Luteolin

Base Information

• Chemical Name: Luteolin
• CAS No.: 491-70-3
• Deprecated CAS: 12671-63-5
• Molecular Formula: C15H10O6
• Molecular Weight: 286.241
• Hs Code.: PRICE
• European Community (EC) Number: 207-741-0
• UNII: KUX1ZNC9J2
• ChEMBL ID: CHEMBL151
• DSSTox Substance ID: DTXSID4074988
• Metabolomics Workbench ID: 23091
• NCI Thesaurus Code: C68467
• Nikkaji Number: J1.554G
• Pharos Ligand ID: 9GVZD45BYUVS
• Wikidata: Q415011
• Wikipedia: Luteolin
• Mol file: 491-70-3.mol

Synonyms:3',4',5,7-Tetrahydroxy-Flavone;3',4',5,7-Tetrahydroxyflavone;Luteolin;Luteoline

Chemical Property of Luteolin

Chemical Property:

• Appearance/Colour: yellow crystalline powder
• Vapor Pressure: 9.03E-16mmHg at 25°C
• Melting Point: ~330 °C(lit.)
• Refractive Index: 1.767
• Boiling Point: 616.1 °C at 760 mmHg
• PKA: 6.50±0.40(Predicted)
• Flash Point: 239.5 °C
• PSA: 111.13000
• Density: 1.654 g/cm³
• LogP: 2.28240
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly, Heated)
• 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
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 286.04773803
• Heavy Atom Count: 21
• Complexity: 447

Purity/Quality:

99% ^*data from raw suppliers

Luteolin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)O
• Recent ClinicalTrials: Influence of Luteolin for Two Weeks on Memory in Healthy Subjects
• Recent NIPH Clinical Trials: Safety analysis of luteolin for prostate cancer
• Indications: This product has antitussive, expectorant effect. The antitussive effect is through suppressing the cough center; the expectorant effect of this product is related to its ability of promoting the secretion of the respiratory tract gland and dissolving the acidic mucopolysaccharides in the sputum. It also has anti-inflammatory, anti-allergic and immune enhancement effect. It also has inhibitory effect on Staphylococcus aureus, Streptococcus pneumoniae and Pseudomonas aeruginosa. It can also be used for the treatment of chronic bronchitis and other respiratory diseases sputum. Luteolin compound prescription is mainly used for relieving cough, eliminating phlegm, diminishing inflammation, treating cardiovascular diseases, and treating amyotrophic lateral sclerosis, severe acute respiratory syndrome (SARS), hepatitis, etc.
• Description: Luteolin is a polyphenolic flavone found in many plants including soybeans and perilla leaves. Luteolin is one of the most potent flavanoid inhibitors of soybean and reticulocyte 15-lipoxygenases, with an IC50 of 0.6 μM. Luteolin has also been found to inhibit the release of TNFα from neutrophils, and to inhibit matrix metalloproteinases. Luteolin is a flavone derived from Honeysuckle(Lonicera japonica Thunb). Luteolin is widely distributed in nature. It can be isolated from a variety of natural herbs, vegetables, and fruits. At present, luteolin is found mainly in honeysuckle, chrysanthemum, Schizonepeta, Ajuga, artichokes, Scutellaria, and Callicarpa nudiflora natural herbs. Dietary sources include celery, broccoli, green pepper, parsley, thyme, dandelion, perilla, chamomile tea, carrots, olive oil, peppermint, rosemary, navel oranges, and oregano. It can also be found in the seeds of the palm Aiphanes aculeata.
• Physical properties: Appearance: yellow needle crystal. Solubility: slightly soluble in water and soluble in alkaline solution (monohydrate). Density, 1.654 g/cm3. Melting point, 330 °C. Boiling point, 616.1 °C (760 mmHg). Flash point, 239.5 °C. Vapor pressure, 9.03E-16 mmHg (25 °C). Acidity, weak acid.
• Uses: Luteolin has been used:to induce and elucidate the apoptotic pathway in renal cell carcinoma 786-O cellsas an additive in M9 minimal medium to induce nodF gene expressionas a reference standard to qualitatively and quantitatively analyse luteolin using reverse phase-high performance liquid chromatography with diode array detector (RP-HPLC-DAD)as a reaction supplement for β-galactosidase assayto elucidate the anti-inflammatory efficacy of luteolin in pseudorabies virus infected RAW264.7 cell line by measuring the anti-inflammatory mediators production and also cell viability and cytotoxicity assay Hydroxylated flavone derivative with strong anti-oxidant and radical scavenging properties. Suggested to play a role in cancer prevention
• Clinical Use: The natural extract containing luteolin has been used in clinical treatment of many diseases. Lamiophlomis rotata Kudo capsule is made from traditional Chinese medicine Lamiophlomis rotata Kudo, which consists of the medicinal components such as flavonoids, saponins, sterols, amino acids, and many trace elements. Among these components, luteolin content is not less than 0.80 mg/g. This capsule is mainly used for a variety of surgical incision pain, postoperative bleeding, fracture, sprain of muscles, rheumatic pain, dysmenorrhea, uterine bleeding, gingival swelling, and bleeding.

