Bisphenol B

242.31

242.31

201-025-1

1RC731TJJA

1775

DTXSID4022442

Crystal or tan granules

29242995

40.5

3.9

odorless slightly brown solid

1.1±0.1 g/cm3

120.5 °C

204-207 °C @ Press: 5 Torr

195.5±17.8 °C

1.589

Approximate solubility per 100 g: acetone 266 g; benzene 2.3 g; carbon tetrachloride <0.1 g; ether 133 g; methanol 166 g; V.M.P. naphtha <0.1 g

Store in a cool, dry place. Store in a tightly closed container.

2.5X10-7 mm Hg at 25 deg C (est)

Henry's Law constant = 1.2X10-11 atm-cu m/mol at 25 °C (est)

pKa = 10.1 at 25 °C (est)

167.17 Ų [M-H]-

Hydroxyl radical reaction rate constant = 8.2X10-11 cu cm/molecule-sec at 25 °C (est)

IRRITANT

36/37/38

26-36/37/39

SM1210200

Stable under normal temperatures and pressures.

P264, P270, P273, P280, P301+P312, P305+P351+P338, P330, P337+P313, P501

H302

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.

IDENTIFICATION AND USE: Bisphenol B is a crystaline or tan granulular substance which is insoluble in water; soluble in acetone; benzene ; ether; methanol; slightly soluble in carbon tetrachloride and naphtha. It is used in the the manufacture of phenolic and polycarbonate resins. HUMAN EXPOSURE AND TOXICITY: Occupational exposure to bisphenol B may occur through dermal contact with this compound at workplaces where it is produced or used. Monitoring and use data indicate that the general population may be exposed to bisphenol B by ingestion of food and dermal contact with this compound or other products containing bisphenol B. ANIMAL STUDIES: In this study, the ability of certain EDCs, bisphenol A (BPA), bisphenol B (BPB), bisphenol F (BPF), 4-n Nonylphenol (NP) and Octylphenol (OP), was investigated to interfere with specific cellular processes, namely, proliferation, by using MCF-7 breast carcinoma cells, and murine bone marrow dendritic cells. The data was correlated on cell growth with the stimulation of cell cycle progression, which could become a step in the development of cancer, and data established a proliferation ranking between the tested EDCs: NP>BPA>OP>BPB>BPF. In addition, the ability of NP, BPA and OP was investigated to induce the differentiation of dendritic cells. The differentiation and activation of these cells could affect a well-regulated immune response and determine an allergic sensitization. It was found that BPA and NP were active in determining differentiation.

Bisphenol B's production and use in the manufacture of phenolic and polycarbonate resins(1,2) may result in its release to the environment through various waste streams(SRC). Bisphenol B can be released from resin linings used as corrosion inhibitors to coat cans in the food industry(2).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 7.4X10+4(SRC), determined from a structure estimation method(2), indicates that bisphenol B is expected to have to be immobile in soil(SRC). Volatilization of bisphenol B from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Bisphenol B is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.5X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Results of aerobic river die-away tests and anaerobic sediment tests suggest that biodegradation of bisphenol B occurs slowly(3).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 7.4X10+4(SRC), determined from a structure estimation method(2), indicates that bisphenol B 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 1.2X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Bisphenol B is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Phenols can undergo sensitized photo-oxidation in surface waters exposed to sunlight via reaction with hydroxyl and peroxy radicals with half-lives on the order of days to weeks at the water surface(4); therefore, photo-oxidation may be an important fate process for bisphenol B in natural water(SRC). According to a classification scheme(5), an estimated BCF of 250(SRC), from an estimated log Kow of 4.13(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Results of aerobic river die-away tests and anaerobic sediment tests suggest that biodegradation of bisphenol B occurs slowly(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bisphenol B, which has an estimated vapor pressure of 2.5X10-7 mm Hg at 25 °C((SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase bisphenol B 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 5 hours(SRC), calculated from its rate constant of 8.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase bisphenol B may be removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of bisphenol B with photochemically-produced hydroxyl radicals has been estimated as 8.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Bisphenol B is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Phenols can undergo sensitized photo-oxidation in surface waters exposed to sunlight via reaction with hydroxyl and peroxy (RO2) radicals with half-lives on the order of days to weeks at the water surface(3); therefore, photo-oxidation may be an important fate process for bisphenol B in natural water(SRC).

An estimated BCF of 250 was calculated in fish for bisphenol B(SRC), using an estimated log Kow of 4.13(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of bisphenol B can be estimated to be 7.4X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that bisphenol B is expected to be immobile in soil. The estimated pKa of bisphenol B is 10.2(3), indicating that this compound will exist predominately in the non-ionized form in the environment(SRC); the anion form of bisphenol B in not expected to adsorb more strongly to soils containing organic carbon and clay than the neutral counterpart(3).

The Henry's Law constant for bisphenol B is estimated as 1.2X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that Bisphenol B is expected to be essentially nonvolatile from water surfaces(2). Bisphenol B's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Bisphenol B is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.5X10-7 mm Hg(SRC), determined from a fragment constant method(1).

Bisphenol B was detected in 9 of 42 tomato samples, at concentrations of 27.1 to 85.7 ug/kg, in samples of peeled canned tomatoes collected from Italian supermarkets. Of the total of 42 tested tomato samples, BPB was detected in 9 samples (21.4%). BPA and BPB were simultaneously present in 8 of the analyzed samples(1).

Occupational exposure to bisphenol B may occur through dermal contact with this compound at workplaces where bisphenol B is produced or used. Monitoring and use data indicate that the general population may be exposed to bisphenol B via ingestion of food and dermal contact with this compound or other products containing bisphenol B. (SRC)

/The researchers/ previously demonstrated that the estrogenicity of either bisphenol A [BPA; 2,2-bis(4-hydroxyphenyl)propane] or bisphenol B [BPB; 2,2-bis(4-hydroxyphenyl)butane] was increased several times after incubation with rat liver S9 fraction. This metabolic activation, requiring both microsomal and cytosolic fractions, was observed with not only rat liver, but also human, monkey, and mouse liver S9 fractions. To characterize the active metabolites of BPA and BPB, /the researchers/ investigated the structures of the isolated active metabolites by negative mode LC/MS/MS and GC/MS. The active metabolite of BPA gave a negative mass peak at [M-H](-) 267 on LC/MS and a single daughter ion at m/z 133 on MS/MS analysis, suggesting an isopropenylphenol dimer structure. Finally, this active metabolite was confirmed to be identical with authentic 4-methyl-2,4-bis(p-hydroxyphenyl)pent-1-ene (MBP) by means of various instrumental analyses. The corresponding peaks of the BPB metabolite were [M-H](-) 295 and m/z 147, respectively, suggesting an isobutenylphenol dimer structure. Further, coincubation of BPA and BPB with rat liver S9 afforded an additional active metabolite(s), which gave a negative mass peak at [M-H](-) 281 and two daughter ion peaks at m/z 133 and m/z 147 on MS/MS analysis. These results strongly suggest that the active metabolite of either BPA or BPB might be formed by recombination of a radical fragment, a one-electron oxidation product of carbon-phenyl bond cleavage. It is noteworthy that the estrogenic activity of MBP, the active metabolite of BPA, is much more potent than that of the parent BPA in several assays, including two reporter assays using a recombinant yeast expressing human estrogen receptor alpha and an MCF-7-transfected firefly luciferase plasmid.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. 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 0.9% saline (NS) 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

2,2-bis(4-hydroxyphenyl)butane

Bisphenol A (BPA) and bisphenol B (BPB) concentrations were determined in peeled canned tomatoes of different brands bought in Italian supermarkets. Tomato samples analyzed were packaged in cans coated with either epoxyphenolic lacquer or low BADGE enamel. A solid phase extraction (SPE) was performed on C-18 Strata E cartridge followed by a step on Florisil cartridge. Detection and quantitation were performed by a reversed phase high-performance liquid chromatography (RP-HPLC) method with both UV and fluorescence detection (FD).

A novel method combining dispersive liquid-liquid microextraction (DLLME) and heart-cutting multidimensional gas chromatography coupled to mass spectrometry was developed for the determination of free and total bisphenol A (BPA) and bisphenol B (BPB) in human urine samples. The DLLME procedure combines extraction, derivatization and concentration of the analytes into one step. Several important variables influencing the extraction efficiency and selectivity such as nature and volume of extractive and dispersive solvents as well as the amount of acetylating reagent were investigated. The temperature and time to hydrolyze BPA and BPB conjugates with a beta-glucuronidase and sulfatase enzyme preparation were also studied. Under the optimized conditions good efficiency extraction (71-93%) and acceptable total DLLME yields (56-77%) were obtained for both analytes. Matrix-matched calibration curves were linear with correlation coefficients higher than 0.996 in the range level 0.1-5 ug/L, and the relative standard deviations (%RSD) were lower than 20% (n=6). The limits of detection were 0.03 and 0.05 ug/L for BPA and BPB, respectively. The applicability of the proposed method for determining urinary free and total BPA and BPB was assessed by analyzing the human urine of a group of 20 volunteers. Free BPA was detected in 45% of the sample whereas total BPA was detected in 85% of the samples at concentrations ranging between 0.39 and 4.99 ug/L. BPB was detected in conjugated form in two samples.|A sensitive HPLC method with fluorescence detection was developed for the determination of bisphenol A (BPA) and bisphenol B (BPB) in human blood serum. The detection limits of the method were 0.18 and 0.20 ng/mL for BPA and BPB, respectively.