Biphenyl-2-ol

Preservative

Personal care product

Fungicides

Active substance -> EU Pesticides database: Approved

Fungicides

Pesticide (O-Phenylphenol) -> USDA PDB

log Kow = 3.09

3.09

3.2

Mild characteristic odor

Sweetish odor

Phenolic odor

1.213 at 77 °F (NTP, 1992) - Denser than water; will sink

1.213 g/cu cm at 25 °C

Relative density (water = 1): 1.2

1.213 @25 °C

Needles from petroleum ether

Colorless to pinkish crystals

White, flaky crystals

less than 0.1 mg/mL at 68.9 °F (NTP, 1992)

FORMS SALTS OF WHICH THOSE OF THE ALKALI METALS ARE WATER-SOLUBLE; THE SODIUM SALT CRYSTALLIZES AS A TETRAHYDRATE, SOLUBILITY CIRCA 1.1 KG/KG WATER (35 °C), GIVING A SOLUTION OF PH 12.0-13.5.

Soluble in fixed alkali hydroxide solutions and most organic solvents.

Soluble in sodium hydroxide

Soluble in ethanol, acetone, benzene, chloroform, and ligroin; very soluble in ethyl ether and pyridine.

Sol in most organic solvents, including ethanol, ethylene glycol, isopropanol, glycolethers, and polyglycols.

255 °F (NTP, 1992)

124 °C

Value: 138 degree C Type: closed cup

124 °C c.c.

Danger

H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P203, P260, P261, P264, P264+P265, P272, P273, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P321, P333+P317, P362+P364, P363, P391, P405, and P501 (click each P-code to see the statement)

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Chemical: [1,1'-Biphenyl]-2-ol

Hazard Traits - Carcinogenicity; Hematotoxicity; Other Toxicological Hazard Traits

Commission Regulation (EC) No 2229/2004

2009/160/EC, 2010/81/EU, Reg. (EU) 2021/1449, Reg. (EU) 2022/1480, Reg. (EU) 2023/2592, Reg. (EU) No 540/2011

Status: Active Update: 09-03-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/2168

Orthophenyl phenol: Does not have an individual approval but may be used under an appropriate group standard

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

This chemical is a combustible solid.

Slight, when exposed to heat or flame; can react with oxidizing materials.

SYMPTOMS: Symptoms of exposure to this compound include eye irritation with possible corneal injury (necrosis); paleness, cyanosis, weakness, sweating, headache, diarrhea, nausea, vomiting, diarrhea, dizziness, fainting, dark urine, central nervous system depression, and deoxyribonuclease inhibition. Chronic exposure may include irritation and lesions of the respiratory system.

A skin, eye, and respiratory tract irritant; May cause injury to heart, gastrointestinal tract, kidneys, liver, and lungs; [ICSC] May cause immunosuppression; [HSDB] May cause corneal damage; [CAMEO] An irritant; [MSDSonline] See Sodium o-phenylphenol.

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - 2-Phenylphenol and Salts (Orthophenylphenol or OPP). EPA 739-R-06-004 (July 2006). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of October 7, 2009: http://www.epa.gov/pesticides/reregistration/status.htm]

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man. Geneva: World Health Organization, International Agency for Research on Cancer, Vol 73 Some Chemicals that Cause Tumours of the Kidney or Urinary Bladder in Rodents and Some Other Substances 674 pp (1999) is available for downloading in pdf form from the IARC Monographs website.[Available from, as of April 8, 2010: http://monographs.iarc.fr/ENG/Monographs/PDFs/index.php]

European Commission, ESIS; IUCLID Dataset, Biphenyl-2-ol (90-43-7) 153 pp. (2000 CD-ROM edition) contains information on use, toxicology, and environmental effects of this chemical as supplied to the European Union by industry.

DHHS/NTP; Toxicology & Carcinogenesis Studies of ortho-Phenylphenol Alone and With 7,12-Dimethylbenz(a)anthracene in Swiss CD-1 Mice (Dermal Studies) Technical Report Series No. 301 (1986) NIH Publication No. 86-2557

Fires involving this chemical can be controlled with a dry chemical, carbon dioxide, foam or Halon extinguisher. (NTP, 1992)

Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Seek medical attention if you feel unwell.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Seek medical attention if you feel unwell.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Seek medical attention if you feel unwell.

