Benzophenone
- CAS
- 119-61-9
- EC
- 2043376
- PubChem CID
- 3102
- Molecular Formula
- C13H10O
- Molecular Weight
- 182.2200 g/mol
Forbidden in cosmetics. Used as a UV filter in sunscreens.
What does it do?
Used as a UV filter in sunscreens.
Details
A substance used as a UV filter in sunscreens. Its use in cosmetic products is forbidden by the European Union.
Benefits
Functions
Restrictions
Function & Use
Masking
UV Absorber
Regulatory note
- EU 1223/2009 Annex IIProhibited
Industry GHS notices (PubChem)
These are industry self-reports to ECHA, not our regulatory assessment.
- H302- Harmful if swallowed
- H320- Causes eye irritation
- H350- May cause cancer
- H351- Suspected of causing cancer
- H373(37.4%)- May cause damage to organs through prolonged or repeated exposure
- H400- Very toxic to aquatic life
- H401- Toxic to aquatic life
- H410- Very toxic to aquatic life with long lasting effects
- H411(74.8%)- Toxic to aquatic life with long lasting effects
What The Sources Say
CIR (Cosmetic Ingredient Review)10
In Vitro Benzophenone-4 The ocular irritation potential of Benzophenone-4 was evaluated using the MatTek EpiOcular™ model, in accordance with OECD TG 492.7 The viability of normal human-derived keratinocytes in the 3-dimensional human tissue model following exposure to the test substance was determined via the MTT cytotoxicity assay. The 3-dimensional tissue construct models the corneal epithelium, with progressively stratified, but not cornified, cells. Tissues were exposed to Benzophenone-4 (solid, 50 mg) for ~ 6 h. The mean % tissue viability of Benzophenone-4 was determined to be 3.6%. Based on the results of this test, Benzophenone-4 was classified as irritating to the human eye. Benzophenone-8 An ocular irritation study on Benzophenone-8 was performed using the bovine corneal opacity and permeability test (OECD TG 437).8 Corneas from 3 animals were exposed to the test substance (20% w/v in paraffin oil; volume = 750 µl) for 4 h. The test substance was then removed from the front opening of the anterior chamber and the epithelium was rinsed. For the evaluation of corneal permeability, the passage of sodium fluorescein dye was measured using ultraviolet-visible (UV/Vis) spectrophotometry. Benzophenone-8 did not cause corneal opacity or permeability, resulting in a mean in vitro irritancy score of 1 after 4 h of exposure. Based on these results, the authors concluded that Benzophenone-8 was not a severe irritant or corrosive agent in the bovine corneal opacity and permeability test. Animal Benzophenones-1, -2, -3, -4, -6, -8, -9, -11, and -12 Most of the ocular irritation tests indicated that Benzophenones-1, -2, -3, -6, -9, -11, and -12 were non-irritating to the eyes of rabbits.1 Some studies indicated that Benzophenones-1, -2, and -4 were slightly to moderately irritating at 100% concentration; however, Benzophenones-1 and -2 were nonirritating when tested at 16% in dimethyl phthalate (DMP) or … [kırpıldı — bölüm toplam 3575 karakter]
In Vitro Benzophenone-1 Effects of Benzophenone-1 on the proliferation and metastasis of MCF-7 human breast cancer cells expressing estrogen receptors were studied.89 The underlying mechanisms for these effects was also studied, including the study of alterations in transcriptional and translational levels of proliferation and metastasis-related markers (cyclin D1, p21, and cathepsin D). Treatment of the cells with Benzophenone-1 (10-7 to 10-5 M) promoted the proliferation of MCF-7 cells in a manner that was similar to the positive control (E2). The addition of Benzophenone-1 also markedly induced the migration of MCF-7 cells in a manner that was similar to E2. Regarding underlying mechanisms of action, an increase in the expression of cyclin D1 and cathepsin D, and a decrease in p21 (at both transcriptional and translational levels) were reported. The authors concluded that Benzophenone-1 may accelerate the growth of MCF-7 breast cancer cells by regulating cell cycle-related genes and promote cancer metastasis through amplification of cathepsin D. A wound healing assay and western blot assay were performed to show the effect of Benzophenone-1 on the migration of BG-1 ovarian cancer cells and the protein expression of epithelial-mesenchymal transition (EMT)-related genes.90 The EMT process is associated with cell migration. Benzophenone-1 (10-6 M) statistically significantly enhanced the migration capability of BG-1 cells by reducing the wounded area in the cell monolayer relative to the control, i.e., in a manner that was similar to E2 (10-9 M). The authors stated that the results of this study indicate that Benzophenone-1 may have the ability to induce ovarian cancer metastasis via regulation of the expression of EMT markers and migration of estrogen receptor- expressing BG-1 ovarian cancer cells. Benzophenone-3 The effect of Benzophenone-3 (concentrations up to 150 µg/l) on cancer cell growth was studied using NCI-H460 lung … [kırpıldı — bölüm toplam 46249 karakter]
