1-Naphthol

144.17

144.17

1817321

201-969-4

2A71EAQ389

9586

DTXSID6021793

Yellow monoclinic needles from water|Colorless prisms (from toluene)

29071510

20.2

2.8

white to off-white Crystalline Flakes

1.0954 g/cm³ @ Temp: 98.7 °C

96 °C

288 °C

125 °C

1.678

soluble in benzene, chloroform, ether and ethanol.

Store in dark!

1 mm Hg ( 94 °C)

4.5 (120 °C, vs air)

LD50 orally in Rabbit: 1870 mg/kg LD50 dermal Rabbit 880 mg/kg

5%

Phenolic odor

Disagreeable, burning taste

5.50e-10 cm3/molecule*sec

6.00e-08 atm-m3/mole|Henry's Law constant = 6.0X10-8 atm-cu m/mole at 25 °C (est)

pKa = 9.34 at 25 °C

Reduces ammoniacal silver nitrate. Sublimable; volatile with steam.|Enthalpy of fusion = 23.1 kJ/mol|Hydroxyl radical reaction rate constant = 1.34X10-12 cu cm/molecule-sec at 25 °C

541.7 °C

4957.4 kJ/mol (crystal) at 298.16 deg K; 5048.5 kJ/mol at 298.16 deg K (gas)

III

6.1

UN 2811 6.1/PG 3

1

21/22-37/38-41-51/53

22-26-37/39-2-61

QL2800000

Xn,N

Stable, but air and light sensitive - store under inert gas. Incompatible with strong bases, strong oxidizing agents.

P273-P280-P302 + P352 + P312-P305 + P351 + P338 + P310-P391

H302-H311-H315-H318-H335-H411

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

The U.S. high production volume (HPV) chemicals are those which are manufactured in or imported into the United States in amounts equal to or greater than one million pounds per year. Robust Summaries include health effects, ecotoxicity data, and environment fate information for selected chemicals. EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans.[Available from, as of January 19, 2006: http://www.epa.gov/hpv/pubs/hpvrstp.htm]|J Am Coll Toxicol 8 (4): 749-68 (1989). Final report on the safety assessment of 1-naphthol.|Hansen AM et al; Int Arch Occup Environ Health 65 (6): 385-94 (1994). Correlation between work process related exposure to polycyclic aromatic hydrocarbons and urinary levels of alpha-naphthol ... in iron foundry workers.|Knobloch T, Engewald W; J High Res Chromat 16 (4): 239-42 (1993). Identification of some polar polycyclic compounds in emissions from brown coal fired residential stoves.|Nasal cavity enzymes involved in xenobiotic metabolism and the effect on the toxicity of inhalants.[Dahl AR, Hadley WM; Crit Rev Toxicol 21 (5): 345-72 (1991)]

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P362, P363, P403+P233, P405, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P333+P313, P361, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 620 companies from 29 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P333+P313, P362, P363, P403+P233, P405, and P501|H311: Toxic in contact with skin [Danger Acute toxicity, dermal]|P260, P264, P270, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P309+P311, P310, P312, P321, P322, P361, P363, P405, and P501

Combustible when exposed to heat or flame.

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. 1-Naphthol is produced, as an intermediate or a final product, by process units covered under this subpart.

In a comprehensive survey of wastewater from 4000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, 1-naphthol was identified in discharges of the following industrial category (positive occurrences, median concn in ppb): timber products (3; 2755.4), printing and publishing (6; 34.3), organic chemicals (10; 5.9)(1). The highest effluent concns for these industrial categories were 3923 ppb, 137 ppb, and 235 ppb, respectively(1). 1-Naphthol was not found in effluent concentrates from 16 advanced waste treatment plants(2).|1-Naphthol concs of 0.060-0.204 mg/g (organic carbon emitted) were detected in the fine particle emissions from fireplace combustion of six species of woods grown in the northern US (red maple, northern red oak, paper birch, eastern white pine, eastern hemlock, balsam fir)(1). 1-Naphthol concs of 0.047-0.332 mg/g (organic carbon emitted) was detected in the fine particle emissions from fireplace combustion of six species of woods grown in the southern US (yellow poplar, white ash, sweet-gum, mockernut hickory, loblolly pine slash pine)(2).

Samples of soil from ponds obtained from 3 different locations around Bhopal, India, where carbaryl was commercially produced for more than a decade, contained mean 1-naphthol concns of 0.466 ppm, 0.279 ppm, and 0.365 ppm(1).

... As model xenobiotics, the substituted aryl compounds aniline, 1-naphthylamine, and 1-naphthol (1-NOH) were investigated herein for their potential to react with HOCl and the transformed into genotoxic products. The compounds were first exposed to HOCl (25-150 uM) in phosphate buffer and afterward used to treat human fibroblasts or purified DNA. DNA single-strand breaks in cells and the binding of HOCl-reacted 1-[14C]NOH to purified DNA were assessed by DNA alkaline elution and scintillation spectrometry, respectively. It was found that neither HOCl nor compounds alone could break cellular DNA. But HOCl-reacted compounds produced up to 400 rad equivalents of DNA breaks. HOCl reaction products of aniline and the model bicyclic aryl compounds differed in their DNA-breaking characteristics. HOCl-reacted 1-[14C]NOH was stable and bound to DNA at up to 124 pmol/mg DNA. Sodium thiosulfate, glutathione, and taurine inhibited the transformation reactions; but only the former two blocked binding of HOCl-reacted 1-NOH to DNA. Ultraviolet spectra showed that HOCl reacted rapidly (<1 min) and equally well with 1-NOH at pH 7.2 or at an intraphagosomal pH of 5.0. Reaction concentrations of HOCl in this study were 2- to 11-fold lower than levels generated in vitro by stimulated neutrophils. These results show that certain aryl compounds can react readily with approximated physiological levels of HOCl (-OCl) to form relatively long-lived products that bind DNA and are genotoxic to human cells.

LD50 Rat oral 2.59 g/kg|LD50 Cat oral 134 mg/kg bw|LD50 Mouse oral 275 mg/kg bw|LD50 Rabbit dermal >10,000 mg/kg /from table/|For more Non-Human Toxicity Values (Complete) data for 1-NAPHTHOL (8 total), please visit the HSDB record page.

/AQUATIC SPECIES/ The effects of temperature, pH, sediment and humic acid on the toxicity and fate of 1-naphthol to the midge larvae, Chironomus riparius, were determined in static 24 hr toxicity tests. Partitioning of (14)C-1-naphthol in systems identical to the toxicity test was examined to determine if results were supported by physical chemical measurements. /In general/, 1-naphthol toxicity increased with increasing temperature. Changes in pH did not affect toxicity except at pH 8 where 1-naphthol was more toxic to the midge at 10 and 20 °C than at pH 4 or 6. In addition, there was no temperature effect at pH 8 as naphthol was equitoxic at all temperatures. The presence of sediment reduced toxicity in the temperate range (20-30 °C) while humic acid had no effect on toxicity at any temperature. Partitioning data did not always support toxicity results, illustrating the importance of coupling bioassays with physical chemical studies when evaluating water soluble chemicals.|/AQUATIC SPECIES/ The short-term toxic effects of both sublethal and lethal concentrations of 1-naphthol were studied by light microscopy examination of the digestive gland-gonad complex of the common periwinkle Littorina littorea. Exposure to naphthol produced severe tissue alterations characterized by disruption of digestive cells and presence of a high number of basophilic cells in the digestive tubules and infiltration of digestive, connective and gonadal tissues by hemocytes. Morphologically, the infiltrating hemocytes comprised of hemocytes with a small nucleus and eosinophilic cytoplasm, and hemocytes with a large nucleus and scarce cytoplasm. In addition, breakdown of ripe ova and resorption of gametes occurred, even at the sublethal concentration of 2.075 mg/L of naphthol, apparently related to phagocytosis by hemocytes. Differences in the hemocytic infiltration incidence were observed between male and female individuals, suggesting a different sensitivity to the experimentally induced stress condition between the two sexes.

1-Naphthol's production and use in the production of agrochemicals, such as carbaryl, drugs, rubber oxidants and dye intermediates(1), may result in its release to the environment through various waste streams(SRC). 1-Naphthol is an environmental degradation product of the pesticide carbaryl(2) that is formed through hydrolysis and biodegradation(3). 1-Naphthol can also be formed in the environment by the aqueous photooxidation of naphthalene(4). 1-Naphthol is released to the atmosphere in particulate matter from the combustion of fireplace wood(5,6). 1-Naphthol is formed in the enzymatic degradation of naphthalene and methylnaphthalenes by fish(7).

TERRESTRIAL FATE: Based on a classification scheme(1), a measured Koc value of 522 (average)(2) indicates that 1-naphthol is expected to have low mobility in soil(SRC). Volatilization of 1-naphthol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.0X10-8 atm-cu m/mole(SRC), based upon its vapor pressure, 2.74X10-4 mm Hg(3), and water solubility, 866 mg/L(2). 1-Naphthol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(SRC). 1-naphthol may react with naturally-occurring compounds in soil, forming persistent, bound residues(4). It may also readily biodegrade(5,6). Over a period of 28 days, 14C-1-naphthol residues (bound complexes) released from moist and flooded clay soil (1.5% organic carbon, pH 7.3) were 14.0 and 15.1%, respectively, with mineralization less than 1%(4). 1-Naphthol (500 ppm) persisted in a Cherzonium soil (pH 7.1-7.5) maintained at a 30% water content for 5 days at 19 °C(5). No transformation products were detected in the soil(5). 1-Naphthol was reduced to trace quantities in flooded soil after 4 days incubation, whereas measurable quantities remained in sterile controls(6). 1-Naphthol also is susceptible to photodegradation(7,8) and therefore may photodegrade on soil surfaces(SRC).|AQUATIC FATE: Based on a classification scheme(1), measured Koc values of 522 (average) to 15,618 in sediment(2), indicate that 1-naphthol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 6.0X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 2.74X10-4 mm Hg(4), and water solubility, 866 mg/L(2). According to a classification scheme(5), an estimated BCF of 31(SRC), from its log Kow of 2.85(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate, provided the compound is not metabolized by the organism(SRC). 1-Naphthol was biodegradable in a variety of screening tests(8-12) and in natural aquatic systems(13). 1-Naphthol also degrades with water through photodegradation(14,15). 1-Naphthol was stable in the dark in sterile seawater(15); in artificial sunlight, 1-naphthol was completely degraded after 2 hr(15). 1-Naphthol was shown to be photodegraded under conditions approximating those in the environment (pH, dissolved oxygen, temperature, UV irradiation)(16); under ambient temperatures, initial 1-naphthol concn (35 mg/L) degraded to 13.2 mg/L after 14 hr of irradiation and to 0.42 mg/L after 4 days(16).|AQUATIC FATE: While carbaryl added to raw Miami River (Ohio) water completely degraded in a little over 1 week, 1-naphthol, its degradation product, was not detected in the water(2). This indicates that 1-naphthol degraded as rapidly as it was formed since other transport processes are reasonably ruled out(SRC). Residues of carbaryl and its degradation product, 1-naphthol, disappeared from irrigation and drainage canal water 6 days after application(3). 1-Naphthol was rapidly dissipated in paddy water(5). Another investigator reported that 1-naphthol was stable in the dark in sterile seawater over a 3 day period, but was degraded to undetectable levels in 96 hr in raw seawater(4). Under artificial sunlight, 1-naphthol was completely degraded after 2 hr(4). In studies in which 1-naphthol was added to filtered seawater adjusted to pH 6.5 and maintained at 16-18 °C, there was a decline in 1-naphthol concn(1). The percent decrease was greater at higher 1-naphthol concns with a 10.8% decline in 24 hr at 4.63 mg/L and 22% in 24 hr at 43.07 mg/L. There was no difference in the decrease when the tanks were kept in the dark. It was believed that the loss was a result of biodegradation(1).|AQUATIC FATE: In an investigation of the fate of 1-naphthol in a simulated estuarine environment, it was found that 1-naphthol was unstable in this environment(1). Both the loss of 1-naphthol and the formation of CO2 was aided by microbial action and light, with simulated daylight having a greater effect than the lack of sterility. The half-lives of 1-naphthol and its mineralization in an unsterile seawater system exposed to simulated sunlight were 7 and 9 days, respectively, whereas in the absence of light they were 15 and 23 days, respectively(1). The loss of 1-naphthol from seawater was much faster in the presence of mud. This was thought to be due to adsorption and enhanced biodegradation due to increased populations of microorganisms in the mud(1). The rate of loss of radioactivity from 1-naphthol-1-14C was nearly the same in dark and light-exposed sterile tanks and this was also true with dark and light-exposed unsterile tanks where the half-life was 2.5 days. Additional experiments showed that 1-naphthol is relatively stable in a light-exposed, oxygen-free environment and that light-induced loss is a photooxidation process(1). In a sterile, light-exposed, oxygen-free environment, the concentration of 1-naphthol decreased 0.3%/day for 30 days. After the addition of oxygen, the rate of decrease rose to 1.6%/day for 40 days. Experiments performed at 16 °C to determine the affect of pH on the stability of 1-naphthol found that 1-naphthol has optimum stability at pH 6.3 (7% loss in 21 days) and is unstable at pH 8.2, the pH of seawater(1). At pH 4.4 and 8.0, stability is considerably reduced from its optimum value and at pH 8.5 1-naphthol was completely degraded in 21 days. A reddish-blue precipitate formed in seawater which had a molecular weight of 454 and contained a stable free radical(1).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-naphthol, which has an extrapolated vapor pressure of 2.74X10-4 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. However, 1-naphthol has been detected in particulate emissions from fireplace combustion of common US woods(3,4). Vapor-phase 1-naphthol 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 0.7 hours(SRC), calculated from its rate constant of 5.5X10-10 cu cm/molecule-sec at 25 °C(5). 1-Naphthol absorbs at wavelengths >290 nm(6) and therefore may be susceptible to direct photolysis by sunlight(SRC). Aromatic phenolic compounds react rapidly in the vapor-phase with ambient atmospheric night-time nitrate radicals(7); therefore, 1-naphthol is expected to degrade in the atmosphere by this process(SRC). Particulate-phase 1-naphthol may be removed from the air by wet or dry deposition(SRC).

The rate constant for the vapor-phase reaction of 1-naphthol with photochemically-produced hydroxyl radicals has been measured as 5.5X10-10 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 0.7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). 1-Naphthol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). 1-Naphthol absorbs at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC). Aromatic phenolic compounds react rapidly in the vapor-phase with ambient atmospheric night-time nitrate radicals(5); therefore, 1-naphthol is expected to degrade in the atmosphere by this process(SRC).|Photolysis experiments on 1-naphthol solutions (pH 7) in a photoreactor using a medium pressure mercury lamp and a pyrex filter (principally 313 and 365 nm radiation) resulted in a photolysis half-life of 29 min(1); in the presence of a riboflavin photosensitizer, the half-life dropped to 0.26 min(1); generally the midday summer sunlight photolysis rates at the latitude of the laboratory (Urbana, IL) were approximately half of those determined under the conditions of the experiment(1). 1-Naphthol was stable in the dark in sterile seawater(2); in artificial sunlight, 1-naphthol was completely degraded after 2 hr(2). 1-Naphthol was shown to be photodegraded under conditions approximating those in the environment (pH, dissolved oxygen, temperature, UV irradiation)(3); under ambient temperatures, initial 1-naphthol concn (35 mg/L) degraded to 13.2 mg/L after 14 hr of irradiation and to 0.42 mg/L after 4 days(3).

An estimated BCF of 31 was calculated for 1-naphthol(SRC), using a log Kow of 2.85(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). There is evidence that 1-naphthol is rapidly transformed in M edulis(4). Experiments conducted with the marine gastropod, Littorina littorea, show that the loss of 1-naphthol in seawater was greater when animals were present in the experimental tanks(4).

524.81 L/kg|Batch equilibrium adsorption studies of 1-naphthol were performed using 16 soils and sediments(1). The Koc average value using ten of these soils was 522 which was in good agreement with that predicted from the octanol-water partition coefficient (hydrophobic adsorption), 432(1); the other six soils and sediments yielded Koc value that were higher (1645, 1733, 2102, 2700, 4198, and 15,618) with the highest value (15, 618) measured in a sediment soil (0.11% organic carbon)(1); it was found that for 1-naphthol, hydrophobic adsorption is dominant only when the ratio of percent organic carbon to percent montorillonite exceeds 0.1% and that adsorption of 1-naphthol is a function of soil and sediment properties(1). According to a classification scheme(2), a Koc value of 522 (average) suggests that 1-naphthol is expected to have low mobility in soil(SRC).|The Koc values of 1-naphthol to Apison (0.11% OC, pH 4.5), Fullerton (0.06% OC, pH 4.4), and Dormont (1.2% OC, pH 4.2) soils were 369,000, >600,000, and 1280, respectively(1); the high sorption of the 1-naphthol in soils with low organic carbon was attributed to its interaction with clay surfaces not coated with humic material(1). The characteristics of the organic sorbent, particularly its polarity and aromaticity greatly influences the partitioning of 1-naphthol(2). The partition coefficient of 1-naphthol to dissolved organic carbon was determined to be 20.1, using a reference soil humic acid(3); this indicates that a substantial faction of 1-naphthol in natural systems may be associated with dissolved organic carbon (DOC) and therefore DOC may significantly influence the fate of 1-naphthol in the environment(3). 1-Naphthol is not adsorbed strongly on kaolinite and bentonite; 75 g of kaolinite or 12 g of bentonite would be required to reduce the a 1 mg/L solution of 1-naphthol to 0.1 mg/L(4); the Freundlich adsorption constant and 1/n for kaolinite is 0.030 and 0.40, respectively(4); for bentonite these Freundlich parameters are 0.260 and 0.55, respectively(4). Koc values ranging from 56 to 562 were measured for 1-naphthol in two sandy VA soils having organic carbon contents of 0.52 and 3.50 percent, respectively(5).

The Henry's Law constant for 1-naphthol is estimated as 6.0X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 2.74X10-4 mm Hg(1), and water solubility, 866 mg/L(2). This Henry's Law constant indicates that 1-naphthol is expected to be essentially nonvolatile from water surfaces(3). No measurable vapor flux of 1-naphthol was found from distilled water solutions at 30 °C and an air flow of 8 mL/min(4). 1-Naphthol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

DRINKING WATER: 1-Naphthol was not found in finished drinking water tested from 15 treatment plants(1).|SURFACE WATER: Samples of pond water obtained from 3 different locations around Bhopal, India, where carbaryl was commercially produced for more than a decade, contained mean 1-naphthol concns of 0.083 ppm, 0.042 ppm, and 0.079 ppm(1).|GROUNDWATER: Samples of groundwater obtained from 2 different locations around Bhopal, India, where carbaryl was commercially produced for more than a decade, contained mean 1-naphthol concns of 0.012 ppm and 0.026 ppm(1). The concs of 1-naphthol in groundwater from a sand aquifer at 2 sites below a former holding pond at a wood-preserving plant in Pensacola, Fl were 0.17 ppm at 6.1 m depth and 0.00, 0.39 and 0.05 ppm at 3.3, 5.8, and 11.0 m depths, respectively(2). The plant used creosote exclusively for the treatment of wood products until 1950 when pentachlorophenol was phased in. The plant was closed in 1981 and site evaluation and sampling occurred between 1981 and 1990. Naphthalene was a major PAH found at the site and there was evidence of active microbial activity in the aquifer(2).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 57,117 workers, including 43,155 females, are potentially exposed to 1-naphthol in the USA(1). All but 1% of exposures are with trade-name products containing 1-naphthol. The NOES Survey does not include farm workers. Occupational exposure to 1-naphthol may occur through inhalation and dermal contact with this compound at workplaces where 1-naphthol is produced or used(SRC). Monitoring data indicate that the general population may be exposed to 1-naphthol via ingestion of contaminated drinking water(SRC).

The occurrence of 1-naphthol in human urine from the Health and Nutrition Examination Survey II (Hanes II), which was based on the analysis of 6846-6936 samples collected from the general population: 1.9% positive, 17.9% trace, 4060 ppb maximum, geometric mean <10 ppb(1). 1-Naphthol conc ranges of 0.4-34.6 mg/L was found in the urine collected directly at the end of the work shift from a group of industrial workers employed in the distillation of naphthalene oil(2). Coke plant workers exposed to naphthalene and other aromatics had mean 1-naphthol urine conc of 0.89 mg/L (working with new technology) and 4.86 mg/L (working with old technology)(2). A good correlation between levels of 1-naphthol in the serum and urine of a farmer applicator and exposure to the pesticide carbaryl was observed indicating that measurement of 1-naphthol can be used to evaluate occupational exposure to carbaryl(3). Mean 1-naphthol conc of 6.5 ppb (range not detectable to 24 ppb) was detected in the urine of 31 subjects from the Great Lakes regions that consume sport fish(4). Geometric mean naphthol (combined 1-naphthol and 2-naphthol) conc of 0.72 ug/L was detected in 14 amniotic fluid samples (70% positive detections)(5). Analyses of urine of 983 adults living in the US (selected from a broad spectrum of the general population as part of the National Health and Nutrition Examination Survey III) detected 1-naphthol in 86% of all samples at a mean conc of 17 ppb and a max conc of 2500 ppb(6). A urine analysis of 119 Japanese workers found a geometric mean 1-naphthol conc of 5.13 ug/L(7); urinary levels were three times higher in cigarette smokers compared to non-smokers(7).

1-Naphthol was selectively toxic to human colorectal tumors compared to corresponding normal colonic tissue removed at surgery and maintained in short-term organ culture. Nineteen of 24 tumors studied have shown a significant differential response. Three human colonic adenocarcinoma xenografts, in the short-term organ culture system, displayed the same response to 1-naphthol as primary tumors removed at surgery. 1-Naphthol, 1,2- and 1,4-naphthoquinone were also toxic to two human colonic adenocarcinoma cell lines, LoVo and COLO 206. The selective toxicity of 1-naphthol is mediated in part through an accumulation of 1-naphthol in the tumor tissue due to impaired conjugation by the tumor. The higher concentrations of 1-naphthol may then exert their toxicity either directly or by formation of naphthoquinones. Some indirect evidence was obtained for the possible involvement of 1,2- or 1,4-naphthoquinone in the cytotoxicity of 1-naphthol. Our studies suggest that further studies are warranted of the possible use of 1-naphthol or related compounds as antitumor agents.

4. 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN), 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OZ FOR 70 KG PERSON (150 LB). /BETA-NAPHTHOL/

