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Luteolin

Luteolin structure

CAS No:
491-70-3
Formula:
C15H10O6
Chemical Name:
Luteolin
Synonyms:
4H-1-Benzopyran-4-one,2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-;Luteolin;Flavone,3′,4′,5,7-tetrahydroxy-;2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one;Luteoline;Luteolol;3′,4′,5,7-Tetrahydroxyflavone;Yama Kariyasu;Digitoflavone;Cyanidenon 1470;Flacitran;5,7,3′,4′-Tetrahydroxyflavone;Weld lake;Cyanidenon;2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyran-4-one;Salifazide;ST 024703;2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one;2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-one;2-(3,4-Dihydroxyphenyl)-5,7-dihydroxychromen-4-one;12671-63-5
Categories:
Cosmetic Ingredient > Skin Conditioning

Description

Luteolin is a falconoid compound, which exhibits anticancer properties.IC50 value:Target: A natural for anticancer.In vitro: Luteolin exerted an anticancer effect against NCI-H460 cells through Sirt1-mediated apoptosis and the inhibition of cell migration [1]. The treatment of luteolin upregulated the expression levels of transforming growth factor β1 (TGF-β1), p21WAF1/CIP1, p27KIP1, Smad4, and Fas in HCC cells. Luteolin induced apoptotic cell death in Hep3B cells while caused G1 arrest

Solid

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 EC 2.3.1.85 (fatty acid synthase) inhibitor, an antineoplastic agent, a vascular endothelial growth factor receptor antagonist, a plant metabolite, a nephroprotective agent, an angiogenesis inhibitor, a c-Jun N-terminal kinase inhibitor, an anti-inflammatory agent, an apoptosis inducer, a radical scavenger and an immunomodulator. It is a 3'-hydroxyflavonoid and a tetrahydroxyflavone. It is a conjugate acid of a 2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-olate luteolin-7-olate(1-).|Luteolin is a naturally-occurring flavonoid, with potential anti-oxidant, anti-inflammatory, apoptosis-inducing and chemopreventive activities. Upon administration, luteolin scavenges free radicals, protects cells from reactive oxygen species (ROS)-induced damage and induces direct cell cycle arrest and apoptosis in tumor cells. This inhibits tumor cell proliferation and suppresses metastasis.|5,7,3',4'-tetrahydroxy-flavone, one of the FLAVONES.

Luteolin Basic Attributes

Molecular Weight：

286.23600

Exact Mass：

286.24

EC Number：

207-741-0

UNII：

KUX1ZNC9J2

DSSTox ID：

DTXSID4074988

NCI Thesaurus Code：

C68467

HScode：

2932999099

Characteristics

PSA：

111.13000

XLogP3：

1.4

Appearance：

Solid

Density：

1.654 g/cm3

Melting Point：

329.5 °C (decomp)

Boiling Point：

616.1ºC at 760 mmHg

Flash Point：

239.5ºC

Refractive Index：

1.767

Water Solubility：

Soluble in aqueous alkaline solutions (1.4 mg/ml), ethanol (~5 mg/ml), dimethyl sulfoxide (7 mg/ml), 1eq. Sodium hydroxide (5 mM), dimethylformamide (~20 mg/ml), water (1 mg/ml) at 25°C and methanol.

Storage Conditions：

2-8ºC

Vapor Pressure：

9.03E-16mmHg at 25°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R36/37/38

safety instructions：

S26-S36

RTECS Number：

LK9275210

Marks：

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

Drug Information

Metabolism/Metabolites：

Luteolin has known human metabolites that include (2S,3S,4S,5R)-6-[5-(5,7-Dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid and Luteolin-7-glucuronide.

MeSH Entry Terms：

3',4',5,7-Tetrahydroxy-Flavone

Luteolin Use and Manufacturing

Uses

Hydroxylated flavone derivative with strong anti-oxidant and radical scavenging properties. Suggested to play a role in cancer prevention.It is used as antitussive, antiphlegm and anti-inflammatory drugs. Hydroxyflavonoid derivatives are strong antioxidants and free radical scavengers, playing an important role in anti-cancer. It is a polyphenolic compound, which belongs to flavonoids. It is a strong antioxidant and free radical scavenger.

Use Classification：

Polyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]

Computed Properties

Molecular Weight:286.24
XLogP3:1.4
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:1
Exact Mass:286.04773803
Monoisotopic Mass:286.04773803
Topological Polar Surface Area:107
Heavy Atom Count:21
Complexity:447
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Acetic acid

Drug Function and Efficacy

It reduces the content of malondialdehyde (MDA) in rabbits with chronic intraocular hypertension, increases the activity of superoxide dismutase (SOD), and reduces the permeability of retinal blood vessels; it improves the grayscale of retinal ganglion cells and the density of active ganglion cells with high cytochrome oxidase activity in rats with acute intraocular hypertension.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Yimaikang Tablets
Ingredients	The chemical components of Erigeron breviscapus extract are mainly flavonoids (main component), lactones, amino acids, polysaccharides, such as pyrofuconic acid (P,romeconic acid) and its glucoside, scutellarin (Scutellarin), apigenin (Api,enin), and luteolin (Luleolin).
Indication	Drug interactions may occur if used with other drugs. Please consult your doctor or pharmacist for details.
Specifications	Each tablet contains 40mg total flavonoids
Manufacturer	Yunnan Baiyao Group Dali Pharmaceutical Co., Ltd.

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