| Revision as of 18:18, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 399328045 of page 4-Methylbenzylidene_camphor for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 02:28, 24 September 2024 edit Citation bot (talk | contribs)Bots5,418,783 edits Altered title. | Use this bot. Report bugs. | Suggested by Spinixster | Category:Sunscreening agents | #UCB_Category 15/41 |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 399326552 |
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|Reference=<ref> at chemicalland21.com</ref> |
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| verifiedrevid = 477222691 |
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|ImageFile=4-Methylbenzylidene camphor.svg |
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| Reference=<ref> at chemicalland21.com</ref> |
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|ImageSize=200px |
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| ImageFile = 4-Methylbenzylidene camphor.svg |
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|IUPACName=(3''E'')-1,7,7-Trimethyl-3--2-norbornanone |
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| ImageAlt = Skeletal formula of 4-methylbenzylidene camphor |
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|OtherNames= 3-(4-Methylbenzylidene)bornan-2-one<br>3-(4-Methylbenzylidene)-dl-camphor |
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| ImageFile1 = 4-Methylbenzylidene-camphor-3D-balls.png |
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| ImageSize1 = 220 |
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| ImageAlt1 = Ball-and-stick model of the 4-methylbenzylidene camphor molecule |
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| IUPACName=(3''E'')-1,7,7-Trimethyl-3--2-norbornanone |
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| OtherNames= 4-Methylbenzylidene camphor<br>3-(4-Methylbenzylidene)bornan-2-one<br>3-(4-Methylbenzylidene)-dl-camphor |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| Abbreviations = 4-MBC |
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| Abbreviations = 4-MBC |
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| 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+ |
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| 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+ |
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| InChIKey = HEOCBCNFKCOKBX-SDNWHVSQBW |
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| InChIKey = HEOCBCNFKCOKBX-SDNWHVSQBW |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = HEOCBCNFKCOKBX-SDNWHVSQSA-N |
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| StdInChIKey = HEOCBCNFKCOKBX-SDNWHVSQSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 36861-47-9 --> |
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| EINECS=253-242-6 |
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| CASNo=36861-47-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=6434217 |
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| UNII = 8I3XWY40L9 |
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| SMILES = O=C2\C(=C\c1ccc(cc1)C)C3CCC2(C)C3(C)C |
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| EINECS=253-242-6 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem=6434217 |
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| SMILES = O=C2\C(=C\c1ccc(cc1)C)C3CCC2(C)C3(C)C |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4939160 |
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| ChemSpiderID = 4939160 |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>18</sub>H<sub>22</sub>O |
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| Formula=C<sub>18</sub>H<sub>22</sub>O |
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| MolarMass=254.37 g/mol |
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| MolarMass=254.37 g/mol |
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| Appearance=White crystalline powder |
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| Appearance=White crystalline powder |
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| Density= |
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| MeltingPt=66-69 °C |
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| MeltingPtC = 66 to 69 |
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| MeltingPt_notes = |
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| Solubility=Insoluble |
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| Solubility=Insoluble |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| FlashPt= |
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| MainHazards='''Xi''' |
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| AutoignitionPt = |
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| FlashPt= |
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| GHSPictograms = {{GHS09}} |
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| GHSSignalWord = Warning |
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| RPhrases= {{R36/37/38}} {{R50}} {{R53}} |
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| HPhrases = {{H-phrases|410}} |
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| SPhrases = {{S26}} {{S37/39}} {{S61}} |
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| PPhrases = {{P-phrases|273|391|501}} |
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|Section4={{Chembox Pharmacology |
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| Legal_status = Banned in Thailand, Palau and Hawaii |
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'''Enzacamene''' (]; also known as '''4-methylbenzylidene camphor''' or '''4-MBC''') is an organic ] ] that is used in the ] industry for its ability to protect the ] against ], specifically UV B radiation. As such, it is used in ] ]s and other skincare products claiming a SPF value. Its tradenames include '''Eusolex 6300''' (]) and '''Parsol 5000''' (]). |
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==Mechanism== |
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All the camphor-derived sunscreens dissipate the photon energy by ]. 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.<ref>''Sun Protection in Man''. Chapter 26: Cantrell, Ann; McGarvey, David J.; Truscott, T. George. Photochemical and photophysical properties of sunscreens.</ref> |
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==Endocrine disruptor== |
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Studies have raised the issue that enzacamene acts as an ]. There is controversy about the ]ic effects of enzacamene and while one study showed only a relatively minor effect.<ref>{{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}}</ref> In addition, there is some evidence that enzacamene may suppress the pituitary-thyroid axis, leading to ].<ref>{{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}}</ref> |
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==Approval status== |
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Enzacamene is approved in Canada by ]. It is not approved for use in the United States by the ] and it is not permitted in Japan nor in Denmark.<ref>{{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}}</ref> |
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==See also== |
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*] |
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==References== |
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{{reflist}} |
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{{Sunscreening agents}} |
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{{Xenobiotic-sensing receptor modulators}} |
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] |
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] |
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] |