rac Naringenin

• CAT Number: R004641
• CAS Number: 67604-48-2
• Molecular Formula: C15H12O5
• Molecular Weight: 272.256
• Purity: ≥95%
• Synonyms: 2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; (R,S)-Naringenin; (+/-)-5,7,4’-Trihydroxyflavanone; 5,7,4’-Trihydroxyflavanone
• Target: Potassium Channel
• Storage: -20°C
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• InChI: InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2
• InChIKey: FTVWIRXFELQLPI-UHFFFAOYSA-N
• SMILES: C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O

Naringenin is a citrus-<wbr></wbr>derived flavonoid that inhibits CYP3A4 activity in human liver microsomes (IC50s = 139-<wbr></wbr>188 μM). At 100 mg/kg/day, naringenin selectively inhibits the transcription of Smad3 and directly down-<wbr></wbr>regulates TGF-<wbr></wbr>β1, significantly reducing lung metastasis in mice with bleomycin-<wbr></wbr>induced pulmonary fibrosis. Naringenin demonstrates both lipid lowering and insulin-<wbr></wbr>like properties in low-<wbr></wbr>density lipoprotein (LDL) receptor-<wbr></wbr>deficient mice fed a Western diet containing 1-<wbr></wbr>3% naringenin by correcting VLDL overproduction, ameliorating hepatic steatosis, and attenuating dyslipidemia without affecting caloric intake or fat absorption.