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Avobenzone (also known as Butyl methoxydibenzoylmethane, BF2AVB) is a dibenzoylmethane derivative that is oil soluble and frequently used in sunscreen products to absorb UVA rays. When combined with mineral UV absorbers like zinc oxide and titanium dioxide, it can degrade more quickly in light; however, this reaction can be mitigated with the proper coating of the mineral particles. To increase the stability of avobenzone, manganese-doped titanium dioxide might be preferable to undoped titanium dioxide. It creates colorful complexes when it reacts with minerals. A chelator is advised by avobenzone manufacturers such as DSM to stop this from occurring. Additionally, they advise against adding heavy metals, PABA and PABA esters, formaldehyde donors, iron and ferric salts, and heavy metals.
Physicochemical Properties
| Molecular Formula | C20H22O3 |
| Molecular Weight | 310.39 |
| Exact Mass | 310.156 |
| Elemental Analysis | C, 77.39; H, 7.14; O, 15.46 |
| CAS # | 70356-09-1 |
| Related CAS # | Avobenzone-13C,d3 |
| PubChem CID | 51040 |
| Appearance | White to light yellow crystalline powder |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 463.6±35.0 °C at 760 mmHg |
| Melting Point | 81-84 °C |
| Flash Point | 203.1±26.0 °C |
| Vapour Pressure | 0.0±1.1 mmHg at 25°C |
| Index of Refraction | 1.545 |
| LogP | 4.81 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 23 |
| Complexity | 405 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O=C(C1=CC=C(C(C)(C)C)C=C1)CC(C2=CC=C(OC)C=C2)=O |
| InChi Key | XNEFYCZVKIDDMS-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C20H22O3/c1-20(2,3)16-9-5-14(6-10-16)18(21)13-19(22)15-7-11-17(23-4)12-8-15/h5-12H,13H2,1-4H3 |
| Chemical Name | 1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione |
| Synonyms | HSDB 7423; HSDB-7423; HSDB7423; Avobenzone; Avobenzonum; Parsol1789; Parsol-1789; Parsol 1789 |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage.(2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets |
Estrogen Receptor (ER) (weak binding activity) [4] - No significant binding to Androgen Receptor (AR) or Progesterone Receptor (PR) [4] |
| ln Vitro |
Avobenzone (EC50=14.1 μM) encourages adipogenesis in hBM-MSCs significantly, with obesogenic chemicals serving as the positive control. During adipogenesis in hBM-MSCs, avobenzone (10 μM) significantly upregulates PPARγ mRNA levels[2]. Avobenzone (1-50 μM; 48 hours) inhibits human trophoblast cells' ability to proliferate[3]. Avobenzone (1-50 μM; 48 hours) brings HTR8/SVneo cells to apoptosis[3]. Avobenzone only demonstrates weak AR antagonistic and ERa agonism[4]. Avobenzone (BF2AVB) induced obesogenic phenotypes in normal human epidermal keratinocytes (NHEK) and human mesenchymal stem cells (hMSC) in a dose-dependent manner. At 50-100 μM, it increased lipid droplet accumulation by ~2.5-fold (NHEK) and ~3.2-fold (hMSC) compared to control, upregulated adipogenic transcription factors (PPARγ, C/EBPα) by ~40-60%, and enhanced fatty acid synthase (FASN) expression by ~55% [2] - It suppressed proliferation and induced apoptosis in human trophoblast cells (HTR-8/SVneo) with an IC50 of ~50 μM for cell viability inhibition. At 50 μM, it increased reactive oxygen species (ROS) production by ~2.8-fold, reduced mitochondrial membrane potential (ΔΨm) by ~45%, upregulated Bax/Bcl-2 ratio by ~3.0-fold, and activated caspase-3/9 (cleaved caspase-3 increased by ~2.2-fold) via mitochondrial disruption [3] - It exhibited weak estrogenic activity in ER reporter gene assays: 100 μM induced luciferase activity by ~1.8-fold (vs. 17β-estradiol, 10 nM: ~8.5-fold), with no androgenic or progestogenic activity at concentrations up to 100 μM [4] - In acetonitrile, it underwent photolysis upon UVA irradiation (365 nm), generating photoproducts via intramolecular hydrogen transfer; no photodegradation was observed in the gas phase [1] - No significant cytotoxicity to NHEK or hMSC at concentrations up to 100 μM (cell viability > 80% by MTT assay), despite obesogenic changes [2] |
| Enzyme Assay |
Nuclear receptor reporter gene assay: HEK293 cells stably transfected with ER/AR/PR expression plasmids and corresponding luciferase reporter plasmids were treated with Avobenzone (BF2AVB) (0.1-100 μM) for 24 hours. Luciferase activity was measured to evaluate receptor activation; 17β-estradiol (ER agonist), dihydrotestosterone (AR agonist), and progesterone (PR agonist) were used as positive controls [4] |
