Estrogen Receptor (ER) (weak binding activity) [4]
- No significant binding to Androgen Receptor (AR) or Progesterone Receptor (PR) [4]

阿伏苯宗 (EC50=14.1 μM) 显着促进 hBM-MSC 的脂肪生成，而致肥胖化学物质作为阳性对照。在 hBM-MSC 的脂肪形成过程中，阿伏苯宗 (10 μM) 显着上调 PPARγ mRNA 水平[2]。阿伏苯宗（1-50 μM；48 小时）抑制人类滋养层细胞的增殖能力[3]。阿伏苯宗（1-50 μM；48 小时）使 HTR8/SVneo 细胞凋亡[3]。阿伏苯宗仅表现出弱的 AR 拮抗作用和 ERa 激动作用[4]。

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阿伏苯宗（Avobenzone, BF2AVB）以剂量依赖性方式诱导正常人表皮角质形成细胞（NHEK）和人间充质干细胞（hMSC）的致肥胖表型。50-100 μM浓度下，使脂滴积累较对照组增加~2.5倍（NHEK）和~3.2倍（hMSC），上调成脂转录因子（PPARγ、C/EBPα）表达~40-60%，增强脂肪酸合酶（FASN）表达~55%[2]
- 抑制人滋养层细胞（HTR-8/SVneo）增殖并诱导凋亡，细胞活力抑制IC50约为50 μM。50 μM浓度下，使活性氧（ROS）生成增加~2.8倍，线粒体膜电位（ΔΨm）降低~45%，Bax/Bcl-2比值上调~3.0倍，通过线粒体损伤激活caspase-3/9（裂解型caspase-3增加~2.2倍）[3]
- 在ER报告基因测定中表现出微弱雌激素活性：100 μM诱导荧光素酶活性~1.8倍（相比17β-雌二醇10 nM：~8.5倍），浓度高达100 μM时无雄激素或孕激素活性[4]
- 在乙腈中经长波紫外线（365 nm）照射发生光解，通过分子内氢转移生成光异构物和降解产物；气相中无明显光降解[1]
- 浓度高达100 μM时，对NHEK或hMSC无明显细胞毒性（MTT法检测细胞活力>80%）[2]

核受体报告基因实验：将稳定转染ER/AR/PR表达质粒及对应荧光素酶报告基因质粒的HEK293细胞，用0.1-100 μM 阿伏苯宗（Avobenzone, BF2AVB）处理24小时。检测荧光素酶活性评估受体激活情况，以17β-雌二醇（ER激动剂）、二氢睾酮（AR激动剂）和孕酮（PR激动剂）作为阳性对照[4]

成脂表型实验：NHEK和hMSC接种于6孔板，用10-100 μM 阿伏苯宗（Avobenzone, BF2AVB）处理14天。油红O染色并通过分光光度法定量脂滴；PCR和Western blot检测PPARγ、C/EBPα及FASN的mRNA和蛋白水平[2]
- 滋养层细胞增殖与凋亡实验：HTR-8/SVneo细胞接种于96孔板（增殖实验）或6孔板（凋亡/线粒体功能实验），用10-100 μM 阿伏苯宗（Avobenzone, BF2AVB）处理48-72小时。MTT法检测细胞活力；DCFH-DA染色检测ROS生成；JC-1染色分析线粒体膜电位；Western blot检测Bax、Bcl-2及裂解型caspase-3/9[3]

Absorption, Distribution and Excretion
Solvents used in sunscreen products can affect the stability and binding affinity of the drug to the skin; generally, alcohol solvents allow sunscreens to penetrate the epidermis the fastest and deepest. Sunscreen agents appear to be absorbed by the intact epidermis, but the degree of absorption varies. /Sunscreen/

Interaction
By absorbing ultraviolet radiation within a specific wavelength range, the penetration of ultraviolet radiation into the epidermis is reduced. The molecular structure of sunscreens affects the absorption amount and wavelength of ultraviolet radiation. /Sunscreen, for external use/

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In vitro experiments showed that avobenzone (BF2AVB) is cytotoxic to human trophoblast cells, with an IC50 of approximately 50 μM; at concentrations up to 100 μM, it showed no significant cytotoxicity to NHEK or hMSCs [2][3]
-It can induce mitochondrial dysfunction (increased ROS, decreased ΔΨm) and apoptosis in trophoblast cells, suggesting that it may have reproductive toxicity [3]
-It exhibits weak estrogenic activity, suggesting that it may have endocrine disrupting properties [4]

[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.

