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Octyl methoxycinnamate

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Octyl methoxycinnamate[1]
Names
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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.157.824 Edit this at Wikidata
UNII
  • InChI=1S/C18H26O3/c1-4-6-7-15(5-2)14-21-18(19)13-10-16-8-11-17(20-3)12-9-16/h8-13,15H,4-7,14H2,1-3H3/b13-10+ checkY
    Key: YBGZDTIWKVFICR-JLHYYAGUSA-N checkY
  • InChI=1/C18H26O3/c1-4-6-7-15(5-2)14-21-18(19)13-10-16-8-11-17(20-3)12-9-16/h8-13,15H,4-7,14H2,1-3H3/b13-10+
    Key: YBGZDTIWKVFICR-JLHYYAGUBM
  • O=C(OCC(CC)CCCC)\C=C\c1ccc(OC)cc1
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)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Octyl methoxycinnamate or ethylhexyl 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 for its use in protection against UV-B rays.[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][medical citation needed][4] 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.[5] Estrogenic and neurological effects were noted in laboratory animals at concentrations close to those experienced by sunscreen users[6][7] and were also shown in test tube experiments.[8][unreliable source?] Octyl methoxycinnamate has been shown to be light sensitive with a decrease in UV absorption efficiency upon light exposure. 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.

See also

References

  1. ^ Merck Index, 11th Edition, 6687.
  2. ^ 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.
  3. ^ Sinister side of sunscreens, Rob Edwards, New Scientist, 7 October 2000
  4. ^ Butt, S; Christensen, T (2000). "Toxicity and Phototoxicity of Chemical Sun Filters". Radiation Protection Dosimetry. 91 (1–3): 283–286. doi:10.1093/oxfordjournals.rpd.a033219. Retrieved 7 June 2015.
  5. ^ 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.
  6. ^ https://web.archive.org/web/20120326182312/http://www.food.dtu.dk/Admin/Public/DWSDownload.aspx?File=%2fFiles%2fFiler%2fPublikationer%2fPhDafhandlinger%2fph.d.-afhandling_Marta_Axelstad.pdf. Archived from the original (PDF) on 26 March 2012. Retrieved 8 July 2011. {{cite web}}: Missing or empty |title= (help); Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  7. ^ "Effects of pre- and postnatal exposure to the UV-filter Octyl Methoxycinnamate (OMC) on the reproductive, auditory and neurological development of rat offspring". Toxicology and Applied Pharmacology. 250: 278–290. doi:10.1016/j.taap.2010.10.031.
  8. ^ http://www.greenyour.com/body/personal-care/sun-care Archived 28 November 2011 at the Wayback Machine

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