Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C18H22O |
| Molecular Weight | 254.3667 |
| Optical Activity | ( + / - ) |
| 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://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aca12ac3-dc05-4f5b-a2b9-dae942bf856c | https://www.ncbi.nlm.nih.gov/pubmed/26888529https://www.ncbi.nlm.nih.gov/pubmed/15926546Curator'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://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aca12ac3-dc05-4f5b-a2b9-dae942bf856c | https://www.ncbi.nlm.nih.gov/pubmed/26888529https://www.ncbi.nlm.nih.gov/pubmed/15926546
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
Enzacamene, ( )-[Bicyclo[2.2.1]-heptan-2-one, 1,7,7-trimethyl-3-[(4-methylphenyl)methylene]-, (1R,3E,4S)-] is one of enantiomer of Enzacamene (4-MBC) -- organic sunscreen components, that protects against UV radiation and may therefore help in the prevention of skin cancer. Enzacamene can exist as a cis-(Z)- and trans-(E)-isomer due to the exocyclic carbon-carbon (styrene) double bond. A commercial Enzacamene from a major supplier of UV filters showed the presence of only the (E)-isomer However, it is known that, upon exposure to light, (E)-4-Enzacamene is photochemically isomerized reversably to (Z)-4-Enzacamene. Both (E)- and (Z)-Enzacamene are chiral and thus consist of enantiomers (optical isomers). In a technical material and in a major brand sun lotion, Enzacamene was shown to consist entirely (>99%) of (E)-isomers and to be racemic. Wastewater showed the presence of both (E)- and (Z)-Enzacamene with a clear excess of (E)-isomers (E >Z). Untreated wastewater showed a nearly racemic composition suggesting that most if not all commercial Enzacamene is racemic. Treated wastewater indicated some excess of (R)- or (S)-stereoisomers ikely as a result of some enantioselective (bio)degradation in wastewater treatment plants. Enantiomers may show different biological behavior with respect to uptake, metabolism, and excretion and often differ in toxicity and other biological effects.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: ultraviolet (UV) radiation Sources: https://www.ncbi.nlm.nih.gov/pubmed/15926546 |
|||
Target ID: ultraviolet (UV) radiation |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | Unknown Approved UseUnknown |
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| Preventing | Unknown Approved UseUnknown |
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| Preventing | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
18 ng/mL |
3.5 g 1 times / day multiple, transdermal dose: 3.5 g route of administration: Transdermal experiment type: MULTIPLE co-administered: |
ENZACAMENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
29 ng/mL |
3.5 g 1 times / day multiple, transdermal dose: 3.5 g route of administration: Transdermal experiment type: MULTIPLE co-administered: |
ENZACAMENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
21 ng/mL |
4 g 1 times / day multiple, transdermal dose: 4 g route of administration: Transdermal experiment type: MULTIPLE co-administered: |
ENZACAMENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
34 ng/mL |
4 g 1 times / day multiple, transdermal dose: 4 g route of administration: Transdermal experiment type: MULTIPLE co-administered: |
ENZACAMENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.98 h |
3.5 g 1 times / day multiple, transdermal dose: 3.5 g route of administration: Transdermal experiment type: MULTIPLE co-administered: |
ENZACAMENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
3.98 h |
3.5 g 1 times / day multiple, transdermal dose: 3.5 g route of administration: Transdermal experiment type: MULTIPLE co-administered: |
ENZACAMENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
3.98 h |
4 g 1 times / day multiple, transdermal dose: 4 g route of administration: Transdermal experiment type: MULTIPLE co-administered: |
ENZACAMENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.98 h |
4 g 1 times / day multiple, transdermal dose: 4 g route of administration: Transdermal experiment type: MULTIPLE co-administered: |
ENZACAMENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Mixtures of environmentally relevant endocrine disrupting chemicals affect mammary gland development in female and male rats. | 2015-07 |
|
| 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. | 2013-10-01 |
|
| 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. | 2013-07-01 |
|
| Monitoring of deiodinase deficiency based on transcriptomic responses in SH-SY5Y cells. | 2013-06 |
|
| Female sexual behavior, estrous cycle and gene expression in sexually dimorphic brain regions after pre- and postnatal exposure to endocrine active UV filters. | 2009-03 |
|
| 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. | 2006-02-01 |
|
| Additive estrogenic effects of mixtures of frequently used UV filters on pS2-gene transcription in MCF-7 cells. | 2005-10-15 |
|
| [Estrogenic activity of ultraviolet absorbers and the related compounds]. | 2005-08 |
|
| Stereoisomer composition of the chiral UV filter 4-methylbenzylidene camphor in environmental samples. | 2005-05-01 |
|
| Interaction of polycyclic musks and UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone receptor (PR) in reporter gene bioassays. | 2005-02 |
|
| Estrogenic activity and estrogen receptor beta binding of the UV filter 3-benzylidene camphor. Comparison with 4-methylbenzylidene camphor. | 2004-07-01 |
|
| Activation of estrogen receptor alpha and ERbeta by 4-methylbenzylidene-camphor in human and rat cells: comparison with phyto- and xenoestrogens. | 2003-04-30 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26888529
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
Mon Mar 31 19:19:33 GMT 2025
by
admin
on
Mon Mar 31 19:19:33 GMT 2025
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| Record UNII |
8I3XWY40L9
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| Record Status |
Validated (UNII)
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NCI_THESAURUS |
C851
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38102-62-4
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100000130022
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8I3XWY40L9
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7899
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36861-47-9
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DB11219
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4292
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SUB169710
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DTXSID8047896
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C87222
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4-METHYLBENZYLIDENE CAMPHOR
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1311507
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8I3XWY40L9
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C038939
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KK-98
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SUB40950
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m7371
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253-242-6
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CHEMBL2104261
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1424222
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| Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE |
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ENANTIOMER -> RACEMATE |
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| Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
USP
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
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