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
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
DescriptionSources: http://www.thedermreview.com/octocrylene/Curator's Comment: description was created based on several sources, including, http://onlinelibrary.wiley.com/doi/10.1111/cod.12205/epdf
Sources: http://www.thedermreview.com/octocrylene/
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
Sources: http://www.google.com/patents/US7037511
Curator's Comment: http://143230426296262911.weebly.com/introduction-to-molecule.html
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
7.8 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31058986 |
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 |
|
3.7 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31058986 |
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 |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
43.3 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31058986 |
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
| Dose | Population | Adverse events |
|---|---|---|
3.7 g 1.3 times / day multiple, topical Recommended Dose: 3.7 g, 1.3 times / day Route: topical Route: multiple Dose: 3.7 g, 1.3 times / day Sources: |
healthy, 3.69 years (range: 0.64-48.15 years) Health Status: healthy Age Group: 3.69 years (range: 0.64-48.15 years) Sex: M+F Sources: |
Other AEs: Dermatitis, Eczema... |
1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
Other AEs: Acne, Dermatitis... Other AEs: Acne (4.8%) Sources: 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%) |
3.1 g 1.2 times / day multiple, topical Recommended Dose: 3.1 g, 1.2 times / day Route: topical Route: multiple Dose: 3.1 g, 1.2 times / day Sources: |
healthy, 6.69 years (range: 0.5-67.95 years) Health Status: healthy Age Group: 6.69 years (range: 0.5-67.95 years) Sex: M+F Sources: |
Other AEs: Dermatitis, Eczema... Other AEs: Dermatitis (2.8%) Sources: Eczema (0.4%) Erythema (0.8%) Skin discomfort (0.8%) Sunburn (1.6%) Conjunctivitis (0.4%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Eczema | 1.3% | 3.7 g 1.3 times / day multiple, topical Recommended Dose: 3.7 g, 1.3 times / day Route: topical Route: multiple Dose: 3.7 g, 1.3 times / day Sources: |
healthy, 3.69 years (range: 0.64-48.15 years) Health Status: healthy Age Group: 3.69 years (range: 0.64-48.15 years) Sex: M+F Sources: |
| Dermatitis | 2.5% | 3.7 g 1.3 times / day multiple, topical Recommended Dose: 3.7 g, 1.3 times / day Route: topical Route: multiple Dose: 3.7 g, 1.3 times / day Sources: |
healthy, 3.69 years (range: 0.64-48.15 years) Health Status: healthy Age Group: 3.69 years (range: 0.64-48.15 years) Sex: M+F Sources: |
| Rosacea | 0.4% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Taste perversion | 0.4% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Conjunctivitis | 0.8% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Seborrhea | 0.8% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Sunburn | 0.8% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Dry skin | 1.2% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Eczema | 1.2% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Erythema | 1.2% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Skin discomfort | 1.2% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Pruritus | 2% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Dermatitis | 2.8% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Acne | 4.8% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Conjunctivitis | 0.4% | 3.1 g 1.2 times / day multiple, topical Recommended Dose: 3.1 g, 1.2 times / day Route: topical Route: multiple Dose: 3.1 g, 1.2 times / day Sources: |
healthy, 6.69 years (range: 0.5-67.95 years) Health Status: healthy Age Group: 6.69 years (range: 0.5-67.95 years) Sex: M+F Sources: |
| Eczema | 0.4% | 3.1 g 1.2 times / day multiple, topical Recommended Dose: 3.1 g, 1.2 times / day Route: topical Route: multiple Dose: 3.1 g, 1.2 times / day Sources: |
healthy, 6.69 years (range: 0.5-67.95 years) Health Status: healthy Age Group: 6.69 years (range: 0.5-67.95 years) Sex: M+F Sources: |
| Erythema | 0.8% | 3.1 g 1.2 times / day multiple, topical Recommended Dose: 3.1 g, 1.2 times / day Route: topical Route: multiple Dose: 3.1 g, 1.2 times / day Sources: |
healthy, 6.69 years (range: 0.5-67.95 years) Health Status: healthy Age Group: 6.69 years (range: 0.5-67.95 years) Sex: M+F Sources: |
| Skin discomfort | 0.8% | 3.1 g 1.2 times / day multiple, topical Recommended Dose: 3.1 g, 1.2 times / day Route: topical Route: multiple Dose: 3.1 g, 1.2 times / day Sources: |
healthy, 6.69 years (range: 0.5-67.95 years) Health Status: healthy Age Group: 6.69 years (range: 0.5-67.95 years) Sex: M+F Sources: |
| Sunburn | 1.6% | 3.1 g 1.2 times / day multiple, topical Recommended Dose: 3.1 g, 1.2 times / day Route: topical Route: multiple Dose: 3.1 g, 1.2 times / day Sources: |
healthy, 6.69 years (range: 0.5-67.95 years) Health Status: healthy Age Group: 6.69 years (range: 0.5-67.95 years) Sex: M+F Sources: |
| Dermatitis | 2.8% | 3.1 g 1.2 times / day multiple, topical Recommended Dose: 3.1 g, 1.2 times / day Route: topical Route: multiple Dose: 3.1 g, 1.2 times / day Sources: |
healthy, 6.69 years (range: 0.5-67.95 years) Health Status: healthy Age Group: 6.69 years (range: 0.5-67.95 years) Sex: M+F Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/28704989/ |
yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Exposure patterns of UV filters, fragrances, parabens, phthalates, organochlor pesticides, PBDEs, and PCBs in human milk: correlation of UV filters with use of cosmetics. | 2010-11 |
|
| Simultaneous determination of UV filters and polycyclic musks in aqueous samples by solid-phase microextraction and gas chromatography-mass spectrometry. | 2010-10-22 |
|
| Stir-bar-sorptive extraction and ultra-high-performance liquid chromatography-tandem mass spectrometry for simultaneous analysis of UV filters and antimicrobial agents in water samples. | 2010-08 |
|
| Octocrylene, an emerging photoallergen. | 2010-07 |
|
| Physicochemical study on microencapsulation of hydroxypropyl-beta-cyclodextrin in dermal preparations. | 2010-06 |
|
| Emergent and unusual allergens in cosmetics. | 2010-05-22 |
|
| Determination of organic UV filters in water by stir bar sorptive extraction and direct analysis in real-time mass spectrometry. | 2010-05 |
|
| Filter-filter interactions. Photostabilization, triplet quenching and reactivity with singlet oxygen. | 2010-04 |
|
| A randomized, controlled comparative study of the wrinkle reduction benefits of a cosmetic niacinamide/peptide/retinyl propionate product regimen vs. a prescription 0.02% tretinoin product regimen. | 2010-03 |
|
| Validation of HPLC method for the simultaneous and quantitative determination of 12 UV-filters in cosmetics. | 2010-02 |
|
| Two cases of photocontact allergy to the new sun filter octocrylene. | 2009-12-15 |
|
| Photostabilization effect of quercetin on the UV filter combination, butyl methoxydibenzoylmethane-octyl methoxycinnamate. | 2009-12-02 |
|
| Ultra-high-performance liquid chromatography-tandem mass spectrometry for determining the presence of eleven personal care products in surface and wastewaters. | 2009-10-16 |
|
| Irradiation of skin and contrasting effects on absorption of hydrophilic and lipophilic compounds. | 2009-08-07 |
|
| Determination of selected UV filters in indoor dust by matrix solid-phase dispersion and gas chromatography-tandem mass spectrometry. | 2009-07-31 |
|
| Determination of personal care products in sewage sludge by pressurized liquid extraction and ultra high performance liquid chromatography-tandem mass spectrometry. | 2009-07-24 |
|
| Addressing technical challenges associated with the FDA's proposed rules for the UVA in vitro testing procedure. | 2009-06-15 |
|
| Non-porous membrane-assisted liquid-liquid extraction of UV filter compounds from water samples. | 2009-06-12 |
|
| A new ecamsule-containing SPF 40 sunscreen cream for the prevention of polymorphous light eruption: a double-blind, randomized, controlled study in maximized outdoor conditions. | 2009-02 |
|
| Incorporation in lipid microparticles of the UVA filter, butyl methoxydibenzoylmethane combined with the UVB filter, octocrylene: effect on photostability. | 2009 |
|
