Nonoxynols | CAS#26027-38-3 | detergents

MedKoo Cat#: 558582 | Name: Nonoxynols

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Description:

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

Nonoxynols is used as detergents, emulsifiers, wetting agents, defoaming agents, etc. Nonoxynol-9, the compound with 9 repeating ethoxy groups, is a spermatocide, formulated primarily as a component of vaginal foams and creams.

Chemical Structure

Nonoxynols

CAS#26027-38-3

Theoretical Analysis

MedKoo Cat#: 558582

Name: Nonoxynols

CAS#: 26027-38-3

Chemical Formula: C17H28O2

Exact Mass: 264.2089

Molecular Weight: 264.41

Elemental Analysis: C, 77.22; H, 10.67; O, 12.10

Price and Availability

Size	Price	Availability	Quantity
25g	USD 220.00

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Synonym

Nonoxynols; Conceptrol; Delfen; Egyptol; Emko;

IUPAC/Chemical Name

2-(4-nonylphenoxy)ethan-1-ol

InChi Key

KUXGUCNZFCVULO-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H28O2/c1-2-3-4-5-6-7-8-9-16-10-12-17(13-11-16)19-15-14-18/h10-13,18H,2-9,14-15H2,1H3

SMILES Code

OCCOc1ccc(CCCCCCCCC)cc1

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

Instruction

View handling instruction

Biological target:

4-Nonylphenol polyethoxylate is an organic compound that is a nonionic surfactant.

In vitro activity:

Using DNA microarray and quantitative RT-PCR techniques, this study observed that N-9 initiated a strong transcriptional upregulation of cyclooxygenase-2 (COX-2) in immortalized human vaginal epithelial cells (VK2/E6E7 cell line). Increased COX-2 protein expression evaluated by immunoblotting was dose- and time-dependent. Reference: Am J Reprod Immunol. 2011 Jun;65(6):569-77. https://pubmed.ncbi.nlm.nih.gov/21241401/

In vivo activity:

This study reports the development of a mouse model of cervicovaginal infection with HPV16 that recapitulates the establishment phase of papillomavirus infection. A widely used vaginal spermicide, nonoxynol-9 (N-9), greatly increased susceptibility to infection. Reference: Nat Med. 2007 Jul;13(7):857-61. https://pubmed.ncbi.nlm.nih.gov/17603495/

	Solvent	mg/mL	mM
Solubility
	DMSO	45.0	170.19
	Ethanol	50.0	189.10

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 264.41 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. Zalenskaya IA, Cerocchi OG, Joseph T, Donaghay MA, Schriver SD, Doncel GF. Increased COX-2 expression in human vaginal epithelial cells exposed to nonoxynol-9, a vaginal contraceptive microbicide that failed to protect women from HIV-1 infection. Am J Reprod Immunol. 2011 Jun;65(6):569-77. doi: 10.1111/j.1600-0897.2010.00964.x. Epub 2011 Jan 18. PMID: 21241401. 2. Jain JK, Li A, Nucatola DL, Minoo P, Felix JC. Nonoxynol-9 induces apoptosis of endometrial explants by both caspase-dependent and -independent apoptotic pathways. Biol Reprod. 2005 Aug;73(2):382-8. doi: 10.1095/biolreprod.104.037168. Epub 2005 Apr 13. PMID: 15829625. 3. Roberts JN, Buck CB, Thompson CD, Kines R, Bernardo M, Choyke PL, Lowy DR, Schiller JT. Genital transmission of HPV in a mouse model is potentiated by nonoxynol-9 and inhibited by carrageenan. Nat Med. 2007 Jul;13(7):857-61. doi: 10.1038/nm1598. Epub 2007 Jul 1. PMID: 17603495.

In vitro protocol:

In vivo protocol:

1. Roberts JN, Buck CB, Thompson CD, Kines R, Bernardo M, Choyke PL, Lowy DR, Schiller JT. Genital transmission of HPV in a mouse model is potentiated by nonoxynol-9 and inhibited by carrageenan. Nat Med. 2007 Jul;13(7):857-61. doi: 10.1038/nm1598. Epub 2007 Jul 1. PMID: 17603495.

1: Smith-McCune K, Chen JC, Greenblatt RM, Shanmugasundaram U, Shacklett BL, Hilton JF, Johnson B, Irwin JC, Giudice LC. Unexpected Inflammatory Effects of Intravaginal Gels (Universal Placebo Gel and Nonoxynol-9) on the Upper Female Reproductive Tract: A Randomized Crossover Study. PLoS One. 2015 Jul 15;10(7):e0129769. doi: 10.1371/journal.pone.0129769. eCollection 2015. PubMed PMID: 26177352; PubMed Central PMCID: PMC4503751. 2: Dooms-Goossens A, Deveylder H, de Alam AG, Lachapelle JM, Tennstedt D, Degreef H. Contact sensitivity to nonoxynols as a cause of intolerance to antiseptic preparations. J Am Acad Dermatol. 1989 Oct;21(4 Pt 1):723-7. PubMed PMID: 2553785. 3: Schwartz JL, Weiner DH, Lai JJ, Frezieres RG, Creinin MD, Archer DF, Bradley L, Barnhart KT, Poindexter A, Kilbourne-Brook M, Callahan MM, Mauck CK. Contraceptive efficacy, safety, fit, and acceptability of a single-size diaphragm developed with end-user input. Obstet Gynecol. 2015 Apr;125(4):895-903. doi: 10.1097/AOG.0000000000000721. PubMed PMID: 25751199. 4: Chhonker YS, Chandasana H, Bala V, Kumar L, Sharma VL, Gupta G, Bhatta RS. Quantitative determination of microbicidal spermicide 'nonoxynol-9' in rabbit plasma and vaginal fluid using LC-ESI-MS/MS: application to pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Aug 15;965:127-32. doi: 10.1016/j.jchromb.2014.06.019. Epub 2014 Jun 21. PubMed PMID: 25016165. 5: Fichorova RN, Mendonca K, Yamamoto HS, Murray R, Chandra N, Doncel GF. A quantitative multiplex nuclease protection assay reveals immunotoxicity gene expression profiles in the rabbit model for vaginal drug safety evaluation. Toxicol Appl Pharmacol. 2015 Jun 15;285(3):198-206. doi: 10.1016/j.taap.2015.02.017. Epub 2015 Mar 25. PubMed PMID: 25818602. 6: Rongxiu L, Guozheng L, Xiaoqun L, Huiyan T. Spermicidal and antifertility effects of an imbibing and soluble nonoxynol-9 diaphragm (ISND) in rabbits. Eur J Contracept Reprod Health Care. 2014 Dec;19(6):465-74. doi: 10.3109/13625187.2014.950729. Epub 2014 Aug 27. PubMed PMID: 25160062. 7: Park S, Hwang IW, Kim JS, Kang HC, Park SY, Gil HW, Song HY, Hong SY. The effects of nonyl phenoxypolyethoxyl ethanol on cell damage pathway gene expression in SK-NSH cells. Korean J Intern Med. 2015 Nov;30(6):873-83. doi: 10.3904/kjim.2015.30.6.873. Epub 2015 Oct 30. PubMed PMID: 26552463; PubMed Central PMCID: PMC4642017. 8: Chakraborty D, Maity A, Jha T, Mondal NB. Spermicidal and contraceptive potential of desgalactotigonin: a prospective alternative of nonoxynol-9. PLoS One. 2014 Sep 22;9(9):e107164. doi: 10.1371/journal.pone.0107164. eCollection 2014. PubMed PMID: 25243914; PubMed Central PMCID: PMC4171379. 9: Kyamwanga IT, Turyakira E, Kilbourne-Brook M, Coffey PS. Potential for revitalisation of the diaphragm for family planning in Uganda: a rapid assessment of the feasibility of introducing the SILCS Diaphragm. Afr J Reprod Health. 2014 Jun;18(2):77-86. PubMed PMID: 25022144. 