レチノイン酸

解説ビタミンA酸ともいう．C20H28O2(300.44)．ビタミンA(レチノール)が酸化されてできるアルデヒド(レチナール)がさらに酸化されてできるカルボン酸．全トランス形レチノイン酸(all trans-retinoic acid)と9-cis-レチノイン酸(9-cis-retinoic acid)とがある．前者は，淡黄色の針状晶．融点180～182 ℃．pKa 4.79±0.20．λmax 350，ε 4500(エタノール)．受容体と結合し，核内で特定の遺伝子の発現を調節することにより細胞の分化などを制御する．この作用機構は，ステロイドホルモン，甲状せんホルモン，活性型ビタミン D3 と似ており，これらホルモンの受容体は，核内受容体スーパーファミリーを形成している．急性前骨髄球性白血病や角化性疾患の治療に用いられる．

用途ビタミン A 誘導体です。生体 内では、上皮細胞の増殖制御などの作用を示 します。

用途細胞の増殖・分化機構の研究用。

説明all-trans Retinoic acid is a metabolite of vitamin A and a ligand for retinoic acid receptors (RARs) with IC50 values of 9, 3, and 10 nM for RARα, RARβ, and RARγ, respectively, in radioligand binding assays. It induces expression of a luciferase reporter in COS-7 cells expressing RARα, RARβ, or RARγ (EC50s = 169, 9, and 2 nM, respectively). all-trans Retinoic acid (17 nmol) reduces papilloma formation induced by phorbol 12-myristate 13-acetate (TPA; ) in mice. It reduces bile duct proliferation, hydroxyproline levels, and liver inflammation in a rat model of α-naphthylisothiocyanate-induced chronic cholestasis and reduces plasma levels of alkaline phosphatase and bile salts in the Mdr2-/- mouse model of cholestasis. all-trans Retinoic acid also reduces hepatic fat accumulation, triglycerides, body weight, and serum glucose levels in mice with Western diet-induced obesity.

使用Physiological metabolite of vitamin A. Effects gene expression via nuclear retinoic acid receptors (RAR); mediates cellular growth and differentiation

一般的な説明Yellow to light-orange crystalline powder.

純化方法Purify the acid by chromatography on silicic acid columns, and eluting it with a small amount of EtOH in hexane. Also dissolve it in Et2O, wash it with H2O, dry (Na2SO4), evaporate and the solid residue is recrystallised from MeOH (0.53g /3.5mL MeOH to give 0.14g) or EtOH. It also recrystallises from i-PrOH, or as the methyl ester from MeOH. UV in MeOH has max at 351nm ( 45,000). 9-Cis-acid forms yellow needles from EtOH, with m 189-190o, and its UV in MeOH has max at 343nm ( 36,500); the 13-cis-acid forms red-orange plates from i-PrOH with m 174-175o, and UV has max at 345nm ( 39,800). Store it in the dark, in an inert atmosphere, at 0o [Robeson et al. J Am Chem Soc 77 4111 1955]. [Beilstein 9 IV 2387.]

定義本品は、ビタミンA酸である。

定義ChEBI: Retinoic acid is a retinoid in which all four exocyclic double bonds have E- (trans-) geometry. It is a naturally occurring derivative of vitamin A (retinol). Retinoids such as tretinoin are important regulators of cell reproduction, proliferation, and differentiation and are used to treat acne and photodamaged skin and to manage keratinization disorders such as ichthyosis and keratosis follicularis.