol:||1. Bonefeld-Jørgensen EC, Long M, Hofmeister MV, Vinggaard AM. Endocrine-disrupting potential of bisphenol A, bisphenol A dimethacrylate, 4-n-nonylphenol, and 4-n-octylphenol in vitro: new data and a brief review. Environ Health Perspect. 2007 Dec;115 Suppl 1(Suppl 1):69-76. doi: 10.1289/ehp.9368. PMID: 18174953; PMCID: PMC2174402. 2. Ji X, Li N, Yuan S, Zhou X, Ding F, Rao K, Ma M, Wang Z. A comparison of endocrine disruption potential of nonylphenol ethoxylate, vanillin ethoxylate, 4-n-nonylphenol and vanillin in vitro. Ecotoxicol Environ Saf. 2019 Jul 15;175:208-214. doi: 10.1016/j.ecoenv.2019.03.060. Epub 2019 Mar 19. PMID: 30901638. 3. . Zalko D, Costagliola R, Dorio C, Rathahao E, Cravedi JP. In vivo metabolic fate of the xeno-estrogen 4-n-nonylphenol in Wistar rats. Drug Metab Dispos. 2003 Feb;31(2):168-78. doi: 10.1124/dmd.31.2.168. PMID: 12527697. 4. Hsieh CY, Miaw CL, Hsieh CC, Tseng HC, Yang YH, Yen CH. Effects of chronic 4-n-nonylphenol treatment on aortic vasoconstriction and vasorelaxation in rats. Arch Toxicol. 2009 Oct;83(10):941-6. doi: 10.1007/s00204-009-0447-6. Epub 2009 Jun 17. PMID: 19533100.|
|In vitro protocol:||1. Bonefeld-Jørgensen EC, Long M, Hofmeister MV, Vinggaard AM. Endocrine-disrupting potential of bisphenol A, bisphenol A dimethacrylate, 4-n-nonylphenol, and 4-n-octylphenol in vitro: new data and a brief review. Environ Health Perspect. 2007 Dec;115 Suppl 1(Suppl 1):69-76. doi: 10.1289/ehp.9368. PMID: 18174953; PMCID: PMC2174402. 2. Ji X, Li N, Yuan S, Zhou X, Ding F, Rao K, Ma M, Wang Z. A comparison of endocrine disruption potential of nonylphenol ethoxylate, vanillin ethoxylate, 4-n-nonylphenol and vanillin in vitro. Ecotoxicol Environ Saf. 2019 Jul 15;175:208-214. doi: 10.1016/j.ecoenv.2019.03.060. Epub 2019 Mar 19. PMID: 30901638.|
|In vivo protocol:||1. Zalko D, Costagliola R, Dorio C, Rathahao E, Cravedi JP. In vivo metabolic fate of the xeno-estrogen 4-n-nonylphenol in Wistar rats. Drug Metab Dispos. 2003 Feb;31(2):168-78. doi: 10.1124/dmd.31.2.168. PMID: 12527697. 2. Hsieh CY, Miaw CL, Hsieh CC, Tseng HC, Yang YH, Yen CH. Effects of chronic 4-n-nonylphenol treatment on aortic vasoconstriction and vasorelaxation in rats. Arch Toxicol. 2009 Oct;83(10):941-6. doi: 10.1007/s00204-009-0447-6. Epub 2009 Jun 17. PMID: 19533100.|
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