Enzacamene

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
CAS Number
  • 36861-47-9 checkY
3D model (JSmol)
  • Interactive image
Abbreviations 4-MBC
ChemSpider
  • 4939160 checkY
ECHA InfoCard 100.048.386 Edit this at Wikidata
EC Number
  • 253-242-6
PubChem CID
  • 6434217
UNII
  • 8I3XWY40L9 checkY
CompTox Dashboard (EPA)
  • DTXSID8047896 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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)
Solubility in water
 Insoluble
Hazards
GHS labelling:
Pictograms
 GHS09: Environmental hazard
Warning
Hazard statements
 H410
Precautionary statements
 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
Chemical compound

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

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.
  • v
  • t
  • e
Sunscreening agents approved by the US FDA or other agencies
  • UVA: 400–315 nm
  • UVB: 315–290 nm
  • Chemical agents unless otherwise noted
UVA filtersUVB filtersUVA+UVB filters
  • v
  • t
  • e
CARTooltip Constitutive androstane receptor
PXRTooltip Pregnane X receptor
See also
Receptor/signaling modulators
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