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HCID 12111Erstellt: 27. Oktober 2026

4,4'-Methylendiphenol

BISPHENOL F · BIS(4-HYDROXYPHENYL)METHANE · Bisphenol F (100μg/mL) · 4,4'-methylenediphenol · p,p'-BPF · PP-BIP-F · NSC 401136 · JACS-620-92-8

https://huagongshe.com/de/chemical/12111

Molekülstruktur von 4,4'-Methylendiphenol

Identifikatoren & physikalische Daten

CAS No.620-92-8
SummenformelC13H12O2
Durchschnittliche Molmasse200,23 g/mol
Monoisotopische Masse200,08372962 g/mol
SMILESOc1ccc(Cc2ccc(O)cc2)cc1
InChIKeyPXKLMJQFEQBVLD-UHFFFAOYSA-N
PubChem CID12111
ChEMBLCHEMBL138061
ChEBICHEBI:34575
EC No.210-658-2
DTXSIDDTXSID9022445
Lokaler Name4,4'-Methylendiphenol

Chemische & physikalische Eigenschaften

XLogP2,9
Polarare Oberfläche (TPSA)40,5
H-Brücken-Donoren2
H-Brücken-Akzeptoren2
Frei drehbare Bindungen2
Schwere Atome15
Formalladung0
Komplexität157
StoffklassenBisphenolOther emerging contaminant and(or) Hormone
LogP (Verteilungskoeffizient)log Kow = 2.91
LöslichkeitSoluble in ethanol, ether, chloroform, alkalislightly soluble in DMSOinsoluble in carbon disulfideDMSO (Slightly), Methanol (Slightly)It is soluble in ethanol, ether, chloroform, alkalislightly soluble in DMSO, insoluble in carbon disulfide and water.
Endocrine DisruptorsPotential endocrine disrupting compound
SiedepunktSublimes297.96°C (rough estimate)
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
Schmelzpunkt162.5 °C162-164 °C
Stability/Shelf LifeStable under recommended storage conditions.
Dissociation ConstantspKa1 = 7.55, pKa2 = 10.80 at 25 °C
Collision Cross Section153.6 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID9022445]155.05 Ų [M-H]-
Dichte1.0907 (rough estimate)
Brechungsindex1.6110 (estimate)
LagerbedingungenSealed in dry,Room Temperature
pKa (Säurekonstante)9.91±0.10(Predicted)
AggregatzustandSolid
FarbeOff-White to Light Red
BRN2049425
Henry-Konstante1.9×106 mol/(m3Pa) at 25℃, HSDB (2015)
InChIInChI=1S/C13H12O2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8,14-15H,9H2
InChIKeyPXKLMJQFEQBVLD-UHFFFAOYSA-N
SMILESC(C1=CC=C(O)C=C1)C1=CC=C(O)C=C1
CAS Datenbank620-92-8(CAS DataBase Reference)
EPA chemische InformationenPhenol, 4,4'-methylenebis- (620-92-8)

Sicherheit & Vorschriften

GHS-EinstufungThis chemical does not meet GHS hazard criteria for 3.8% (5 of 130) of reports.DangerH315 (80.8%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 130 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Regulatorische InformationenHazard Traits - Hazard Trait UndefinedPhenol, 4,4'-methylenebis-: Does not have an individual approval but may be used under an appropriate group standard
Toxic Combustion ProductsSpecial hazards arising from the substance or mixture: Carbon oxides.
Hazard Classes and CategoriesSkin Irrit. 2 (80.8%)
Hazardous Reactivities and IncompatibilitiesIncompatible materials: Strong oxidizing agents.
BrandbekämpfungsverfahrenSuitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.
LagerbedingungenKeep container tightly closed in a dry and well-ventilated place.
ReinigungsverfahrenACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
EntsorgungsverfahrenSRP: 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

Anwendungen & Verwendung

Verwenden

4,4'-Dihydroxydiphenylmethane, is also used as a bisphenol derivative with antioxidant activities. Bisphenol F has been reported to exhibit estrogen agonistic properties. Bisphenol F is used to make epoxy resins and coatings for various applications, such as lacquers, varnishes, liners, adhesives, plastics, water pipes, dental sealants, and food packaging.

