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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
Structure of ENZACAMENE, (+)-

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

HIDE SMILES / InChI

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

Description
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.

Originator

Sources: Journal de Chimie Physique et de Physico-Chimie Biologique (1984), 81, (10), 629-34.

Approval Year

Targets

Targets

Conditions

Conditions

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as perpetrator​
PubMed

PubMed

TitleDatePubMed
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

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 Mon Mar 31 22:47:15 GMT 2025
Edited
by admin
on Mon Mar 31 22:47:15 GMT 2025
Record UNII
7576E1028E
Record Status Validated (UNII)
Record Version
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Name Type Language
ENZACAMENE, (+)-
Common Name English
BICYCLO(2.2.1)HEPTAN-2-ONE, 1,7,7-TRIMETHYL-3-((4-METHYLPHENYL)METHYLENE)-, (1R,3E,4S)-
Preferred Name English
BICYCLO(2.2.1)HEPTAN-2-ONE, 1,7,7-TRIMETHYL-3-((4-METHYLPHENYL)METHYLENE)-, (1R-(1.ALPHA.,3E,4.ALPHA.))-
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID70865901
Created by admin on Mon Mar 31 22:47:15 GMT 2025 , Edited by admin on Mon Mar 31 22:47:15 GMT 2025
PRIMARY
FDA UNII
7576E1028E
Created by admin on Mon Mar 31 22:47:15 GMT 2025 , Edited by admin on Mon Mar 31 22:47:15 GMT 2025
PRIMARY
CAS
95342-41-9
Created by admin on Mon Mar 31 22:47:15 GMT 2025 , Edited by admin on Mon Mar 31 22:47:15 GMT 2025
PRIMARY
PUBCHEM
7019255
Created by admin on Mon Mar 31 22:47:15 GMT 2025 , Edited by admin on Mon Mar 31 22:47:15 GMT 2025
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER