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NP-40
NP-40
NP-40
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NP-40
Names
Other names
Polyethylene glycol nonylphenyl ether; Nonyl phenoxypolyethoxylethanol; Nonoxynol-40
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 500-024-6
UNII
UN number 3082
  • InChI=1S/C19H32O3/c1-2-3-4-5-6-7-8-9-18-10-12-19(13-11-18)22-17-16-21-15-14-20/h10-13,20H,2-9,14-17H2,1H3
    Key: BLXVTZPGEOGTGG-UHFFFAOYSA-N
  • CCCCCCCCCC1=CC=C(C=C1)OCCOCCO
Properties
H(C2H4O)nO(C6H4)C9H19
Molar mass Variable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

NP-40 (also known as Tergitol-type NP-40 and nonyl phenoxypolyethoxylethanol[1]) is a commercially available detergent with CAS Registry Number 9016-45-9. NP-40 is an ethoxylated nonylphenol for non-ionic surfactants and can act as emulsifier and demulsifier agent.

NP-40 is often used to break open all membranes within a cell, including the nuclear membrane [citation needed]. To break only the cytoplasmic membrane, other detergents such as digitonin can be used.

NP-40 has applications in paper and textile processing, in paints and coatings, and in agrochemical manufacturing.

Care should be taken to avoid confusing NP-40 with Nonidet P-40 (octyl phenoxypolyethoxylethanol) which is currently out of production. Nonidet P-40 ("Non-Ionic Detergent") was originally manufactured and trademarked by the Shell Chemical Company,[2] but was phased out of production in the early 2000s. Confusingly, biochemical protocols published between the 1960s[3] and 2000s refer to Shell's Nonidet P-40 as NP-40. Shell's original Nonidet P-40 had a hydrophilic-lipophilic balance (HLB) value of 13.5,[4] as opposed to 12.9 for the currently available IGEPAL CA-630,[5] indicating that the currently available compound is more potent than the compound used in older publications. Indeed, according to a 2017 report,[6] an additional dilution factor of 10 was required for the currently available NP-40 ("Nonidet P-40 substitutes") to match the activity of the previously available, and now discontinued, Shell's Nonidet P-40.

See also

[edit]

References

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

NP-40

View on Grokipedia
from Grokipedia
NP-40 is a non-ionic, non-denaturing widely employed in biochemistry and for cell , solubilization, and extraction of cytoplasmic proteins while maintaining their native conformation. It functions as a mild that disrupts lipid-lipid and lipid-protein interactions without denaturing proteins, making it suitable for applications such as , subcellular fractionation, and proteomic studies. Originally produced by Shell Chemical Company under the trade name , this has been a staple in protocols for decades, though its manufacture was discontinued, leading to the adoption of chemically equivalent substitutes from other suppliers. Chemically, NP-40 belongs to the class of polyoxyethylene alkyl phenyl ethers, with an average molecular weight of approximately 603–617 Da and a structure consisting of a nonylphenyl (or equivalent octylphenyl in substitutes) hydrophobic tail linked to a polyoxyethylene hydrophilic chain of 9–10 ethylene oxide units (formula: C15H24O(C2H4O)n or C14H22O(C2H4O)n for substitutes). Key physical properties include a (CMC) of 0.05–0.29 mM, a of 80°C, an aggregation number of 149, and a (HLB) value of 13–14, which contribute to its effectiveness in aqueous buffers at concentrations typically ranging from 0.1% to 1% (v/v). These attributes allow NP-40 to form micelles that encapsulate hydrophobic regions of proteins, aiding in their isolation without interference from strong ionic interactions, unlike anionic detergents such as SDS. In practice, NP-40 is often included in lysis buffers for techniques requiring gentle extraction, such as the isolation of membrane-bound complexes or nuclear extracts, though it is less effective for membrane proteins compared to other non-ionic detergents like Triton X-100. Commercial formulations, such as 10% (w/v) solutions, are purified to minimize contaminants like aldehydes and oxidants, ensuring low background in downstream assays like or Western blotting. Due to environmental concerns over ethoxylates, modern substitutes are formulated to be eco-friendly while retaining equivalent performance in tubulin polymerization and other intracellular assays; as of 2025, restrictions on APEs in consumer products have been implemented in regions like and , prompting further development of non-APE alternatives for use.

