2-ethylhexyl-4-methoxycinnamate

Synonyms: "octylmethoxycinnamate", "octinoxate", "octyl methoxycinnamate", "parsol", "escalol", "2-ethylhexyl p-methoxycinnamate"

Source: 2-ethylhexyl-4-methoxycinnamate is mainly used in cosmetics.

Identifiers:

IUPAC Name: 2-ethylhexyl (E)-3-(4-methoxyphenyl)prop-2-enoate
CAS Number: 5466-77-3
PubChem ID: 5355130
InChiKey: YBGZDTIWKVFICR-JLHYYAGUSA-N
Canonical SMILES: CCCCC(CC)COC(=O)C=CC1=CC=C(C=C1)OC

Structural Properties:

Molecular Formula: C₁₈H₂₆O₃
Molecular Weight: 290.397

Pharmacophore Features:

Number of bond donors: 0
Number of bond acceptors: 2
Number of atoms different from hydrogen: 21

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2D structure (.sdf)
3D structure (.sdf)
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Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors

Carbone S, Szwarcfarb B, Reynoso R, Ponzo OJ, Cardoso N, Ale E, Moguilevsky JA, Scacchi P. 2010. In vitro effect of octyl - methoxycinnamate (OMC) on the release of Gn-RH and amino acid neurotransmitters by hypothalamus of adult rats. Exp Clin Endocrinol Diabetes 118(5):298-303.

Klammer H, Schlecht C, Wuttke W, Jarry H. 2005. Multi-organic risk assessment of estrogenic properties of octyl-methoxycinnamate in vivo - A 5-day sub-acute pharmacodynamic study with ovariectomized rats. Toxicology 215(1-2):90-96.

Klammer H, Schlecht C, Wuttke W, Schmutzler C, Gotthardt I, Kohrle J, Jarry H. 2007. Effects of a 5-day treatment with the UV-filter octyl-methoxycinnamate (OMC) on the function of the hypothalamo-pituitary-thyroid function in rats. Toxicology 238(2-3):192-199.

Rachon D, Rimoldi G, Wuttke W. 2006. In vitro effects of benzophenone-2 and octyl-methoxycinnamate on the production of interferon-gamma and interleukin-10 by murine splenocytes. Immunopharmacol Immunotoxicol 28(3):501-510.Seidlova-Wuttke D, Jarry H, Christoffel J, Rimoldi G, Wuttke W. 2006. Comparison of effects of estradiol (E2) with those of octylmethoxycinnamate (OMC) and 4-methylbenzylidene camphor (4MBC)--2 filters of UV light - on several uterine, vaginal and bone parameters. Toxicol Appl Pharmacol 210(3):246-254.