Enzacamene

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).

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 (JSmol)
Abbreviations 4-MBC
ChemSpider
ECHA InfoCard 100.048.386
EC Number
  • 253-242-6
UNII
  • InChI=1S/C18H22O/c1-12-5-7-13(8-6-12)11-14-15-9-10-18(4,16(14)19)17(15,2)3/h5-8,11,15H,9-10H2,1-4H3/b14-11+ checkY
    Key: HEOCBCNFKCOKBX-SDNWHVSQSA-N checkY
  • InChI=1/C18H22O/c1-12-5-7-13(8-6-12)11-14-15-9-10-18(4,16(14)19)17(15,2)3/h5-8,11,15H,9-10H2,1-4H3/b14-11+
    Key: HEOCBCNFKCOKBX-SDNWHVSQBW
  • O=C2\C(=C\c1ccc(cc1)C)C3CCC2(C)C3(C)C
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
GHS labelling:
GHS09: Environmental hazard
Warning
H410
P273, P391, P501
Pharmacology
Legal status
  • Banned in Thailand, Palau and Hawaii
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Mechanism

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

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

Approval status

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 nor in Denmark.[5]

See also

References
  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. 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.
  5. Garcia, Sandra E. (2023-08-12). "U.S. Sunscreen Is Stuck in the '90s. Is This a Job for Congress?". The New York Times. ISSN 0362-4331. Retrieved 2023-08-13.
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