H7779

Retinoic acid p-hydroxyanilide

≥95%

• Synonyme(s) : 4-HPR, Fenretinide, N-(4-Hydroxyphenyl)retinamide
• Formule empirique (notation de Hill) : C₂₆H₃₃NO₂
• CAS Number: 65646-68-6
• Poids moléculaire : 391.55
• Numéro MDL: MFCD00792674
• Code UNSPSC : 12352106
• ID de substance PubChem : 24278472
• Nomenclature NACRES : NA.77

Propriétés

• Source biologique: synthetic (organic)
• Niveau de qualité: 200
• Essai: ≥95%
• Forme: powder
• Couleur: yellow to yellow-orange
• Température de stockage: −20°C
• Chaîne SMILES: CC1=C(\C=C\C(C)=C\C=C\C(C)=C\C(=O)Nc2ccc(O)cc2)C(C)(C)CCC1
• InChI: 1S/C26H33NO2/c1-19(11-16-24-21(3)10-7-17-26(24,4)5)8-6-9-20(2)18-25(29)27-22-12-14-23(28)15-13-22/h6,8-9,11-16,18,28H,7,10,17H2,1-5H3,(H,27,29)/b9-6+,16-11+,19-8+,20-18+
• Clé InChI: AKJHMTWEGVYYSE-FXILSDISSA-N

Description

Description générale

Retinoic acid p-hydroxyanilide is a synthetic analog of retinoid.

Application

Retinoic acid p-hydroxyanilide has been used:

• as a synthetic retinoid to induce apoptosis in SEB-1 sebocytes
• as a medium supplement for C2C12 myoblasts to test its effect on ceramide formation
• to test in cytotoxicity in T-cell acute lymphoblastic leukemia (T-ALL)

Actions biochimiques/physiologiques

Retinoic acid p-hydroxyanilide, also called fenretinide, increases reactive oxygen species, activates caspases and induces apoptosis. It also inhibits dihydroceramide desaturase, leading to a decrease in ceramide biosynthesis. Fenretinide may elicit anticancer activity in cultured human breast cancer cells. It acts as an insulin antagonist and may be useful in treating insulin resistance. Fenretinide or 4-HPR has chemotherapeutic potential and is cytotoxic to retinoic acid-resistant cancers.

Vitamin A acid analogue with antiproliferative activity; induces apoptosis in malignant hemopoietic cell lines.

Informations sur la sécurité

• Pictogrammes: GHS08,GHS07
• Mention d'avertissement: Danger
• Mentions de danger: H302 + H312 + H332,H315,H319,H335,H360
• Conseils de prudence: P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P305 + P351 + P338 - P308 + P313
• Classification des risques: Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• Organes cibles: Respiratory system
• Code de la classe de stockage: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges