benzylidene camphor

Synonyms: "benzal camphor", "3-benzylidene-1,7,7-trimethyl-norbornan-2-one", "(3E)-3-benzylidene-1,7,7-trimethyl-norbornan-2-one", "2-benzylidene-4,7,7-trimethylbicyclo[2.2.1]heptan-3-one", "1,7,7-trimethyl-3-(phenylmethylene)-bicyclo[2.2.1]heptan-2-one".

Source: benzylidene camphor is used as a UV filter in sunscreens.

Identifiers:

IUPAC Name: 3-benzylidene-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
CAS Number: 15087-24-8
PubChem ID: 27021
InChiKey: OIQXFRANQVWXJF-UHFFFAOYSA-N
Canonical SMILES: CC1(C2CCC1(C(=O)C2=CC3=CC=CC=C3)C)C

Structural Properties:

Molecular Formula: C₁₇H₂₀O
Molecular Weight: 240.346

Pharmacophore Features:

Number of bond donors: 0
Number of bond acceptors: 1
Number of atoms different from hydrogen: 18

Downloads

2D structure (.sdf)
3D structure (.sdf)
3D structure (.mol2)
3D structure (.pdb)
3D structure (.pdbqt)

Search Similar molecules

Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors

Faass O, Schlumpf M, Reolon S, Henseler M, Maerkel K, Durrer S, Lichtensteiger W. 2009. Female sexual behavior, estrous cycle and gene expression in sexually dimorphic brain regions after pre- and postnatal exposure to endocrine active UV filters. Neurotoxicology 30(2):249-260. DOI: 10.1016/j.neuro.2008.12.008. URL: https://www.sciencedirect.com/science/article/pii/S0161813X08002441.
Kunz PY, Fent K. 2006. Multiple hormonal activities of UV filters and comparison of in vivo and in vitro estrogenic activity of ethyl-4-aminobenzoate in fish. Aquat Toxicol 79(4):305-324. DOI: 10.1016/j.aquatox.2006.06.016. URL: https://www.sciencedirect.com/science/article/pii/S0166445X06002700.
Kunz PY, Galicia HF, Fent K. 2006. Comparison of in vitro and in vivo estrogenic activity of UV filters in fish. Toxicol Sci 90(2):349-361 DOI: 10.1093/toxsci/kfj082. URL: https://academic.oup.com/toxsci/article/90/2/349/1658390Kunz PY, Gries T, Fent K. 2006. The ultraviolet filter 3-benzylidene camphor adversely affects reproduction in fathead minnow (Pimephales promelas). Toxicol Sci 93(2):311-321. DOI: 10.1093/toxsci/kfl070. URL: https://academic.oup.com/toxsci/article/93/2/311/1707808Schlumpf.
M, Jarry H, Wuttke W, Ma R. 2004. Estrogenic activity and estrogen receptor beta binding of the UV filter 3-benzylidene camphor. Comparison with 4-methylbenzylidene camphor. Toxicology 199(2-3):109-120. DOI: 10.1016/j.tox.2004.02.015. URL: https://www.sciencedirect.com/science/article/pii/S0300483X04001167?via%3Dihub.
Schlumpf M, Schmid P, Durrer S, Conscience M, Maerkel K, Henseler M, Gruetter M, Herzog I, Reolon S, Ceccatelli R, Faass O, Stutz E, Jarry H, Wuttke W, Lichtensteiger W. 2004. Endocrine activity and developmental toxicity of cosmetic UV filters - an update. Toxicology 205(1-2):113-122. DOI: 10.1016/j.tox.2004.06.043. URL: https://www.sciencedirect.com/science/article/pii/S0300483X04003713.
Schreurs RH, Sonneveld E, Jansen JH, Seinen W, van der Burg B. 2005. Interaction of polycyclic musks and UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone receptor (PR) in reporter gene bioassays. Toxicol Sci 83(2):264-272. DOI: 10.1093/toxsci/kfi035. URL: https://academic.oup.com/toxsci/article/83/2/264/1713967.