10: Coleman JS, Fuchs E, Aung WS, Marzinke MA, Bakshi RP, Spiegel HML, Robinson J, Hendrix CW. Feasibility of radiolabeled small molecule permeability as a quantitative measure of microbicide candidate toxicity. Contraception. 2016 Apr;93(4):331-336. doi: 10.1016/j.contraception.2016.01.002. Epub 2016 Jan 6. PubMed PMID: 26772905; PubMed Central PMCID: PMC4783221. 11: Ensign LM, Lai SK, Wang YY, Yang M, Mert O, Hanes J, Cone R. Pretreatment of human cervicovaginal mucus with pluronic F127 enhances nanoparticle penetration without compromising mucus barrier properties to herpes simplex virus. Biomacromolecules. 2014 Dec 8;15(12):4403-9. doi: 10.1021/bm501419z. Epub 2014 Nov 11. PubMed PMID: 25347518; PubMed Central PMCID: PMC4261994. 12: Mirabelli MF, Chramow A, Cabral EC, Ifa DR. Analysis of sexual assault evidence by desorption electrospray ionization mass spectrometry. J Mass Spectrom. 2013 Jul;48(7):774-8. doi: 10.1002/jms.3205. PubMed PMID: 23832933. 13: Vincent KL, Vargas G, Wei J, Bourne N, Motamedi M. Monitoring vaginal epithelial thickness changes noninvasively in sheep using optical coherence tomography. Am J Obstet Gynecol. 2013 Apr;208(4):282.e1-7. doi: 10.1016/j.ajog.2013.01.025. Epub 2013 Jan 17. PubMed PMID: 23333551; PubMed Central PMCID: PMC3610851. 14: Mauck CK, Lai JJ, Weiner DH, Chandra N, Fichorova RN, Dezzutti CS, Hillier SL, Archer DF, Creinin MD, Schwartz JL, Callahan MM, Doncel GF. Toward early safety alert endpoints: exploring biomarkers suggestive of microbicide failure. AIDS Res Hum Retroviruses. 2013 Nov;29(11):1475-86. doi: 10.1089/AID.2012.0345. Epub 2013 Aug 30. PubMed PMID: 23885658. 15: Grimes DA, Lopez LM, Raymond EG, Halpern V, Nanda K, Schulz KF. Spermicide used alone for contraception. Cochrane Database Syst Rev. 2013 Dec 5;(12):CD005218. doi: 10.1002/14651858.CD005218.pub4. Review. PubMed PMID: 24307556. 16: Li W, Huang Z, Wu Y, Wang H, Zhou X, Xiao Z, Ding X, Xu J. Effectiveness of an optimized benzalkonium chloride gel as vaginal contraceptive: a randomized controlled trial among Chinese women. Contraception. 2013 Jun;87(6):756-65. doi: 10.1016/j.contraception.2012.09.012. Epub 2012 Oct 22. PubMed PMID: 23089047. 17: Musah RA, Vuong AL, Henck C, Shepard JR. Detection of the spermicide nonoxynol-9 via GC-MS. J Am Soc Mass Spectrom. 2012 May;23(5):996-9. doi: 10.1007/s13361-012-0353-7. Epub 2012 Feb 23. PubMed PMID: 22359093. 18: Mauck CK, Weiner DH, Lai JJ, Schwartz JL. Colposcopy: still useful in microbicide safety trials? Sex Transm Dis. 2012 Jun;39(6):465-9. doi: 10.1097/OLQ.0b013e3182500f33. PubMed PMID: 22592833. 19: Buyze J, Goetghebeur E. Crossover studies with survival outcomes. Stat Methods Med Res. 2013 Dec;22(6):612-29. doi: 10.1177/0962280211402258. Epub 2011 Jun 29. PubMed PMID: 21715438. 20: Michel M, Dompmartin A, Moreau A, Leroy D. Contact photosensitivity to nonoxynol used in antiseptic preparations. Photodermatol Photoimmunol Photomed. 1994 Oct;10(5):198-201. PubMed PMID: 7880758.