Octyl methoxycinnamate
Names | |
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IUPAC name
(RS)-2-Ethylhexyl (2E)-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 | |
ATC code | D02 |
5466-77-3 | |
ChEMBL | ChEMBL1200608 |
ChemSpider | 4511170 |
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Jmol-3D images | Image |
PubChem | 5355130 |
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UNII | 4Y5P7MUD51 |
Properties | |
Molecular formula |
C18H26O3 |
Molar mass | 290.40 g·mol−1 |
Density | 1.01 g/cm3 |
Melting point | −25 °C (−13 °F; 248 K) |
Boiling point | 198 °C (388 °F; 471 K) |
Hazards | |
NFPA 704 | |
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
verify (what is: / ?) | |
Infobox references | |
Octyl methoxycinnamate (INCI) or octinoxate (USAN), trade names Eusolex 2292 and Uvinul MC80, is an organic compound that is an ingredient in some sunscreens and lip balms. It is an ester formed from methoxycinnamic acid and (RS)-2-ethylhexanol. It is a clear liquid that is insoluble in water.
Its primary use is in sunscreens and other cosmetics to absorb UV-B rays from the sun, protecting the skin from damage. It is also used to reduce the appearance of scars.
Uses
Often used as an active ingredient in sunscreens combined with oxybenzone and titanium oxide.[2]
Safety studies
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.[3] However, a more recent 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 human keratinocytes.[4] Estrogenic effects were noted in laboratory animals at concentrations close to those experienced by sunscreen users[5] and were also shown in test tube experiments.[6]
See also
- Amiloxate, a chemically related sunscreening agent
- Cinoxate, another cinnamic acid based sunscreen ingredient
- Sunscreen controversy
References
- ↑ Merck Index, 11th Edition, 6687.
- ↑ Serpone N, Salinaro A, Emeline AV, Horikoshi S, Hidaka H, Zhao JC. 2002. An in vitro systematic spectroscopic examination of the photostabilities of a random set of commercial sunscreen lotions and their chemical UVB/UVA active agents. Photochemical & Photobiological Sciences 1(12): 970-981.
- ↑ Sinister side of sunscreens, Rob Edwards, New Scientist, 7 October 2000
- ↑ Hayden, C. G. J.; Cross, S. E.; Anderson, C.; Saunders, N. A.; Roberts, M. S. (2005). "Sunscreen Penetration of Human Skin and Related Keratinocyte Toxicity after Topical Application". Skin Pharmacology and Physiology 18 (4): 170–174. doi:10.1159/000085861. PMID 15908756.
- ↑ http://www.food.dtu.dk/Admin/Public/DWSDownload.aspx?File=%2fFiles%2fFiler%2fPublikationer%2fPhDafhandlinger%2fph.d.-afhandling_Marta_Axelstad.pdf
- ↑ http://www.greenyour.com/body/personal-care/sun-care
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