Urinary excretion of (14)C following topical application of ((14)C)naphth-1-ol indicated that about 50% was absorbed percutaneously in man.|Sixty-two workers of a carbochemical plant exposed to benzene, naphthalene, toluene, o-xylene, p-xylene, phenol and pyridine were examined. In urine samples collected before and after occupational exposure significant differences in concn values of phenol (21.7-97.6 mg/l), 1-naphthol (0.1-9.38 mg/l), hippuric acid (95.5-873.9 mg/l) and m-methylhippuric acid (29.0-93.5 mg/l) were found. There was a correlation between benzene and naphthalene in the breathing zone air and phenol and 1-naphthol in the urine of coke plant workers.|Chemical exposure of assemblers handling creosote impregnated wood and of a single worker chiselling coal tar pitch layer was assessed by measuring airborne naphthalene and various polycyclic aromatic hydrocarbons, and by measurement of urinary excretion of 1-naphthol and 1-pyrenol. The sum concn polycyclic aromatic hydrocarbon and of 4-6 aromatic ring containing polycyclic aromatic hydrocarbons were high, 440 ug/cu m and 290 ug/cu m, respectively, when chiselling. In the assemblers workplace, the polycyclic aromatic hydrocarbons concn were about 1/50 of this value. Regarding airborne naphthalene concn the situation was reversed (assemblers, 1000 ug/cu m; chiseller, 160 ug/cu m). Correspondingly, the assemblers urinary 1-naphthol concn were 15-20 times higher than those of the chiseller. The urinary 1-pyrenol concn of the chiseller was 2-4 times higher than among the assemblers. As the estimated pyrene inhalation doses among the assemblers could account only for 2%-25% of the 24 hr pyrenol excretion in the urine, the skin was presumably the main route of uptake. ...|Oral administration of 45 mg alpha-Naphthol/kg bw resulted in 95% of the administered dose being eliminated within 72 hr after treatment in male mice.

Yields 1-napthhyl-alpha-D-glucoside ... in blowfly and in grass grub; yields 1-naphthyl phosphate in fly and in grass grub. /from table/|Yields 1-naphthyl-beta-D-glucuronide in rat, in rabbit, in fly and in mouse. /from table/|Yields 1-naphthyl sulfate in rat, rabbit, mouse, guinea pig, fly, and grass grub. /from table/|After 0.1 mmol 1-naphthol injected into intestinal loops (rat in vivo), 70-90% in intestinal venous blood was present as 1-naphthol glucuronide. For 1.0 and 2.0 mmol injections, proportion of 1-naphthol present as 1-naphthol glucuronide was 25-50%.|For more Metabolism/Metabolites (Complete) data for 1-NAPHTHOL (8 total), please visit the HSDB record page.|1-Naphthol has known human metabolites that include 1-Naphthyl glucuronide.

The mechanism(s) of toxicity of 1-naphthol and two of its possible metabolites, 1,2- and 1,4-naphthoquinone, to freshly isolated rat hepatocytes has been studied. 1-Naphthol and both naphthoquinones exhibited a dose-dependent toxicity to hepatocytes. [1-14C]-1-Naphthol was metabolised by hepatocytes predominantly to its glucuronic acid and sulphate ester conjugates, but small amounts of covalently bound products were also formed. Blebbing on the surface of the hepatocytes was observed following exposure to 1-naphthol and the naphthoquinones, together with a dose-dependent decrease in intracellular glutathione (GSH), which preceded the onset of cytotoxicity. The toxicity of 1-naphthol and the naphthoquinones was potentiated by dicoumarol, an inhibitor of DT-diaphorase (NAD(P)H:quinone oxidoreductase). This enhanced toxicity was accompanied by a greater amount of surface blebbing, an increased depletion of intracellular GSH, particularly in the case of 1-naphthol and 1,4-naphthoquinone, and a decreased metabolism of 1-naphthol to its conjugates with variable effects on the amount of covalently bound products formed. These results support the suggestion that the toxicity of 1-naphthol may be mediated by the formation of 1,2-naphthoquinone and/or 1,4-naphthoquinone, which may then be metabolised by one electron reduction to naphthosemiquinone radicals. These, in turn, may covalently bind to important cellular macromolecules or enter a redox cycle with molecular oxygen thereby generating active oxygen species. Both of these processes appear to play a role in producing the cytotoxic effects of 1-naphthol.

