enzacamene

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477222691

| Reference=[http://www.chemicalland21.com/specialtychem/finechem/3-(4-METHYLBENZYLIDEN)CAMPHOR.htm 3-(4-METHYLBENZYLIDEN)CAMPHOR] at chemicalland21.com

| ImageFile = 4-Methylbenzylidene camphor.svg

| ImageAlt = Skeletal formula of 4-methylbenzylidene camphor

| ImageFile1 = 4-Methylbenzylidene-camphor-3D-balls.png

| ImageSize1 = 220

| ImageAlt1 = Ball-and-stick model of the 4-methylbenzylidene camphor molecule

| IUPACName=(3E)-1,7,7-Trimethyl-3-[(4-methylphenyl)methylene]-2-norbornanone

| OtherNames= 4-Methylbenzylidene camphor
3-(4-Methylbenzylidene)bornan-2-one
3-(4-Methylbenzylidene)-dl-camphor

|Section1={{Chembox Identifiers

| Abbreviations = 4-MBC

| 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+

| InChIKey = HEOCBCNFKCOKBX-SDNWHVSQBW

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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+

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HEOCBCNFKCOKBX-SDNWHVSQSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo=36861-47-9

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 8I3XWY40L9

| EINECS=253-242-6

| PubChem=6434217

| SMILES = O=C2\C(=C\c1ccc(cc1)C)C3CCC2(C)C3(C)C

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4939160

}}

|Section2={{Chembox Properties

| Formula=C18H22O

| MolarMass=254.37 g/mol

| Appearance=White crystalline powder

| Density=

| MeltingPtC = 66 to 69

| MeltingPt_notes =

| BoilingPt=

| Solubility=Insoluble

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|Section3={{Chembox Hazards

| FlashPt=

| AutoignitionPt =

| GHSPictograms = {{GHS09}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|410}}

| PPhrases = {{P-phrases|273|391|501}}

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|Section4={{Chembox Pharmacology

| Legal_status = Banned in Thailand, Palau and Hawaii

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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.Sun Protection in Man. Chapter 26: Cantrell, Ann; McGarvey, David J.; Truscott, T. George. Photochemical and photophysical properties of sunscreens.

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.{{cite journal |author=Mueller SO |author2= Kling M |author3=Arifin Firzani P |title=Activation of estrogen receptor alpha and ERbeta by 4-methylbenzylidene-camphor in human and rat cells: comparison with phyto- and xenoestrogens |journal=Toxicol. Lett. |volume=142 |issue=1–2 |pages=89–101 |date=April 2003 |pmid=12765243 |doi= 10.1016/S0378-4274(03)00016-X|display-authors=etal}} In addition, there is some evidence that enzacamene may suppress the pituitary-thyroid axis, leading to hypothyroidism.{{cite journal| journal=Endocrine Abstracts |date=2006 |volume=11 |pages=OC60 |title=4-Methylbenzylidene-camphor (4MBC) causes pituitary effects comparable to hypothyroidism |author=IH Hamann |author2=C Schmutzler |author3=P Kirschmeyer|author4=H Jarry |author5=J Köhrle |name-list-style=amp |url=http://www.endocrine-abstracts.org/ea/0011/ea0011oc60.htm}}

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.{{Cite news |last=Garcia |first=Sandra E. |date=2023-08-12 |title=U.S. Sunscreen Is Stuck in the '90s. Is This a Job for Congress? |language=en-US |work=The New York Times |url=https://www.nytimes.com/2023/08/12/style/sunscreen-fda-regulation-aoc.html |access-date=2023-08-13 |issn=0362-4331}}

See also

References

{{reflist}}

{{Sunscreening agents}}

{{Xenobiotic-sensing receptor modulators}}

Category:Sunscreening agents

Category:Enones

Category:4-Tolyl compounds