Technology Process of Luteolin

There total 88 articles about Luteolin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (520-36-5) → 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on (491-70-3)

Guidance literature:

With C₉H₈IO₄Pol; In dimethyl sulfoxide; at 25 ℃; for 2h;

DOI:10.1016/j.tet.2010.06.014

Reference yield: 89.0%

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one (855-97-0) → 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on (491-70-3)

Guidance literature:

With pyridine hydrochloride; at 190 ℃; for 6h; Inert atmosphere;

DOI:10.3184/174751915X14404221529907

Reference yield: 80.0%

2-(3,4-bis(benzyloxy)phenyl)-5,7-dihydroxy-4H-chromen-4-one (58124-13-3) → 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on (491-70-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In N,N-dimethyl-formamide; Ambient temperature;

upstream raw materials:

diosmetin

luteolin 7-O-glucoside

luteolin-5-O-β-D-glucopyranoside

7-O-lactoyl-luteolin

Downstream raw materials:

5-hydroxy-3',4',7-trimethoxyflavone

luteolin tetraacetate

5,7-bis-benzoyloxy-2-(3,4-bis-benzoyloxy-phenyl)-chromen-4-one

7-methylluteoline

Refernces

FLAVONOID PROFILES OF NEW ZEALAND LIBOCEDRUS AND RELATED GENERA

10.1016/0031-9422(90)85105-O

The research aimed to investigate the flavonoid compounds present in New Zealand Libocedrus species, specifically Libocedrus bidwillii and L. plumosa, and to assess their chemotaxonomic significance. The study's purpose was to support or challenge the existing classification of these species within the Cupressaceae family by analyzing their flavonoid profiles. The conclusions drawn from the research indicated that while the two Libocedrus species shared similar flavonoid types, they were distinct enough to be differentiated, with L. plumosa characterized by the presence of myricetin 3-rhamnoside and L. bidwillii by the presence of a di-acylated quercetin 3-rhamnoside. The chemicals used in the process included various flavonoids such as kaempferol, quercetin, apigenin, luteolin, amentoflavone, and biflavonoids like 7-O-methyl-2,3-dihydroamentoflavone.

Design and discovery of flavonoid-based HIV-1 integrase inhibitors targeting both the active site and the interaction with LEDGF/p75

10.1016/j.bmc.2014.04.016

The research focuses on the design and discovery of flavonoid-based HIV-1 integrase inhibitors that target both the active site of the enzyme and its interaction with LEDGF/p75. The purpose of this study is to develop novel inhibitors that can combat HIV-1 by inhibiting the viral replication process, specifically the integration of viral DNA into the host genome, which is catalyzed by HIV integrase (IN). The researchers synthesized a series of flavonoid derivatives with the aim of improving the inhibitory activity against IN and disrupting the IN-LEDGF/p75 interaction, which is crucial for viral integration. The study concluded that certain flavonoids, particularly those containing a catechol or β-ketoenol structure, showed potent inhibitory activity against both the catalytic function of IN and the IN-LEDGF/p75 interaction. Notably, the introduction of a hydrophilic morpholine group at the phenolic hydroxyl position resulted in sub- to low-micromolar IN-LEDGF/p75 inhibitory activity. The chemicals used in this process included various flavonoid derivatives, such as quercetin, baicalein, genistein, luteolin, chrysin, apigenin, and naringenin, along with synthetic reagents like acetic anhydride, benzyl bromide, potassium carbonate, and palladium catalysts for the synthesis and modification of these flavonoids.