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . For contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Ketones and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ketones and related compounds/|Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Administer activated charcoal ... . Do not use emetics. Cover skin burns with dry, sterile dressings after decontamination ... . Maintain body temperature. /Phenols and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors for hypotension with a normal fluid volume. Watch for signs of fluid overload ... Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam (Valium). ... Use proparacaine hydrochloride to assist eye irrigation ... . /Phenols and related compounds/

/SIGNS AND SYMPTOMS/ ... Produces crampy abdominal pain, nausea, vomiting, and sometimes convulsions. Intestinal or percutaneous absorption may lead to severe nephritis, liver injury, and acute hemolytic anemia. Lens opacities and retinal changes have been described. Alpha isomer is said to be even more toxic. /beta-Naphthol/|/SIGNS AND SYMPTOMS/ 1. ...Diarrhea. 2. Headache, profuse perspiration, listlessness, confusion. 3. In severe poisoning, coma with or without convulsions. ...5. Acute intravascular hemolysis ... characteristic sign ... in persons with red /blood/ cell glucose-6-phosphate dehydrogenase deficiency. ... Begins on third day ... accompanied by ... leukocytosis, fever, hemoglobinuria ... renal insufficiency ... disturbances in liver function. 6. In absence of adequate supportive treatment, death may result from acute renal failure or kernicterus in young. /Naphthalene/|/SIGNS AND SYMPTOMS/ Conjunctivitis, corneal burns, dermatitis, headache, nausea, vomiting, abdominal pain, hepatomegaly, jaundice, splenomegaly, albuminuria, hematuria; unconsciousness, convulsion (fits).|/BIOMONITORING/ In Nigeria, severe /neonatal jaundice/ (NNJ) is common in babies exposed to mothballs and other icterogenic agents. High-performance liquid chromatographic (HPLC) method was employed for quantitative analysis of 1 and 2-naphtol in the urine of 50 neonates aged one to 19 days. Five of the 25 babies who had a history of exposure to mothballs, and none of the babies without a history of exposure had 1-naphtol in their urine. The value of 1-naphtol ranged between 0.75 and 11.69 ug/mL with mean of 5 +/- 5 ug/mL. The overall correlation coefficient (r) between bilirubin values and 1-naphtol was 0.1 while it was 1 in the three G-6-PD deficient infants. The procedure will be very useful in the evaluation of infants with unexplained NNJ, anemia, acute hemolytic jaundice and hemoglobinuria if naphthalene poisoning is suspected.

1-hydroxynaphthalene

Pesticide, fertilizer, and other agricultural chemical manufacturing|1-Naphthalenol: ACTIVE|Two stage catalytic process is claimed to give an overall yield of 72% with an overall efficiency of 97%.

FLUORESCENCE ANALYSIS.|GAS CHROMATOGRAPHIC DETERMINATION OF MICROAMOUNTS OF CARBARYL & 1-NAPHTHOL IN NATURAL WATER AS SOURCES OF WATER SUPPLIES.|Method: EPA-OGWDW/TSC 531.2; Procedure: high performance liquid chromatography; Analyte: 1-naphthol; Matrix: finished drinking waters; Detection Limit: 0.063 ug/L.|Method: USGS-NWQL O-1131-95; Procedure: high performance liquid chromatography; Analyte: 1-naphthol; Matrix: filtered natural-water samples; Detection Limit: 0.007 ug/L.

DETECTION LIMITS OF 1- & 2-NAPHTHOL, GUAIACOL, & THYMOL ON READY-TO-USE FILMS & SILICA GEL G LAYERS.|The validity of determination of alpha-Naphthol in urine as a marker for exposure to polycyclic aromatic hydrocarbons.|Development of a selective enzyme linked immunosorbent assay for 1-naphthol, the major metabolite of carbaryl.|Quantitative analysis of 1-napthol in urine of neonates exposed to moth balls by high performance liquid chromatography.

Cosmetics -> Hair dyeing|Environmental transformation -> Pesticide transformation products (metabolite, successor)

1-Napthol is a known environmental transformation product of Napropamide.