Nomenclature and History

Definition and Synonyms

NP-40 is a non-ionic, non-denaturing primarily used for solubilizing proteins and in biochemical applications. It functions by disrupting lipid bilayers without denaturing proteins, making it suitable for maintaining the native structure of membrane-bound complexes during extraction and purification processes. Common synonyms for NP-40 include Nonidet P-40, which was the original trademarked product manufactured by Shell Chemical Company as octylphenoxypolyethoxyethanol, and IGEPAL CA-630, a chemically indistinguishable substitute also based on the octyl variant. TERGITOL NP-40 refers to the nonylphenoxypolyethoxyethanol variant, often used interchangeably in similar applications. The CAS number for the octyl variant (IGEPAL CA-630 and original Nonidet P-40) is 9002-93-1, while the nonyl variant (TERGITOL NP-40 and NP-40 alternatives) is 9016-45-9. Following the discontinuation of Shell's , the term "NP-40" has become a generic designation applied to these ethoxylated alkylphenols, leading to interchangeable usage across octyl and nonyl formulations in settings. This nomenclature shift arose from the need for substitutes that replicate the original product's performance in non-denaturing conditions.

Development and Commercial Availability

NP-40, originally marketed as , was developed by Shell Chemical Company in the mid-1950s as a non-ionic primarily for industrial applications such as emulsification and detergency. The product, consisting of octylphenoxypolyethoxyethanol, gained widespread use due to its mild, non-denaturing properties, with initial production focused on sectors like and processing. By the , it had become a standard in various formulations, supported by Shell's patents on ethoxylate technologies around that era. Shell discontinued production of Nonidet P-40 in the early 2000s, shifting focus away from alkylphenol ethoxylates amid changing manufacturing priorities and emerging regulatory pressures. This phase-out prompted other manufacturers to produce generic versions under the NP-40 label, including Rhodia's IGEPAL CA-630 and Dow Chemical's TERGITOL NP-series, which are chemically equivalent substitutes. European Union restrictions on related alkylphenol ethoxylates, beginning in the early 2000s with limits on nonylphenol variants and extending to octylphenol types by the mid-decade, further influenced the market transition to alternatives. Today, NP-40 remains commercially available as purified, sterile solutions, typically at concentrations like 10% w/v or 70% in water, supplied by laboratory reagent providers such as (under TERGITOL™ NP-40) and (as NP-40 alternatives). These products are positioned as direct replacements for the original Shell formulation, ensuring compatibility in research and industrial protocols while adhering to modern purity standards.

Chemical Properties

Molecular Structure

NP-40 is a nonionic surfactant classified as an alkylphenol ethoxylate, featuring a hydrophobic alkyl-substituted phenyl core linked to a hydrophilic chain of ethylene oxide units, which confers amphipathic properties essential for its function as a detergent. The original formulation has the general chemical formula C8H17C6H4(OCH2CH2)nOHC_8H_{17}C_6H_4(OCH_2CH_2)_nOH, where n≈9−10n \approx 9-10 (with an average of 9.5 ethoxy units). A nonyl variant, often used as a substitute (e.g., Tergitol NP-40), possesses the formula C9H19C6H4(OCH2CH2)nOHC_9H_{19}C_6H_4(OCH_2CH_2)_nOH, also with n≈9−10n \approx 9-10. This structure yields a (HLB) value of approximately 13-14 for both variants, reflecting moderate hydrophilicity suitable for emulsification. The molecular weight ranges from 600 to 650 g/mol, varying with the extent of ; for instance, the original octyl variant with nine ethoxy units has a molecular weight of approximately 603 g/mol. The non-ionic nature of NP-40, arising from the linkages in the chain, contributes to its non-denaturing effects on proteins in settings.

