Octinoxate | CAS#5466-77-3 | UVB blocker

MedKoo Cat#: 464486 | Name: Octinoxate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Octinoxate is an ultraviolet B (UVB) blocker. Topical application of Octinoxate prevents UV-induced edema and formation of cyclobutane pyrimidine dimers, a marker of DNA damage, in mouse skin. Octinoxate is estrogenic, increasing uterine weight in female rats (ED50 = 934 mg/kg per day). It also induces bleaching of A. pulchra coral. Formulations containing 2-EHMC have been used as sunscreens.

Chemical Structure

Octinoxate

CAS#5466-77-3

Theoretical Analysis

MedKoo Cat#: 464486

Name: Octinoxate

CAS#: 5466-77-3

Chemical Formula: C18H26O3

Exact Mass: 290.1882

Molecular Weight: 290.40

Elemental Analysis: C, 74.45; H, 9.02; O, 16.53

Price and Availability

Size	Price	Availability
10g	USD 450.00	2 Weeks
25g	USD 650.00	2 Weeks
100g	USD 950.00	2 Weeks

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Synonym

Octinoxate; 2-EHMC; 2EHMC; 2 EHMC; 2-Ethylhexyl p-methoxycinnamate; 2-Ethylhexyl 4-methoxycinnamate; NSC 26466; NSC26466; NSC-26466; OMC; Octyl 4-methoxycinnamate; Octyl 4 methoxycinnamate;

IUPAC/Chemical Name

2-ethylhexyl (E)-3-(4-methoxyphenyl)acrylate

InChi Key

YBGZDTIWKVFICR-JLHYYAGUSA-N

InChi Code

InChI=1S/C18H26O3/c1-4-6-7-15(5-2)14-21-18(19)13-10-16-8-11-17(20-3)12-9-16/h8-13,15H,4-7,14H2,1-3H3/b13-10+

SMILES Code

O=C(OCC(CC)CCCC)/C=C/C1=CC=C(OC)C=C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Octinoxate is an ultraviolet B (UVB) blocker.

In vitro activity:

The present work proposed to understand how long-term exposure to OMC (octylmethoxycinnamate) affects vascular homeostasis. Endothelium-denuded human umbilical artery (HUA) rings were incubated in an organ bath system. Long-term effects of exposure to OMC (0.001-50 μmol/L) were evaluated on the contractile responses of HUA to the application of the contractile agents, serotonin (5-HT) and histamine (Hist). To investigate in more detail the vascular mode of action of OMC, through which it impairs the vascular homeostasis of HUA, the activity and expression of different 5-HT and Hist-receptors involved in contractility processes were studied. Reference: Biomedicines. 2022 May 3;10(5):1054. https://pubmed.ncbi.nlm.nih.gov/35625791/

In vivo activity:

This study examined the effects of the sunscreen agent Octylmethoxycinnamate (OMC) on photoaging of the skin induced by chronic UV exposure in hairless albino Crl:SKH1-Hrhr (SKH-1) mice. This study demonstrated that the expression of MMPs was elevated by UV irradiation, whereas the topical application of OMC inhibited the upregulation of MMPs. Furthermore, UV-induced wrinkle formation was decreased by OMC treatment. Reference: Int J Mol Sci. 2018 Jun 22;19(7):1836. https://pubmed.ncbi.nlm.nih.gov/29932111/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	103.00
	DMSO	15.5	53.37
	Ethanol	85.0	292.70
	Water	0.7	2.31

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 290.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Cahova J, Blahova J, Mares J, Hodkovicova N, Sauer P, Kroupova HK, Svobodova Z. Octinoxate as a potential thyroid hormone disruptor - A combination of in vivo and in vitro data. Sci Total Environ. 2023 Jan 15;856(Pt 1):159074. doi: 10.1016/j.scitotenv.2022.159074. Epub 2022 Sep 29. PMID: 36181807. 2. Lorigo M, Quintaneiro C, Breitenfeld L, Cairrao E. UV-B Filter Octylmethoxycinnamate Is a Modulator of the Serotonin and Histamine Receptors in Human Umbilical Arteries. Biomedicines. 2022 May 3;10(5):1054. doi: 10.3390/biomedicines10051054. PMID: 35625791; PMCID: PMC9139053. 3. Phelan-Dickinson SJ, Palmer BC, Chen Y, DeLouise LA. The UVR Filter Octinoxate Modulates Aryl Hydrocarbon Receptor Signaling in Keratinocytes via Inhibition of CYP1A1 and CYP1B1. Toxicol Sci. 2020 Sep 1;177(1):188-201. doi: 10.1093/toxsci/kfaa091. PMID: 32603427; PMCID: PMC7553703. 4. Kim SY, Lamichhane S, Ju JH, Yun J. Protective Effect of Octylmethoxycinnamate against UV-Induced Photoaging in Hairless Mouse via the Regulation of Matrix Metalloproteinases. Int J Mol Sci. 2018 Jun 22;19(7):1836. doi: 10.3390/ijms19071836. PMID: 29932111; PMCID: PMC6073923.

