 | |
| Names | |
|---|---|
| IUPAC name 2-ethylhexyl (E)-3-(4-methoxyphenyl)prop-2-enoate | |
| Other names Ethylhexyl methoxycinnamate Octinoxate Uvinul MC80 (E)-3-(4-methoxyphenyl) prop-2-enoic acid 2-ethylhexyl ester | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| DrugBank | |
| ECHA InfoCard | 100.157.824 |
| EC Number |
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| KEGG | |
| UNII | |
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| Properties | |
| C18H26O3 | |
| Molar mass | 290.403 g·mol−1 |
| Density | 1.01 g/cm3 |
| Melting point | −25 °C (−13 °F; 248 K) |
| Boiling point | 198 to 200 °C (388 to 392 °F; 471 to 473 K) |
| Pharmacology | |
| D02BA02 (WHO) | |
| Legal status |
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| Hazards | |
| GHS labelling:[1] | |
  | |
| Warning | |
| H315,H319,H335,H411 | |
| P261,P264,P264+P265,P271,P273,P280,P302+P352,P304+P340,P305+P351+P338,P319,P321,P332+P317,P337+P317,P362+P364,P391,P403+P233,P405,P501 | |
| NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Octyl methoxycinnamate orethylhexyl methoxycinnamate (INCI) oroctinoxate (USAN), trade namesEusolex 2292 andUvinul MC80, is anorganic compound that is an ingredient in somesunscreens andlip balms. It is anester formed frommethoxycinnamic acid and2-ethylhexanol. It is a liquid that is insoluble in water.
It is primarily used in sunscreens and other cosmetics to absorbUV-B rays from thesun, protecting the skin from damage. It is also used to reduce the appearance of scars.
Octyl methoxycinnamate is the most commonactive ingredient in sunscreens for protection againstUV-B rays.[2][3] It may be combined withoxybenzone andtitanium oxide.[2]
Studies have evaluated the efficacy of octyl methoxycinnamate in preventing postoperative peritoneal adhesions and determined that octyl methoxycinnamate covering peritoneal surfaces decreases adhesion formation. This effect is more notable when octyl methoxycinnamate is applied before the induction of trauma.[4]
Chromophore groups, such as C=C, C=O, and O-N=O, have loosely held electrons that are excited by radiation. Hence, octyl methoxycinnamate is able to absorb radiation when the electron energy level is increased to an excited state.[5]
The UV spectra of octyl methoxycinnamate contains a maximum at 310 nm.[6]
Olefin metathesis has been widely studied. One of the synthesis pathways for octyl methoxycinnamate includes cross metathesis. The high efficiency of the nitro-Grela catalyst has been used in the cross metathesis oftrans-anethole with 2-ethylhexyl acrylate to produce octyl methoxycinnamate (86% yield).[7]
 | This sectionneeds morereliable medical references forverification or relies too heavily onprimary sources. Please review the contents of the section andadd the appropriate references if you can. Unsourced or poorly sourced material may be challenged andremoved.Find sources: "Octyl methoxycinnamate" – news ·newspapers ·books ·scholar ·JSTOR(April 2013) |
One study performed in 2000 raised safety concerns about octyl methoxycinnamate by demonstrating toxicity to mouse cells at concentrations lower than typical levels in sunscreens.[8][9][medical citation needed] However, another study concluded that octyl methoxycinnamate and other sun screening agents do not penetrate the outer skin in sufficient concentration to cause any significant toxicity to the underlying humankeratinocytes.[10]
Estrogenic and neurological effects were noted in laboratory animals at concentrations close to those experienced by sunscreen users[11][12] and were also shownin vitro.[citation needed] Octyl methoxycinnamate has been shown to be light sensitive with a decrease in UV absorption efficiency upon light exposure.[13] This degradation causes formation of the Z-octyl-p-methoxycinnamate from the E-octyl-p-methoxycinnamate. In contrast, the OMC does not show degradation when kept in darkness for extended periods of time.[citation needed]
A study carried out in 2017 by the Research Centre for Toxic Compounds in the Environment at Masaryk University, Czech Republic, indicates that octyl methoxycinnamate (EHMC) may damage human cell DNA. When exposed to sun rays, the spatial arrangement of its molecules changes and isomerisation takes place. While until now only unchanged EHMC has been researched, Massaryk University researchers focused on its isomers and found out that it has a significant genotoxic effect under lab conditions. It means that it may potentially damage human DNA and cause genome mutations which may lead to serious health risks.[14]
In swimming pools with hypochlorite in aqueous solution, octyl methoxycinnamate has been shown to produce chlorine-substituted intermediates. The chlorination intermediates of octyl methoxycinnamate demonstrated weak mutagenic effects on the Salmonella typhimurium TA 100 strain. The reactions depended on the pH, compound structures, and chlorine dose.[15]
Concern about effects oncoral reefs resulted in a bill in thestate legislature of Hawaii to limit use of sunscreens containing octyl methoxycinnamate andoxybenzone.[16][17]
For the same reasons, the government ofPalau signed a law in 2018 (becoming effective in 2020) that restricted the sale and use of sunscreen and skincare products that contain a list of ten different chemicals, including the UV filters octyl methoxycinnamate, oxybenzone and octocrylene, with fines ofUS$1,000 for retailers who violate the law and the power to confiscate such products from non-commercial users.[18]
Octinoxate contains a stereocenter and a double bond. It has the following stereoisomers[19][20] Therefore, octinoxate could consist of the following four stereoisomers:
| Enantiomers of Octinoxate | ||
|---|---|---|
| (R)-shape | (S)-shape | |
| (E)-shape | -Octinoxat_Structural_Formula_V2.svg) | -Octinoxat_Structural_Formula_V2.svg) |
| (Z)-shape | -Octinoxat_Structural_Formula_V2.svg) | -Octinoxat_Structural_Formula_V2.svg) |
