Dive into helpful resources on chemistry fundamentals and see how to spot bad science. The high-strength polymer PEEK is prepared from derivatives of benzophenone. Key West has also banned the sale of sunscreens that contain the ingredients oxybenzone (and octinoxate). The allergic contact dermatitis to BP-3 was noticed for the first time in 1972 [28]. If you do not allow these cookies we will not know when you have visited our site, and will not be able to monitor its performance. UV-filters belong to the products, which should influence only the skin surface. packaging We can find benzophenone-3 naturally occurring in flowering plants. In addition, as an ingredient in non-food plastic packaging, it helps to prevent sun damage and fading of the product inside the packaging. label [44] observed that the aquatic insect Chironomus riparius, continuously exposed to BP-3, showed the impaired development in the subsequent generation. Benzophenone is an FDA-approved active ingredient found in many sunscreen products. On the other hand, a dose-dependent estrogenic effect was noticed in rats exposed to high doses of BP-3 per os [69]. If you need to go back and make any changes, you can always do so by going to our Privacy Policy page. Benzophenone is a widely used building block in organic chemistry, being the parent diarylketone. Do not miss our News, the Watch-out database, and the Library of Documents! In the 1980s, BP-3 was the most popular as a sunscreen formulation [ 1 ]. Uses [11] It is used, along with other benzophenones, in sunscreens, hair sprays, and cosmetics because they help prevent potential damage from sunlight exposure. EU Cosmetics Regulation Moreover, the antagonistic activity of BP-3 has been detected in yeast expressing human ER [67]. However, the prolonged (7-day) exposure to BP-3 reduced astrocyte and neuron viability by 25% and 36%, respectively. Percutaneous absorption of the sunscreen benzophenone-3 after repeated whole-body applications, with and without ultraviolet irradiation, Concentrations of the sunscreen agent benzophenone-3 in residents of the United States: National Health and Nutrition Examination Survey 20032004, Commission Regulation (EU) 2017/238 of 10 February 2017 amending Annex VI to Regulation (EC) No 1223/2009 of the European Parliament and of the Council on cosmetic products C/2017/0716, Sunscreen Drug Products for Over-the-Counter Human Use, in Federal Register, Food and Drug Administration, HHS. It is a pale-yellow solid that is readily soluble in most organic solvents. Binder et al. [20] proposed that BP-3 undergoes an electron-driven internal conversion to its keto-tautomer, as the central mechanisms for its protective, antioxidative activity. However, the negative effects that may be induced by BP-3 on human health, cannot be clearly stated due to an insufficient number of performed studies. It possesses anti-aging properties. The modification concerns two substances, Benzophenone-3 and Octocrylene. No regulations have come of this study yet. Benzophenone-3 and Octocrylene are organic compounds used for UV filters, and Octocrylene is also used as a light stabilizer, underscores Cosmeservice. 2018 Feb;17 (1):15-19. doi: 10.1111/jocd.12449. The global DNA hypomethylation and diminished activity of enzymes related to this process suggest the chromosomal instability and inappropriate gene expression pattern, leading to an increased risk of neurodevelopmental disorders or nerve degenerations. The resulting diradical will abstract a hydrogen atom from a suitable hydrogen donor to form a ketyl radical. 1. The directive, known as the empowering consumers for the green transition, received Read more. the contents by NLM or the National Institutes of Health. The draft Regulation aims to implement the Scientific Committees findings in the EU cosmetics regulatory framework. In animal experiments, BP-3 applied topically on the skin has been detected in the liver, heart, kidneys, spleen, muscle and testes [12]. Benzophenone is a widely used building block in organic chemistry, being the parent diarylketone. Skrkowska A, Maciejska A, Pomierny B, et al.. UV filters Benzophenone helps to protect against UV rays that could damage or deteriorate consumer products such as sunglasses, shoes and sports equipment. Michler's ketone has dimethylamino substituents at each para position. According to the draft, BP-3 entry in Annex VIto the EU Cosmetics Regulation will be amended as follow: Frederiksen H, Nielsen O, Koch HM, et al.. Changes in urinary excretion of phthalates, phthalate substitutes, bisphenols and other polychlorinated and phenolic substances in young Danish men; 2009-2017, Kosmetyki ochrony przeciwsonecznej. [45] noticed that the exposure to oxybenzone changed the expression of oestrogen receptors and , GPR30 and PPAR-, leading to the neurotoxicity, induction of apoptosis and impairment in cell survival. approximately 20 g benzophenone, i.e. A European multicentre photopatch test study, Patch test reactions associated with sunscreen products and the importance of testing to an expanded series: retrospective analysis of North American Contact Dermatitis Group data, 2001 to 2010. Karsili TN, Marchetti B, Ashfold MN, Domcke W. Ab initio study of potential ultrafast internal conversion routes in oxybenzone, caffeic acid, and ferulic acid: implications for sunscreens. In consumer products like sunglasses, shoes and sports equipment, benzophenone helps to protect against UV rays that could damage or deteriorate the product. In Europe, BP-3 was . Data from epidemiological and animal-based studies have suggested a relationship between the exposure to harmful environmental factors in early life and the risk of neurodegenerative disorders in adulthood. Almeida SDS, Rocha TL, Qualhato G, et al.. Sunscreen: FDA regulation, and environmental and health impact BP-3-induced apoptosis and neurotoxicity was associated with global DNA hypomethylation and specific hypomethylation of the GPER1 and BAX genes. Aug. 10, 2021 6:10 AM PT. Prenatal exposure of mice to subcutaneous BP-3 injection revealed activation of apoptosis, loss of the mitochondrial membrane potential, impairment of autophagy and alteration of epigenetic and post-translational status in the brain of mice embryos [16, 84]. News The previous in vitro study demonstrated that some chemical UV filters, including BP-3, can induce Ca2+ signals via the cationic channel of sperm (CatSper) Ca2+ channel, similar to progesterone [58]. Oxybenzone helps protect skin from the suns harmful UV rays by absorbing UV radiation and dissipating it as heat. Benzophenone Accumulates over Time from the Degradation of Octocrylene Additionally, Benzophenone-3 could be incidentally ingested (maximum use concentrations up to 0.5% in lipstick). Moreover, the increased vulnerability to oxidative stress and cytotoxicity was observed in rat thymocytes exposed to BP-3 [80]. The ACC mark, Responsible Care, the hands logo mark, CHEMTREC, TRANSCAER, and americanchemistry.com are registered service marks of the American Chemistry Council, Inc. May also be known as: Benzophenone-3 (BP3), Benzophenone-1, -4, -5, -9, -11, Oxybenzone. Nowadays, more and more researches are being conducted into the harmfulness of BP-3 on animals. [29] The major metabolite detected was DHB and very small amounts of THB were found. In this same study, the repeated, 30-day application of BP-3 at the dose of 5 mg/kg on the skin of 8-week-old male and female rats did not show the significant behavioural changes [9]. "Hazardous Substances Data Bank". Krause M, Frederiksen H, Sundberg K, et al.. Maternal exposure to UV filters and associations to maternal thyroid hormones and IGF-I/IGFBP3 and birth outcomes. The consumer care products containing BP-3 are widely used by the general public. Knowledge about the impact of BP-3 on foetal and neonatal development in humans is negligible and controversial. UK Subscribe now to the ToxPartner newsletter. This compound was also detected in all urine samples of young men from the general Danish population [7]. Recent update on Kojic Acid: the SCCS opinion, Warning label requirements for certain Hair and Eyelash Dyes / Lyrial, Atranol and Chloroatranol totally prohibited in the EU, https://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:32022R1176&from=EN, https://members.wto.org/crnattachments/2021/TBT/EEC/21_6560_00_e.pdf, https://members.wto.org/crnattachments/2021/TBT/EEC/21_6560_01_e.pdf, http://tbtims.wto.org/en/RegularNotifications/View/174842?FromAllNotifications=True, Q&A on the regulatory requirements to sell cosmetic products in Iceland, Norway, Liechtenstein, and Switzerland, Green claims: the EU proposal for new requirements, Is your product a cosmetic in the United States? However, the impact of BP-3 on human health requires a careful assessment. Non-Exhaustive List of Banned Substances, Directive 94/33/EC on Young People at Work, 20 August 1994, as amended by Dir 2014/27/EU, March 5, 2014 (Based on Table 3 of Annex VI to CLP, inter alia) . [9] This interaction contributes to oxybenzone's light-absorption properties. By measuring BP-3 in urine, scientists can estimate the amount of BP-3 that has entered peoples bodies. Derivatives of benzophenone, such as benzophenone-2 (BP2) and oxybenzone (benzophenone-3 or BP3) are common ingredients in sunscreen. We use cookies to ensure that we give you the best experience on our website. Benzophenone (also known as diphenylketone) 2. [27][28] To form DHB the methoxy functional group undergoes O-dealkylation; to form THB the same ring is hydroxylated. Benzophenone-3 (BP-3) is a naturally occurring chemical found in some flowering plants. What is BP-3 and where does it come from? Pollack AZ, Mumford SL, Krall JR, et al.. Exposure to phthalates and phenols during pregnancy and offspring size at birth. After topical application to human volunteers, results revealed that up to 1% of the applied dose was found in the urine. The endocrine disruption can also occur by altering normal hormone levels by the inhibition or stimulation of production and/or metabolism of hormones. For leave-on products: o Not to be used in sunscreen products and products marketed for exposure to natural or artificial UV light. Community members who have kept a low