Nonylphenol

log Kow = 5.71 (average of 3 isomers)

5.76

0.9494 at 77 °F (USCG, 1999) - Less dense than water; will float

0.950 at 20 °C/4 °C

0.950 @ 20°C

Pale-yellow, viscous liquid

Clear, straw colored

Colorless

In water, 4.90 mg/L at 25 °C

In water, 6.35 mg/L at 25 °C

Practically insoluble in dilute aqueous sodium hydroxide. Soluble in benzene, chlorinated solvents, aniline, heptane, aliphatic alcohols, ethylene glycol.

Soluble in most organic solvents

285 °F (USCG, 1999)

285 °F

285 °F (141 °C)(closed cup)

300 °F (Open cup)

579 °F at 760 mmHg (USCG, 1999)

293-297 °C

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P264, P270, P273, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P318, P321, P330, P363, P391, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.1% (2 of 1869) of reports.

Danger

H302 (99.8%): Harmful if swallowed [Warning Acute toxicity, oral]

Chemical: Phenol, nonyl-

Hazard Traits - Bioaccumulation; Endocrine Toxicity; Environmental tox

Phenol, nonyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, nonyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

SP - indicates a substance that is identified in a proposed Significant New Use Rule.

Restricted substance: Nonylphenol C6H4(OH)C9H19

Substance: Nonylphenol

Corrosive to skin; [Quick CPC] High inhalation exposure may cause respiratory tract irritation; [ICSC] A technical mixture of monoalkyl phenols (primarily para substituted) whose side chains are isomeric branched-alkyl radicals; [Merck Index] Short-term exposure to skin causes first-degree burns; [CHRIS] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Harmful by ingestion; [Aldrich MSDS]

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 3/29/96; Reporting date: 5/29/96.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Nonylphenol (mixed isomers) is included on this list. Effective date: 3/29/96; Sunset date: 6/30/98.

NONYLPHENOL behaves as a very weak organic acid. Incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Likely to react exothermically with concentrated sulfuric acid and nitric acid.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Nonylphenol is produced, as an intermediate or a final product, by process units covered under this subpart.

Alcohol foam, dry chemical, or carbon dioxide. Water or foam may cause frothing. Cool exposed containers with water.

If material on fire or involved in fire: Use dry chemical or carbon dioxide. Do not use water on material itself. If large quantities of combustibles are involved, use water in flooding quantities as spray and fog. Use water spray to knock-down vapors. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.

Environmental considerations - water spill: Neutralize with agricultural lime (CaO), crushed limestone (CaCO3), or sodium bicarbonate (NaHCO3). If dissolved, in region of 10 ppm of greater concentration, apply activated carbon at ten times the spilled amount. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.

Environmental considerations - land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash or cement powder. Neutralize with agricultural lime (CaO), crushed limestone (CaCO3) or sodium bicarbonate (NaHCO3).

Environmental considerations - air spill: Apply water spray or mist to knock down vapors.

Accidental Release Measures. Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Spray into incinerator or burn in paper packaging. Additional flammable solvent may be added.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. Do not use water on material itself. Neutralize spilled material with crushed limestone, soda ash, or lime.

Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. If contact with the material anticipated, wear appropriate chemical protective clothing.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

0.19 [mg/m3]

2.1 [mg/m3]

13 [mg/m3]

Rubber gloves and splash-proof goggles. (USCG, 1999)

Rubber gloves and splash-proof goggles.

Wear skin protection and self-contained breathing apparatus.

Skin protection: Handle with gloves.

Eye/face protection: Tightly fitting safety goggles. Faceshield (8-inch minimum). Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

For more Personal Protective Equipment (PPE) (Complete) data for NONYLPHENOL (6 total), please visit the HSDB record page.

Nonylphenol has been detected in human breast milk, blood, and urine(1). Breast milk from German women contained nonylphenol levels of 0.3 ug/kg(2). Adipose tissues collected from surgeries in Italy between 2005 and 2007 contained nonylphenol concentrations of 10-226 ng/g with a mean concentration of 122 ng/g(3).

The aim of this study was to assess the toxicological risks arising from the coexistence of polyethylene glycol coated single-walled carbon nanotubes (SWCNTs-PEG) and a known environmental contaminant: 4-nonylphenol (NP). To this end, in vitro toxicity assays involving the exposure of 3T3-L1 cells (mouse embryonic fibroblasts) to SWCNTs-PEG alone or in combination with NP for 24 or 48 h were performed. Experimental treatments were conducted in both presence (10%) and absence of serum in order to evaluate its influence on the toxicity of SWCNTs-PEG. Although the results provided no unambiguous evidences of synergistic toxicity between SWCNTs-PEG and NP, some specific treatments with mixtures (SWCNTs-PEG+NP) resulted in an unexpected combined toxicity in relation to the individual treatments. Only in those cases the interaction between SWCNTs-PEG and NP could have a synergistic effect on the resulting toxicity. The addition of 10% serum increased the stability of SWCNTs-PEG in the culture medium-possibly by steric repulsions-and reduced the toxicity of nanoparticles as a result. Overall, the serum had a "protective effect" on cells against all treatments: SWCNTs-PEG, NP or their mixtures (SWCNTs-PEG+NP). Raman spectroscopy allowed the intracellular distribution of SWCNTs-PEG to be elucidated.

This study investigated the effects that 4-nonylphenol (NP) has on CYP1A1 expression in Hepa-1c1c7 cell cultures. NP alone did not affect CYP1A1-specific 7-ethoxyresorufin-O-deethylase (EROD) activity. In contrast, the 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)-inducible EROD activities were markedly reduced upon concomitant treatment with TCDD and NP in a dose-dependent manner. Treatment with tamoxifen, an anti-estrogen that acts through the estrogen receptor, did not affect the suppressive effects that NP has on TCDD-inducible EROD activity. The TCDD-inducible CYP1A1 mRNA levels were markedly suppressed upon concomitant treatment with TCDD and NP that is consistent with their effects on EROD activity. A transient transfection assay using dioxin-response element (DRE)-linked luciferase and an electrophoretic mobility shift assay revealed that NP reduced the transformation of the aryl hydrocarbon (Ah) receptor to a form capable of binding specifically to the DRE sequence of the CYP1A1 gene promoter. These results suggest that the down-regulation of CYP1A1 gene expression by NP in Hepa-1c1c7 cells might be an antagonism of the DRE-binding potential of the nuclear Ah receptor, but is not mediated through the estradiol receptor.

LC50; Species: Pimephales promelas (fathead minnow) weight 220 mg; Conditions: flow-through bioassay, dissolved oxygen 7.4 (4.6-8.8) mg/L, water hardness 44.9 (42.4-46.6) mg/L as calcium carbonate, pH 6.9-7.7, alkalinity 42.9 (39.6-61.4) mg/L calcium carbonate, temp: 26.4 + or - 1.4 °C; Concentration: 0.164 (0.145-0.186) mg/L for 48 hr /Purity 91% 4-nonylphenol, 4% 2-nonylphenol, 2% nonylphenol/

LC50; Species: Pimephales promelas (fathead minnow) weight 220 mg; Conditions: flow-through bioassay, dissolved oxygen 7.4 (4.6-8.8) mg/L, water hardness 44.9 (42.4-46.6) mg/L as calcium carbonate, pH 6.9-7.7, alkalinity 42.9 (39.6-61.4) mg/L calcium carbonate, temp: 26.4 + or - 1.4 °C; Concentration: 0.137 (0.34-0.140) mg/L for 72 hr /Purity 91% 4-nonylphenol, 4% 2-nonylphenol, 2% nonylphenol/

LC50; Species: Pimephales promelas (fathead minnow) weight 220 mg; Conditions: flow-through bioassay, dissolved oxygen 7.4 (4.6-8.8) mg/L, water hardness 44.9 (42.4-46.6) mg/L as calcium carbonate, pH 6.9-7.7, alkalinity 42.9 (39.6-61.4) mg/L calcium carbonate, temp: 26.4 + or - 1.4 °C; Concentration: 0.135 (0.098-0.187) mg/L for 96 hr /Purity 91% 4-nonylphenol, 4% 2-nonylphenol, 2% nonylphenol/

LC50; Species: Bay Mussel; Concentration: 3.0 mg/L for 96 hr /Conditions of bioassay not specified/

For more Ecotoxicity Values (Complete) data for NONYLPHENOL (14 total), please visit the HSDB record page.

TERRESTRIAL FATE: Nonylphenol is a mixture of isomeric monoalkyl phenols, predominately para substituted with a nine-carbon chain(1). Based on a classification scheme(2), a measured Koc range of 10,000 to 50,000 in a variety of soils(3,4), indicates that nonylphenol is expected to be immobile in soil(SRC). Volatilization of nonylphenol from moist soil surfaces is expected to occur given an estimated Henry's Law constant of 5.6X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 9.4X10-5 mm Hg(5), and water solubility, 4.9 mg/L(6). However, adsorption to soil is expected to attenuate volatilization(SRC). Nonylphenol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(5). Acclimation and lag periods can be important factors in biodegradation rates(7,8). Most dissipation studies of nonylphenol in soil found primary degradation half-lives of 2.1-51 days(7). Results of photolysis tests in water(9) suggest that some photodegradation of nonylphenol may occur on soil surfaces exposed to sunlight(SRC).

AQUATIC FATE: Nonylphenol is a mixture of isomeric monoalkyl phenols, predominately para substituted with a nine-carbon chain(1). Based on a classification scheme(2), measured Koc range of 6.91X10+4 to 3.98X10+5 for suspended material and sediment(3), indicates that nonylphenol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 5.6X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 9.4X10-5 mm Hg(5), and water solubility, 4.9 mg/L(6). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 10 and 77 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is about 10 years if adsorption is considered(7). According to a classification scheme(8), BCFs ranging from 87-1250(9-11), suggests the potential for bioconcentration in aquatic organisms is moderate to very high(SRC). However, under most conditions, depuration in fish will be rapid which suggest that long-term bioconcentration may be low(SRC). Acclimation and lag periods can be important factors in biodegradation rates(9,12). The results from simulation tests demonstrate that nonylphenol degrades and dissipates with a half-life range 2.5-56 days in surface water and 13.6-99 days in sediment under aerobic conditions(12). Dissipation from the surface water may be caused by adsorption to sediment(12). Different results exist for biodegradation in sediment under anaerobic conditions with half-lives of 46.2 days (primary degradation) to >703 days(12). Results of photolysis tests in water(13) suggest that some photodegradation of nonylphenol may occur in surface waters exposed to sunlight(SRC). Hydrolysis is a negligible removal processes for nonylphenol in the aquatic environment(14).

ATMOSPHERIC FATE: Nonylphenol is a mixture of isomeric monoalkyl phenols, predominately para substituted with a nine-carbon chain(1). According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(2), nonylphenol, which has a vapor pressure of 9.4X10-5 mm Hg at 25 °C(3), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase nonylphenol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 7.5 hours(SRC), calculated from its rate constant of 5.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(4). Based on analogy to measured rate constants for various alkylphenols(5), the rate constant for the vapor-phase reaction of nonylphenol with atmospheric nitrate radicals is about 1.0X10-11 cu cm/molecule-sec at 25 °C(SRC); this corresponds to an atmospheric half-life of about 5 minutes at an atmospheric concentration of 2.5X10+8 nitrate radicals per cu cm(6). The nitrate radical (NO3) is the dominant atmospheric oxidant during the night-time in most atmospheric environments(7), therefore, night-time degradation appears to be a major environmental sink for nonylphenol(SRC). Particulate-phase nonylphenol may be removed from the air by wet and dry deposition(SRC). Phenol and alkylphenols absorb at wavelengths >290 nm(8) and therefore, by analogy, nonylphenol may be susceptible to direct photolysis by sunlight(SRC).

Nonyphenol was identified in raw beef samples (concentration not specified)(1). Nonylphenol concentrations of 1.47-4.52 ug/kg dry weight were detected in farm vegetables (cabbage, spinach, lettuce, mustard, eggplant, cowpea, bitter gourd, ash gourd and leek) collected from 27 vegetable farms in the Pearl River Delta region of South China in 2009 and 2010(2). Results of analysis of 60 different foodstuffs commercially available in Germany for nonylphenols indicated the nonylphenols are ubiquitous in foods(3); the concentration of nonylphenols on a fresh weight basis varied from 0.1 to 19.4 ug/kg(3).

IDENTIFICATION AND USE: Nonylphenol (NP) is a pale-yellow, viscous liquid. it is used as nonionic surfactant (nonbiodegradable), lubricating-oil additives, stabilizers, petroleum demulsifiers, fungicides, antioxidants for plastics and rubber. NP is also used as a heat stabilizer to protect polymers with repeating units of chlorine or bromine against heat or UV degradation. Nonylphenol is used to produce tris(4-nonyl-phenyl) phosphite (TNPP). TNPP is also used as a stabilizer in plastic food packaging. Although it does contain residual nonylphenol, TNPP has been approved for this use by the Food and Drug Administration (FDA). FDA also lists nonylphenol as an indirect food contact substance. Barium and calcium salts of nonylphenol are used as heat stabilizers for poly vinyl chloride (PVC). Nonylphenol is also used as a catalytic diluent in epoxy resins. HUMAN EXPOSURE AND TOXICITY: NP appears to increases the risk of developing inflammatory bowel disease by promoting or prolonging adverse progression of inflammation in the gastrointestinal tract. NP is an estrogenic compound that alters pS2, MUC1 and ER gene expression in MCF-7 cells. ANIMAL STUDIES: Nonylphenol caused a skin sensitization reaction in 18 of 20 animals dosed. Nonylphenol, mixed isomers have been tested externally on the eyes of rabbits, and according to the degree of injury observed after 24 hr, have been rated on a scale of 1 to 10 (the most severely injurious substances have been rated 10), a 10. In another study, rats were exposed to 200, 650, or 2,000 ppm NP in their diet for 3 months. The treatment caused a small decr in BW and food consumption in the 2,000 ppm dose group. No treatment-related clinical or histopathological changes, including effects on endocrine organs, estrous cycling, or sperm measurements were noted up to 2,000 ppm exposure. NP is a male and female reproductive toxicant in rats at concentrations equal to or greater than 650 ppm based on decreased epididymal sperm density and testicular spermatid head counts in males, and increased estrous cycle length and decreased ovarian weights observed in females. ECOTOXICITY STUDIES: NP is classified among the endocrine disruptor chemicals with estrogen-like properties. It is widely used in many industries and to dilute pesticides in agriculture, and is known to affect the reproductive system of many aquatic and semi-aquatic organisms. NP has a dose-independent potential of feminization of the male gonad, called ovotestis, developed in the left testis in all nonylphenol- groups in the Japanese quail embryo. Exposure to high environmentally relevant concentrations of NP can affect molecular endpoints related to reproduction in the copper redhorse. Lab toxicity studies indicated that the most sensitive organism to nonylphenol was Daphnia pulex followed by rainbow trout (salmo gairdneri) embryos and juveniles. NP-induced oxidative stress could damage the chorion of unfertilized eggs and lead to a decline in gamete quality in female Chinese rare minnow. The nonylphenol did not affect honeybee populations.

Based on an analysis of 60 different foodstuffs and food consumption rates in Germany, the daily intake of nonylphenol was calculated to be 7.5 ug/day(1); for infants exclusively fed with breast milk or infant formulas, daily intakes are estimated to 0.2 and 1.4 ug/day respectively(1).

/BIRDS and MAMMALS/ Sex reversal effects of nonylphenol and bisphenol A on the gonads in F1(AWExWE) Japanese quail (Coturnix japonica) embryos were investigated using an in vivo screening model developed previously. The F1 (AWExWE) Japanese quail are a useful avian model because sex differentiation is confirmed by the plumage color before hatching, ruled by a criss-cross inheritance. The nonylphenol at 200, 2,000, 20,000, and 200,000 ng/egg and bisphenol A at 20, 200, 2,000, and 20,000 ng/egg were injected into the egg white just before incubation. At 16 days of incubation, embryos were subjected to a complete necropsy, and their gonads were both grossly observed and examined histopathologically and morphometrically. Grossly, genetic sex was confirmed because plumage color coincided completely with the external sex phenotype of the gonads in all embryos. Histopathologically, feminization of the male gonad, called ovotestis, developed in the left testis in all nonylphenol- and bisphenol A-treated groups. The incidence of the lesion in all treated groups was significantly higher than that in the control group, whereas there were no dose-dependent changes in the incidence and area of the ovotestis in both nonylphenol- and bisphenol A-treated groups. The present study revealed that nonylphenol and bisphenol A have a dose-independent potential of ovotestis induction in the Japanese quail embryo.

/AQUATIC SPECIES/ The copper redhorse, Moxostoma hubbsi, is an endangered species endemic to Quebec. The presence of contaminants, in particular endocrine disrupting chemicals (EDCs), in its habitat has been advanced as partly responsible for the reproductive difficulties encountered by the species. In the present study, immature copper redhorse were exposed to the estrogenic surfactant nonylphenol (NP; 1, 10 and 50 ug/L) and the synthetic estrogen 17a-ethinylestradiol (EE2; 10 ng/L) for 21 days in a flow-through system. The endpoints investigated included general health indicators (hepatosomatic index and hematocrit), thyroid hormones, sex steroids, brain aromatase activity, plasma and mucus vitellogenin (VTG), cytochrome P4501A protein expression and ethoxyresorufin-O-deethylase activity, heat shock protein 70 (HSP70) and muscle acetylcholinesterase. Exposure to 10 ng EE2/L significantly increased brain aromatase activity. Exposure to 50 ug NP/L resulted in a significant reduction of plasma testosterone concentrations and a significant induction of hepatic HSP70 protein expression. NP at 50 ug/L also induced plasma and mucus VTG. The presence of elevated VTG levels in the surface mucus of immature copper redhorse exposed to NP, and its correlation to plasma VTG, supports the use of mucus VTG as a non-invasive biomarker to evaluate copper redhorse exposure to EDCs in the environment and contribute to restoration efforts of the species. The results of the present study indicate that exposure to high environmentally relevant concentrations of NP and EE2 can affect molecular endpoints related to reproduction in the copper redhorse.

/AQUATIC SPECIES/ The effects of hexestrol (HXS) and nonylphenol (NP) on plasma vitellogenin (Vtg) concentration in barfin plaice Liopsetta pinnifasciata was studied during spring and autumn experiment. In L. pinnifasciata two "complete" forms of Vtgs, namely VtgAa and VtgAb, were previously described which may be separated due to molecular mass of their largest polypeptide in SDS-PAGE. In spring, the injection of HXS led to an increase in Vtg concentrations in both females and males. SDS-PAGE analysis of plasma from HXS-exposed fish produced only one prominent band at a molecular mass of 180kDa that corresponds to an increase in VtgAb levels. NP injected in fish in spring induced statistically significant increasing of Vtg concentration in males, and only one type of Vtg, as in case of HXS, accumulated in plasma. In autumn, the injection of HXS results to the increase of Vtg concentration in the plasma of females and males, electrophoretic analysis of plasma proteins showed that only a 98kDa polypeptide, corresponding to the VtgAa-type showed a significant increase. The blood plasma ratios of VtgAa and VtgAb in experimental fish are discussed in relation to the season and stage of reproductive cycle.

/AQUATIC SPECIES/ ...In this study, the effects of /nonylphenol/ NP on gonadal differentiation and development in Rivulus marmoratus (Osteichthyes, Cyprinodontiformes), a self-fertilizing, hermaphroditic species, were examined. Starting at hatching, fish were exposed to 150 or 300 g/L NP (nominal concentrations) in a static system with daily renewal. The measured concentration of NP in the test water decreased rapidly; half-life was 8.0 hr. After 60 days of exposure to NP, fish were kept in uncontaminated water for 20 days and were then preserved for histological examination. No fish exposed to 300 g/L NP (N=8) and only two of nine fish exposed to 150 g/L NP developed testicular tissue, compared with nine of 13 water-control fish and five of nine solvent-control fish. Oogenesis was also significantly inhibited by NP. None of the fish exposed to 300 g/L and only two of nine fish exposed to 150 g/L NP had vitellogenic oocytes, compared with seven of 11 water-control fish (not including males) and six of nine solvent-control fish. Dysplasia of the gonadal lumen also occurred in fish exposed to 300 g/L NP. These changes, including testicular agenesis, have not been previously reported in fish exposed to NP.

For more Ecotoxicity Excerpts (Complete) data for NONYLPHENOL (15 total), please visit the HSDB record page.

Nonylphenol was identified in raw beef samples (concentration not provided)(1). The concentration of nonylphenol in wild mallard ducks (Anas Boscas) ranged from 0.03 to 1.20 mg/kg dry weight sampled near the Glatt River, Switzerland between 1984-85(2). Nonylphenol concentrations of <0.7-134 ng/g were detected in the livers of surf scoter sea ducks (Melanitta perspicillata) collected from Vancouver Harbor in 2001(3).

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 3/29/96; Reporting date: 5/29/96.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Nonylphenol (mixed isomers) is included on this list. Effective date: 3/29/96; Sunset date: 6/30/98.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Nonylphenol is produced, as an intermediate or a final product, by process units covered under this subpart.

Nonylphenol (NP) and 4-Octylphenol (4OP) have shown estrogenic properties both in vivo and in vitro. Researchers have known for years that estrogens induce a wide number of hepatotoxic actions in rodents. In order to study the acute hepatic effects exerted by NP and 4OP on rat liver the following endpoints were evaluated: relative liver weight (RLW), morphology, cell cycle and ploidy status, monooxygenase enzymes content and levels of both, cytosolic estrogen receptor (cER) and microsomal binding sites for estrogens (mEBS). Immature male Sprague-Dawley rats were injected intraperitoneally (i.p.) with 60 mg/kg of NP or 4OP for 1, 5 or 10 days. Despite the fact that RLW of the animals was not modified but any treatment, the histopathological study revealed the presence of an increase in the percentage of both, mitotic activity and Ki-67-labeling index (LI) in the livers from animals treated with alkylphenols in absence of any degenerative lesion. Furthermore, all the livers from alkylphenols-treated groups showed the presence of abnormal mitosis and c-mitosis. Although the levels of both, cER and cytochrome P450 (Cyt. P450) were not affected by any treatment, concentration of the mEBS was decreased after 10 days of treatment with alkylphenols. These findings taken together suggest that the exposition to alkylphenols induce cell proliferation and spindle disturbances and that these compounds are capable of modulating the expression of putative membrane receptors for estrogens.

In this study, the pharmacokinetic behavior of 4-nonylphenol (NP) was investigated in human volunteers...Both after intravenous and oral application, the elimination half-life of the parent compound from the blood was 2-3 hr.

Serum toxicokinetics of total NP /in Sprague-Dawley rats/, measured following gavage administration, showed rapid absorption and elimination (average half-times 0.8 and 3.5 h, respectively).

Mass spectrometry was used to quantify NP and metabolites in serum and endocrine-responsive tissues from dietary exposure in Sprague-Dawley rats. Tissue accumulation of NP aglycone was observed despite the predominance of glucuronidation in blood.

Only about 1% of the oral dose entered circulation.

Mass spectrometry was used to quantify NP and metabolites in serum and endocrine-responsive tissues from dietary exposure in Sprague-Dawley rats. Tissue accumulation of NP aglycone was observed despite the predominance of glucuronidation in blood. Serum toxicokinetics of total NP, measured following gavage administration, showed rapid absorption and elimination (average half-times 0.8 and 3.5 h, respectively). NP was similarly administered by gavage to pregnant dams and total and aglycone NP were measured in dam serum and fetuses to show placental transfer into serum and brain.

...juvenile salmon...were exposed in vivo to waterborne [3H]-4-n-NP for a period up to 72 h or were administered a single oral dose of [3H]-4-n-NP. In vitro biotransformation of NP was studied by exposure of cultured salmon hepatocytes to [3H]-4-n-NP in the presence or absence of a CYP1A-inducer, -naphthoflavone (NF). Our results show that 4-n-NP was mainly metabolized in vivo, to its corresponding glucuronide conjugates and hydroxylates. The major route of excretion was the bile. The half-life of residues in carcass and muscle was between 24 and 48 h in both waterborne and dietary exposure. In whole body autoradiography, intragastric administered [3H]-4-n-NP was mainly present in the gastrointestinal tract and bile. NP-derived radioactivity in fish exposed via water was more evenly distributed in the organs compared to intragastric exposure and were observed in the intestinal contents, liver, kidney, gills, skin, abdominal fat and brain. In vitro pretreatment of hepatocytes with NF had no effect on rates or patterns of NP biotransformation. The in vitro metabolic rate of NP were 118 pmol NP metabolized/h/0.5x106 cells without NF, and 98 pmol NP metabolized/h/0.5x106 cells when NF was added to the culture medium./4-nonylphenol/

In this study, the pharmacokinetic behavior of 4-nonylphenol (NP) was investigated in human volunteers...Bioavailability after oral application (determined by oral and intravenous AUCs) was about 20%. NP seems to distribute into the lipid phase of the body within 2 h.

Used as a chemical intermediate, an additive to plastics and rubber, a stabilizer in drilling muds, a demulsifier in petroleum, and a disinfectant; [HSDB] Used in the chemical, leather processing, paper/pulp, polymers, and textiles industries; Used as a disinfectant, intermediate, lubricant additive, softener, stabilizer, surface-active agent, anti-oxidizing agent, and denaturing agent; [IUCLID]

Petroleum Production and Refining [Category: Industry]

Shale and clay stabilizer in drilling muds.

Nonionic surfactant (nonbiodegradable), lubricating-oil additives, stabilizers, petroleum demulsifiers, fungicides, antioxidants for plastics and rubber.

Bactericides; dyes; drugs; adhesives

Used as a heat stabilizer to protect polymers with repeating units of chlorine or bromine against heat or UV degradation

(1974) 3.66X10+8 GRAMS (PRINCPL CUSTMS DISTS)

(1975) 2.58X10+8 GRAMS (PRINCPL CUSTMS DISTS)

(1984) 6.48x10+8 G /ALKYL PHENOLS/

2023: 75,000 - <500,000 lb

(1972) 4.56X10+10 GRAMS

(1975) 3.08X10+10 GRAMS

(1984) 7.34X10+10 g

(1991) 82,116,000 kg

For more U.S. Production (Complete) data for NONYLPHENOL (6 total), please visit the HSDB record page.

55% as a chemical intermediate for surfactants, 25% as a chemical intermediate for plastic and rubber antioxidants, 15% as a chemical intermediate for lube oil additives, and 5% in other uses (1977).

CHEMICAL PROFILE: Nonylphenol. Surfactants (primarily industrial and institutional), 70%; rubber and plastic antioxidants, 20%; other, including lube oil additives, 10%.

CHEMICAL PROFILE: Nonylphenol. Demand: 1985: 185 million lb; 1986: 190 million lb; 1990 /projected/: 215 million lb.

CHEMICAL PROFILE: Nonylphenol. Surfactants (primarily industrial and institutional), 70%; rubber and plastic antioxidants, 20%; other, including lube oil additives, 10%.

CHEMICAL PROFILE: Nonylphenol. Demand: 1988: 200 million lb; 1989: 202 million lb; 1993 /projected/: 210 million lb. (Imports and exports are minor.)

A technical grade mixture of monoalkyl phenols, predominantly para substituted. The side chains are isomeric branched-alkyl radicals.

Grade: Technical.

PURITY: 90% PARA-ISOMER, PLUS 4% ORTHO-ISOMER & 5% 2,4-DINONYLPHENOL.

90% 4-isomer and 10% 2-isomer.

For more Formulations/Preparations (Complete) data for NONYLPHENOL (6 total), please visit the HSDB record page.

Information on 11 consumer products that contain Nonylphenol in the following categories is provided:

Information on 17 consumer products that contain Nonyl phenol in the following categories is provided:

Not Known or Reasonably Ascertainable

Phenol, nonyl-: ACTIVE

Constituent of an oil spill remover (80% nonyl/octyl phenol ethylene oxide condensate; 20% methyl cyclohexanol).

Inert pesticide ingredient, Approved for Nonfood Use Only