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
DescriptionCurator's Comment: description was created based on several sources, including, http://onlinelibrary.wiley.com/doi/10.1111/cod.12205/epdf
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.
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
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 (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 Sources: avobenzone titanium dioxide |
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... |
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 Sources: avobenzone titanium dioxide |
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%) 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 (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 Sources: avobenzone titanium dioxide |
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%) 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 (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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effects of active sunscreen ingredient combinations on the topical penetration of the herbicide 2,4-dichlorophenoxyacetic acid. | 2003 Feb |
|
| Contact allergy to octocrylene. | 2003 Jan |
|
| Active ingredients in sunscreens act as topical penetration enhancers for the herbicide 2,4-dichlorophenoxyacetic acid. | 2004 Mar 15 |
|
| 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 |
|
| Sunscreen penetration of human skin and related keratinocyte toxicity after topical application. | 2005 Jul-Aug |
|
| Assay of common sunscreen agents in suncare products by high-performance liquid chromatography on a cyanopropyl-bonded silica column. | 2005 Jun 15 |
|
| Sunscreens - which and what for? | 2005 Nov-Dec |
|
| Contact allergy to octocrylene in sunscreen with recurrence from passive transfer of a cosmetic. | 2005 Oct |
|
| Fate and removal of polycyclic musks, UV filters and biocides during wastewater treatment. | 2006 Aug |
|
| Concentrations and specific loads of UV filters in sewage sludge originating from a monitoring network in Switzerland. | 2006 Feb |
|
| Evaluation of the photostability of different UV filter combinations in a sunscreen. | 2006 Jan 13 |
|
| Occurrence of UV filters 4-methylbenzylidene camphor and octocrylene in fish from various Swiss rivers with inputs from wastewater treatment plants. | 2006 Mar 1 |
|
| Octocrylene: really non-allergenic? | 2006 May |
|
| A validated method for the determination of traces of UV filters in fish using LC-MS/MS. | 2006 Nov |
|
| Sunscreen enhancement of UV-induced reactive oxygen species in the skin. | 2006 Oct 15 |
|
| Occurrence and behavior of four of the most used sunscreen UV filters in a wastewater reclamation plant. | 2007 Aug |
|
| Determination of UV filters and antimicrobial agents in environmental water samples. | 2007 Feb |
|
| Study of the efficacy of 18 sun filters authorized in European Union tested in vitro. | 2007 Jun |
|
| Photostability and efficacy studies of topical formulations containing UV-filters combination and vitamins A, C and E. | 2007 Oct 1 |
|
| 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 |
|
| Sunscreens cause coral bleaching by promoting viral infections. | 2008 Apr |
|
| 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 Feb 1 |
|
| Region-specific growth effects in the developing rat prostate following fetal exposure to estrogenic ultraviolet filters. | 2008 Jul |
|
| Incorporation in lipid microparticles of the UVA filter, butyl methoxydibenzoylmethane combined with the UVB filter, octocrylene: effect on photostability. | 2009 |
|
| Two cases of photocontact allergy to the new sun filter octocrylene. | 2009 Dec 15 |
|
| 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 Feb |
|
| Determination of personal care products in sewage sludge by pressurized liquid extraction and ultra high performance liquid chromatography-tandem mass spectrometry. | 2009 Jul 24 |
|
| Non-porous membrane-assisted liquid-liquid extraction of UV filter compounds from water samples. | 2009 Jun 12 |
|
| Addressing technical challenges associated with the FDA's proposed rules for the UVA in vitro testing procedure. | 2009 Nov-Dec |
|
| Irradiation of skin and contrasting effects on absorption of hydrophilic and lipophilic compounds. | 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 |
|
| 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 Aug |
|
| Validation of HPLC method for the simultaneous and quantitative determination of 12 UV-filters in cosmetics. | 2010 Feb |
|
| Octocrylene, an emerging photoallergen. | 2010 Jul |
|
| Physicochemical study on microencapsulation of hydroxypropyl-beta-cyclodextrin in dermal preparations. | 2010 Jun |
|
| 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 Mar |
|
| Photostabilization effect of quercetin on the UV filter combination, butyl methoxydibenzoylmethane-octyl methoxycinnamate. | 2010 Mar-Apr |
|
| Determination of organic UV filters in water by stir bar sorptive extraction and direct analysis in real-time mass spectrometry. | 2010 May |
|
| Emergent and unusual allergens in cosmetics. | 2010 May-Jun |
|
| 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 |
|
| Simultaneous determination of UV filters and polycyclic musks in aqueous samples by solid-phase microextraction and gas chromatography-mass spectrometry. | 2010 Oct 22 |
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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C851
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CFR |
21 CFR 352.20
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1477411
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3395
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m8115
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4719
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C088673
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C84027
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6197-30-4
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OCTOCRYLENE
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DB09535
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ACTIVE MOIETY