profile so far now want to make . [83] showed that this compound is capable of inhibiting an autophagy and disturbing the epigenetic state of primary neuronal cell cultures by the inhibition of global DNA methylation as well as reduction of the activity of histone deacetylases (HDACs) and histone acetyl transferases (HATs). [5] Without it, opaque or dark packaging would be required. According to Aker et al. The continuous and long-term exposure of the developing organism to a mix of chemicals contained in UV filters, which may act as endocrine disruptors or neurotoxins, could have consequences for its health in adult life. CMR substances As a photoprotective agent, it has an absorption profile spanning from 270 to 350nm with absorption peaks at 288 and 350nm. 3. That's what makes it so popular as an ingredient for sunscreen. Received 2020 Oct 18; Accepted 2020 Dec 16. More research is needed to assess the human health effects of exposure to BP-3. Fernndez MF, Arrebola JP, Jimnez-Daz I, et al.. Bisphenol A and other phenols in human placenta from children with cryptorchidism or hypospadias. The above mechanisms were related to phototoxic potential of benzophenones in HaCaT cell line exposed to sunlight or UV radiation [38, 39]. Under California Proposition 65, there is no safe harbor for benzophenone in any personal care products, including sunscreens, anti-aging creams, and moisturizers. The U.S. Food and Drug Administration (FDA) has approved benzophenone-3 (BP3), also known as oxybenzone, as an active ingredient in sunscreen. Associations of prenatal environmental phenol and phthalate biomarkers with respiratory and allergic diseases among children aged 6 and 7 years, Association of prenatal exposure to phenols and parabens with birth size: a systematic review and meta-analysis, The relationship between prenatal exposure to BP-3 and Hirschsprungs disease. BP-3 has also frequently been reported as a factor playing a key role in endocrine disruption [6680]. On the other hand, manufacturers that place cosmetic products on the EU market in compliance with the previous requirements until January 28, 2023, have until July 28, 2023, to make those available on the EU market. Apart from the allergic reaction, benzophenone-1 metabolite of BP-3 can induce of photogenotoxicity and apoptosis via release of cytochrome c and Smac/DIABLO in human keratinocytes under UV radiation [36]. This interference with normal plant metabolism led to the inhibition of photosynthesis and respiration, restriction of carbohydrate synthesis and ATP regeneration, limiting the energy available for metabolic processes, and even leading to plants death [25]. Benzophenone is persistent, bioaccumulative and toxic (PBT). In the mouse neuronal cells culture, Wnuk et al. aluminium chloride) catalyst: since benzoyl chloride can itself be produced by the reaction of benzene with phosgene the first synthesis proceeded directly from those materials. The ban was to be effective as of January 1, 2021. Benzophenone - Proposition 65 Warnings Website On the other hand, there is evidence that BP-3 can cross blood-tissue barriers, such as the blood-follicle barrier or the blood-placental barrier [59]. BP-3 also is used in plastic products to block and prevent UV rays from altering the plastic and the contents inside. Once applied, a small amount of BP-3 passes through the skin into the body. The regulatory definition. In the Fourth National Report on Human Exposure to Environmental Chemicals (Fourth Report), CDC scientists measured BP-3 in the urine of 2,517 participants aged six years and older who took part in the National Health and Nutrition Examination Survey (NHANES) during 20032004. Benzophenone-3 - Truth In Aging Benzophenone-3 (CAS 131-57-7) is an organic aromatic ketone found in some flowering plants. European Multicentre Photopatch Test Study (EMCPPTS) Taskforce . At the moment, in cosmetics, it is used as a UV filter up to a maximum concentration of 6% and up to 0.5% to protect the cosmetic formulation. [11] Benzophenones can leach from food packaging, and are widely used as photo-initiators to activate a chemical that dries ink faster. ", "Questions and Answers: FDA posts deemed final order and proposed order for over-the-counter sunscreen", "UV Spectral Properties of Benzophenone. In addition, a Cosmetic Ingredient Review (CIR) expert scientific panel states that benzophenone and its derivatives (benzophenone-1, -3, -4, -5, -9 and -11) are safe as typically used in cosmetics and personal care products. Your email address will not be published. EU In people, BP-3 is detected in serum in concentrations ten times higher than other chemical filters [10]. In 2021, the SCCS noted that there is "inconclusive, and at best equivocal" evidence for Benzophenone-3 as an endocrine-disrupting substance. [73] showed that the urinary BP-3 levels were associated with earlier menarche but Wolff et al. It is a white solid that is soluble in organic solvents. Biomonitoring data can also help scientists plan and conduct research on exposure and health effects. It is also found, in concentrations up to 1%, in nail polishes. These 3 