Movatterモバイル変換


[0]ホーム

URL:


Jump to content
WikipediaThe Free Encyclopedia
Search

Enzacamene

From Wikipedia, the free encyclopedia
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)
Abbreviations4-MBC
ChemSpider
ECHA InfoCard100.048.386Edit this at Wikidata
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 mass254.37 g/mol
AppearanceWhite crystalline powder
Melting point66 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 theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Enzacamene (INN; also known as4-methylbenzylidene camphor or4-MBC) is an organiccamphorderivative that is used in thecosmetic industry for its ability to protect theskin againstUV, specifically UV B radiation. As such, it is used insunscreenlotions and other skincare products claiming a SPF value. Its tradenames includeEusolex 6300 (Merck) andParsol 5000 (DSM).

Mechanism

[edit]

All the camphor-derived sunscreens dissipate the photon energy bycis-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 enzacamene acts as anendocrine disruptor. There is controversy about theestrogenic 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 tohypothyroidism.[4]

Approval status

[edit]

Enzacamene is approved in Canada byHealth Canada. It is not approved for use in the United States by theFood and Drug Administration and it is not permitted in Japan nor in Denmark.[5]

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. ^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. Retrieved2023-08-13.
Sunscreening agentsapproved by theUS FDA or other agencies
  • UVA: 400–315 nm
  • UVB: 315–290 nm
  • Chemical agents unless otherwise noted
UVA filters
UVB filters
UVA+UVB filters
CARTooltip Constitutive androstane receptor
PXRTooltip Pregnane X receptor
Retrieved from "https://en.wikipedia.org/w/index.php?title=Enzacamene&oldid=1247388463"
Categories:
Hidden categories:

[8]ページ先頭

©2009-2025 Movatter.jp