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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-OYEVUCPFSA-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+/m0/s1

HIDE SMILES / InChI

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]-, (1S,3E,4R)-] 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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: ultraviolet (UV) radiation
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Stereoisomer composition of the chiral UV filter 4-methylbenzylidene camphor in environmental samples.
2005 May 1

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.
Name Type Language
ENZACAMENE, (-)
Common Name English
BICYCLO(2.2.1)HEPTAN-2-ONE, 1,7,7-TRIMETHYL-3-((4-METHYLPHENYL)METHYLENE)-, (1S,3E,4R)-
Systematic Name English
Code System Code Type Description
PUBCHEM
6989205
Created by admin on Sat Dec 16 09:55:27 GMT 2023 , Edited by admin on Sat Dec 16 09:55:27 GMT 2023
PRIMARY
CAS
852541-30-1
Created by admin on Sat Dec 16 09:55:27 GMT 2023 , Edited by admin on Sat Dec 16 09:55:27 GMT 2023
PRIMARY
FDA UNII
955UIJ2GWS
Created by admin on Sat Dec 16 09:55:27 GMT 2023 , Edited by admin on Sat Dec 16 09:55:27 GMT 2023
PRIMARY