potential migration in air, soil or water
effects on animal, aquatic and plant life
and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.
Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material
Contaminated packaging: Dispose of as unused product.
Preventive MeasuresACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Do not let product enter drains.Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.
Personal Protective Equipment (PPE)Eye/face protection: Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).Skin protection: Handle with gloves.Body Protection: Impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
KörperbelastungBisphenol F was detected in 60% of human breast milk samples collected from 20 healthy voluntary donors living in Hunan Province, China, at 0.010-0.166 ug/L. In 116, 22 and 20 urine samples collected July-August 2014 from people living in an electronic waste dismantling, rural reference and urban reference areas of China, respective bisphenol F concentrations were <LOQ-8.68, <LOQ-0.855 and <LOQ-3.04 ng/mL(2).Urine samples collected from adult volunteers in Atlanta, GA contained bisphenol F at the following concentrations(1).[Table#8071]
WechselwirkungenThe estrogenic activities of BPA, BPAF, BPAP, BPF were tested based on recombinant gene yeast assay. Six mixtures were designed based on the result of the test,each of which had an equitoxic ratio ray (EC10 or EC50). The EC50 values are 6.81 x 10(-6) mol/L, 7.44 x 10(-7) mol/L, 1.43 x 10(-5) mol/L, 7.52 x 10(-6) mol/L for BPA, BPAF, BPAP and BPF respectively,which reveals that the estrogenic activities order among the four bisphenols was BPAF> BPA> BPF> BPAP. The experiment shows that when BPA mixes with BPAF, BPAP and BPF in different ratios individually, different combination effects are produced. ...
UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 15,000(SRC), determined from a structure estimation method(2), indicates that bisphenol F is expected to be immobile in soil(SRC). Volatilization of bisphenol F from moist soil surfaces is not expected(SRC) given an estimated Henry's Law constant of 5.2X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Bisphenol F is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.7X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). A 1% of theoretical BOD using activated sludge in the Japanese MITI test(3) suggests that biodegradation is not an important environmental fate process in soil(SRC). In contrast, bisphenol F was readily biodegradable in modified river and seawater die-away tests(4-5) including complete mineralization within 22 days in various microcosms(4).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 15,000(SRC), determined from a structure estimation method(2), indicates that bisphenol F 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 5.2X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Bisphenol F is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(4), BCFs of 3.8-18 measured in carp(5), suggest bioconcentration in aquatic organisms is low. 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(6)therefore, photo-oxidation may have some importance as a fate process for Bisphenol F in natural water(SRC). In 22-day aerobic river die-away tests using river water samples, bisphenol F showed complete degradation or complete primary degradation(7). Biodegradation of bisphenol F was 8-58% after 30 days using an aerobic degradation test and seawater microcosms following a 6-12 day lag period(8)biodegradation of bisphenol F was >92% after 60 days(8).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bisphenol F, which has an estimated vapor pressure of 3.7X10-7 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 F 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 F may be removed from the air by wet or dry deposition(SRC).
LebensmitteluntersuchungswerteBisphenol F was detected in two of eleven canned beverages purchased in Barcelona supermarketsconcentration in a sample of orange soda was 0.218 g/L and concentration in a sample of lemon soda was 0.141 ug/L(1). Bisphenol F was not detected in beverages packaged in poly(ethylene terephthalate) containers, but was detected in the same beverages packaged in cans at <LOQ-0.39 ng/mLit was also detected in canned foods at <LOQ-35 ng/g, beverage and food products were purchased Feb 2014 from a supermarket in Beijing, China(2). Bisphenol F was detected in 6 of 36 honey samples purchased 2015 and 2016 from supermarkets from various European and non-European countries at 1.69-31.6 ng/g(3). Bisphenol F has been detected in prepared mustards containing ground white mustard (Sinapis alba) seeds, mustards containing only brown (Brassica juncea) or black (Brassica nigra) seeds did not contain bisphenol F(4).In 267 food samples divided into nine categories collected 2008, 2011 and 2012 from retail grocery stores in Albany, NY, bisphenol F was detected at the following concentrations(1):[Table#8072]
