Nonaethylene Glycol Nonylphenyl Ether

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Cat Number

API0232282

CAS Number

26571-11-9

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Product Detail Description Scientific Support Customer Q&A

CAS Number

26571-11-9

EINECS

247-816-5

Storage

Store at room temperature

Synonyms

Nonoxynol-9; Delfen; NONOXINOL 9; Nonoxinolum 9

Molecular Formula

C33H60O10

Molecular Weight

616.8

Smiles

CCCCCCCCCC1=CC=C(C=C1)OCCOCCOCCOCCOCCOCCOCCOCCOCCO

General Description

Nonaethylene glycol nonylphenyl ether is a non-ionic surfactant belonging to the class of alkylphenol ethoxylates, with a hydrophobic nonylphenyl group and a hydrophilic polyethylene glycol chain containing nine ethylene oxide units. Its chemical structure is C₉H₁₉C₆H₄O(CH₂CH₂O)₉H. The compound is a clear to slightly hazy liquid, miscible with water and organic solvents. It is also known as Nonoxynol-9.

Mechanism of Action

Nonoxynol-9 acts as a surfactant by disrupting the lipid membrane of spermatozoa and certain microorganisms, leading to cell lysis and immobilization. It also inactivates the envelope of viruses, such as HIV, by disrupting the lipid bilayer. The spermicidal activity is concentration-dependent, with higher concentrations providing greater efficacy. The compound has no systemic absorption and acts locally at the site of application.

Application

Nonoxynol-9 is indicated as a vaginal spermicide for the prevention of pregnancy, used as a topical contraceptive. It is also used as a lubricant and as a preservative in various pharmaceutical and cosmetic products. The compound is effective in reducing the risk of pregnancy when used alone or with barrier methods.

In a randomized noninferiority trial comparing the spermicide C31G gel with nonoxynol-9, 932 women received C31G and 633 received nonoxynol-9. Six-month pregnancy probabilities were identical (12.0%) in both groups, establishing noninferiority. Twelve-month probabilities were 13.8% for C31G versus 19.8% for nonoxynol-9. No serious adverse events occurred in the C31G group. Three-quarters of users in both groups reported liking the product. C31G provides a new marketable option for spermicidal contraception.

Fig. 1 Cumulative probability of pregnancy over time among users of C31G and Conceptrol® (Kaplan-Meier method) in the modified intent-to-treat (MITT) group. (Burke AE, et al., 2010)

References

Burke AE, et al. Contraceptive efficacy, acceptability, and safety of C31G and nonoxynol-9 spermicidal gels: a randomized controlled trial. Obstet Gynecol. 2010;116(6):1265-1273.

Does Nonaethylene Glycol Nonylphenyl Ether require protection from light and oxidation during storage?

Yes, as a surfactant with ether linkages, it is susceptible to peroxide formation and photodegradation. Store in airtight, light‑resistant containers under inert gas (nitrogen) at controlled room temperature (15–25°C).

What is the recommended storage temperature for Nonaethylene Glycol Nonylphenyl Ether?

Store at controlled room temperature (15–25°C). Avoid excessive heat above 30°C, which can accelerate oxidation and formation of degradation products.

Is Nonaethylene Glycol Nonylphenyl Ether stable in liquid formulations for pharmaceutical use?

Formulated solutions are stable when protected from light and stored at room temperature.

How is the peroxide impurity (an oxidation product) monitored in Nonaethylene Glycol Nonylphenyl Ether?

Peroxide value is measured using a validated titrimetric method, ensuring it remains within pharmaceutical or cosmetic specifications.