chemicals have similar structures, but also ketoprofen is metabolized into various benzophenones structurally similar to BP-3 during sunlight exposure [35]. Effects of maternal and lactational exposure to 2-hydroxy-4-methoxybenzone on development and reproductive organs in male and female rat offspring, NTP technical report on the toxicity studies of 2-hydroxy-4-methoxybenzophenone (CAS No. Kunisue T, Chen Z, Buck Louis GM, et al.. Urinary concentrations of benzopheone-type UV filters in U.S. women and their association with endometriosis, Estrogenic activity of UV filters determined by an in vitro reporter gene assay and an in vivo transgenic zebrafish assay, Multiple hormonal activities of UV-filters and comparison of in vivo and in vitro estrogenic activity of ethyl-4-aminobenzoate in fish. The most disturbing findings are that foetuses and babies are exposed to BP-3 as this UV filter was found in human milk and it can easily cross the blood-brain barrier after being topically applied. The four chemicals are Oxybenzone (Benzophenone-3, BP-3), Octinoxate (Ethylhexyl methoxycinnamate), 4-Methylbenzylid Camphor (4MBC) and Butylparaben. [56] demonstrated the presence of BP-3 in human milk and in the plastic containers for milk storing, indicating that the exposure to this compound may take place not only during foetal development but also in the early stages of babys life. 2022 Upcoming EU cosmetic ingredient bans and restrictions An official website of the United States government. In biological applications, benzophenones have been used extensively as photophysical probes to identify and map peptideprotein interactions. The site is secure. Pomierny B, Krzyanowska W, Broniowska , et al.. Benzophenone-3 passes through the blood-brain barrier, increases the level of extracellular glutamate and induces apoptotic processes in the hippocampus and frontal cortex of rats, Prenatal exposure to benzophenone-3 impairs autophagy, disrupts RXRs/PPAR signaling, and alters epigenetic and post-translational statuses in brain neurons. 8600 Rockville Pike [48], Revised as of 2012, Health Canada allows oxybenzone for cosmetic use up to 6%. Toxicopathological Effects of the Sunscreen UV Filter, Oxybenzone A vast majority of community members have roots in Punjab in northwestern India. The 'Substance identity' section is calculated from substance identification information from all ECHA databases. Until this situation is clarified, pregnant women and children should pay special attention to the composition of sunscreens. October 5, 2018 The FDA is amending its food additive regulations in response to two food additive petitions, to no longer allow for the use of a total of 7 synthetic flavoring substances and. If your sunscreen or cosmetic product contains Oxybenzone (Benzophenone-3, BP-3), Octinoxate (Ethylhexyl methoxycinnamate), 4-Methylbenzylid Camphor (4MBC) or Butylparaben (butyl p-hydroxybenzoate). The https:// ensures that you are connecting to the The overproduction of reactive oxygen species (ROS), which adversely affects the structure and function of proteins, DNA and membrane lipids was observed in higher plant cells exposed to BP-3. Simultaneous occurrence of urticarial and contact sensitivities. Benzophenone-3 or oxybenzone is an organic compound having the chemical formula C 14 H 12 O 3. Occasionally, wearing products containing BP-3 has resulted in a skin allergy or photo allergy, a skin reaction that occurs with exposure to sunlight. Large scale purification may be more economical using devices which utilize adsorbents such as the aforementioned alumina or molecular sieves. Furthermore, it is possible that BP-3 can be transmitted by carrier proteins in plasma, can act with human serum albumin and displace drugs and other substances, like sex and thyroid hormones, interfering the proper functioning of the human organism [11]. WTO. Oxybenzone belongs to the class of aromatic ketones known as benzophenones. Evaluation of the estrogenic and oxidative stress effects of the UV filter 3-benzophenone in zebrafish (Danio rerio) eleuthero-embryos, Significant inhibition of photosynthesis and respiration in leaves of Cucumis sativus L. by oxybenzone, an active ingredient in sunscreen, The toxicological effects of oxybenzone, an active ingredient in suncream personal care products, on prokaryotic alga Arthrospira sp. The recent studies, after combined prenatal and adult dermal exposure to BP-3, also confirmed the proapoptotic changes, the raise of oxidative stress associated with reduction in the antioxidant capacity and an increase in the level of extracellular glutamate in frontal cortex and hippocampus of male offsprings. [53], The Palau government has signed a law that restricts the sale and use of sunscreen and skincare products that contain oxybenzone, and nine other chemicals. Face products, hand products, and lip products, excluding propellant and pump spray products. fragrance ingredient At the moment, in cosmetics, it is used as a UV filter up to a maximum concentration of 6% and up to 0.5% to protect the cosmetic formulation.
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