Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H22O |
| Molecular Weight | 254.3667 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC=C(C=C1)\C=C2/[C@H]3CC[C@@](C)(C2=O)C3(C)C
InChI
InChIKey=HEOCBCNFKCOKBX-RELGSGGGSA-N
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+/t15-,18+/m1/s1
| Molecular Formula | C18H22O |
| Molecular Weight | 254.3667 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 1 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/15926546https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aca12ac3-dc05-4f5b-a2b9-dae942bf856c | https://www.ncbi.nlm.nih.gov/pubmed/26888529Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25694030 | https://www.ncbi.nlm.nih.gov/pubmed/26888529
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15926546https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aca12ac3-dc05-4f5b-a2b9-dae942bf856c | https://www.ncbi.nlm.nih.gov/pubmed/26888529
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25694030 | https://www.ncbi.nlm.nih.gov/pubmed/26888529
4-Methylbenzylidene-camphor (4-MBC, also known as ENZACAMENE) is an organic sunscreen components, that protects against UV radiation and may therefore help in the prevention of skin cancer. Recently was reveled, that 4-MBC was a teratogen and influenced muscular and neuronal development, which might result in developmental defects.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: ultraviolet (UV) radiation |
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Target ID: ultraviolet (UV) radiation |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | Unknown Approved UseUnknown |
|||
| Preventing | Unknown Approved UseUnknown |
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| Preventing | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Activation of estrogen receptor alpha and ERbeta by 4-methylbenzylidene-camphor in human and rat cells: comparison with phyto- and xenoestrogens. | 2003 Apr 30 |
|
| [Estrogenic activity of ultraviolet absorbers and the related compounds]. | 2005 Aug |
|
| Stereoisomer composition of the chiral UV filter 4-methylbenzylidene camphor in environmental samples. | 2005 May 1 |
|
| Additive estrogenic effects of mixtures of frequently used UV filters on pS2-gene transcription in MCF-7 cells. | 2005 Oct 15 |
|
| Comparison of effects of estradiol (E2) with those of octylmethoxycinnamate (OMC) and 4-methylbenzylidene camphor (4MBC)--2 filters of UV light - on several uterine, vaginal and bone parameters. | 2006 Feb 1 |
|
| Female sexual behavior, estrous cycle and gene expression in sexually dimorphic brain regions after pre- and postnatal exposure to endocrine active UV filters. | 2009 Mar |
|
| Effects of in vivo exposure to UV filters (4-MBC, OMC, BP-3, 4-HB, OC, OD-PABA) on endocrine signaling genes in the insect Chironomus riparius. | 2013 Jul 1 |
|
| Monitoring of deiodinase deficiency based on transcriptomic responses in SH-SY5Y cells. | 2013 Jun |
|
| Simultaneous determination of the UV-filters benzyl salicylate, phenyl salicylate, octyl salicylate, homosalate, 3-(4-methylbenzylidene) camphor and 3-benzylidene camphor in human placental tissue by LC-MS/MS. Assessment of their in vitro endocrine activity. | 2013 Oct 1 |
|
| Mixtures of environmentally relevant endocrine disrupting chemicals affect mammary gland development in female and male rats. | 2015 Jul |
Patents
Sample Use Guides
Apply liberally 15 minutes before sun exposure
Reapply: immediately after towel drying. At least every 2 hours
Route of Administration:
Topical
Zebrafish embryos were exposed to various concentrations of 4-Methylbenzylidene camphor (4-MBC/ ENZACAMENE) in embryo medium for 3 days. A high concentration of 4-MBC was used for the purpose of phenotypic screening. Embryos exposed to 15 μM of 4-MBC displayed abnormal axial curvature and exhibited impaired motility. Exposure effects were found to be greatest during the segmentation period, when somite formation and innervation occur. Immunostaining of the muscle and axon markers F59, znp1, and zn5 revealed that 4-MBC exposure leads to a disorganized pattern of slow muscle fibers and axon pathfinding errors during the innervation of both primary and secondary motor neurons.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:41:06 GMT 2023
by
admin
on
Sat Dec 16 09:41:06 GMT 2023
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| Record UNII |
7576E1028E
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| Record Status |
Validated (UNII)
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| Record Version |
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| Related Record | Type | Details | ||
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RACEMATE -> ENANTIOMER |