Milk ConcentrationsBisphenol F was detected in 60% of human breast milk samples collected from 20 healthy voluntary donors living in Hunan Province, China, at 0.010-0.166 ug/L(1).
ToxizitätsübersichtIDENTIFICATION AND USE: Bisphenol F is a mixture of isomeric and oligomeric products. Bisphenol F is used to make epoxy resins and coatings for various applications, such as lacquers, varnishes, liners, adhesives, plastics, water pipes, dental sealants, and food packaging. HUMAN STUDIES: Retrospective review of results of patch-testing with plastics and glues allergens was conducted. In total, 444 patients were patch-tested with up to 56 plastics and glues allergens in the specialized series and up to five plastics and glues allergens in a baseline series. Positive-reaction rates were compared to other patch testing reports. Of patients, 97 (22%) had irritant reactions, and 201 (45%) had at least one allergic reaction. Bis(2-dimethylaminoethyl) ether 1%, benzoyl peroxide 1%, epoxy resin, bisphenol F 0.25%, 2-hydroxyethyl methacrylate 2%, and 2-hydroxyethyl acrylate 0.1% had the highest allergy reaction rates. Testing with specialized series identified 193 patients with plastics and glues allergy, of whom 162 were not identified by testing with baseline series alone. Occupational exposure to bisphenol F may occur through inhalation of dust and dermal contact with this compound at workplaces where it is produced or used. Monitoring data indicate that the general population is exposed to bisphenol F via inhalation of house dust, ingestion of soda, and possibly dermal contact with consumer products containing resins and coatings made with bisphenol F. Bisphenol F caused mainly necrotic changes in in human peripheral blood mononuclear cells. Bisphenol F was anti-androgenic in the human cell lines. Bisphenol F was effective on HepG2 cell DNA fragmentation at non-cytotoxic concentrations, but it did not induced a positive response in the micronucleus assay. ANIMAL STUDIES: Bisphenol F was orally administered to young rats for at least 28 days. No clear endocrine mediated changes were detected, and it was concluded bisphenol F had no endocrine mediated effects. The main effect of the chemical was liver toxicity based on clinical biochemical parameters and liver weight, but without histopathological changes. Decreased body weight accompanied by decreased serum total cholesterol, glucose, and albumin values were observed in the female rats given bisphenol F. When estrogenic activities of bisphenols were tested using recombinant gene yeast assay, bisphenol F was the most potent of the group. Bisphenol F did not induce any genic mutation in bacteria in the Ames test.
Average Daily IntakeThe average daily intake (ADI) of bisphenol F for different age groups was calculated using food concentrations from a survey collected 2008, 2011 and 2012 in Albany, NY(1).[Table#8070]The average intake of the sum of 9 bisphenols (including bisphenol F) by the mouthing of baby teeters for 1 hour by 12 month old infants is reported as 1.40-1.51 ng/kg body weight/day(1).
Ongoing Test StatusEPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPAICSS Dashboard ApplicationAvailable from, as of November 16, 2017: http://actor.epa.gov/dashboard/]
Effluent ConcentrationsBisphenol F was detected not quantified in leachate collected from a municipal landfill in Sweden in 1990(1).
Soil Adsorption/MobilityUsing a structure estimation method based on molecular connectivity indices(1), the Koc of bisphenol F can be estimated to be 15,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that bisphenol F is expected to be immobile in soil.
Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ Retrospective review of results of patch-testing with plastics and glues allergens at our institution between 2000 and 2007. In total, 444 patients were patch-tested with up to 56 plastics and glues allergens in the specialized series and up to five plastics and glues allergens in a baseline series. Positive-reaction rates were compared to other patch testing reports. Of patients, 97 (22%) had irritant reactions, and 201 (45%) had at least one allergic reaction. Bis(2-dimethylaminoethyl) ether 1%, benzoyl peroxide 1%, epoxy resin, bisphenol F 0.25%, 2-hydroxyethyl methacrylate 2%, and 2-hydroxyethyl acrylate 0.1% had the highest allergy reaction rates. Testing with specialized series identified 193 patients with plastics and glues allergy, of whom 162 were not identified by testing with baseline series alone./ENDOCRINE MODULATION/ Concerning endocrine activities, /bisphenol F/ BPF increased the luciferase activity in HepG2 cells transiently transfected with a concentration dependant pattern, dihyroxybenzophenone (DHB) also induced a positive response but at highest concentrations. Estrogenic responses in the HepG2 cells differed with the estrogen receptor (ER) involved. Using MDA-kb2 cell line stably transfected with pMMTV-neo-Luc, only BPF was anti-androgenic at the highest concentration (1.0x10-5 M). /Investigators/ demonstrated using human cell lines, especially HepG2, /that/ BPF was the most toxic compound in term of ... endocrine activities compared to DHB and BPF-OH, the free metabolites identified in rat urine when BPF was administrated to rats./ENDOCRINE MODULATION/ Bisphenol F, bisphenol A, fluorine-containing bisphenol A (bisphenol AF), and other diphenylalkanes were found to be estrogenic in a bioassay with MCF7 human breast cancer cells in culture (E-SCREEN assay). Bisphenols promoted cell proliferation and increased the synthesis and secretion of cell type-specific proteins. When ranked by proliferative potency, the longer the alkyl substituent at the bridging carbon, the lower the concentration needed for maximal cell yieldthe most active compound contained two propyl chains at the bridging carbon. Bisphenols with two hydroxyl groups in the para position and an angular configuration are suitable for appropriate hydrogen bonding to the acceptor site of the estrogen receptor. Our data suggest that estrogenicity is influenced not only by the length of the substituents at the bridging carbon but also by their nature. .../GENOTOXICITY/ Bisphenol A (BPA) and bisphenol F (BPF) are widely used to manufacture plastics and epoxy resins. Both compounds have been shown to be present in the environment and are food contaminants, with, as a result, a low but chronic exposure of humans. However, the fate and possible bioactivation of these compounds at the level of human cell lines was not completely elucidated yet. In this study, /the researchers/ investigated the ability of human cells (intestinal cell line: LS174T, hepatoma cell line: HepG2, and renal cell line: ACHN) to biotransform BPA and BPF, and focused on the cytotoxicity and genotoxicity of these two bisphenols, through the use of a novel and efficient genotoxic assay based on the detection of histone H2AX phosphorylation. BPA and BPF were extensively metabolized in HepG2 and LS174T cell lines, with stronger biotransformation capabilities in intestinal cells than observed in liver cells. Both cell lines produced the glucuronide as well as the sulfate conjugates of BPA. Conversely, the ACHN cell line was found to be devoid of any metabolic capabilities for the two examined bisphenols. Cytotoxicity was tested for BPA, BPF, as well as one metabolite of BPF produced in vivo in rat, namely dihydroxybenzophenone (DHB). In the three cell lines used, /the researchers/ observed similar ranges of toxicity, with DHB being weakly cytotoxic, BPF exhibiting an intermediary cytotoxicity, and BPA being the most cytotoxic compound tested. BPA and DHB were not found to be genotoxic, whatever the cell line examined. BPF was clearly genotoxic in HepG2 cells. These results demonstrate that some human cell lines extensively metabolize bisphenols and establish the genotoxic potential of bisphenol F.For more Human Toxicity Excerpts (Complete) data for Bisphenol F (7 total), please visit the HSDB record page.
Artificial Pollution SourcesBisphenol F's production and use in making epoxy resins and coatings for various applications such as lacquers, varnishes, liners, adhesives, plastics, water pipes, dental sealants and food packaging(1) may result in its release to the environment through various waste streams(SRC).
Wassergefährdungsklasse (WGK)2
TSCA-Inventar-StatusTSCA listed
Zollcode29072990
RTECS-Nr.SL9625000
R-Sätze (R)36/37/38
ToxizitätLD50 oral in rat: 4950mg/kg
GefahrensymboleXi
Sicherheitshinweise (S)26-36
Lagerklasse11 - Combustible Solids
Gefahrstoffdaten620-92-8(Hazardous Substances Data)
GefahrenklasseAquatic Chronic 2Eye Irrit. 2Repr. 2Skin Irrit. 2Skin Sens. 1