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Isorhamnetin

CAT: 0013-GTR19161916-02Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19161916-02Size:5 mg
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Description
Red turnip, goldenrod, mustard leaf, ginkgo biloba. (In Vitro) :Isorhamnetin is a plant flavonoid that occurs in fruits and medicinal herbs. Isorhamnetin binds directly to MEK1 in an ATP-noncompetitive manner and to PI3-K in an ATP-competitive manner. In vitro and ex vivo kinase assay data show that Isorhamnetin inhibits the kinase activity of MAP/ERK kinase (MEK) 1 and PI3-K and the inhibition is due to direct binding with Isorhamnetin. Isorhamnetin inhibits the Akt/mTOR and MEK/ERK signaling pathways, and promotes the activity of the mitochondrial apoptosis signaling pathway. The inhibitory effects of Isorhamnetin on breast cancer cells are determined using the CCK-8 method. Isorhamnetin inhibits the proliferation of numerous breast cancer cells (IC50, ~10 μM), including MCF7, T47D, BT474, BT-549, MDA-MB-231 and MDA-MB-468, whereas less inhibitory activity is observed in the MCF10A normal breast epithelial cell line (IC50, 38 μM) . (In Vivo) :Photographic data shows that Isorhamnetin treatment suppresses tumor development in mice. The average volume of tumors in untreated mice increases over time and reaches a volume of 623 mm3 at 4 weeks post-inoculation; however, at this time, in mice treated with 1 or 5 mg/kg Isorhamnetin, the average tumor volume is only 280 or 198 mm3, respectively. At the end of the study, Isorhamnetin treatment (1 or 5 mg/kg) reduces tumor weight compared with the untreated control group.
CAS Number
480-19-3
Product Name Alternative
3'-O-methyl Quercetin
Purity
>98% (HPLC)
Solubility
DMSO: 10 mM
Smiles
O=C1C (O) =C (C2=CC=C (O) C (OC) =C2) OC3=CC (O) =CC (O) =C13
Molecular Formula
C16H12O7
Molecular Weight
316.27
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
3,5,7-trihydroxy-2- (4-hydroxy-3-methoxyphenyl) -4H-chromen-4-one

Chemical Information

Isorhamnetin

Isorhamnetin is a monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group. It has a role as a metabolite, an anticoagulant and an EC 1.14.18.1 (tyrosinase) inhibitor. It is a monomethoxyflavone, a tetrahydroxyflavone and a 7-hydroxyflavonol. It is functionally related to a quercetin. It is a conjugate acid of an isorhamnetin(1-).

CAS Number480-19-3
PubChem CID5281654
IUPAC Name3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
Molecular FormulaC16H12O7
Molecular Weight316.26
XLogP1.9
Topological Polar Surface Area116
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Heavy Atom Count23
Formal Charge0
Complexity503
SMILES
COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O
InChI
InChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
InChIKey
IZQSVPBOUDKVDZ-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Isorhamnetin
CAS: 480-19-3
CID: 5281654
Formula: C16H12O7
MW: 316.26
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight316.26
XLogP31.9
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Exact Mass316.05830272
Monoisotopic Mass316.05830272
Topological Polar Surface Area116 Ų
Heavy Atom Count23
Formal Charge0
Complexity503
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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