| Cell Assay |
Adipogenic phenotype assay: NHEK and hMSC were seeded in 6-well plates, treated with Avobenzone (BF2AVB) (10-100 μM) for 14 days. Lipid droplets were stained with Oil Red O and quantified by spectrophotometry; PPARγ, C/EBPα, and FASN mRNA/protein levels were detected by PCR and Western blot [2] - Trophoblast cell proliferation and apoptosis assay: HTR-8/SVneo cells were seeded in 96-well plates (proliferation) or 6-well plates (apoptosis/mitochondrial function) and treated with Avobenzone (BF2AVB) (10-100 μM) for 48-72 hours. Cell viability was detected by MTT assay; ROS production was measured by DCFH-DA staining; mitochondrial membrane potential was analyzed by JC-1 staining; Bax, Bcl-2, and cleaved caspase-3/9 were detected by Western blot [3] |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion Solvents used in sunscreen products affect the stability and binding of the drug to the skin; in general, alcoholic solvents allow for the most rapid and deepest epidermal penetration of sunscreens. It appears that sunscreen agents are absorbed by the intact epidermis to varying degrees. /Sunscreens/ |
| Toxicity/Toxicokinetics |
Interactions Diminish the penetration of ultraviolet (UV) light through the epidermis by absorbing UV radiation within a specific wavelength range. The amount and wavelength of UV radiation absorbed are affected by the molecular structure of the sunscreen agent. /Sunscreen agents, topical/ In vitro, Avobenzone (BF2AVB) showed cytotoxicity to human trophoblast cells with an IC50 of ~50 μM; no significant cytotoxicity to NHEK or hMSC at concentrations up to 100 μM [2][3] - It induced mitochondrial dysfunction (ROS elevation, ΔΨm reduction) and apoptosis in trophoblast cells, suggesting potential reproductive toxicity [3] - It exhibited weak estrogenic activity, indicating potential endocrine-disrupting properties [4] |
| References |
[1]. A new insight into the photochemistry of avobenzone in gas phase and acetonitrile from ab initio calculations. Phys Chem Chem Phys. 2016;18(32):22168-22178. [2]. A long-wave UVA filter avobenzone induces obesogenic phenotypes in normal human epidermal keratinocytes and mesenchymal stem cells. Arch Toxicol. 2019;93(7):1903-1915. [3]. Avobenzone suppresses proliferative activity of human trophoblast cells and induces apoptosis mediated by mitochondrial disruption. Reprod Toxicol. 2018;81:50-57. [4]. Interaction of polycyclic musks and UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone receptor (PR) in reporter gene bioassays. Toxicol Sci. 2005;83(2):264-272. |
| Additional Infomation |
Avobenzone is a member of dihydrochalcones. Avobenzone is dibenzoyl methane derivative. It is oil soluble ingredient. Avobenzone has the ability to absorb ultraviolet light over wider range of wavelengths. It is included in many commercially available sunscreens which are used as wide spectrum sunscreens. Avobenzone is very sensitive to light, to increase its stability and duration of action, photostablizers are added in the sunscreen product. Avobenzone has an absorption maximum of 357 nm. Sunscreens containing avobenzone is indicated for providing protection from the sun. In addition to limiting the skin's exposure to the sun, using sunscreen agents may help reduce long-term sun damage such as premature aging of the skin and skin cancer. Avobenzone is a sunscreen blocker. Avobenzone is a topical, broad range UV protector and blocks UVA I, UVA II, and UVB wavelengths, thereby limiting the impact of UV rays on skin. (NCI05) See also: Avobenzone; ecamsule; octocrylene (component of); Avobenzone; Octinoxate; Oxybenzone (component of); Avobenzone; Octinoxate (component of) ... View More ... Drug Indication Sun protection factor, added in the sunscreen products for its wide spectrum ultraviolet absorption properties. Mechanism of Action It blocks UVA I, UVA II, and UVB wavelengths, thereby limiting the impact of UV rays on skin. Diminish the penetration of ultraviolet (UV) light through the epidermis by absorbing UV radiation within a specific wavelength range. The amount and wavelength of UV radiation absorbed are affected by the molecular structure of the sunscreen agent. Diminish the penetration of ultraviolet (UV) light