| In vitro assessments of UVA protection by popular sunscreens available in the United States. | 2008-12 |
|
| Region-specific growth effects in the developing rat prostate following fetal exposure to estrogenic ultraviolet filters. | 2008-07 |
|
| Sunscreens cause coral bleaching by promoting viral infections. | 2008-04 |
|
| Multiclass determination of sunscreen chemicals in water samples by liquid chromatography-tandem mass spectrometry. | 2008-02-15 |
|
| Development of a method for the determination of UV filters in water samples using stir bar sorptive extraction and thermal desorption-gas chromatography-mass spectrometry. | 2008-02-01 |
|
| Allergic and photoallergic contact dermatitis from ketoprofen: evaluation of cross-reactivities by a combination of photopatch testing and computerized conformational analysis. | 2008 |
|
| Development of a human in vivo method to study the effect of ultraviolet radiation and sunscreens in melanocytic nevi. | 2008 |
|
| Photostability and efficacy studies of topical formulations containing UV-filters combination and vitamins A, C and E. | 2007-10-01 |
|
| Occurrence and behavior of four of the most used sunscreen UV filters in a wastewater reclamation plant. | 2007-08 |
|
| Study of the efficacy of 18 sun filters authorized in European Union tested in vitro. | 2007-06 |
|
| Determination of UV filters and antimicrobial agents in environmental water samples. | 2007-02 |
|
| A validated method for the determination of traces of UV filters in fish using LC-MS/MS. | 2006-11 |
|
| Sunscreen enhancement of UV-induced reactive oxygen species in the skin. | 2006-10-15 |
|
| Fate and removal of polycyclic musks, UV filters and biocides during wastewater treatment. | 2006-08 |
|
| Octocrylene: really non-allergenic? | 2006-05 |
|
| Occurrence of UV filters 4-methylbenzylidene camphor and octocrylene in fish from various Swiss rivers with inputs from wastewater treatment plants. | 2006-03-01 |
|
| Concentrations and specific loads of UV filters in sewage sludge originating from a monitoring network in Switzerland. | 2006-02 |
|
| Evaluation of the photostability of different UV filter combinations in a sunscreen. | 2006-01-13 |
|
| Contact allergy to octocrylene in sunscreen with recurrence from passive transfer of a cosmetic. | 2005-10 |
|
| [Estrogenic activity of ultraviolet absorbers and the related compounds]. | 2005-08 |
|
| Assay of common sunscreen agents in suncare products by high-performance liquid chromatography on a cyanopropyl-bonded silica column. | 2005-06-15 |
|
| Occurrence of some organic UV filters in wastewater, in surface waters, and in fish from Swiss Lakes. | 2005-02-15 |
|
| Sunscreens - which and what for? | 2004-12-13 |
|
| Sunscreen penetration of human skin and related keratinocyte toxicity after topical application. | 2004-09-28 |
|
| Determination of sixteen UV filters in suncare formulations by high-performance liquid chromatography. | 2004-09-17 |
|
| Occurrence of UV filter compounds from sunscreens in surface waters: regional mass balance in two Swiss lakes. | 2004-05 |
|
| 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. | 2004-03-26 |
|
| Active ingredients in sunscreens act as topical penetration enhancers for the herbicide 2,4-dichlorophenoxyacetic acid. | 2004-03-15 |
|
| Effects of active sunscreen ingredient combinations on the topical penetration of the herbicide 2,4-dichlorophenoxyacetic acid. | 2003-02 |
|
| Contact allergy to octocrylene. | 2003-01 |
Sample Use Guides
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.
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Food Contact Sustance Notif, (FCN No.) |
FCN NO. 217
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CFR |
21 CFR 352.10
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NCI_THESAURUS |
C851
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CFR |
21 CFR 352.20
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1477411
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m8115
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4719
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OCTOCRYLENE
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ACTIVE MOIETY