Enzacamene

From Wikipedia, the free encyclopedia
  (Redirected from 4-Methylbenzylidene camphor)
Jump to: navigation, search
Enzacamene[1]
Skeletal formula of 4-methylbenzylidene camphor
Ball-and-stick model of the 4-methylbenzylidene camphor molecule
Names
IUPAC name
(3E)-1,7,7-Trimethyl-3-[(4-methylphenyl)methylene]-2-norbornanone
Other names
4-Methylbenzylidene camphor
3-(4-Methylbenzylidene)bornan-2-one
3-(4-Methylbenzylidene)-dl-camphor
Identifiers
3D model (Jmol)
Abbreviations 4-MBC
ChemSpider
ECHA InfoCard 100.048.386
EC Number 253-242-6
Properties
C18H22O
Molar mass 254.37 g/mol
Appearance White crystalline powder
Melting point 66 to 69 °C (151 to 156 °F; 339 to 342 K)
Insoluble
Hazards
Main hazards Xi
R-phrases R36/37/38 R50 R53
S-phrases S26 S37/39 S61
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Enzacamene (INN; also known as 4-methylbenzylidene camphor or 4-MBC) is an organic camphor derivative that is used in the cosmetic industry for its ability to protect the skin against UV, specifically UV B radiation. As such, it is used in sunscreen lotions and other skincare products claiming a SPF value. Its tradenames include Eusolex 6300 (Merck) and Parsol 5000 (DSM).

Mechanism[edit]

All the camphor-derived sunscreens dissipate the photon energy by cis-trans isomerisation. However, for enzacamene the quantum yield for this isomerization is only between 0.13-0.3. This low quantum yield means that other photochemical processes are also occurring.[2]

Endocrine disruptor[edit]

Studies have raised the issue that enzacameneacts an endocrine disruptor. There is controversy about the estrogenic effects of enzacamene and while one study showed only a relatively minor effect,[3] a study in Switzerland showed significant uterine growth in immature rodents.[4] In addition, there is some evidence that enzacamene may suppress the pituitary-thyroid axis, leading to hypothyroidism.[5]

Approval status[edit]

Enzacamene is approved in Canada by Health Canada. It is not approved for use in the United States by the Food and Drug Administration and it is not permitted in Japan.

See also[edit]

References[edit]

  1. ^ 3-(4-METHYLBENZYLIDEN)CAMPHOR at chemicalland21.com
  2. ^ Sun Protection in Man. Chapter 26: Cantrell, Ann; McGarvey, David J.; Truscott, T. George. Photochemical and photophysical properties of sunscreens.
  3. ^ Mueller SO; Kling M; Arifin Firzani P; et al. (April 2003). "Activation of estrogen receptor alpha and ERbeta by 4-methylbenzylidene-camphor in human and rat cells: comparison with phyto- and xenoestrogens". Toxicol. Lett. 142 (1-2): 89–101. doi:10.1016/S0378-4274(03)00016-X. PMID 12765243. 
  4. ^ Sun Block has Endocrine Disruptor Chemicals, New Scientist, April 18, 2001
  5. ^ IH Hamann; C Schmutzler; P Kirschmeyer; H Jarry & J Köhrle (2006). "4-Methylbenzylidene-camphor (4MBC) causes pituitary effects comparable to hypothyroidism". Endocrine Abstracts. 11: OC60.