Physical and Chemical Characteristics

NP-40 is typically a clear, at . Certain commercial formulations, such as Tergitol NP-40, are supplied as a 70% that may solidify below approximately 2°C and requires gentle heating to restore liquidity. It exhibits high solubility in water, forming solutions exceeding 10% w/v, and is compatible with most polar organic solvents such as alcohols and chlorinated hydrocarbons, but shows limited in non-polar solvents like hydrocarbons. The (CMC) of NP-40 is approximately 0.02–0.3 mM at 25°C, varying slightly with the specific and temperature, which marks the threshold for formation driven by its amphipathic structure. In a 1% aqueous solution, NP-40 maintains a neutral to slightly alkaline of 6–8 and demonstrates stability across a range of 4–10, resisting degradation under these conditions. Its is approximately 1.06 g/mL at 20°C, with a exceeding 200°C for the pure and non-flammable behavior under standard laboratory conditions. NP-40 effectively reduces , achieving around 50 dynes/cm in a 1% solution at 25°C compared to water's 72 dynes/cm, facilitating emulsification and wetting in various systems. Key properties include a of approximately 80°C and an aggregation number of 149, which influence its behavior in aqueous environments.

Biological and Laboratory Applications

Role in Cell Lysis and Protein Extraction

NP-40, a non-ionic , plays a key role in cell lysis by disrupting plasma membranes to facilitate the extraction of intracellular proteins, particularly from mammalian cells, while maintaining their native structure. Its mechanism involves the formation of micelles above its (approximately 0.0179% w/v), which incorporate and solubilize membrane lipids and associated proteins, enabling the release of cytoplasmic contents and the isolation of integral membrane proteins without disrupting their folding or function. In practice, NP-40 is typically employed at concentrations of 0.1-1% for selective , where it effectively permeabilizes the plasma membrane while leaving nuclear and membranes intact, allowing of soluble proteins. For more comprehensive total cell , including disruption of nuclear membranes, concentrations of 1-2% are used, often in combination with mechanical or enzymatic aids to enhance efficiency. This approach is particularly advantageous over ionic detergents like SDS, as NP-40 preserves protein-protein interactions and enzymatic activities essential for downstream functional assays, reducing denaturation and maintaining biological relevance. Specific applications include the isolation of membrane-bound receptors, such as from viral envelopes, where NP-40 solubilizes lipid bilayers to yield functional protein complexes. It is also routinely used in assays to extract and capture interacting proteins from cell lysates, leveraging its mild nature to retain native complexes for analysis. However, NP-40 is less effective against the rigid layer of bacterial cell walls, often requiring combination with agents like or mechanical disruption for efficient in prokaryotic systems.

Use in Specific Buffers and Protocols

NP-40 is a key component in radio assay (RIPA) buffer, typically formulated at 1% concentration alongside 1% sodium deoxycholate and 0.1% SDS in a base of 50 mM Tris-HCl (pH 7.4–8.0), 150 mM NaCl, and 1 mM EDTA, enabling efficient extraction of whole-cell proteins including cytoplasmic, membrane-bound, and some nuclear fractions under mildly denaturing conditions. This composition disrupts cell membranes while preserving protein-antibody interactions for downstream applications like and Western blotting. A standard protocol for NP-40-based lysis begins with harvesting cells by at 500 × g for 5 minutes at , followed by resuspension in ice-cold 1× (such as RIPA or NP-40 buffer) supplemented with inhibitors at a ratio of 1 mL per 10^7 cells. The suspension is then incubated for 30 minutes on ice with gentle vortexing every 10 minutes to allow complete , after which it is at 13,000 × g for 10–15 minutes at to pellet debris and collect the supernatant containing solubilized proteins. This process is performed at throughout to minimize protein degradation and maintain enzymatic activity. In nuclear extraction protocols like NE-PER, NP-40 is used at a lower concentration of approximately 0.075–0.1% in the cytoplasmic extraction buffer (e.g., with 10 mM pH 7.6, 60 mM KCl, and 1 mM EDTA) to selectively release cytoplasmic proteins while leaving nuclei intact for subsequent isolation. For mammalian cells, NP-40 buffers are typically applied directly after or scraping, whereas plant cell protocols incorporate mechanical grinding or enzymatic pretreatment (e.g., with ) before adding the buffer to overcome rigid cell walls, often using similar 1% NP-40 formulations adapted for tissue homogenization. Concentrations of NP-40 in protocols vary by application; for gentle solubilization in preparation, 0.5% NP-40 in a Tris-based buffer suffices to extract proteins without excessive denaturation, while 1% is standard for robust whole-cell . at 4°C during incubation and is critical to preserve protein integrity and prevent aggregation. NP-40 has been a standard in radioimmunoprecipitation assays since the , where its inclusion in RIPA buffer facilitated the solubilization of radiolabeled cellular proteins for immunoprecipitation studies.

Industrial and Other Applications

Cleaning and Surfactant Uses

NP-40, known chemically as an octylphenol ethoxylate with approximately 9-10 units, functions as a nonionic with strong and emulsifying capabilities. By reducing the surface tension of aqueous solutions to around 31 mN/m, it promotes rapid penetration and spreading on hard surfaces, making it suitable for degreasers and cleaners that target oily residues. Its hydrophilic-lipophilic balance (HLB) value of 13 supports stable emulsion formation, aiding in the dispersion of hydrophobic contaminants in water-based formulations. This low (CMC) of about 177 ppm allows efficient performance without excessive foaming in controlled-foam applications. In household and laboratory cleaning, NP-40 is formulated into detergents for removing oils, greases, and proteinaceous soils from glassware, , and surfaces, often at concentrations of 0.1-5% to balance efficacy and cost. For instance, it appears in industrial metal cleaners, floor polishes, and hard-surface sprays, where it enhances soil removal in soak, spray, or steam-cleaning systems without leaving residues that interfere with subsequent processes. In laboratory contexts, dilute solutions (around 1%) effectively clean laboratory ware by emulsifying and facilitating rinsing. Within the textile and paper industries, NP-40 serves as a agent in aqueous steps, such as , scouring, and pulp treatment, where it improves dye penetration and uniform distribution by lowering interfacial tension between fibers and liquids. In applications, it aids in the emulsification of oils during finishing, typically at 1-2% in baths to ensure even without affecting fabric integrity. For production, it facilitates pulp dispersion and coating adhesion, contributing to smoother and reduced defects. Spray cleaners for industrial maintenance often incorporate 1-2% NP-40 to provide quick and emulsification of contaminants on machinery.

Agrochemical and Oilfield Applications

In agrochemical applications, NP-40 serves as a nonionic functioning primarily as a agent and spreader in formulations, facilitating uniform distribution and enhanced of active ingredients to plant surfaces such as leaves and stems. This role is critical for improving the efficacy of herbicides, insecticides, and fungicides by reducing and promoting better coverage, with typical use rates in tank mixes ranging from 0.125% to 0.25% by volume to achieve effective formation without excessive foaming. Its HLB value of approximately 13 makes it suitable for water-based dispersions, where it aids in the solubilization and stability of hydrophobic pesticides. In the oilfield sector, NP-40 is employed to emulsify oil-water mixtures in fluids, helping to stabilize suspensions and reduce friction during operations. It also contributes to (EOR) processes, particularly in EOR systems under high-salinity conditions, where ethoxylates lower interfacial tension between oil and water phases to mobilize residual hydrocarbons. Although NP-40 exhibits biodegradability under aerobic conditions in standard tests, its degradation products, such as octylphenol, raise environmental concerns due to persistence and endocrine-disrupting potential. As a result, its use in and oilfield applications is increasingly restricted under regulations like EU REACH (as of 2021) and EPA guidelines, promoting eco-friendly alternatives to minimize long-term environmental impact.

