H7779

Retinoic acid p-hydroxyanilide

≥95%

• Synonym(e): 4-HPR, Fenretinide, N-(4-Hydroxyphenyl)retinamide
• Empirische Formel (Hill-System): C₂₆H₃₃NO₂
• CAS-Nummer: 65646-68-6
• Molekulargewicht: 391.55
• NACRES: NA.77
• PubChem Substance ID: 24278472
• UNSPSC Code: 12352106
• MDL number: MFCD00792674
• Assay: ≥95%
• Form: powder

Eigenschaften

• biological source: synthetic (organic)
• Quality Segment: 200
• assay: ≥95%
• form: powder
• color: yellow to yellow-orange
• storage temp.: −20°C
• SMILES string: 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+
• InChI key: AKJHMTWEGVYYSE-FXILSDISSA-N

Beschreibung

General description

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)

Biochem/physiol Actions

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.

Sicherheitshinweise

• pictograms: GHS08,GHS07
• signalword: Danger
• hcodes: H302 + H312 + H332,H315,H319,H335,H360
• pcodes: P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Lagerklasse: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges