U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C24H27NO2
Molecular Weight 361.4767
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OCTOCRYLENE

SMILES

CCCCC(CC)COC(=O)C(C#N)=C(C1=CC=CC=C1)C2=CC=CC=C2

InChI

InChIKey=FMJSMJQBSVNSBF-UHFFFAOYSA-N
InChI=1S/C24H27NO2/c1-3-5-12-19(4-2)18-27-24(26)22(17-25)23(20-13-8-6-9-14-20)21-15-10-7-11-16-21/h6-11,13-16,19H,3-5,12,18H2,1-2H3

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including, http://onlinelibrary.wiley.com/doi/10.1111/cod.12205/epdf

Octocrylene is a compound often used as an additive in sun screen, and is thought to have skin moisturizing effects because of its emollient properties. What makes this chemical such a popular additive to sun block, is its ability to neutralize UV radiation dissipated by sunlight, and to minimize skin damage from prolonged sun exposure. Octocrylene is also often combined with avobenzone, another common sunscreen ingredient often appearing on ingredient labels. Because of its effectiveness, the chemical has been approved across the globe for use in cosmetics and skin care products, but the concentrations of this ingredient are usually limited to no more than 10 or 12 percent. However, the use of this chemical doesn’t just stop with sunscreen for face and arms, but can extend to a variety of other products, like hair spray, tannin oil, BB cream, conditioner, and CC cream, among others. Octocrylene may cause contact and photocontact allergy.

Originator

Curator's Comment: http://143230426296262911.weebly.com/introduction-to-molecule.html

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
ANTHELIOS 20

Approved Use

Help prevent sunburns.

Launch Date

2006
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.7 ng/mL
2.7 g single, topical
dose: 2.7 g
route of administration: Topical
experiment type: SINGLE
co-administered:
OCTOCRYLENE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
7.8 ng/mL
2.7 g 4 times / day steady-state, topical
dose: 2.7 g
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
OCTOCRYLENE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
43.3 h
2.7 g 4 times / day steady-state, topical
dose: 2.7 g
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
OCTOCRYLENE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
3.7 g 1.3 times / day multiple, topical (median)
Recommended
Dose: 3.7 g, 1.3 times / day
Route: topical
Route: multiple
Dose: 3.7 g, 1.3 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 3.69 years (range: 0.64-48.15 years)
n = 79
Health Status: healthy
Age Group: 3.69 years (range: 0.64-48.15 years)
Sex: M+F
Population Size: 79
Sources:
Other AEs: Dermatitis, Eczema...
Other AEs:
Dermatitis (2.5%)
Eczema (1.3%)
Sources:
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Other AEs: Acne, Dermatitis...
Other AEs:
Acne (4.8%)
Dermatitis (2.8%)
Dry skin (1.2%)
Eczema (1.2%)
Erythema (1.2%)
Pruritus (2%)
Rosacea (0.4%)
Seborrhea (0.8%)
Skin discomfort (1.2%)
Sunburn (0.8%)
Conjunctivitis (0.8%)
Taste perversion (0.4%)
Sources:
3.1 g 1.2 times / day multiple, topical (median)
Recommended
Dose: 3.1 g, 1.2 times / day
Route: topical
Route: multiple
Dose: 3.1 g, 1.2 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 6.69 years (range: 0.5-67.95 years)
n = 246
Health Status: healthy
Age Group: 6.69 years (range: 0.5-67.95 years)
Sex: M+F
Population Size: 246
Sources:
Other AEs: Dermatitis, Eczema...
Other AEs:
Dermatitis (2.8%)
Eczema (0.4%)
Erythema (0.8%)
Skin discomfort (0.8%)
Sunburn (1.6%)
Conjunctivitis (0.4%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Eczema 1.3%
3.7 g 1.3 times / day multiple, topical (median)
Recommended
Dose: 3.7 g, 1.3 times / day
Route: topical
Route: multiple
Dose: 3.7 g, 1.3 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 3.69 years (range: 0.64-48.15 years)
n = 79
Health Status: healthy
Age Group: 3.69 years (range: 0.64-48.15 years)
Sex: M+F
Population Size: 79
Sources:
Dermatitis 2.5%
3.7 g 1.3 times / day multiple, topical (median)
Recommended
Dose: 3.7 g, 1.3 times / day
Route: topical
Route: multiple
Dose: 3.7 g, 1.3 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 3.69 years (range: 0.64-48.15 years)
n = 79
Health Status: healthy
Age Group: 3.69 years (range: 0.64-48.15 years)
Sex: M+F
Population Size: 79
Sources:
Rosacea 0.4%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Taste perversion 0.4%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Conjunctivitis 0.8%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Seborrhea 0.8%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Sunburn 0.8%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Dry skin 1.2%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Eczema 1.2%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Erythema 1.2%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Skin discomfort 1.2%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Pruritus 2%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Dermatitis 2.8%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Acne 4.8%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Conjunctivitis 0.4%
3.1 g 1.2 times / day multiple, topical (median)
Recommended
Dose: 3.1 g, 1.2 times / day
Route: topical
Route: multiple
Dose: 3.1 g, 1.2 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 6.69 years (range: 0.5-67.95 years)
n = 246
Health Status: healthy
Age Group: 6.69 years (range: 0.5-67.95 years)
Sex: M+F
Population Size: 246
Sources:
Eczema 0.4%
3.1 g 1.2 times / day multiple, topical (median)
Recommended
Dose: 3.1 g, 1.2 times / day
Route: topical
Route: multiple
Dose: 3.1 g, 1.2 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 6.69 years (range: 0.5-67.95 years)
n = 246
Health Status: healthy
Age Group: 6.69 years (range: 0.5-67.95 years)
Sex: M+F
Population Size: 246
Sources:
Erythema 0.8%
3.1 g 1.2 times / day multiple, topical (median)
Recommended
Dose: 3.1 g, 1.2 times / day
Route: topical
Route: multiple
Dose: 3.1 g, 1.2 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 6.69 years (range: 0.5-67.95 years)
n = 246
Health Status: healthy
Age Group: 6.69 years (range: 0.5-67.95 years)
Sex: M+F
Population Size: 246
Sources:
Skin discomfort 0.8%
3.1 g 1.2 times / day multiple, topical (median)
Recommended
Dose: 3.1 g, 1.2 times / day
Route: topical
Route: multiple
Dose: 3.1 g, 1.2 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 6.69 years (range: 0.5-67.95 years)
n = 246
Health Status: healthy
Age Group: 6.69 years (range: 0.5-67.95 years)
Sex: M+F
Population Size: 246
Sources:
Sunburn 1.6%
3.1 g 1.2 times / day multiple, topical (median)
Recommended
Dose: 3.1 g, 1.2 times / day
Route: topical
Route: multiple
Dose: 3.1 g, 1.2 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 6.69 years (range: 0.5-67.95 years)
n = 246
Health Status: healthy
Age Group: 6.69 years (range: 0.5-67.95 years)
Sex: M+F
Population Size: 246
Sources:
Dermatitis 2.8%
3.1 g 1.2 times / day multiple, topical (median)
Recommended
Dose: 3.1 g, 1.2 times / day
Route: topical
Route: multiple
Dose: 3.1 g, 1.2 times / day
Co-administed with::
ecamsule
avobenzone
titanium dioxide
Sources:
healthy, 6.69 years (range: 0.5-67.95 years)
n = 246
Health Status: healthy
Age Group: 6.69 years (range: 0.5-67.95 years)
Sex: M+F
Population Size: 246
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Contact allergy to octocrylene.
2003 Jan
Development and validation of a non-aqueous reversed-phase high-performance liquid chromatographic method for the determination of four chemical UV filters in suncare formulations.
2004 Mar 26
Occurrence of UV filter compounds from sunscreens in surface waters: regional mass balance in two Swiss lakes.
2004 May
Determination of sixteen UV filters in suncare formulations by high-performance liquid chromatography.
2004 Sep 17
[Estrogenic activity of ultraviolet absorbers and the related compounds].
2005 Aug
Occurrence of some organic UV filters in wastewater, in surface waters, and in fish from Swiss Lakes.
2005 Feb 15
Multiclass determination of sunscreen chemicals in water samples by liquid chromatography-tandem mass spectrometry.
2008 Feb 15
Incorporation in lipid microparticles of the UVA filter, butyl methoxydibenzoylmethane combined with the UVB filter, octocrylene: effect on photostability.
2009
Determination of selected UV filters in indoor dust by matrix solid-phase dispersion and gas chromatography-tandem mass spectrometry.
2009 Jul 31
Addressing technical challenges associated with the FDA's proposed rules for the UVA in vitro testing procedure.
2009 Nov-Dec
Ultra-high-performance liquid chromatography-tandem mass spectrometry for determining the presence of eleven personal care products in surface and wastewaters.
2009 Oct 16
Filter-filter interactions. Photostabilization, triplet quenching and reactivity with singlet oxygen.
2010 Apr
Octocrylene, an emerging photoallergen.
2010 Jul
Physicochemical study on microencapsulation of hydroxypropyl-beta-cyclodextrin in dermal preparations.
2010 Jun
Determination of organic UV filters in water by stir bar sorptive extraction and direct analysis in real-time mass spectrometry.
2010 May
Exposure patterns of UV filters, fragrances, parabens, phthalates, organochlor pesticides, PBDEs, and PCBs in human milk: correlation of UV filters with use of cosmetics.
2010 Nov
Patents

Sample Use Guides

Apply 15 minutes before sun exposure.
Route of Administration: Topical
The study was performed in vitro using a Franz type diffusion cell. Only one of the products contained octocrylene and the concentration was 70 g/L (~7%). The sunscreen product was applied to human skin (surface area = 1.13 -1.23 cm2). Following 8-hr topical applications of the products it was reported that no octocrylene was detected in the receptor fluid suggesting that penetration through the skin was minimal to non-existent.
Name Type Language
OCTOCRYLENE
INCI   MI   ORANGE BOOK   USAN   USP   USP-RS  
INCI   USAN  
Official Name English
ANTHELIOS SX COMPONENT OCTOCRYLENE
Common Name English
OCTOCRYLENE [USP MONOGRAPH]
Common Name English
OCTOCRYLENE [USAN]
Common Name English
Octocrilene [WHO-DD]
Common Name English
2-CYANO-3,3-DIPHENYL-2-PROPENOIC ACID, 2-ETHYLHEXYL ESTER
Common Name English
OCTOCRYLENE COMPONENT OF CAPITAL SOLEIL
Common Name English
2-Ethylhexyl 2-cyano-3,3-diphenylacrylate
Systematic Name English
OCTOCRYLENE [INCI]
Common Name English
CAPITAL SOLEIL COMPONENT OCTOCRYLENE
Common Name English
NSC-760433
Code English
2-PROPENOIC ACID, 2-CYANO-3,3-DIPHENYL-, 2-ETHYLHEXYL ESTER
Common Name English
OCTOCRYLENE COMPONENT OF ANTHELIOS SX
Common Name English
octocrilene [INN]
Common Name English
OCTOCRYLENE [MI]
Common Name English
OCTOCRYLENE [ORANGE BOOK]
Common Name English
OCTOCRYLENE [USP-RS]
Common Name English
OCTOCRYLENE [USP IMPURITY]
Common Name English
OCTOCRILENE [MART.]
Common Name English
OCTOCRILENE
INN   MART.   WHO-DD  
INN  
Official Name English
Classification Tree Code System Code
Food Contact Sustance Notif, (FCN No.) FCN NO. 217
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
CFR 21 CFR 352.10
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
NCI_THESAURUS C851
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
CFR 21 CFR 352.20
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
228-250-8
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
PRIMARY
RS_ITEM_NUM
1477411
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
PRIMARY
DRUG CENTRAL
3395
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PRIMARY
MERCK INDEX
m8115
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
PRIMARY Merck Index
INN
4719
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PRIMARY
MESH
C088673
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
PRIMARY
PUBCHEM
22571
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
PRIMARY
NCI_THESAURUS
C84027
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
PRIMARY
CAS
6197-30-4
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
PRIMARY
WIKIPEDIA
OCTOCRYLENE
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
PRIMARY
EVMPD
SUB09413MIG
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
PRIMARY
NSC
760433
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID9025299
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
PRIMARY
SMS_ID
100000083846
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
PRIMARY
DAILYMED
5A68WGF6WM
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
PRIMARY
ChEMBL
CHEMBL1201147
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
PRIMARY
RXCUI
77674
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
PRIMARY RxNorm
FDA UNII
5A68WGF6WM
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
PRIMARY
DRUG BANK
DB09535
Created by admin on Fri Dec 15 15:26:19 GMT 2023 , Edited by admin on Fri Dec 15 15:26:19 GMT 2023
PRIMARY