Safety and Regulatory Aspects

Health and Handling Precautions

NP-40, a non-ionic surfactant, presents low via oral exposure, with an LD50 value ranging from 1,900 to 5,000 mg/kg in rats, classifying it as under GHS Category 4. Dermal exposure shows low toxicity, with an LD50 exceeding 3,000 mg/kg in rabbits. It acts as a mild irritant to (GHS Category 2), potentially causing redness and discomfort upon contact, and is classified as causing serious eye damage (GHS Category 1), leading to severe , , and possible corneal injury. Inhalation of vapors or mists may irritate the , with an LC50 of 1.15 mg/L in rats over 4 hours, classifying it as harmful if inhaled (GHS Category 4). Available toxicological data do not indicate carcinogenicity, mutagenicity, or for NP-40, though specific studies are limited. Safe handling of NP-40 in laboratory and industrial settings requires , including gloves (with breakthrough time of at least 480 minutes), tightly fitting safety goggles, and protective clothing to prevent skin and eye contact. Adequate ventilation is essential to minimize inhalation risks, and respiratory protection such as an ABEK filter mask should be used if vapors or aerosols are generated. The material should be stored in tightly closed containers at (typically 15–30°C) in a dry, well-ventilated area, away from strong oxidizers, acids, or bases to prevent incompatible reactions. As a non-ionic surfactant, NP-40 exhibits lower reactivity risks compared to ionic counterparts, reducing hazards from chemical interactions under normal conditions. In the event of exposure, first aid measures include immediately rinsing skin or eyes with copious amounts of water for at least 15 minutes while removing contaminated clothing or contact lenses; attention is advised for persistent irritation or eye exposure. For inhalation, move the affected individual to fresh air and provide oxygen if breathing is difficult, seeking professional evaluation. If ingested, rinse the mouth, do not induce vomiting, and consult a physician promptly, as aspiration into the lungs poses a risk. NP-40 is non-flammable with a above 93°C (typically 110–251°C depending on ), but it should not be mixed with strong acids or bases to avoid potential exothermic reactions or . Safety Data Sheets emphasize good industrial hygiene practices, such as washing hands after handling and prohibiting eating, drinking, or smoking in work areas.

Environmental Impact and Regulations

NP-40, an octylphenol ethoxylate , undergoes biodegradation in environmental matrices primarily through microbial action, yielding octylphenol (OP) as a key intermediate product. This degradation process is often incomplete under aerobic conditions in plants and natural waters, leading to the persistence of OP, which acts as an affecting reproductive processes in aquatic organisms. OP exhibits low biodegradability and high hydrophobicity, with a log Kow value of approximately 4.5, facilitating its accumulation in sediments and biota. The ecotoxicity of NP-40 and its degradation products is pronounced in aquatic ecosystems, particularly impacting and . Acute toxicity tests report LC50 values ranging from 1 to 10 mg/L for non-ionic like NP-40 across various , including , daphnids, and . Chronic exposure to OP disrupts endocrine functions, such as vitellogenin induction in male , and contributes to declines in sensitive aquatic communities. Furthermore, OP bioaccumulates in aquatic food chains due to its lipophilic nature, with concentrations magnifying from water to and higher trophic levels like . Regulatory frameworks worldwide address the environmental risks posed by ethoxylates, including octylphenol ethoxylates (OPEs), through restrictions targeting their release into aquatic environments. In the , OPEs are listed as substances of very high concern (SVHC) under REACH Annex XIV, requiring authorization for use after the sunset date of January 4, 2021; exemptions apply to scientific , product development, and in vitro diagnostics as of November 2025. The U.S. Environmental Protection Agency (EPA) classifies and their ethoxylates as chemicals of high concern, with action plans and significant new use rules implemented since 2010 to phase out uses leading to environmental release, while allowing controlled industrial and laboratory applications. Globally, bans on APEs in laundry detergents have been enacted in regions like the (since 2013 for certain formulations) and other areas, driven by concerns over wastewater effluent. Laboratory use of NP-40 remains permitted under these regimes, but stringent waste disposal protocols are mandated to mitigate environmental release. In the U.S. and EU, lab-generated NP-40 waste is classified as hazardous and must be collected for or specialized treatment rather than discharged to drains or sewers, in compliance with local resource conservation and recovery acts. To address persistence issues, regulatory bodies and industry promote readily biodegradable variants, though octylphenol-based forms like NP-40 are deemed environmentally problematic due to the persistence of their phenolic byproducts.

