Octocrylene targets UV radiation for absorption and dissipation. Upon exposure to UV light, the compound undergoes electronic transitions that allow it to dissipate harmful energy as heat. It inhibits 17β-estradiol- or dihydrotestosterone-induced transactivation of estrogen receptor α (ERα) or the androgen receptor. The compound acts as a photosensitizer, resulting in increased production of free radicals under illumination.

In vitro, Octocrylene absorbs UV radiation in the 290–380 nm range and converts light energy into harmless heat through intramolecular hydrogen bonding. It inhibits ERα or androgen receptor transactivation. The compound can penetrate into the skin where it acts as a photosensitizer. Its photostability and UV absorption properties have been characterized in various in vitro assays.

In vivo, Octocrylene is used as an ingredient in sunscreens and cosmetics. It protects the skin from UV damage by absorbing UVB and short-wave UVA radiation. The compound stabilizes avobenzone in sunscreen formulations. It can penetrate into the skin and act as a photosensitizer. Its endocrine-disrupting potential has been noted through ERα and androgen receptor inhibition.

In vitro UV absorption assays for Octocrylene involve measuring its absorbance spectrum using UV-Vis spectrophotometry. The compound's absorbance is measured at various wavelengths to determine its UV absorption profile (peak at 303 nm). Photostability is assessed by exposing the compound to UV radiation and measuring absorbance over time. For receptor studies, ERα and androgen receptor transactivation is measured using reporter gene assays.

In vitro cell-based assays for Octocrylene are conducted in skin cells and cells expressing ERα or androgen receptors. Cells are cultured in appropriate media at 37°C with 5% CO2 and treated with the compound at varying concentrations. For phototoxicity studies, cells are exposed to UV radiation and cell viability is assessed. Receptor transactivation is assessed using reporter gene assays. Cell viability is assessed by standard assays. Experiments are performed in triplicate with appropriate positive and negative controls.

Octocrylene in vivo studies are conducted in animal models for sunscreen efficacy and toxicology. Animals are treated with Octocrylene via topical application. UV protection efficacy is assessed by measuring skin redness or sunburn following UV exposure. For toxicology studies, animals are exposed to the compound and endocrine effects are assessed. Animals are monitored for clinical signs. Skin tissues are collected for histopathological analysis. Studies are conducted in accordance with institutional animal care guidelines.

Octocrylene (MW 361.48 g/mol, C24H27NO2) is an organic UV filter of the cyanoacrylate class. It is a viscous liquid formed by the condensation of a diphenylcyanoacrylate with 2-ethylhexanol. The compound is oil-soluble and has excellent photostability. It absorbs UVB and short UVA with peak at 303 nm. Pharmacokinetic properties such as skin penetration and systemic absorption have been characterized in clinical studies.

Octocrylene is generally recognized as safe for use in sunscreens and cosmetics at approved concentrations. The compound can penetrate into the skin and act as a photosensitizer. It inhibits ERα and androgen receptor transactivation. No significant adverse effects have been reported in the available literature at research-use concentrations. The compound is intended for research use only. Standard safety precautions should be followed when handling. Comprehensive toxicological evaluation is available from cosmetic safety studies.

[1]Int J Environ Res Public Health. 2022 May 16;19(10):6037

[2]Review of the safety of octocrylene used as an ultraviolet filter in cosmetics. J Eur Acad Dermatol Venereol. 2019 Nov;33 Suppl 7:25-33.

2-Ethylhexyl-2-cyano-3,3-diphenylacrylate is a yellow, viscous liquid, insoluble in water. (NTP, 1992) Octocrylene is a diarylmethane. Octocrylene is a compound commonly used as an additive in sunscreens, believed to have moisturizing properties due to its skin-softening effects. This chemical is a common additive in sunscreens because it neutralizes ultraviolet radiation from sunlight and minimizes damage to the skin caused by prolonged sun exposure. Octocrylene is also frequently used in combination with avobenzone (another common sunscreen ingredient, often found on ingredient labels). Due to its effectiveness, this chemical is approved for use in cosmetics and skincare products worldwide, but its concentration is typically limited to 10% or 12%. However, the use of this chemical is not limited to sunscreens for the face and arms; it can be extended to various other products such as hairspray, tannin oil, BB cream, conditioner, and CC cream. Octocrylene may cause contact sensitization and photosensitivity. See also: Avobenzone; Ekachenox; Octocrylene (ingredient); Avobenzone; Octocrylene (ingredient); Octyl salicylate; Octocrylene (ingredient)... See more...

---

Drug Indications
In the United States, octocrylene has been evaluated by the FDA and is considered safe for use at concentrations not exceeding 10% in formulations. Similarly, the European Union allows it at concentrations not exceeding 10% in formulations, while Health Canada allows a maximum usage concentration of 12%.

---

Mechanism of Action
Octocrylene is an effective oil-soluble liquid UVB filter. It has excellent properties for dissolving crystalline ultraviolet filters. Due to its excellent photostability, it is used as a photostable agent. The conjugated acrylate moiety absorbs UVB and short-wave UVA (ultraviolet light) wavelengths in the 280-320 nm range, thus protecting the skin from direct DNA damage. The ethylhexanol moiety is a fatty alcohol that, due to its hydrophobicity, can be used as a emollient.
Octocrylene (Octocrilene) is an organic UV filter of the cyanoacrylate class that absorbs UVB and short UVA radiation (peak 303 nm). It is an oil-soluble liquid UVB filter with excellent photostability and dissolving properties. The compound stabilizes avobenzone and is used in sunscreens and cosmetics. It inhibits ERα and androgen receptor transactivation. Its molecular formula is C24H27NO2 with a molecular weight of 361.48 g/mol.All applications are limited to non-human research use.

C24H27NO2

361.4767

361.204

6197-30-4

22571

Light yellow to yellow ointment

1.1±0.1 g/cm3

478.5±33.0 °C at 760 mmHg

−10 °C(lit.)

239.5±12.1 °C

0.0±1.2 mmHg at 25°C

1.546

7.53

0

3

10

27

510

0

O(C(/C(/C#N)=C(\C1C([H])=C([H])C([H])=C([H])C=1[H])/C1C([H])=C([H])C([H])=C([H])C=1[H])=O)C([H])([H])C([H])(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

FMJSMJQBSVNSBF-UHFFFAOYSA-N

InChI=1S/C24H27NO2/c1-3-5-12-19(4-2)18-27-24(26)22(17-25)23(20-13-8-6-9-14-20)21-15-10-7-11-16-21/h6-11,13-16,19H,3-5,12,18H2,1-2H3

2-ethylhexyl 2-cyano-3,3-diphenylprop-2-enoate

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

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

DMSO : ≥ 100 mg/mL (~276.64 mM)
Ethanol : ~50 mg/mL (~138.32 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (6.92 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (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 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

---

Solubility in Formulation 2: 2.5 mg/mL (6.92 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 ultrasonication.
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.

---

View More

Solubility in Formulation 3: ≥ 2.5 mg/mL (6.92 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.)