A citrus-derived flavonoid
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Naringenin

Item No. 14173

Technical Information
Formal Name
2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
CAS Number
67604-48-2
Synonyms
  • S-Dihydrogenistein
  • NSC 11855
  • NSC 34875
  • Salipurol
Molecular Formula
C15H12O5
Formula Weight
Purity
≥98%
Formulation
A crystalline solid
DMF: 10 mg/mlDMF:PBS (pH 7.2) (1:1): 0.50 mg/mlDMSO: 5 mg/mlEthanol: 2.5 mg/ml
λmax
213, 225, 289 nm
SMILES
OC(C=C1)=CC=C1C2CC(C3=C(O)C=C(O)C=C3O2)=O
InChi Code
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
InChi Key
FTVWIRXFELQLPI-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Naringenin is a citrus-derived flavonoid that inhibits CYP3A4 activity in human liver microsomes (IC50s = 139-188 μM).1,2 At 100 mg/kg/day, naringenin selectively inhibits the transcription of Smad3 and directly down-regulates TGF-β1, significantly reducing lung metastasis in mice with bleomycin-induced pulmonary fibrosis.3 Naringenin demonstrates both lipid lowering and insulin-like properties in low-density lipoprotein (LDL) receptor-deficient mice fed a Western diet containing 1-3% naringenin by correcting VLDL overproduction, ameliorating hepatic steatosis, and attenuating dyslipidemia without affecting caloric intake or fat absorption.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fuhr, U., Klittich, K., and Staib, A.H. Inhibitory effect of grapefruit juice and its bitter principal, naringenin, on CYP1A2 dependent metabolism of caffeine in man. Br. J. Clin. Pharmacol. 35(4), 431-436 (1993).

    2. Ho, P.C., and Saville, D.J. Inhibition of human CYP3A4 activity by grapefruit flavonoids, furanocoumarins and related compounds. J. Pharm. Pharm. Sci. 4(3), 217-227 (2001).

    3. Du, G., Jin, L., Han, X., et alNaringenin: A potential immunomodulator for inhibiting lung fibrosis and metastasis. Cancer Res. 69(7), 3205-3212 (2009).

    4. Mulvihill, E.E., Allister, E.M., Sutherland, B.G., et alNaringenin prevents dyslipidemia, apolipoprotein B overproduction, and hyperinsulinemia in LDL receptor-null mice with diet-induced insulin resistance. Diabetes 58(10), 2198-2210 (2009).