through the epidermis by absorbing UV radiation within a specific wavelength range. The amount and wavelength of UV radiation absorbed are affected by the molecular structure of the sunscreen agent. /Sunscreen agents, topical/ Therapeutic Uses Daily use of a sunscreen with a high SPF (greater than 15) on usually exposed skin is recommended for residents of areas of high ... /solar radiation/ who work outdoors or ... /enjoy/ regular outdoor recreation. Daily use of a sunscreen can reduce the cumulative ... /solar/ exposure that causes actinic keratoses and squamous-cell carcinoma. Sunscreen agents are indicated for the prevention of sunburn. In addition to limiting the skin's exposure to the sun, using sunscreen agents regularly when in the sun may help reduce long-term sun damage such as premature aging of the skin and skin cancer. /Sunscreen agents, topical; Included in US product labeling/ Sunscreen preparations should be applied uniformly and generously to all exposed skin surfaces, including lips, before exposure to UVB radiation. Two applications of the sunscreen may be needed for maximum protection. PABA-containing sunscreens are most effective when applied 1-2 hours before exposure to sunlight. Sunscreen products that are not water resistant should be reapplied after swimming, towel-drying, or profuse sweating and, because most sunscreens are easily removed from the skin, reapplication every 1-2 hours or according to the manufacturer's directions usually is required to provide adequate protection from UVB light. /Sunscreens/ Drug Warnings The manufacturers of sunscreen preparations with propellants warn that concentrating and subsequently inhaling the fumes from these preparations may be harmful or fatal. /Propellants/ Because the absorptive characteristics of skin of children younger than 6 months of age may differ from those of adults and because the immaturity of metabolic and excretory pathways of these children may limit their ability to eliminate any percutaneously absorbed sunscreen agent, sunscreen products should be used in children younger than 6 months of age only as directed by a clinician. It is possible that the characteristics of geriatric skin also differ from those of skin in younger adults, but these characteristics and the need for special considerations regarding use of sunscreen preparations in this age group are poorly understood. /Sunscreens/ Little information is available regarding the safety of chronic sunscreen usage, but commercially available physical and chemical sunscreens appear to have a low incidence of adverse effects. Derivatives of PABA, benzophenone, cinnamic acid, and salicylate and 2-phenylbenzimidazole-5-sulfonic acid have caused skin irritation including burning, stinging, pruritus, and erythema on rare occasions. /Sunscreens/ Sunscreens should not be used as a means of extending the duration of solar exposure, such as prolonging sunbathing, and should not be used as a substitute for clothing on usually unexposed sites, such as the trunk and buttocks. /Sunscreens/ For more Drug Warnings (Complete) data for AVOBENZONE (11 total), please visit the HSDB record page. Avobenzone (BF2AVB) is a synthetic long-wave UVA (320-400 nm) sunscreen filter [2][4] - Its photochemical properties: in acetonitrile, it undergoes photolysis upon UVA irradiation via intramolecular hydrogen transfer, forming photoisomers and degradation products; it is more stable in the gas phase [1] - Beyond sunscreen activity, it exhibits obesogenic effects in skin and stem cells via upregulating adipogenic transcription factors [2] - It has potential reproductive toxicity by inhibiting trophoblast cell proliferation and inducing mitochondrial-mediated apoptosis [3] - It shows weak estrogenic activity without androgenic or progestogenic effects, suggesting mild endocrine-disrupting potential [4] - It is widely used in sunscreen formulations, but its in vitro toxicological effects (endocrine disruption, reproductive cell toxicity) highlight the need for safety evaluation [2][3][4] |
Solubility Data
| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (8.05 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.05 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2218 mL | 16.1088 mL | 32.2175 mL | |
| 5 mM | 0.6444 mL | 3.2218 mL | 6.4435 mL | |
| 10 mM | 0.3222 mL | 1.6109 mL | 3.2218 mL |