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Luteolin

CAT: 0804-HY-N0162-08Size: 5 gDry Ice: NoHazardous: No
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CAT#:0804-HY-N0162-08Size:5 g
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Description
Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3].
CAS Number
491-70-3
Product Name Alternative
Luteoline; Luteolol; Digitoflavone
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Apoptosis; Autophagy; Endogenous Metabolite; Keap1-Nrf2
Type
Natural Products
Related Pathways
Apoptosis; Autophagy; Metabolic Enzyme/Protease; NF-κB
Applications
Cancer-programmed cell death
Field of Research
Cancer; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/Luteolin.html
Purity
99.51
Solubility
DMSO : ≥ 100 mg/mL
Smiles
O=C1C=C(C2=CC=C(O)C(O)=C2)OC3=CC(O)=CC(O)=C13
Molecular Formula
C15H10O6
Molecular Weight
286.24
Precautions
H302, H315, H319, H335
References & Citations
[1]Ma L, et al. Luteolin exerts an anticancer effect on NCI-H460 human non-small cell lung cancer cells through the induction of Sirt1-mediated apoptosis. Mol Med Rep. 2015 Sep;12 (3) :4196-4202.|[2]Abu-Elsaad N, et al. Protection against nonalcoholic steatohepatitis through targeting IL-18 and IL-1alpha by luteolin. Pharmacol Rep. 2019 Aug;71 (4) :688-694.|[3]Xiuwen Tang, et al. Luteolin inhibits Nrf2 leading to negative regulation of the Nrf2/ARE pathway and sensitization of human lung carcinoma A549 cells to therapeutic drugs. Free Radic Biol Med. 2011 Jun 1;50 (11) :1599-609.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
Launched

Chemical Information

Luteolin

Luteolin is a tetrahydroxyflavone in which the four hydroxy groups are located at positions 3', 4', 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers. It has a role as an antineoplastic agent, an angiogenesis inhibitor, a radical scavenger, an immunomodulator, a vascular endothelial growth factor receptor antagonist, an anti-inflammatory agent, an apoptosis inducer, an EC 2.3.1.85 (fatty acid synthase) inhibitor, a nephroprotective agent, a plant metabolite and a c-Jun N-terminal kinase inhibitor. It is a 3'-hydroxyflavonoid and a tetrahydroxyflavone. It is a conjugate acid of a luteolin-7-olate.

CAS Number491-70-3
PubChem CID5280445
IUPAC Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
Molecular FormulaC15H10O6
Molecular Weight286.24
XLogP1.4
Topological Polar Surface Area107
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count1
Heavy Atom Count21
Formal Charge0
Complexity447
SMILES
C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)O
InChI
InChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H
InChIKey
IQPNAANSBPBGFQ-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Luteolin
CAS: 491-70-3
CID: 5280445
Formula: C15H10O6
MW: 286.24
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight286.24
XLogP31.4
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count1
Exact Mass286.04773803
Monoisotopic Mass286.04773803
Topological Polar Surface Area107 Ų
Heavy Atom Count21
Formal Charge0
Complexity447
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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