オクトクリレン
2-シアノ-3,3-ジフェニルアクリル酸2-エチルヘキシル · α-シアノ-β-フェニルベンゼンアクリル酸2-エチルヘキシル · ユビヌルN-539 · α-シアノ-β-フェニルけい皮酸2-エチルヘキシル · 2-シアノ-3,3-ジフェニルプロペン酸2-エチルヘキシル · 3,3-ジフェニル-2-シアノアクリル酸2-エチルヘキシル · 2-シアノ-3,3-ジフェニル-2-プロペン酸2-エチルヘキシル · オクトクリレン
識別子と物理属性
| CAS No. | 6197-30-4 |
|---|---|
| 分子式 | C24H27NO2 |
| 平均分子量 | 361.5 g/mol |
| 単同位体質量 | 361.2041791 g/mol |
| SMILES | CCCCC(CC)COC(=O)C(C#N)=C(c1ccccc1)c1ccccc1 |
| InChIKey | FMJSMJQBSVNSBF-UHFFFAOYSA-N |
| PubChem CID | 22571 |
| ChEMBL | CHEMBL1201147 |
| ChEBI | CHEBI:135526 |
| EC No. | 228-250-8 |
| DTXSID | DTXSID9025299 |
| 現地名 | オクトクリレン |
化学・物理的性質
| XLogP | 7.1 |
|---|---|
| 極性表面積 | 50.1 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 10 |
| 重原子数 | 27 |
| 形式電荷 | 0 |
| 複雑度 | 510 |
| 物質分類 | UV filter |
| 化粧品 | Uv absorberUv filter |
| 香料 | Fragrance Ingredient (2-_Propenoic acid, 2-_cyano-_3,_3-_diphenyl-_, 2-_ethylhexyl ester) -> IFRA transparency List |
| 溶解度 | Insoluble (NTP, 1992)クロロホルム（微量）、メタノール（微量） |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Food Contact Substances | FCS -> FDA Cumulative Estimated Daily Intake (CEDI)FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications |
| Physical Description | 2-ethylhexyl-2-cyano-3,3-diphenylacrylate is a yellow viscous liquid. Insoluble in water. (NTP, 1992) |
| Collision Cross Section | 193.47 Ų [M+H]+ [CCS Type: TWBuffer gas: N2Ionization: GC-APCI+] |
| 融点 | -10 °C (lit.) |
| 沸点 | 218 °C/1.5 mmHg (lit.) |
| 密度 | 1.051 g/mL at 25 °C (lit.) |
| 蒸気圧 | 0Pa at 25℃ |
| 屈折率 | n20/D 1.567(lit.) |
| 引火点 | >230 °F |
| 貯蔵条件 | 15-25°C |
| 外観・状態 | Oil |
| 色 | 無色～淡黄色 |
| 臭い | Mild characteristic odor |
| Merck | 14,6756 |
| 化粧品成分の機能 | 光安定剤紫外線吸収剤UVフィルター |
| 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 |
| InChIKey | FMJSMJQBSVNSBF-UHFFFAOYSA-N |
| SMILES | CCCCC(CC)COC(=O)\C(C#N)=C(/c1ccccc1)c2ccccc2 |
| LogP（分配係数） | 6.1 at 23℃ |
| CAS データベース | 6197-30-4(CAS DataBase Reference) |
| EPAの化学物質情報 | 2-Ethylhexyl 2-cyano-3,3-diphenylacrylate (6197-30-4) |
| Absorption | uv max: 303 nm |
化学的特性
Clear yellow viscous liquid with mild characteristic odor, Miscible in methanol, n-butanol, ethyl acetate, mineral oil, hexane, toluene. Immiscible in water. Octocrylene is an effective oil soluble liquid UV‐B filter. It has excellent dissolving properties for crystalline UV filters.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 2.5% (16 of 645) of reports.WarningH410 (42.6%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]P273, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 645 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: 2-Propenoic acid, 2-cyano-3,3-diphenyl-, 2-ethylhexyl ester2-Propenoic acid, 2-cyano-3,3-diphenyl-, 2-ethylhexyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-cyano-3,3-diphenyl-, 2-ethylhexyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 09-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14858Octocrylene: Does not have an individual approval but may be used under an appropriate group standard |
| 火災危険 | Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992) |
| 反応性グループ | Nitriles |
| Reactivity Alerts | Polymerizable |
| Reactivity Profile | 2-ETHYLHEXYL-2-CYANO-3,3-DIPHENYLACRYLATE is an acrylate ester derivative. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Aquatic Chronic 1 (42.6%) |
| 消火 | This compound is not very flammable but any fire involving this compound may produce dangerous vapors. You should evacuate the area. All firefighters should wear full-body protective clothing and use self-contained breathing apparatuses. You should extinguish any fires involving this chemical with a dry chemical, carbon dioxide, foam, or halon extinguisher. (NTP, 1992) |
用途
説明
Octocrylene (OCT) is a viscous, clear, colorlesss oi introduced in commercial sunscreens and anti-ageing creams about 15 years ago. It is the 2-ethylhexyl ester of 2-cyano-3,3-diphenylacrylic acid, with the extended conjugation of the acid portion that absorbs UVB and short-wave UVA (ultraviolet) rays, with wavelengths from 280 to 320 nm, which promote tanning but also contribute to the onset of sunburn and skin cancer. It is used in various body care products, in concentrations up to 10%, to provide an adequate sun-protection factor or to protect the body care formulations themselves from UV radiation[1].
使用
Octocrylene is an ingredient used in sunscreens for its ability to absorb UV rays, protecting the skin from sun damage. It is chemically related to cinnamates. It can be used to boost SPF and improve water resistance in a given formulation. Octocrylene is photostable and can improve the photostability of other sunscreens. It is expensive and can present difficulties in formulation.
一般的な説明
Yellow viscous liquid. Insoluble in water.