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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

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.

Originator

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

Approval Year

Targets

Targets

Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
Activation of estrogen receptor alpha and ERbeta by 4-methylbenzylidene-camphor in human and rat cells: comparison with phyto- and xenoestrogens.
2003 Apr 30
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
Mixtures of environmentally relevant endocrine disrupting chemicals affect mammary gland development in female and male rats.
2015 Jul
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 Sat Dec 16 09:41:06 UTC 2023
Edited
by admin
on Sat Dec 16 09:41:06 UTC 2023
Record UNII
7576E1028E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ENZACAMENE, (+)-
Common 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
BICYCLO(2.2.1)HEPTAN-2-ONE, 1,7,7-TRIMETHYL-3-((4-METHYLPHENYL)METHYLENE)-, (1R,3E,4S)-
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID70865901
Created by admin on Sat Dec 16 09:41:06 UTC 2023 , Edited by admin on Sat Dec 16 09:41:06 UTC 2023
PRIMARY
FDA UNII
7576E1028E
Created by admin on Sat Dec 16 09:41:06 UTC 2023 , Edited by admin on Sat Dec 16 09:41:06 UTC 2023
PRIMARY
CAS
95342-41-9
Created by admin on Sat Dec 16 09:41:06 UTC 2023 , Edited by admin on Sat Dec 16 09:41:06 UTC 2023
PRIMARY
PUBCHEM
7019255
Created by admin on Sat Dec 16 09:41:06 UTC 2023 , Edited by admin on Sat Dec 16 09:41:06 UTC 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER