Octinoxate

Octinoxate (Octyl methoxycinnamate) is a thyroid hormone receptor agonist, reducing the levels of triiodothyronine (T3) and thyroxine (T4) and transcription levels of genes related to type II deiodinase (deio2) in Japanese Medaka. Octinoxate is commonly used as a safe ultraviolet (UV) filter used in the aquatic environment. Octinoxate inhibits CYP1A1 and CYP1B1 to regulate hyaluronan (HA) (HY-B0633A) metabolism in a PI3K pathway-dependent manner in human keratinocytes. Octinoxate also exhibits an anti-estrogenic and anti-androgenic effect in vitro and in vivo[1][2][3][4][5].

Product Specifications

CAS Number

[5466-77-3]

Product Name Alternative

Octyl methoxycinnamate

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Androgen Receptor; Cytochrome P450; Estrogen Receptor/ERR; Thyroid Hormone Receptor

Type

Natural Products

Related Pathways

Metabolic Enzyme/Protease; Vitamin D Related/Nuclear Receptor

Field of Research

Endocrinology; Metabolic Disease

Assay Protocol

https://www.medchemexpress.com/Octinoxate.html

Concentration

10mM

Purity

99.89

Solubility

Ethanol : 140 mg/mL (ultrasonic)

Smiles

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

Molecular Formula

C18H26O3

Molecular Weight

290.40

Precautions

H302, H315, H319, H335

References & Citations

[1]Cahova J, et al. 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.|[2]Ka Y, et al. Waterborne exposure to avobenzone and octinoxate induces thyroid endocrine disruption in wild-type and thrαa-/- zebrafish larvae[J]. Ecotoxicology. 2022 Aug;31 (6) :948-955. |[3]Phelan-Dickinson SJ, et al. The UVR Filter Octinoxate Modulates Aryl Hydrocarbon Receptor Signaling in Keratinocytes via Inhibition of CYP1A1 and CYP1B1[J]. Toxicol Sci. 2020 Sep 1;177 (1) :188-201. |[4]Chang KY, et al. Organic ultraviolet filters regulate hyaluronan metabolism in human epidermal keratinocytes through the phosphatidylinositol 3-kinase pathway[J]. Toxicol In Vitro. 2023 Feb;86:105511. |[5]Schmutzler C, et al. Endocrine disruptors and the thyroid gland--a combined in vitro and in vivo analysis of potential new biomarkers. Environ Health Perspect. 2007 Dec;115 Suppl 1 (Suppl 1) :77-83.