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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
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

Sotiropoulos, J.|El Batouti, N.
2
Sources: Journal de Chimie Physique et de Physico-Chimie Biologique (1984), 81, (10), 629-34.

Approval Year

2010
465
Targets

Targets

Primary TargetPharmacologyConditionPotency
ultraviolet (UV) radiation
3
Target ID: ultraviolet (UV) radiation
Inhibitor
8297
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8429
Unknown

Approved Use

Unknown
Preventing
Approved
8429
Unknown

Approved Use

Unknown
Preventing
Approved
8429
Unknown

Approved Use

Unknown
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
Estrogenic activity and estrogen receptor beta binding of the UV filter 3-benzylidene camphor. Comparison with 4-methylbenzylidene camphor.
2004 Jul 1
[Estrogenic activity of ultraviolet absorbers and the related compounds].
2005 Aug
Interaction of polycyclic musks and UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone receptor (PR) in reporter gene bioassays.
2005 Feb
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

Patents

20020106390
4

Sample Use Guides

In Vivo Use Guide
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
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 Fri Dec 15 18:44:18 UTC 2023
Edited
by admin
on Fri Dec 15 18:44:18 UTC 2023
Record UNII
8I3XWY40L9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ENZACAMENE
INN   MART.   USAN   USP   WHO-DD  
USAN   INN  
Official Name English
ENZACAMENE [USP MONOGRAPH]
Common Name English
3-(4-Methylbenzylidene)camphor
Systematic Name English
Enzacamene [WHO-DD]
Common Name English
ENZACAMENE [USAN]
Common Name English
ENZACAMENE [MART.]
Common Name English
enzacamene [INN]
Common Name English
BICYCLO(2.2.1)HEPTAN-2-ONE, 1,7,7-TRIMETHYL-3-((4-METHYLPHENYL)METHYLENE)-
Systematic Name English
METHYL BENZYLIDENE CAMPHOR
USP-RS  
Systematic Name English
4-METHYLBENZYLIDENE CAMPHOR
INCI   MI  
INCI  
Official Name English
Enzacamene D-L form [WHO-DD]
Common Name English
ENZACAMENE D-L FORM
WHO-DD  
Common Name English
(±)-3-(P-METHYLBENZYLIDENE)CAMPHOR
Common Name English
4-METHYLBENZYLIDENE CAMPHOR [INCI]
Common Name English
4-METHYLBENZYLIDENE CAMPHOR [MI]
Common Name English
METHYL BENZYLIDENE CAMPHOR [USP-RS]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C851
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
Code System Code Type Description
PUBCHEM
7019255
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY
CAS
38102-62-4
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
SUPERSEDED
SMS_ID
100000130022
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY
DAILYMED
8I3XWY40L9
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY
INN
7899
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY
CAS
36861-47-9
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY
DRUG BANK
DB11219
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY
DRUG CENTRAL
4292
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY
EVMPD
SUB169710
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY
EPA CompTox
DTXSID8047896
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY
NCI_THESAURUS
C87222
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY
WIKIPEDIA
4-METHYLBENZYLIDENE CAMPHOR
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY
RXCUI
1311507
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY RxNorm
FDA UNII
8I3XWY40L9
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY
MESH
C038939
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY
USAN
KK-98
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY
EVMPD
SUB40950
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY
MERCK INDEX
m7371
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
253-242-6
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY
ChEMBL
CHEMBL2104261
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY
RS_ITEM_NUM
1424222
Created by admin on Fri Dec 15 18:44:18 UTC 2023 , Edited by admin on Fri Dec 15 18:44:18 UTC 2023
PRIMARY
Related Record Type Details
Structure of ENZACAMENE, (-)
ENANTIOMER -> RACEMATE
Structure of ENZACAMENE, (+)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of CAMPHOR (SYNTHETIC)
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
USP
Related Record Type Details
Structure of ENZACAMENE
ACTIVE MOIETY
NIH
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ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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