Irritation In Vitro Benzophenone-3 The hen’s egg-chorioallantoic membrane test (HET-CAM) was used to evaluate the irritation potential of a sunscreen formulation composed of polymeric nanocapsules loading Benzophenone-3.111 The nanocapsules contained poly(ℇ-caprolactone), carrot oil, a non-ionic surfactant, and Benzophenone-3 (0.005 wt%). The eggs were incubated for 10 d, after which the membrane was removed and the CAM was exposed. The formulation was then added on the embryonated hen’s egg membrane, and effects were studied for 300 s. As a positive control (for vascular hemorrhage and lysis), 300 µl of sodium hydroxide solution (0.1 M), was applied. Sodium chloride solution (0.9 wt%) was applied as a negative control. The diluted (distilled water) formulation (300 µl) was applied to eggs also. The assay was monitored for any event (hemorrhage, lysis, and coagulation) for 300 s. The formulation was classified as a non-irritant. Benzophenone-4 The dermal corrosion potential of Benzophenone-4 was determined using a three-dimensional human epidermis model, according to OECD Test TG 431.7 Before dosing, the tissues were moistened with sterile water (25 µl). Approximately 25 mg of solid test article was evenly applied to the apical surface of each tissue. Each treatment with test article or control was conducted in duplicate. The exposure period for the test articles and controls was 3 and 60 min. For the 60-min exposure, the dosed tissues were placed in an incubator for the remainder of the 60-min exposure period. The MTT assay was performed using tissues transferred to 24-well plates. The mean optical density for the test chemical was determined to be 2.098 and 0.315 for the 3-min endpoint and 1-h endpoint, respectively. The mean % tissue viability, compared to the negative control (n = 3), was determined to be 85.7 % and 13.4 % for the 3-min endpoint and 1-h endpoint, respectively. Based on these values, … [kırpıldı — bölüm toplam 35293 karakter]
Retrospective and Multicenter Studies Benzophenone-3 Over 3400 patients (age range: 3 to 96 years) with suspected allergic contact dermatitis were evaluated and then patch tested by 12 North American Contact Dermatitis Group dermatologists with a screening series of 50 allergens.136 The patients were patch tested (July 1, 1996 to June 30, 1998) using Finn chambers on Scanpor tape. The patches remained in place for 48 hours, and sites were evaluated initially at 48 to 72 h, and, again, between 72 and 168 h after initial placement. A positive allergic patch test result was generally interpreted as a 1+, 2+, or 3+ reaction manifested by erythematous papules, vesicles, or a spreading reaction with crust and ulceration. The relevance of the patch test reactions was determined in combination with the patient’s history and skin examination findings, and were integrated to determine the diagnostic group. Of the 4094 patients patch tested with 3% Benzophenone-3, 0.5% had allergic reactions (73.7% relevant reactions, i.e., definite, probable, or possible relevance to patient’s present dermatitis). A North American Contact Dermatitis Group (NACDG) study that was performed involved 5800 patients who were patch tested with Benzophenone-3 (3% in petrolatum).137 Patch testing was performed from July of 1998 to December of 2000. The patches remained in place for 48 h. Test sites were evaluated twice, initially at 48 h to 70 h and, again, at between 72 h and 178 h after initial placement. A positive allergic patch test result was interpreted to be a +, ++, or +++ reaction. Reactions of these types were manifested by erythematous papules, vesicles, or a spreading reaction with crust and ulceration. The incidence of positive reactions was 0.6%. The relevance of this incidence of positive reactions was classified as follows: 20.6% (definite relevance), 50% (possible relevance) and 2.9% (past relevance). … [kırpıldı — bölüm toplam 35692 karakter]
General Structure Benzophenones-1 to -12 are substituted derivatives of 2-hydroxybenzo- phenone, which conforms to the structure: I Substituents include hydroxy, methoxy, octyloxy, sulfonyl, methyl, and chloride groups. Benzophenones* may be mono- di-, tri-, or tetra-substituted. Among the many preparative methods for individual Benzophenones, the most common is the Friedel-Crafts reaction.(1-4) Benzophenones-3, -6, and -8 are components of and can be extracted from certain flower pigments.(5) General Properties The most important property of the Benzophenones is their ability to absorb and dissipate ultraviolet (UV) radiation. When UV light passes through a Benzo- phenone solution, certain frequencies or wavelengths are selectively absorbed. Electromagnetic energy is transferred to the Benzophenone molecule; as a result, outer electrons are promoted from their lowest-energy ground state to higher- energy excited states. Since only certain states are possible in any given mole- cule, and since the energy difference between any ground state and excited state must equal the energy added by the quantum, only certain frequencies of radia- tion can be absorbed by a particular Benzophenone. Excited molecules are relatively short-lived and tend to return to their ground states after approximately *Throughout this report the term “Benzophenone(# is used although all compounds reviewed are 2-hydroxybenzophenones. Distributed for Comment Only -- Do Not Cite or Quote … [kırpıldı — bölüm toplam 135874 karakter]
+5 more records.
IARC (International Agency for Research on Cancer)1
IARC Group 2B - Possibly carcinogenic to humans. Limited evidence in humans and insufficient evidence in experimental animals (or vice versa). (Monograph volume: 101). Caveat: IARC classifies HAZARD, not RISK - it says 'can cause cancer under some conditions', not 'causes cancer at cosmetic use levels'. Route and dose must be assessed separately. Data is a 01/2021 snapshot.
ToxValDB (EPA Toxicity Value Database)7
EPA ToxValDB skin/eye data — endpoint: Eye Irritation, classification: Category 2B. Caveat: this is an aggregated record; dose, species and route of exposure must be considered together.
EPA ToxValDB skin/eye data — endpoint: Skin Irritation, classification: Classification not possible. Caveat: this is an aggregated record; dose, species and route of exposure must be considered together.
EPA ToxValDB skin/eye data — endpoint: Skin Sensitization, classification: Not classified. Caveat: this is an aggregated record; dose, species and route of exposure must be considered together.
EPA ToxValDB skin/eye data — endpoint: skin sensitisation: in vivo (non-LLNA), classification: Not likely to be sensitizing, species: guinea pig, study: skin sensitization, guideline: equivalent or similar to OECD Guideline 406 (Skin Sensitisation) Maximisation test, year: 1978. Caveat: this is an aggregated record; dose, species and route of exposure must be considered together.
EPA ToxValDB skin/eye data — endpoint: skin irritation: in vivo, classification: Moderate or Mild Irritation, species: rabbit, study: skin irritation, guideline: other guideline: Draize method 1944 no guideline followed, year: 1977. Caveat: this is an aggregated record; dose, species and route of exposure must be considered together.
+2 more records.
EPA ToxCast (high-throughput in vitro screening)1
EPA ToxCast ER model: NO estrogen receptor activity found (AUC agonist=0.04, antagonist=0). Tested in 18 in vitro assays. Caveat: this is an in vitro screening model with no dose or exposure context; it does NOT mean an effect occurs in humans at cosmetic use levels.
Scientific References
- CIR - Amended Safety Assessment ofCosmetic Ingredient Review (CIR), Personal Care Products Council(2019)
- EPA CompTox Chemicals Dashboard - DSSTox identifiers mapped to CAS (2021r1)US EPA, Center for Computational Toxicology and Exposure
- EU CosIng - Cosmetic Ingredient Database full exportEuropean Commission, DG GROW
- IARC Monographs - Benzophenone (Group 2B - Possibly carcinogenic to humans)IARC — WHO Uluslararası Kanser Araştırmaları Ajansı
- OpenFDA Cosmetic Adverse Events (api.fda.gov/cosmetic/event)US FDA — unvalidated adverse event reports
- PubChem - CID-Synonym-filtered bulk + PUG REST propertiesNCBI / National Library of Medicine
- ToxCast ER model - Benzophenone (DTXSID0021961)US EPA — ToxCast / CompTox
- ToxValDB - cancerUS EPA — ToxValDB v97
- ToxValDB - genotoxicityUS EPA — ToxValDB v97
- ToxValDB - skin/eyeUS EPA — ToxValDB v97