Octocrylene
(Synonyms: 奥克立林) 目录号 : GC30116
A UV filter
Cas No.:6197-30-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Octocrylene is a UV filter.1,2 It stabilizes the full-spectrum UVA blocker avobenzone to UV radiation.1 Octocrylene inhibits 17β-estradiol- or dihydrotestosterone-induced transactivation of estrogen receptor α (ERα) or the androgen receptor in S. cerevisiae expressing the human receptors (IC50s = 2.17 and 0.627 mM, respectively).2 Topical application of octocrylene (15 or 30% w/v) increases thymidine incorporation in a mouse local lymph node assay (LLNA), indicating allergenic activity.3 Octocrylene has been found in influent and effluent wastewater.4 Formulations containing octocrylene have been used in sunscreen products.
1.Beasley, D.G., and Meyer, T.A.Characterization of the UVA protection provided by avobenzone, zinc oxide, and titanium dioxide in broad-spectrum sunscreen productsAm. J. Clin. Dermatol.11(6)413-421(2010) 2.Kunz, P.Y., and Fent, K.Multiple hormonal activities of UV filters and comparison of in vivo and in vitro estrogenic activity of ethyl-4-aminobenzoate in fishAquat. Toxicol.79(4)305-324(2006) 3.Karlsson, I., Broecke, K.V., M?rtensson, J., et al.Clinical and experimental studies of octocrylene's allergenic potencyContact Dermatitis64(6)343-352(2011) 4.Balmer, M., Buser, H.-R., Müller, M.D., et al.Occurrence of some organic UV filters in wastewater, in surface waters, and in fish from Swiss lakesEnviron. Sci. Technol.39(4)953-962(2005)
| Cas No. | 6197-30-4 | SDF | |
| 别名 | 奥克立林 | ||
| Canonical SMILES | O=C(OCC(CC)CCCC)/C(C#N)=C(C1=CC=CC=C1)\C2=CC=CC=C2 | ||
| 分子式 | C24H27NO2 | 分子量 | 361.48 |
| 溶解度 | DMSO : ≥ 130 mg/mL (359.63 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.7664 mL | 13.832 mL | 27.664 mL |
| 5 mM | 0.5533 mL | 2.7664 mL | 5.5328 mL |
| 10 mM | 0.2766 mL | 1.3832 mL | 2.7664 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Review of the safety of Octocrylene used as an ultraviolet filter in cosmetics
J Eur Acad Dermatol Venereol 2019 Nov;33 Suppl 7:25-33.31588614 10.1111/jdv.15945
Octocrylene or octocrilene is an organic ultraviolet (UV) filter which absorbs mainly UVB radiation and short UVA wavelengths. It is used in various cosmetic products to either provide an appropriate sun protection factor in sunscreen products or to protect cosmetic formulations from UV radiation. There is no discussion that UV filters are beneficial ingredients in cosmetics since they protect from skin cancer, but Octocrylene has been recently incriminated to potentially induce adverse effects on the endocrine system in addition to having allergic and/or photoallergic potential. However, the substance has the advantage to work synergistically with other filters allowing a beneficial broad photoprotection, e.g. it stabilizes the UVA filter avobenzone (i.e. butylmethoxydibenzoylmethane). Like all chemicals used in cosmetics, the safety profile of Octocrylene is constantly under assessment by the European Chemical Agency (ECHA) since it has been registered according to the European regulation Registration, Evaluation, Authorisation and Restriction of Chemicals. Summaries of safety data of Octocrylene are publicly available on the ECHA website. This review aims to present the main safety data from the ECHA website, as well as those reported in scientific articles from peer-reviewed journals. The available data show that Octocrylene does not have any endocrine disruption potential. It is a rare sensitizer, photocontact allergy is more frequent and it is considered consecutive to photosensitization to ketoprofen. Based on these results, Octocrylene can be considered as safe when used as a UV filter in cosmetic products at a concentration up to 10%.
Sunscreens
Adv Exp Med Biol 2014;810:429-63.25207381 10.1007/978-1-4939-0437-2_25
Sunscreens have become since more than 40 years the most popular means of protection against UV radiation (UVR) in Western countries. Organic and inorganic filters with different absorption spectrum exist. They filter or scatter UVR. Protection from UVB is quantified as a minimal erythema dose-based sun protection factor. UVA protection testing is less standardized: Persistent pigment darkening and critical wavelength are currently used methods. Marketing and labeling of sunscreens underlay national regulation which explains major differences between the European and the US sunscreen market. Sunscreens are most performing in sunburn prevention. Broad spectrum UVB and UVA protection and regular application in sufficient amounts are essential for prevention of skin cancers, UV-induced immunosuppression, and skin aging. A significant benefit from regular sunscreen use has not yet been demonstrated for primary prevention of basal cell carcinoma and melanoma. Concerning the prevention of actinic keratoses, squamous cell carcinomas, and skin aging, the effect of sunscreens is significant, but it remains incomplete. Some organic UV filters (PABA derivatives, cinnamates, benzophenones, and Octocrylene) have been described to cause photoallergy. Percutaneous absorption and endocrine disrupting activity of small-sized organic and nano-sized inorganic UV filters have been reported. On lesional skin and in pediatric settings, these products should be used with caution. Cutaneous vitamin D synthesis depending on skin-carcinogenic UVB radiation, the potential risk of vitamin D deficiency by sunscreen use has become a major subject of public health debate. Sunscreens indeed impair vitamin D synthesis if they are used in the recommended amount of 2 mg/cm2, but not in lesser thickness below 1.5 mg/cm2 that corresponds better to what users apply in real life conditions. Large molecular last generation UVB-UVA broad spectrum sunscreens have a better benefit-risk ratio than former organic filters: They offer better protection in the UVA band, they are non toxic and non allergenic. A better outcome of sunscreen efficacy especially in primary skin cancer prevention may be achieved with these molecules.
Contact and photocontact allergy to Octocrylene: a review
Contact Dermatitis 2014 Apr;70(4):193-204.24628344 10.1111/cod.12205
Octocrylene is an ultraviolet (UV)B and UVAII absorber that was introduced some 15 years ago, and is now widely used in sunscreen agents and skin care cosmetics. Since 2003, several studies, notably from France, Belgium, Spain, and Italy, have reported an increasing number of patients with photocontact allergy to Octocrylene. This reaction is seen mainly in adult patients who have previously used topical products containing the non-steroidal anti-inflammatory drug ketoprofen. Photosensitization to ketoprofen leads, in many cases, to photocontact allergy to Octocrylene; the mechanism of this reaction is unknown. Contact allergy to Octocrylene also occurs, but is far less frequent, and is seen, in most cases, in children, resulting from the use of octocrylene-containing sunscreen products. In this article, (photo)contact allergy to Octocrylene is fully reviewed.
Sunscreen Ingredient Octocrylene's Potency to Disrupt Vitamin D Synthesis
Int J Mol Sci 2022 Sep 5;23(17):10154.36077552 PMC9456232
Octocrylene is a widely used ingredient in sunscreen products, and it has been observed that the use of sunscreen has been increasing over the last few decades. In this paper, we investigated the way in which sunscreen's ingredient Octocrylene may disrupt normal vitamin D synthesis pathway, resulting in an imbalance in vitamin D levels in the body. The key techniques used for this insilico investigation were molecular docking, molecular dynamic (MD) simulation, and MMPBSA-based assessment. Vitamin D abnormalities have become very common in human health. Unknown exposure to chemicals may be one of the important risk factors. In molecular docking analysis, Octocrylene exhibited a binding energy of -11.52 kcal/mol with vitamin D binding protein (1KXP) and -11.71 for the calcitriol native ligand. Octocrylene had a binding potency of -11.152 kcal/mol with the vitamin D receptor (1DB1), and calcitriol had a binding potency of -8.73 kcal/mol. In addition, Octocrylene has shown binding energy of -8.96 kcal/mol with CYP2R1, and the calcitriol binding energy was -10.36 kcal/mol. Regarding stability, the root-mean-square deviation (RMSD), the root-mean-square fluctuation (RMSF), the radius of gyration, hydrogen bonding, and the solvent-accessible surface area (SASA) exhibited that Octocrylene has a stable binding pattern similar to calcitriol. These findings revealed that incessant exposure to Octocrylene may disrupt normal vitamin D synthesis.
Octocrylene, an emerging photoallergen
Arch Dermatol 2010 Jul;146(7):753-7.20644036 10.1001/archdermatol.2010.132
Background: Octocrylene is a new emerging photoallergen. We report and discuss 50 cases of photoallergic contact dermatitis from Octocrylene use and/or positive photopatch test reactions to this UV filter and draw attention to the unexpected association in adults with a history of photoallergic contact dermatitis from ketoprofen. Observations: Patients were divided in 3 groups: group A comprised 11 children; group B, 28 adults with a history of photoallergy from sunscreen products; and group C, 14 adults systematically tested with Octocrylene because of a history of photoallergy from ketoprofen. All patients but 3 in group C had positive test reactions to Octocrylene. Ten of 11 children in group A and 9 of 28 adults in group B had positive patch test reactions to Octocrylene. One child in group A, the other 19 adults in group B, and 11 of 14 adults in group C had positive photopatch test reactions to Octocrylene. All adults in group C and 24 of 28 adults in group B had a history of photoallergy from ketoprofen and positive patch test or photopatch test reactions to other allergens that are often positive in patients with photoallergy from ketoprofen, especially fragrance components. Conclusions: Octocrylene appears to be a strong allergen leading to contact dermatitis in children and mostly photoallergic contact dermatitis in adults with an often-associated history of photoallergy from ketoprofen. Patients with photoallergy from ketoprofen frequently have positive photopatch test reactions to Octocrylene. These patients need to be informed of sunscreen products not containing Octocrylene, benzophenone-3, or fragrances.