3-(4-methylbenzylidene)camphor

Synonyms: "3-(4'-methylbenzylidene)camphor", "4-methylbenzylidene camphor", "neo heliopan MBC", "parsol 5000"

Source: 3-(4-methylbenzylidene)camphor is a chiral sunscreen agent used in cosmetic products.

Identifiers:

IUPAC Name: (2E)-4,7,7-trimethyl-2-[(4-methylphenyl)methylidene]bicyclo[2.2.1]heptan-3-one
CAS Number: 36861-47-9
PubChem ID: 6434217
InChiKey: HEOCBCNFKCOKBX-SDNWHVSQSA-N
Canonical SMILES: CC1=CC=C(C=C1)C=C2C3CCC(C2=O)(C3(C)C)C

Structural Properties:

Molecular Formula: C₁₈H₂₂O
Molecular Weight: 254.367

Pharmacophore Features:

Number of bond donors: 0
Number of bond acceptors: 1
Number of atoms different from hydrogen: 19

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2D structure (.sdf)
3D structure (.sdf)
3D structure (.mol2)
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Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors

Durrer S, Ehnes C, Fuetsch M, Maerkel K, Schlumpf M, Lichtensteiger W. 2007. Estrogen sensitivity of target genes and expression of nuclear receptor co-regulators in rat prostate after pre- and postnatal exposure to the ultraviolet filter 4-methylbenzylidene camphor. Environ Health Perspect 115 (Suppl 1):42-50.

Durrer S, Maerkel K, Schlumpf M, Lichtensteiger W. 2005. Estrogen target gene regulation and coactivator expression in rat uterus after developmental exposure to the ultraviolet filter 4-methylbenzylidene camphor. Endocrinology 146(5):2130-2139.

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.

Maerkel K, Durrer S, Henseler M, Schlumpf M, Lichtensteiger W. 2007. Sexually dimorphic gene regulation in brain as a target for endocrine disrupters: Developmental exposure of rats to 4-methylbenzylidene camphor. Toxicol Appl Pharmacol 218(2):152-165.

Seidlova-Wuttke D, Christoffel J, Rimoldi G, Jarry H, Wuttke W. 2006. Comparison of effects of estradiol with those of octylmethoxycinnamate and 4-methylbenzylidene camphor on fat tissue, lipids and pituitary hormones. Toxicol Appl Pharmacol 214(1):1-7.