Unusual Fire and Explosion Hazards: Violent steam generation or eruption may occur upon application of direct water stream to hot liquids. Do not permit dust to accumulate. When suspended in air dust can pose an explosion hazard. Minimize ignition sources. If dust layers are exposed to elevated temperatures, spontaneous combustion may occur. Dense smoke is produced when product burns. / DOWICIDE* 1 ANTIMICROBIAL/

Special Protective Equipment for Firefighters: Wear positive-pressure self-contained breathing apparatus (SCBA) and protective fire fighting clothing (includes fire fighting helmet, coat, trousers, boots, and gloves). If protective equipment is not available or not used, fight fire from a protected location or safe distance. / DOWICIDE* 1 ANTIMICROBIAL/

Fire Fighting Procedures: Keep people away. Isolate fire and deny unnecessary entry. Cool surroundings with water to localize fire zone. Do not use direct water stream. May spread fire. Burning liquids may be moved by flushing with water to protect personnel and minimize property damage. Water fog, applied gently may be used as a blanket for fire extinguishment. Contain fire water run-off if possible. / DOWICIDE* 1 ANTIMICROBIAL/

Extinguishing Media: Water fog or fine spray. Dry chemical fire extinguishers. Carbon dioxide fire extinguishers. Foam. Do not use direct water stream. May spread fire. Alcohol resistant foams (ATC type) are preferred. General purpose synthetic foams (including AFFF) or protein foams may function, but will be less effective. Water fog, applied gently may be used as a blanket for fire extinguishment. / DOWICIDE* 1 ANTIMICROBIAL/

Use dry chemical, carbon dioxide, water spray, or alcohol foam extinguishers ... If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors or shows any signs of deforming), withdraw immediately to a secure position.

Store in tightly closed containers in a cool, well-ventilated area away from water. Sources of ignition, such as smoking and open flames, are prohibited where o-phenylphenol is used, handled, or stored in a manner that could create a potential fire or explosion hazard.

Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Evacuate persons not wearing protective equipment from area of spill or leak until clean-up is complete. Remove all ignition sources. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waterse.

If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.

After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, you should dampen the solid spill material with alcohol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with alcohol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.

Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Adipose specimens collected in the United States in fiscal year 1982 were analyzed for general volatile and semivolatile organic compounds. Of 46 samples collected, o-phenylphenol was detected in 22 samples (5 samples from people between the ages of 0-14 yrs, 6 samples from people between the ages of 15-44 and 11 samples from people aged 45 or greater)(1). In an analysis of serum from 10 infants exposed to germicidal solutions containing o-phenylphenol, o-phenylphenol was found in the serum of 7 infants at levels of 500-1900 ng/ml(2). In a study comparing semen samples from Danish farmers consuming organically grown commodities as opposed to traditional farmers, the acceptable daily intake of o-phenylphenol among organic farmers was 0.02 mg/kg/day, 1.1% above the acceptable daily intake(3).

o-Phenylphenol is rapidly and almost completely excreted in urine as water soluble conjugates and can be quantified using several chromatographic methods. In an occupational study 11 volunteers were treated with 10 consecutive 3 mL applications of undiluted hand disinfectant containing 2 percent o-phenylphenol. The formula was rubbed on the hands for 1 minute, rinsed under running water for 30 seconds, and dried with a paper towel. The total 24 hour urine samples were collected over a 4-day period post treatment and were analyzed by steam distillation followed by gas chromatography. The total o-phenylphenol excreted by the subjects ranged from 2.95 to 7.22 mg, with an average of 4.45 mg on the first day, 1.08 mg on the second day, and only traces on the third and fourth days. 600 mg of o-phenylphenol was applied to each subject, therefore only about 1 percent was absorbed dermally and the remaining washed off(1).

The serum of 10 infants with hyperbilirubinaemia who had been exposed to a gemicidal phenolic solution containing 9.8 percent o-phenylphenol was analyzed for the presence of three gemicidal phenols. o-Phenylphenol was detected in the serum of 7 infants with concentrations ranging from 500-1900 ng/L(1).

To investigate pesticides as exposure biomarkers during pregnancy, 100 amniotic fluid samples, slated for disposal, were collected at approximately 18 weeks gestation. o-Phenylphenol was detected in 30 percent of the samples with a geometric mean of 0.13 ug/L(1).

