Octyl methoxycinnamate

Octyl methoxycinnamate[1]
IUPAC name 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
CAS number	5466-77-3 Y
PubChem	5355130
ChemSpider	4511170 Y
UNII	4Y5P7MUD51 Y
ChEMBL	CHEMBL1200608 N
Jmol-3D images	Image 1
SMILES O=C(OCC(CC)CCCC)\C=C\c1ccc(OC)cc1
InChI 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+ Y Key: YBGZDTIWKVFICR-JLHYYAGUSA-N Y 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
Properties
Molecular formula	C18H26O3
Molar mass	290.397
Density	1.01 g/cm3
Melting point	-25 °C
Boiling point	198-200 °C
N methoxycinnamate (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 2-ethylhexanol. It is a clear liquid that is insoluble in water.

Its primary use is in suncreens and other cosmetics to absorb UV-B and UV-A rays from the sun, protecting the skin from damage. It is also used to reduce the appearance of scars.

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.^[2] 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.^[3] Estrogenic effects were noted in laboratory animals at concentrations close to those experienced by sunscreen users.^{[4][dead link][5]} A study published in 2011 explored the effects of pre- and post-natal exposure to high doses of octyl methoxycinnamate in rats and showed, for example, that the testes weight and testoserone levels were significantly reduced in male rats.^[6]

See also

• Cinoxate, another cinnamic acid based sunscreen ingredient
• sunscreen controversy

References

1. ^ Merck Index, 11th Edition, 6687.
2. ^ Sinister side of sunscreens, Rob Edwards, New Scientist, 07 October 2000
3. ^ 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. 
4. ^ Skin deep Cosmetics Database
5. ^ http://www.food.dtu.dk/Admin/Public/DWSDownload.aspx?File=%2fFiles%2fFiler%2fPublikationer%2fPhDafhandlinger%2fph.d.-afhandling_Marta_Axelstad.pdf
6. ^ Axelstad, M; Boberg, J; Hougaard, KS; Christiansen, S; Jacobsen, PR; Mandrup, KR; Nellemann, C; Lund, SP et al. (2011). "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 (3): 278–90. doi:10.1016/j.taap.2010.10.031. PMID 21059369.