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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

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

Primary TargetPharmacologyConditionPotency
Target ID: ultraviolet (UV) radiation
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
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

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 17 01:03:05 UTC 2022
Edited
by admin
on Sat Dec 17 01:03:05 UTC 2022
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 Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
Code System Code Type Description
CAS
38102-62-4
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
SUPERSEDED
DAILYMED
8I3XWY40L9
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
PRIMARY
INN
7899
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
PRIMARY
CAS
36861-47-9
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
PRIMARY
DRUG BANK
DB11219
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
PRIMARY
DRUG CENTRAL
4292
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
PRIMARY
EVMPD
SUB169710
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
PRIMARY
EPA CompTox
DTXSID8047896
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
PRIMARY
NCI_THESAURUS
C87222
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
PRIMARY
WIKIPEDIA
4-METHYLBENZYLIDENE CAMPHOR
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
PRIMARY
RXCUI
1311507
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
PRIMARY RxNorm
FDA UNII
8I3XWY40L9
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
PRIMARY
MESH
C038939
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
PRIMARY
USAN
KK-98
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
PRIMARY
EVMPD
SUB40950
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
PRIMARY
MERCK INDEX
M7371
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
PRIMARY Merck Index
ECHA (EC/EINECS)
253-242-6
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
PRIMARY
ChEMBL
CHEMBL2104261
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
PRIMARY
RS_ITEM_NUM
1424222
Created by admin on Sat Dec 17 01:03:05 UTC 2022 , Edited by admin on Sat Dec 17 01:03:05 UTC 2022
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
USP
Related Record Type Details
ACTIVE MOIETY