The mean concentration of o-phenylphenol in personal air samples in Jacksonville, Florida in summer (1986), spring (1987) and winter (1988) was 79.7, 55.6 and 39.7 ng/cu m, respectively(1). o-Phenylphenol was also detected in personal air samples in Springfield, Massachusetts in spring (1987) and winter (1987) at 16.2 and 11.3 ng/cu m, respectively(1).

F344/DuCrj rats were fed 10,000 or 20,000 mg sodium o-phenylphenol/kg diet, mixed with 2000 mg/kg thiabendazole in diet. The mean body weight of both sexes of both dose groups showed a statistically significant reduction throughout the study. The survival rates were not affected. At a dose level of 1.0% OPP-Na 1/15 males developed a papilloma and 11/15 carcinomas of the urinary bladder, while females were not affected. At a dose level of 2.0% OPP-Na 4/15 males developed papillomas and 10/15 carcinomas of the urinary bladder. 6/15 females showed papillomas and also 6/15 carcinomas of the urinary bladder. Transitional cell hyperplasia of the renal pelvis appeared in 2/15 males and 3/15 females at the 2.0% dose level. Thiabendazole apparently enhanced the carcinogenic effects of OPP-Na in the rat urinary bladder. /Sodium o-phenylphenol/

LD50; Species: Anas platyrhynchos (Mallard duck) oral >2250 mg a.i./kg /99.2%/ /from table/

LC50; Species: Anas platyrhynchos (Mallard duck) dietary >5620 ppm (subacute) /99.2%/ /from table/

LC50; Species: Colinus virginianus (Bobwhite quail) dietary >5620 (subacute) /99.2%/ /from table/

EC50; Species: Daphnia magna (Water flea, 6-24 hr old); Concentration: 2.1 mg/L for 24 hr; Effect: immobilization /Conditions of bioassay not specified in source examined/

For more Ecotoxicity Values (Complete) data for o-Phenylphenol (26 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6,700(SRC), determined from a log Kow of 3.09(2) and a regression-derived equation(3), indicates that o-phenylphenol is expected to be immobile in soil(SRC). Volatilization of o-phenylphenol from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 1.05X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.0X10-3 mm Hg(4), and water solubility, 700 mg/L(5). o-Phenylphenol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Utilizing the Japanese MITI test, o-phenylphenol reached 47-86% of its theoretical BOD in 2 weeks(6), indicating that biodegradation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6,700(SRC), determined from a log Kow of 3.09(2) and a regression-derived equation(3), indicates that o-phenylphenol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces may occur(4) based upon an estimated Henry's Law constant of 1.05X10-6 atm-cu m/mole(5), derived from its vapor pressure, 2.0X10-3 mm Hg(6), and water solubility, 700 mg/L(7). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 46 days and 366 days, respectively(SRC). The volatilization half-life from a model pond is about 490 days when adsorption is considered(8). According to a classification scheme(9), an estimated BCF of 51(SRC), from its log Kow(2) and a regression-derived equation(10), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation in water is expected to occur based on a 50% reduction of carbon-14 labeled o-phenylphenol observed in approximately 1 week in river water(11).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), o-phenylphenol, which has a vapor pressure of 2.0X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase o-phenylphenol 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 1.4 hours(SRC), calculated from its rate constant of 2.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Reaction to nitrate radical may be important based on o-phenylphenol structural similarity to phenol. Phenol has a half-life of 12 minutes in night-time air based on its reaction with nitrate radical; the rate constant for this reaction is 3.8X10-12 cu cm/molecule sec(4). By analogy to phenol, o-phenylphenol may degrade very rapidly in night-time air(4). o-Phenylphenol oxidizes in contact with air to form phenylbenzoquinone(5).

In a compilation of various data from US Food and Drug Administration studies for fiscal years 1970-1976, o-phenylphenol was positively detected in 101 of 448 large domestic fruit samples at an avg concn of 0.293 ppm(1); it was infrequently detected in fish and shellfish (1 positive sample), in leaf and stem vegetables (10 positive samples), and in vine and ear vegetables (5 positive samples)(1). In an analysis of imported fruits and bananas in Kyoto, Japan, o-phenylphenol residues of 0.1-3.2 ppm were found in all citrus fruits, but no residues were found in bananas(2). o-Phenylphenol concns of 2.3 ppm were found in whole lemons used for making marmalade(3).

Analysis of 324 food composites collected from 27 US cities between Oct 1980 and Mar 1982 (as part of the US FDA Total Diet Studies) detected o-phenylphenol in 2 cereal and grain products at an avg concn of 0.007 ppm(1). Analysis of 240 food composites collected from 20 US cities between Oct 1979 and Sept 1980 (as part of the US FDA Total Diet Studies) detected o-phenylphenol in 1 fruit product at a concn of 0.005 ppm(2). Analysis of 2250 food composites collected from US cities between Jun 1969 and July 1976 (as part of the US FDA Total Diet Studies for fiscal years 1970-1976) detected o-phenylphenol in 27 composites (primarily fruits) at levels ranging from a trace (0.001 ppm) to 0.40 ppm(3).

The concentration of o-phenylphenol found in foods as a preservative range from 10-12 ppm(1). Fourteen kinds of fruits, 22 kinds of vegetables, and 7 other food items were selected to represent the average Belgian diet from April 1991-March 1993 and analyzed for pesticide content(2). o-Phenylphenol was detected in 27.3% of orange and lemon samples with a mean concentration of 0.153 ppm for oranges and 0.133 ppm for lemons(2). From a variety of Spanish oranges, 86 percent contained levels of o-phenylphenol <10 mg/kg(3). The pesticide content of 27,065 food samples from CA, FL, IN, MA, MI, NC, NY, OR, VA and WI were analyzed for fiscal years 1988-89(3). o-Phenylphenol was not detected in fiscal year 1988 but was detected in fiscal year 1989 in 0.053% of the samples with 2 samples having significantly high levels (concn exceeded state or federal tolerance level)(4). In 1990, 15,919 food samples acquired from 18 states (AR, CA, CT, DE, FL, GA, IN, ME, MI, MN, NY, OR, PA, RI, VA, WA, WI, WY) were analyzed and found to have detectable amounts of o-phenylphenol (concn not specified)(5). A study near the city of Valencia in 2000-2001 analyzed fruits and vegetables by MSPD-LCMS. o-Phenylphenol was detected in 54 percent of the samples. The concentrations found ranged between 0.005-3.34 mg/kg. The average concentrations were 2 ug/kg in chard, 100 ug/kg in onion, 0.8 ug/kg in pepper, 3 ug/kg in banana, 30 ug/kg in lemon, 309 ug/kg in orange, and 165 ug/kg in tangerine(6). In Hyogo Prefecture, Japan a pesticide monitoring study detected o-phenylphenol in oranges (0.27 ug/g), grapefruit (0.12 ug/g), lemons (0.09 ug/g, and 0.66 ug/g)(7).

FOOD INTAKE: The 1971-1976 US dietary intake of o-phenylphenol has been calculated to be 0.03 ug/kg body wt/day(1). Based on results from the USFDA's Total Diet Studies, the US dietary intake for fiscal years 1978, 1979, 1980, and 1981/82 has been estimated to be 0.038, 0.046, 0.015, and 0.047 ug/kg body wt/day(2).

The average daily intake (ADI) of o-phenylphenol, was calculated to be 20 ug/kg body wt/day. The estimated daily intakes as a percentage of ADI for several fruits and vegetables were 0.0009 in chard, 0.18 in onion, 0.00060 in pepper, 0.006 in banana, 0.013 in lemon, 1.3 in orange, and 0.13 in tangerine for a total of 1.623(1).

/BIRDS and MAMMALS/ In order to establish the toxicity of 2-phenylphenol to avian species, the /Environmental Protection/ Agency required an acute oral toxicity study... The preferred test species is either mallard duck (a waterfowl) or bobwhite quail (an upland game bird). The results ... are provided in the table. The results indicate that 2-phenylphenol is slightly toxic to avian species on an acute oral basis.

/BIRDS and MAMMALS/ A subacute dietary study... was required /by EPA/ for the wood preservation use of 2-phenylphenol. Results of these studies are provided in the Table. The results indicate that 2-phenylphenol is practically non-toxic to avian species on a subacute dietary basis.

/AQUATIC SPECIES/ In order to establish the acute toxicity of pesticides to freshwater fish, the /Environmental Protection/ Agency requires freshwater fish toxicity studies ... The preferred test species are rainbow trout (a coldwater fish) and bluegill sunfish (a warmwater fish). Results of submitted studies ... indicate that orthophenylphenol and its sodium salt are moderately toxic to freshwater fish. The guideline requirements for freshwater fish acute studies (850.1075/72-1a and c) have been fulfilled.

/AQUATIC SPECIES/ Exposure of sea urchin sperm to 0.00001 M, 0.000001 M o-phenylphenol (OPP) for 10 min. did not result in any spermiotoxic effect. Mitotic abnormalities, namely % total mitotic aberrations, mean number of mitoses per embryo, and metaphase/anaphase ratio were induced by OPP.

Cough. Sore throat.

Redness.

Redness. Pain.

No acute symptoms expected.

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=90-43-7]

o-Phenylphenol was detected in raw wastewater from a textile finishing plant, probably from use as a dye carrier(1). Wastewater sampled from publicly owned treatment works in Decatur, IL and Bensenville, IL in 1980 contained o-phenylphenol(2). Levels of less than 0.008 ppm were found in sewage samples taken from Phoenix, AZ, but no detections were made in groundwater samples following a rapid infiltration method of sewage disposal(3). o-Phenylphenol was detected in discharges from two of five US leather tanning plants in 1978 and in effluent and sludge from a water treatment plant in Putnam, CT(4). In a four year study carried out in West Germany, o-phenylphenol was found at levels of 0.1-10 ppb in samples from a water filtration plant, at levels of <1-95 ppb in sanatoria wastewater, and at levels 0.1-1.0 ppb in Ruhr River water(4). A survey of sewage waste treatment plants in Germany found that o-phenylphenol was routinely found in influents in concentrations up to 2.6 ug/L (5). Another study at a German sewage treatment plant found that influent contained 1.89 ug/L o-phenylphenol and following treatment effluent had 0.015 ug/L, a 99.2 percent reduction(6). Composite five to seven day samples of chlorinated and unchlorinated primary-treated municipal wastewater were collected at the Iona Island treatment plant in Vancouver, Canada during a 62 day exposure of juvenile chinook salmon from June-August 1983(7). o-Phenylphenol was detected, concn not specified, in the base/neutral fraction of Iona Island wastewater and sludge(7).

Tolerances are established for combined residues of the fungicide o-phenylphenol and sodium o-phenylphenate, each expressed as o-phenylphenol, from postharvest application of either in or on the following food commodities: [Table#3537]

The Agency has completed its assessment of the dietary, occupational, drinking water, and ecological risks associated with the use of pesticide products containing the active ingredient OPP and salts. The Agency has determined that OPP containing products are eligible for reregistration provided that: (i) current data gaps and confirmatory data needs are addressed; (ii) the risk mitigation measures outlined in this document are adopted; and (iii) label amendments are made to reflect these measures where necessary. ... Based on its evaluation of OPP and salts, the Agency has determined that OPP products, unless formulated and used as specified in this document, would present risks inconsistent with FIFRA. Accordingly, should a registrant fail to implement any of the risk mitigation measures identified in this document, the Agency may take regulatory action to address the risk concerns from the use of OPP. If all changes outlined in this document are incorporated into the product formulations, then all current risks for OPP and its salts will be substantially mitigated for the purposes of this determination. Once an Endangered Species assessment is completed, further changes to these registrations may be necessary as explained in Section III of this document.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. o-Phenylphenol is found on List B. Case No: 2575; Pesticide type: fungicide, antimicrobial; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED /Reregistration Eligibility Decision/ document.; Active ingredient (AI): o-phenylphenol; Data Call-in (DCI) Date(s): 8/2/91, 5/12/95, 10/13/95; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

D08AE06

D - Dermatologicals

QD - Dermatologicals

... A genome-wide transcriptome analysis of the cellular responses of Pseudomonas aeruginosa (P. aeruginosa) exposed to 0.82 mM OPP for 20 and 60 minutes /was performed/ ... Ortho-phenylphenol (OPP) upregulated the transcription of genes encoding ribosomal, virulence and membrane transport proteins after both treatment times. After 20 minutes of exposure to 0.82 mM OPP, genes involved in the exhibition of swarming motility and anaerobic respiration were upregulated. After 60 minutes of OPP treatment, the transcription of genes involved in amino acid and lipopolysaccharide biosynthesis were upregulated. Further, the transcription of the ribosome modulation factor (rmf) and an alternative sigma factor (rpoS) of RNA polymerase were downregulated after both treatment times. Results from this study indicate that after 20 minutes of exposure to OPP, genes that have been linked to the exhibition of anaerobic respiration and swarming motility were upregulated. This study also suggests that the downregulation of the rmf and rpoS genes may be indicative of the mechanism by which OPP causes decreases in cell viability in P. aeruginosa. Consequently, a protective response involving the upregulation of translation leading to the increased synthesis of membrane related proteins and virulence proteins is possibly induced after both treatment times. In addition, cell wall modification may occur due to the increased synthesis of lipopolysaccharide after 60 minutes exposure to OPP. This gene expression profile can now be utilized for a better understanding of the target cellular pathways of OPP in P. aeruginosa and how this organism develops resistance to OPP.

A genome-wide transcriptome analysis of the cellular responses of Staphylococcus aureus (S. aureus) when exposed to 0.82 mM of ortho-phenylphenol (OPP) for 20 and 60 min /was performed/ ... OPP downregulated the biosynthesis of many amino acids, which are required for protein synthesis. In particular, the genes encoding the enzymes of the diaminopimelate (DAP) pathway which results in lysine biosynthesis were significantly downregualted. Intriguingly, ... the transcription of genes encoding ribosomal proteins was upregulated by OPP and at the same time, the genes encoding iron acquisition and transport were downregulated. The genes encoding virulence factors were upregulated and genes encoding phospholipids were downregulated upon 20 min exposure to OPP ... Using microarray analysis ... revealed novel information regarding the mode of action of OPP on Staphylococcus: OPP inhibits anabolism of many amino acids and highly downregulates the genes that encode the enzymes involved in the DAP pathway. Lysine and DAP are essential for building up the peptidoglycan cell wall. It was concluded that the mode of action of OPP is similar to the mechanism of action of some antibiotics. The discovery of this phenomenon provides useful information that will benefit further antimicrobial research on S. aureus.

Ortho-phenylphenol (OPP) was well absorbed in the male B6C3F1 mouse, with 84 and 98% of the administered radioactivity recovered in the 0-48-hr urine of animals administered a single oral dose of 15 or 800 mg/kg respectively. High absorption and rapid elimination were also seen in the female and male F344 rat with 86 and 89% respectively of a single oral dose (27-28 mg/kg) found in the urine in 24 hr. OPP was also rapidly eliminated from human volunteers following dermal exposure for 8 hr (0.006 mg/kg), with 99% of the absorbed dose in the urine in 48 hr.. Sulfation of OPP was found to be the major metabolic pathway at low doses in all three species, accounting for 57, 82 and 69% of the urinary radioactivity in the male mouse (15 mg/kg, po), male rat (28 mg/kg, po) and male human volunteers (0.006 mg/kg, dermal). OPP-glucuronide was also present in all species, representing 29, 7 and 4% of the total urinary metabolites in the low dose groups of mouse, rat and human volunteers respectively. Conjugates of 2-phenylhydroquinone (PHQ) in these single-dose studies accounted for 12, 5 and 15% of the dose in mouse, rat and human, respectively. Little or no free OPP was found in any species. No free PHQ or PBQ was found in the mouse, rat or human (LOD = 0.1-0.6%). A novel metabolite, the sulfate conjugate of 2,4'-dihydroxybiphenyl, was identified in rat and man, comprising 3 and 13% of the low dose respectively. Dose-dependent shifts in metabolism were seen in the mouse for conjugation of parent OPP, indicating saturation of the sulfation pathway. Dose-dependent increases in total PHQ were also observed in mouse. This study was initiated to elucidate a mechanistic basis for the difference in carcinogenic potential for OPP between rat and mouse. However, the minor differences seen in the metabolism of OPP in these two species do not appear to account for the differences in urinary bladder toxicity and tumor response between mouse and rat.

Dogs & cats also excrete urinary sulfonic acid & glucuronic acid metabolites of o-phenylphenol, although the parent compound predominates.

(14)C-ortho-Phenylphenol was applied onto the skin of the forearm of 6 volunteers for 8 hr at a dose of 0.4 mg/person (0.006 mg/kg bw). ... Sulfation was the major metabolic pathway, accounting for 69% of the metabolites, while conjugates of 2-phenylhydroquinone accounted for 15%. Little or no free ortho-phenylphenol was present in the urine, & no free 2-phenylhydroquinone or 2-phenyl-1,4-benzoquinone was detected.

ortho-Phenylphenol was converted to phenylhydroquinone by microsomal cytochrome P450 in vitro. Phenylhydroquinone was oxidized to phenylquinone by cumene hydroperoxide-supported microsomal cytochrome P450, & phenylquinone was reduced back to phenylhydroquinone by cytochrome P450 reductase, providing direct evidence of redox cycling of ortho-phenylphenol.

For more Metabolism/Metabolites (Complete) data for o-Phenylphenol (12 total), please visit the HSDB record page.

2-phenylphenol has known human metabolites that include 2,5-dihydroxybiphenyl.

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.

Substances used on inanimate objects that destroy harmful microorganisms or inhibit their activity. Disinfectants are classed as complete, destroying SPORES as well as vegetative forms of microorganisms, or incomplete, destroying only vegetative forms of the organisms. They are distinguished from ANTISEPTICS, which are local anti-infective agents used on humans and other animals. (From Hawley&apos;s Condensed Chemical Dictionary, 11th ed)

Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.

The pharmacokinetics and metabolism of uniformly labeled 14C/13C-ortho-phenylphenol (OPP) were followed in six human male volunteers given a single 8 hr dermal dose of 6 ug OPP/kg body weight formulated as a 0.4% (w/v) solution in isopropyl alcohol. The application site was covered with a non-occlusive dome allowing free movement of air, but preventing the loss of radioactivity due to physical contact. At 8 hr post-exposure the non-occlusive dome was removed, the dose site was wiped with isopropyl alcohol containing swabs and the skin surface repeatedly stripped with tape. Blood specimens, urine, and feces were collected from each volunteer over a 5 day post-exposure period and were analyzed for radioactivity and metabolites (urine only). Following dermal application, peak plasma levels of radioactivity were obtained within 4 hr post-exposure and rapidly declined with virtually all of the absorbed dose rapidly excreted into the urine within 24 hr post-exposure. A one-compartment pharmacokinetic model was used to describe the time-course of OPP absorption and clearance in male human volunteers. Approximately 43% of the dermally applied dose was absorbed through the skin with an average absorption half-life of 10 hr. Once absorbed the renal clearance of OPP was rapid with an average half-life of 0.8 hr. The rate limiting step for renal clearance was the relatively slower rate of dermal absorption; therefore the pharmacokinetics of OPP in humans was described by a 'flip-flop' single compartment model. Overall, the pharmacokinetics were similar between individuals, and the model parameters were in excellent agreement with the experimental data. Approximately 73% of the total urinary radioactivity was accounted for as free OPP, OPP-sulfate and OPP-glucuronide conjugates. The sulfate conjugate was the major metabolite (approximately 69%). Therefore, total urinary OPP equivalents (acid-labile conjugates+free OPP) can be used to estimate the systemically absorbed dose of OPP. The rapid excretion of OPP and metabolites into the urine following dermal exposure indicates that OPP is unlikely to accumulate in humans upon repeated exposure ...

Male F344 rats were treated with 0, 15, 50, 125, 250, 500, 1000 mg/kg of ortho-phenylphenol (OPP) and its radiocarbon analogue via oral gavage. The dosed rats were euthanized after 24 hr, and the proteins were extracted from the liver, kidney, and bladder. The amount of radioactivity associated with the extracted protein was quantified ... Protein binding in liver and kidney exhibited a linear or modest curvilinear relationship over the dose range studied. In the urinary bladder, however, a pronounced nonlinear relationship between protein adduct levels and administered dose was observed. The measured protein adduct levels were in agreement with the predicted concentrations of phenylbenzoquinone based on a proposed mechanism involving free phenylhydroquinone autoxidation in the urine. Unlike protein binding, DNA adducts measured from the same bladder samples did not show a significant difference from the control group ...

The validity of in vitro and in vivo methods for the prediction of percutaneous penetration in humans was assessed using the fungicide ortho-phenylphenol (OPP) (log Po/w 3.28, MW 170.8, solubility in water 0.7 g/L). In vivo studies were performed in rats and human volunteers, applying the test compound to the dorsal skin and the volar aspect of the forearm, respectively. In vitro studies were performed using static diffusion cells with viable full-thickness skin membranes (rat and human), nonviable epidermal membranes (rat and human), and a perfused pig ear model. For the purpose of conducting in vitro/in vivo comparisons, standardized experimental conditions were used with respect to dose (120 ug OPP/sq cm), vehicle (60% aqueous ethanol), and exposure duration (4 hr). In human volunteers, the potentially absorbed dose (amount applied minus dislodged) was 105 ug/sq cm, while approximately 27% of the applied dose was excreted with urine within 48 hr. In rats these values were 67 ug/sq cm and 40%, respectively. In vitro methods accurately predicted human in vivo percutaneous absorption of OPP on the basis of the potential absorbed dose. With respect to the other parameters studied (amount systemically available, maximal flux), considerable differences were observed between the various in vitro models ...

Excreted in mammals principally as the parent compound & as the glucuronide & sulfate conjugates.

For more Absorption, Distribution and Excretion (Complete) data for o-Phenylphenol (7 total), please visit the HSDB record page.

Used as a dye intermediate, germicide, fungicide, disinfectant, and plasticizer; to manufacture rubber chemicals; in food packaging; as a preservative in water-oil emulsions; antimicrobial preservative in cosmetics; [HSDB] Used as an antimicrobial additive in the manufacture of metalworking fluids, leather, adhesives, and textiles; [Merck Index]

Metal Machining [Category: Heat or Machine]

For 2-phenylphenol (USEPA/OPP Pesticide Code: 064103) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Used in products predominantly as a disinfectant, antimicrobial, preservative, antioxidant, and sanitizing agent in various industries.

Wood preserving ... used for sapstain control in freshly cut lumber

Fungicide for citrus (postharvest use); disinfectant (eg, for cutting oils, timber, + paper); dyestuff carrier for polyester fibers

(1976) 6.01X10+6 g (Princpl custms dists)

(1978) 3.00X10+7 g (Princpl custms dists)

(1976) Probably greater than 4.54x10+5 g

(1978) Probably greater than 4.54x10+5 g

Current global production is estimated to be less than 10 million pounds per year.

[1,1'-Biphenyl]-2-ol is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).[EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program.

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3538]

By hydrogenation of 2-cyclohexylidenecyclohexanone produced by the base catalyzed dimerization of cyclohexanone.

Either synthesized directly or isolated as a byproduct in the production of phenol by the hydrolysis of monochlorobenzene.

Prepared from phenyl ether.

Biphenyl (sulphonation/alkali fusion; coproduced with p-phenylphenol). Chlorobenzene (arylation/base-catalyzed hydrolysis; coproduced with p-phenylphenol). Xylenol, mixed (fractionation/alkali extraction; coproduced with biphenyl)

For more Methods of Manufacturing (Complete) data for o-Phenylphenol (7 total), please visit the HSDB record page.

Coldcide 0.25%: Active Ingredients 0.2750% Glutaral, 0.0027% 4-tert-Amylphenol, 0.0137% o-Phenylphenol

Staphene Disinfectant Spray And Deodorizer: Active Ingredients 53.096% Ethyl alcohol, 0.077% 2-Benzyl-4-chlorophenol, 0.074% 4-tert-Amylphenol , 0.041% o-Phenylphenol , 0.042% Alkyl* dimethyl benzyl ammonium chloride *(60%C14, 30%C16, 5%C1 8, 5%C12), 0.042% Alkyl* dimethyl ethylbenzyl ammonium chloride *(50%C12, 30%C14,17%C16, 3%C18)

Easy-Dab Bacteriostatic Creme Cleanser: Active Ingredient 0.05% o-Phenylphenol

Steriphene II Brand Disinfectant Deodorant: Active Ingredients 64.000% Ethyl alcohol, 0.071% 2-Benzyl-4-chlorophenol, 0.051% o-Phenylphenol

For more Formulations/Preparations (Complete) data for o-Phenylphenol (92 total), please visit the HSDB record page.

Cosmetics product ingredient: o-Phenylphenol

Information on 25 consumer products that contain o-Phenylphenol in the following categories is provided:

Food Additives -> PRESERVATIVE -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Food Additives -> PRESERVATIVE -> JECFA Functional Classes

Food Additives -> PRESERVATIVE -> JECFA Functional Classes

Food Additives -> PRESERVATIVE -> JECFA Functional Classes

Food Additives -> PRESERVATIVE -> JECFA Functional Classes

[1,1'-Biphenyl]-2-ol: ACTIVE

The tendency /of o-phenylphenol/ to scald citrus fruits is reduced by addition of hexamine.

Water sol sodium salt of o-phenylphenol is used for protecting water extendable paints against decomposition prior to use and is employed as a preservative for proteins and other types of decomposable adhesives. In dish washing formulations, vegetable wax, and in paper dipping for food storage. /o-Phenylphenol sodium/

Canadian tolerance on apples and pears: 5 ppm.

Should not be used on growing plants.

For more General Manufacturing Information (Complete) data for o-Phenylphenol (6 total), please visit the HSDB record page.