Alternatives and Comparisons

Common Substitutes

NP-40, a non-ionic historically used in biochemical applications, has prompted the adoption of several alternatives due to its original discontinuation by the manufacturer. is a widely used substitute for NP-40, featuring a similar as an octylphenol ethoxylate with approximately 9-10 units in its polyoxyethylene chain. However, as of 2025, Triton X-100 faces phase-out under EU REACH regulations (sunset date September 2025) and similar environmental restrictions globally due to its degradation into endocrine-disrupting compounds, prompting further shifts to eco-friendly options. This non-ionic detergent maintains a comparable (CMC) to NP-40, around 0.24 mM, making it suitable for membrane solubilization tasks. Triton X-100 is commercially available from major suppliers such as and . Tween 20 and Tween 80, known as polysorbates, serve as milder non-ionic alternatives based on structures ethoxylated with polyoxyethylene chains. Tween 20, or polyoxyethylene monolaurate (molecular weight 1228), has a CMC of 0.06 mM, while Tween 80, or polyoxyethylene monooleate (molecular weight 1310), exhibits a lower CMC of 0.01 mM. These are less aggressive for solubilization compared to NP-40 but are effective in protein extraction protocols. Both are readily available from suppliers including and . Brij-35 acts as an alkyl chain variant substitute, consisting of polyoxyethylene lauryl ether with a lauryl (C12) hydrophobic tail and 23 units (molecular formula C12H26O(CH2CH2O)23, molecular weight approximately 1225). Its CMC is 0.09 mM, and it lacks the phenolic component of NP-40, potentially reducing environmental concerns. Brij-35 is used in and protein isolation and is commercially supplied by companies like and Anatrace. With Triton's phase-out, Brij-35 and similar alcohol ethoxylates are gaining prominence as biodegradable alternatives. n-Dodecyl-β-D-maltoside (DDM) represents a glycoside-based non-ionic alternative, featuring a dodecyl (C12) alkyl chain attached to a β-D-maltoside hydrophilic head. With a CMC of approximately 0.17 mM, it is employed for specialized protein solubilization, particularly in studies. DDM is available from suppliers such as GoldBio and , often labeled for proteomic applications. Its superior biodegradability makes it a preferred option amid regulatory pressures on ethoxylates. All these substitutes are commercially accessible from reputable laboratory suppliers like and , frequently marketed explicitly as NP-40 alternatives.

Performance Differences

NP-40 and exhibit comparable lysis efficiency for mammalian cells, both effectively solubilizing plasma membranes in buffers like RIPA at concentrations around 1%, though subtle differences in protein recovery have been noted in some protocols where NP-40 yields marginally higher amounts of certain membrane-bound proteins. In contrast, Tween-20 is generally less effective for robust membrane disruption due to its higher and milder action, often requiring combination with other agents for complete cell . For plant cells, which possess rigid cell walls, both NP-40 and are typically supplemented with mechanical or enzymatic methods, but is frequently favored in protocols for its slightly better penetration in fibrous tissues. Regarding environmental profiles, NP-40 and face restrictions due to their classification as alkylphenol ethoxylates, which degrade slowly into persistent endocrine-disrupting compounds like and octylphenol, posing risks to aquatic life. As of 2025, Triton's regulatory phase-out in the and elsewhere has accelerated adoption of greener options. In comparison, Brij-35 and n-dodecyl-β-D-maltoside (DDM) offer superior biodegradability as alcohol ethoxylates and glycoside-based , respectively, breaking down more readily under aerobic conditions without forming toxic byproducts. NP-40 was historically cheaper and more widely available than , but its phase-out in many regions due to regulatory pressures has reversed this advantage, making alternatives like Brij-35 more cost-competitive for routine use. requires dark storage to prevent UV-induced formation and degradation, whereas NP-40 and DDM show greater stability under ambient light. In specific applications, 1% NP-40 in RIPA buffer is largely interchangeable with , though NP-40 may provide slightly higher protein recovery in assays for cytoplasmic extracts. DDM is preferred for due to its low interference with formation and maintenance of native protein conformations.
DetergentCMC (mM)HLBLysis Strength (Relative)
NP-400.05–0.2913.0Mild (mammalian membranes)
0.2313.5Mild (similar to NP-40)
Brij-350.0916.9Mild (gentler)
DDM0.1715.6Mild (s)
Tween-200.05916.7Very mild (less disruptive)

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  58. https://www.goldbio.com/products/n-dodecyl-b-d-maltoside-ddm
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  65. https://www.mdpi.com/2073-4352/7/7/197
  66. https://www.aatbio.com/resources/biological-detergents-properties-and-applications/nonidet-p-40-substitute
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