n-Nonylphenol | CAS#25154-52-3 | GPR30 agonist

MedKoo Cat#: 591913 | Name: 4-n-Nonylphenol

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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).

Chemical Structure

4-n-Nonylphenol

CAS#104-40-5 (4-n-Nonyl phenol)

Theoretical Analysis

MedKoo Cat#: 591913

Name: 4-n-Nonylphenol

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

Price and Availability

Size	Price	Availability
100mg	USD 90.00	Ready to ship
200mg	USD 150.00	Ready to ship
500mg	USD 250.00	Ready to ship
1g	USD 450.00	Ready to ship
2g	USD 750.00	Ready to ship

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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

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot# A21A10S06

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

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/

Preparing Stock Solutions

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:

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.

1: Fan X, Kubwabo C, Wu F, Rasmussen PE. Analysis of Bisphenol A, Alkylphenols, and Alkylphenol Ethoxylates in NIST SRM 2585 and Indoor House Dust by Gas Chromatography-Tandem Mass Spectrometry (GC/MS/MS). J AOAC Int. 2018 Jun 26. doi: 10.5740/jaoacint.18-0071. [Epub ahead of print] PubMed PMID: 29945692. 2: Nichols J, Fay K, Bernhard MJ, Bischof I, Davis J, Halder M, Hu J, Johanning K, Laue H, Nabb D, Schlechtriem C, Segner H, Swintek J, Weeks J, Embry M. Reliability of In Vitro Methods used to Measure Intrinsic Clearance of Hydrophobic Organic Chemicals by Rainbow Trout: Results of an International Ring Trial. Toxicol Sci. 2018 May 14. doi: 10.1093/toxsci/kfy113. [Epub ahead of print] PubMed PMID: 29767801. 3: Dong H, Zeng X, Bai W. Solid phase extraction with high polarity Carb/PSA as composite fillers prior to UPLC-MS/MS to determine six bisphenols and alkylphenols in trace level hotpot seasoning. Food Chem. 2018 Aug 30;258:206-213. doi: 10.1016/j.foodchem.2018.03.074. Epub 2018 Mar 19. PubMed PMID: 29655724. 4: Wang L, Kang Y, Liang S, Chen D, Zhang Q, Zeng L, Luo J, Jiang F. Synergistic effect of co-exposure to cadmium (II) and 4-n-nonylphenol on growth inhibition and oxidative stress of Chlorella sorokiniana. Ecotoxicol Environ Saf. 2018 Jun 15;154:145-153. doi: 10.1016/j.ecoenv.2018.02.039. Epub 2018 Feb 22. PubMed PMID: 29459164. 5: Li J, Jiang J, Pang SY, Zhou Y, Gao Y, Yang Y, Sun S, Liu G, Ma J, Jiang C, Wang L. Transformation of Methylparaben by aqueous permanganate in the presence of iodide: Kinetics, modeling, and formation of iodinated aromatic products. Water Res. 2018 May 15;135:75-84. doi: 10.1016/j.watres.2018.02.014. Epub 2018 Feb 10. PubMed PMID: 29454924. 6: Li J, Zhou Q, Wu Y, Yuan Y, Liu Y. Investigation of nanoscale zerovalent iron-based magnetic and thermal dual-responsive composite materials for the removal and detection of phenols. Chemosphere. 2018 Mar;195:472-482. doi: 10.1016/j.chemosphere.2017.12.093. Epub 2017 Dec 19. PubMed PMID: 29274993. 7: Holmes BE, Smeester L, Fry RC, Weinberg HS. Identification of endocrine active disinfection by-products (DBPs) that bind to the androgen receptor. Chemosphere. 2017 Nov;187:114-122. doi: 10.1016/j.chemosphere.2017.08.105. Epub 2017 Aug 22. PubMed PMID: 28843117. 8: Silvani L, Riccardi C, Eek E, Papini MP, Morin NAO, Cornelissen G, Oen AMP, Hale SE. Monitoring alkylphenols in water using the polar organic chemical integrative sampler (POCIS): Determining sampling rates via the extraction of PES membranes and Oasis beads. Chemosphere. 2017 Oct;184:1362-1371. doi: 10.1016/j.chemosphere.2017.06.083. Epub 2017 Jun 21. PubMed PMID: 28693101. 