WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H464486
CAS#: 5466-77-3
Description: 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.
Hodoodo Cat#: H464486
Name: Octinoxate
CAS#: 5466-77-3
Chemical Formula: C18H26O3
Exact Mass: 290.19
Molecular Weight: 290.403
Elemental Analysis: C, 74.45; H, 9.02; O, 16.53
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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMF | 30.0 | 103.00 | |
| DMSO | 30.0 | 103.00 | |
| Ethanol | 30.0 | 103.00 |
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: | |
| In vitro protocol: | |
| In vivo protocol: |
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.
