6027. 4-Methylbenzylidene Camphor

Nomenclature

CAS number: 36861-47-9
1,7,7-Trimethyl-3-[(4-methylphenyl)methylene]bicyclo[2.2.1]heptan-2-one; 3-(4′-methylbenzylidene)camphor; 4-MBC; Eusolex 6300 (Merck KGaA).
C18H22O; mol wt 254.37.
C 84.99%, H 8.72%, O 6.29%.

Description and references

Ultraviolet filter in sunscreens. Prepn: J.-C. Richer, A. Rossi, Can. J. Chem. 50, 1376 (1972). TLC identification in cosmetics: D. H. Liem, L. T. H. Hilderink, Int. J. Cosmet. Sci. 1, 341 (1979); electrokinetic chromatography determn of enantiomers in cosmetic formulations: B. Gómara et al., Electrophoresis 26, 3952 (2005). Photostability: A. Deflandre, G. Lang, Int. J. Cosmet. Sci. 10, 53 (1988); eidem, Cosmet. Toiletries 103, 69 (1988). In vivo assessment of photostability: M. Cambon et al., J. Cosmet. Sci. 52, 1 (2001). Uterotrophic activity: H. Tinwell et al., Environ. Health Perspect. 110, 533 (2002). Evaluation of androgenic activity: R. Ma et al., Toxicol. Sci. 74, 43 (2003).

Chemical structure

Properties

Crystals from absolute ethanol, mp 98.5-99.5°. [α]D24 +429° (c = 1.615 in benzene). uv max (95% ethanol): 226, 301 nm (ε 7300, 20500).

Therapeutic Category

Ultraviolet screen.

Keywords

Ultraviolet Screen