Avobenzone belongs to the dihydrochalcone class of compounds. Avobenzone is a dibenzoylmethane derivative and is an oil-soluble component. Avobenzone absorbs a wide range of ultraviolet (UV) wavelengths. Many commercially available sunscreens contain avobenzone and are used as broad-spectrum sunscreens. Avobenzone is very photosensitive, and photostable agents are added to sunscreens to improve its stability and duration of action. The maximum absorption wavelength of avobenzone is 357 nanometers. Sunscreens containing avobenzone are suitable for providing sun protection. In addition to limiting the time skin is exposed to sunlight, using sunscreens helps reduce long-term sun damage, such as premature skin aging and skin cancer. Avobenzone is a sunscreen agent. Avobenzone is a topical broad-spectrum UV protectant that blocks UVA I, UVA II, and UVB wavelengths, thereby reducing UV damage to the skin. (NCI05)
See also: Avobenzone; Ekaminol; Octocrylene (ingredient); Avobenzone; Octyl Methoxycinnamate; Oxybenzone (ingredient); Avobenzone; Octyl Methoxycinnamate (ingredient)...See more...

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Drug Indications
Sun Protection Factor (SPF) is added to sunscreen products due to its broad-spectrum UV absorption properties.

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Mechanism of Action
It blocks UVA I, UVA II, and UVB wavelengths, thereby limiting the effects of ultraviolet radiation on the skin. By absorbing ultraviolet radiation within a specific wavelength range, it reduces the penetration of ultraviolet radiation into the epidermis. The amount and wavelength of ultraviolet radiation absorbed are affected by the molecular structure of the sunscreen agent.
By absorbing ultraviolet radiation within a specific wavelength range, it reduces the penetration of ultraviolet radiation into the epidermis. The amount and wavelength of ultraviolet radiation absorbed are affected by the molecular structure of the sunscreen agent. /Sunscreen, for external use/

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Therapeutic use
It is recommended that people living in areas with high sun intensity and who frequently work or engage in outdoor recreational activities use a high SPF (greater than 15) sunscreen daily on normally exposed skin. Daily use of sunscreen can reduce cumulative sun exposure, thereby reducing the risk of actinic keratosis and squamous cell carcinoma.
Sunscreen is intended to prevent sunburn. In addition to limiting the time skin is exposed to sunlight, regular use of sunscreen in the sun can help reduce long-term sun damage, such as premature skin aging and skin cancer. /Sunscreen, for external use; included on US product label/
Sunscreen should be applied evenly and in sufficient quantity to all exposed skin surfaces, including the lips, before exposure to UVB radiation. For best protection, it may be necessary to apply sunscreen twice. Sunscreens containing para-aminobenzoic acid (PABA) are most effective when applied 1-2 hours before sun exposure. Non-waterproof sunscreens should be reapplied after swimming, towel drying, or heavy sweating. Because most sunscreens wash off easily, they typically need to be reapplied every 1-2 hours or as directed by the manufacturer to provide adequate UVB protection. /Sunscreen/

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Drug Warnings
Manufacturers of sunscreens using propellants warn that inhaling the fumes produced by these formulations can be harmful or even fatal. /Propellants/
Because the skin absorption characteristics of infants under 6 months of age may differ from those of adults, and their metabolic and excretory pathways are not yet fully developed, their ability to clear transdermally absorbed sunscreens may be limited. Therefore, infants under 6 months of age should only use sunscreen products under the guidance of a clinician. Older adults' skin characteristics may differ from those of younger adults, but these characteristics and the special considerations for using sunscreen products in this age group are not yet fully understood. /Sunscreen/
Information on the safety of long-term use of sunscreens is limited, but commercially available physical and chemical sunscreens appear to have a low incidence of adverse reactions. Derivatives of para-aminobenzoic acid (PABA), benzophenone, cinnamic acid, salicylic acid, and 2-phenylbenzimidazole-5-sulfonic acid can cause skin irritation in rare cases, including burning, stinging, itching, and erythema. /Sunscreen/
Sunscreen should not be used to prolong sun exposure, such as for extended sunbathing, nor should it be used as a substitute for clothing on normally unexposed areas (such as the torso and buttocks). /Sunscreen Agents/
For more complete data on drug warnings for avobenzone (11 in total), please visit the HSDB records page.

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Avobenzone (BF2AVB) is a synthetic long-wave UVA (320-400 nm) sunscreen [2][4]
- Its photochemical properties: In acetonitrile, it undergoes photolysis under UVA irradiation via intramolecular hydrogen transfer, forming photoisomers and degradation products; it is more stable in the gas phase [1]
- In addition to its sunscreen activity, it can also exhibit obesity-inducing effects in skin and stem cells by upregulating adipose-derived transcription factors [2]
- It has potential reproductive toxicity and can exert its effects by inhibiting trophoblast cell proliferation and inducing mitochondrial-mediated apoptosis [3]
- It exhibits weak estrogenic activity without androgenic or progesterone effects, indicating that it has a slight 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 assessment [2][3][4]

C20H22O3

310.39

310.156

C, 77.39; H, 7.14; O, 15.46

70356-09-1

Avobenzone-13C,d3

51040

White to light yellow crystalline powder

1.1±0.1 g/cm3

463.6±35.0 °C at 760 mmHg

81-84 °C

203.1±26.0 °C

0.0±1.1 mmHg at 25°C

1.545

4.81

43.37

0

3

6

23

405

0

O=C(C1=CC=C(C(C)(C)C)C=C1)CC(C2=CC=C(OC)C=C2)=O

XNEFYCZVKIDDMS-UHFFFAOYSA-N

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

1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione

HSDB 7423; HSDB-7423; HSDB7423; Avobenzone; Avobenzonum; Parsol1789; Parsol-1789; Parsol 1789

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

注意： (1). 本产品在运输和储存过程中需避光。  (2). 请将本产品存放在密封且受保护的环境中（例如氮气保护），避免吸湿/受潮。

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

配方 1 中的溶解度: 2.5 mg/mL (8.05 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (这些助溶剂从左到右依次添加，逐一添加), 悬浮液；超声助溶。
例如，若需制备1 mL的工作液，可将100 μL 25.0 mg/mL澄清DMSO储备液加入900 μL 20% SBE-β-CD生理盐水溶液中，混匀。
*20% SBE-β-CD 生理盐水溶液的制备（4°C，1 周）：将 2 g SBE-β-CD 溶解于 10 mL 生理盐水中，得到澄清溶液。

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配方 2 中的溶解度: ≥ 2.5 mg/mL (8.05 mM) (饱和度未知) in 10% DMSO + 90% Corn Oil (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将 100 μL 25.0 mg/mL 澄清 DMSO 储备液添加到 900 μL 玉米油中并混合均匀。

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请根据您的实验动物和给药方式选择适当的溶解配方/方案：
1、请先配制澄清的储备液(如：用DMSO配置50 或 100 mg/mL母液(储备液));
2、取适量母液，按从左到右的顺序依次添加助溶剂，澄清后再加入下一助溶剂。以 下列配方为例说明 (注意此配方只用于说明，并不一定代表此产品 的实际溶解配方):
10% DMSO → 40% PEG300 → 5% Tween-80 → 45% ddH2O (或 saline);
假设最终工作液的体积为 1 mL, 浓度为5 mg/mL: 取 100 μL 50 mg/mL 的澄清 DMSO 储备液加到 400 μL PEG300 中，混合均匀/澄清；向上述体系中加入50 μL Tween-80，混合均匀/澄清；然后继续加入450 μL ddH2O (或 saline)定容至 1 mL；
3、溶剂前显示的百分比是指该溶剂在最终溶液/工作液中的体积所占比例;
4、 如产品在配制过程中出现沉淀/析出，可通过加热(≤50℃)或超声的方式助溶;
5、为保证最佳实验结果，工作液请现配现用！
6、如不确定怎么将母液配置成体内动物实验的工作液，请查看说明书或联系我们;
7、 以上所有助溶剂都可在 Invivochem.cn网站购买。