9: Liu L, Zhou X, Lu Y, Shan D, Xu B, He M, Shi H, Qian Y. Facile screening of potential xenoestrogens by an estrogen receptor-based reusable optical biosensor. Biosens Bioelectron. 2017 Nov 15;97:16-20. doi: 10.1016/j.bios.2017.05.026. Epub 2017 May 18. PubMed PMID: 28549265. 10: Křesinová Z, Linhartová L, Filipová A, Ezechiáš M, Mašín P, Cajthaml T. Biodegradation of endocrine disruptors in urban wastewater using Pleurotus ostreatus bioreactor. N Biotechnol. 2018 Jul 25;43:53-61. doi: 10.1016/j.nbt.2017.05.004. Epub 2017 May 11. PubMed PMID: 28502780. 11: Rajasärkkä J, Pernica M, Kuta J, Lašňák J, Šimek Z, Bláha L. Drinking water contaminants from epoxy resin-coated pipes: A field study. Water Res. 2016 Oct 15;103:133-140. doi: 10.1016/j.watres.2016.07.027. Epub 2016 Jul 15. PubMed PMID: 27448038. 12: Del Rio M, Palomino Cabello C, Gonzalez V, Maya F, Parra JB, Cerdà V, Turnes Palomino G. Metal Oxide Assisted Preparation of Core-Shell Beads with Dense Metal-Organic Framework Coatings for the Enhanced Extraction of Organic Pollutants. Chemistry. 2016 Aug 8;22(33):11770-7. doi: 10.1002/chem.201601329. Epub 2016 Jul 8. PubMed PMID: 27388932. 13: Hanson AM, Ickstadt AT, Marquart DJ, Kittilson JD, Sheridan MA. Environmental estrogens inhibit mRNA and functional expression of growth hormone receptors as well as growth hormone signaling pathways in vitro in rainbow trout (Oncorhynchus mykiss). Gen Comp Endocrinol. 2017 May 15;246:120-128. doi: 10.1016/j.ygcen.2016.07.002. Epub 2016 Jul 5. PubMed PMID: 27388662. 14: Jia Y, Su H, Wong YL, Chen X, Dominic Chan TW. Thermo-responsive polymer tethered metal-organic framework core-shell magnetic microspheres for magnetic solid-phase extraction of alkylphenols from environmental water samples. J Chromatogr A. 2016 Jul 22;1456:42-8. doi: 10.1016/j.chroma.2016.06.004. Epub 2016 Jun 4. PubMed PMID: 27318505. 15: Zhang Y, Liu Y, Dong H, Li X, Zhang D. The nonylphenol biodegradation study by estuary sediment-derived fungus Penicillium simplicissimum. Environ Sci Pollut Res Int. 2016 Aug;23(15):15122-32. doi: 10.1007/s11356-016-6656-7. Epub 2016 Apr 20. PubMed PMID: 27094271. 16: Kim BM, Lee MC, Kang HM, Rhee JS, Lee JS. Genomic organization and transcriptional modulation in response to endocrine disrupting chemicals of three vitellogenin genes in the self-fertilizing fish Kryptolebias marmoratus. J Environ Sci (China). 2016 Apr;42:187-195. doi: 10.1016/j.jes.2015.08.006. Epub 2015 Oct 1. PubMed PMID: 27090710. 17: Salgueiro-González N, Turnes-Carou I, Viñas L, Besada V, Muniategui-Lorenzo S, López-Mahía P, Prada-Rodríguez D. Occurrence of alkylphenols and bisphenol A in wild mussel samples from the Spanish Atlantic coast and Bay of Biscay. Mar Pollut Bull. 2016 May 15;106(1-2):360-5. doi: 10.1016/j.marpolbul.2016.03.003. Epub 2016 Mar 19. PubMed PMID: 27001713. 18: Xu LJ, Chu W, Lee PH, Wang J. The mechanism study of efficient degradation of hydrophobic nonylphenol in solution by a chemical-free technology of sonophotolysis. J Hazard Mater. 2016 May 5;308:386-93. doi: 10.1016/j.jhazmat.2016.01.075. Epub 2016 Feb 1. PubMed PMID: 26855185. 19: Takeshita J, Seki M, Kamo M. Criteria for deviation from predictions by the concentration addition model. Environ Toxicol Chem. 2016 Jul;35(7):1806-14. doi: 10.1002/etc.3334. Epub 2016 May 10. PubMed PMID: 26660330. 20: Wang X, Deng C. Preparation of C₁₈-functionalized magnetic polydopamine microspheres for the enrichment and analysis of alkylphenols in water samples. Talanta. 2016 Feb 1;148:387-92. doi: 10.1016/j.talanta.2015.11.008. Epub 2015 Nov 4. PubMed PMID: 26653464.

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