In vitro protocol:

In vivo protocol:

1. Phelan-Dickinson SJ, Palmer BC, Chen Y, DeLouise LA. The UVR Filter Octinoxate Modulates Aryl Hydrocarbon Receptor Signaling in Keratinocytes via Inhibition of CYP1A1 and CYP1B1. Toxicol Sci. 2020 Sep 1;177(1):188-201. doi: 10.1093/toxsci/kfaa091. PMID: 32603427; PMCID: PMC7553703. 2. Kim SY, Lamichhane S, Ju JH, Yun J. Protective Effect of Octylmethoxycinnamate against UV-Induced Photoaging in Hairless Mouse via the Regulation of Matrix Metalloproteinases. Int J Mol Sci. 2018 Jun 22;19(7):1836. doi: 10.3390/ijms19071836. PMID: 29932111; PMCID: PMC6073923.

1: Lorigo M, Quintaneiro C, Maia CJ, Breitenfeld L, Cairrao E. UV-B filter octylmethoxycinnamate impaired the main vasorelaxant mechanism of human umbilical artery. Chemosphere. 2021 Mar 24;277:130302. doi: 10.1016/j.chemosphere.2021.130302. Epub ahead of print. PMID: 33789217. 2: Serpone N. Sunscreens and their usefulness: have we made any progress in the last two decades? Photochem Photobiol Sci. 2021 Feb;20(2):189-244. doi: 10.1007/s43630-021-00013-1. Epub 2021 Feb 18. PMID: 33721254. 3: Fivenson D, Sabzevari N, Qiblawi S, Blitz J, Norton BB, Norton SA. Sunscreens: UV filters to protect us: Part 2-Increasing awareness of UV filters and their potential toxicities to us and our environment. Int J Womens Dermatol. 2020 Sep 9;7(1):45-69. doi: 10.1016/j.ijwd.2020.08.008. PMID: 33537395; PMCID: PMC7838327. 4: Lorigo M, Quintaneiro C, Breitenfeld L, Cairrao E. UV-B Filter Octylmethoxycinnamate Alters the Vascular Contractility Patterns in Pregnant Women with Hypothyroidism. Biomedicines. 2021 Jan 26;9(2):115. doi: 10.3390/biomedicines9020115. PMID: 33530401; PMCID: PMC7912698. 5: Chu S, Kwon BR, Lee YM, Zoh KD, Choi K. Effects of 2-ethylhexyl-4-methoxycinnamate (EHMC) on thyroid hormones and genes associated with thyroid, neurotoxic, and nephrotoxic responses in adult and larval zebrafish (Danio rerio). Chemosphere. 2021 Jan;263:128176. doi: 10.1016/j.chemosphere.2020.128176. Epub 2020 Aug 29. PMID: 33297144. 6: Teeranachaideekul V, Morakul B, Boonme P, Pornputtapitak W, Junyaprasert V. Effect of Lipid and Oil Compositions on Physicochemical Properties and Photoprotection of Octyl Methoxycinnamate-loaded Nanostructured Lipid Carriers (NLC). J Oleo Sci. 2020;69(12):1627-1639. doi: 10.5650/jos.ess20093. PMID: 33268665. 7: O'Malley E, McLachlan MS, O'Brien JW, Verhagen R, Mueller JF. The presence of selected UV filters in a freshwater recreational reservoir and fate in controlled experiments. Sci Total Environ. 2021 Feb 1;754:142373. doi: 10.1016/j.scitotenv.2020.142373. Epub 2020 Sep 16. PMID: 33254898. 8: Agozzino M, Licata G, Giorgio CMR, Babino G, Lupoli A, Sperduti I, Argenziano G, Ardigò M. Reflectance Confocal Microscopy Assessment of the Depigmenting Agents Complex for Melasma Treatment. J Clin Aesthet Dermatol. 2020 Sep;13(9):41-44. Epub 2020 Sep 1. PMID: 33133340; PMCID: PMC7577329. 9: Peyrot C, Mention MM, Brunissen F, Allais F. Sinapic Acid Esters: Octinoxate Substitutes Combining Suitable UV Protection and Antioxidant Activity. Antioxidants (Basel). 2020 Aug 24;9(9):782. doi: 10.3390/antiox9090782. PMID: 32847133; PMCID: PMC7554726. 10: Phelan-Dickinson SJ, Palmer BC, Chen Y, DeLouise LA. The UVR Filter Octinoxate Modulates Aryl Hydrocarbon Receptor Signaling in Keratinocytes via Inhibition of CYP1A1 and CYP1B1. Toxicol Sci. 2020 Sep 1;177(1):188-201. doi: 10.1093/toxsci/kfaa091. PMID: 32603427; PMCID: PMC7553703. 11: Peyrot C, Mention MM, Brunissen F, Balaguer P, Allais F. Innovative Bio- Based Organic UV-A and Blue Light Filters from Meldrum's Acid. Molecules. 2020 May 6;25(9):2178. doi: 10.3390/molecules25092178. PMID: 32384797; PMCID: PMC7248827. 12: do Prado AH, Araújo VHS, Eloy JO, Fonseca-Santos B, Pereira-da-Silva MA, Peccinini RG, Chorilli M. Synthesis and Characterization of Nanostructured Lipid Nanocarriers for Enhanced Sun Protection Factor of Octyl p-methoxycinnamate. AAPS PharmSciTech. 2020 Apr 29;21(4):125. doi: 10.1208/s12249-019-1547-0. PMID: 32350635. 13: Lozano C, Matallana-Surget S, Givens J, Nouet S, Arbuckle L, Lambert Z, Lebaron P. Toxicity of UV filters on marine bacteria: Combined effects with damaging solar radiation. Sci Total Environ. 2020 Jun 20;722:137803. doi: 10.1016/j.scitotenv.2020.137803. Epub 2020 Mar 7. PMID: 32197158. 14: Xu H, Lu G, Xue C. Effects of Sulfamethoxazole and 2-Ethylhexyl-4-Methoxycinnamate on the Dissimilatory Nitrate Reduction Processes and N2O Release in Sediments in the Yarlung Zangbo River. Int J Environ Res Public Health. 2020 Mar 11;17(6):1822. doi: 10.3390/ijerph17061822. PMID: 32168922; PMCID: PMC7143930. 15: Suh S, Pham C, Smith J, Mesinkovska NA. The banned sunscreen ingredients and their impact on human health: a systematic review. Int J Dermatol. 2020 Sep;59(9):1033-1042. doi: 10.1111/ijd.14824. Epub 2020 Feb 28. PMID: 32108942; PMCID: PMC7648445. 16: Zhong X, Downs CA, Li Y, Zhang Z, Li Y, Liu B, Gao H, Li Q. Comparison of toxicological effects of oxybenzone, avobenzone, octocrylene, and octinoxate sunscreen ingredients on cucumber plants (Cucumis sativus L.). Sci Total Environ. 2020 Apr 20;714:136879. doi: 10.1016/j.scitotenv.2020.136879. Epub 2020 Jan 22. PMID: 32018996. 17: Matta MK, Florian J, Zusterzeel R, Pilli NR, Patel V, Volpe DA, Yang Y, Oh L, Bashaw E, Zineh I, Sanabria C, Kemp S, Godfrey A, Adah S, Coelho S, Wang J, Furlong LA, Ganley C, Michele T, Strauss DG. Effect of Sunscreen Application on Plasma Concentration of Sunscreen Active Ingredients: A Randomized Clinical Trial. JAMA. 2020 Jan 21;323(3):256-267. doi: 10.1001/jama.2019.20747. Erratum in: JAMA. 2020 Mar 17;323(11):1098. PMID: 31961417; PMCID: PMC6990686. 18: Benjatikul K, Mahamongkol H, Wongtrakul P. Sunscreen Properties of Marl. J Oleo Sci. 2020;69(1):73-82. doi: 10.5650/jos.ess19232. PMID: 31902898. 19: da Silva Fernandes A, Brito LB, Oliveira GAR, Ferraz ERA, Evangelista H, Mazzei JL, Felzenszwalb I. Evaluation of the acute toxicity, phototoxicity and embryotoxicity of a residual aqueous fraction from extract of the Antarctic moss Sanionia uncinata. BMC Pharmacol Toxicol. 2019 Dec 19;20(Suppl 1):77. doi: 10.1186/s40360-019-0353-3. PMID: 31852531; PMCID: PMC6921389. 20: Narla S , Lim HW . Sunscreen: FDA regulation, and environmental and health impact. Photochem Photobiol Sci. 2020 Jan 22;19(1):66-70. doi: 10.1039/c9pp00366e. PMID: 31845952.