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Product FOB Price Min.Order Supply Ability Supplier
Luteolin Powder Sophora Japonica Extract 98% Luteolin
Cas No: 491-70-3
USD $ 310.0-310.0 / Kilogram 1 Kilogram 5000 Kilogram/Week ShangHai Soyoung Biotechnology Inc Contact Supplier
Factory price Luteolin 98% CAS 491-70-3
Cas No: 491-70-3
USD $ 265.65-270.32 / Kilogram 25 Kilogram 100 Metric Ton/Year Guang'an Hongyi Bio-technology Co., Ltd Contact Supplier
peanut shell extract luteolin 98%
Cas No: 491-70-3
USD $ 192.0-192.0 / Kilogram 1 Kilogram 1 Metric Ton/Month Changsha Staherb Natural Ingredients Co.,Ltd Contact Supplier
E-0070 Luteolin
Cas No: 491-70-3
No Data No Data Metric Ton/Day shanghai Tauto Biotech Co., Ltd Contact Supplier
Mignonette extract
Cas No: 491-70-3
USD $ 14.0-14.0 / Kilogram 1 Kilogram 300 Kilogram/Month Greenutra Resource Inc Contact Supplier
Luteolin Manufacturer/High quality/Best price/In stock
Cas No: 491-70-3
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
High quality Luteolin with best price cas:491-70-3
Cas No: 491-70-3
USD $ 250.0-350.0 / Kilogram 1 Kilogram 99999 Kilogram/Year Hangzhou Dingyan Chem Co., Ltd Contact Supplier
Luteolin
Cas No: 491-70-3
USD $ 800.0-1000.0 / Kilogram 1 Kilogram 500 Metric Ton/Day Kono Chem Co.,Ltd Contact Supplier
High purity Luteolin
Cas No: 491-70-3
USD $ 2.0-2.0 / Gram 100 Gram 100 Metric Ton/Month Hebei yanxi chemical co.,LTD. Contact Supplier
Bulk price Peanut Shell / Peanut shells Extract Luteolin 98% powder
Cas No: 491-70-3
USD $ 0.32-0.35 / Gram 100 Gram 100000000 Kilogram/Year Xi'an Quanao Biotech Co., Ltd. Contact Supplier

491-70-3 Usage

Natural Flavonoids

Luteolin is a very typical kind of natural flavonoid and belongs to weak acidic tetrahydroxy flavonoids. It is widely distributed in the plant kingdom and is mainly presented in honeysuckle, chrysanthemum, Nepeta, Herba Ajuga and some other drugs as well as many kinds of vegetables such as thyme, Brussels sprouts, cabbage, cauliflower, beets, broccoli and carrots. Moreover, it is also distributed in the form of glycosides in celery, green pepper, and basil leaves as well as the fruit shell of the legume plant Arachis hypogaea, Ajuga decumbus, Lonicera japonica Thunb, Gentianaceae plant Gentianopsis paludosa, and Valerianaceae plant Valeriana amurensis Smir. The pure product of Luteolin appears as yellow crystalline powder. Figure 1 the pale yellow powder of luteolin and its sources of plant.

Solubility

Luteolin is a golden needles product containing a crystal water molecule that is precipitated from ethanol. It is soluble in alcohol and diethyl ether; slightly soluble in hot water, and insoluble in cold water. Its aqueous solution exhibits pleasing yellow and can be dissolved in 10% aqueous solution of sodium hydroxide and appears as dark yellow color. It is stable under normal conditions.

Extraction Method

According to the report of the literature, method for extracting the active ingredient luteolin from the peanut shell includes solvent method, ultrasonic method, microwave method and supercritical CO2 method, wherein the solvent extraction method is the most widely used with the major extraction solvents used being methanol, acetone and ethyl acetate.

Pharmacological activity

1. Luteolin has various kinds of pharmacological activities. Plants rich in luteolin content are often used as a traditional Chinese medicine for treatment of disease. With the deepening of the study on luteolin, researchers have found that it have anti-cancer activities including inhibiting the proliferation of tumor cell, inducing the apoptosis of tumor cells as well as sensitizing anti-cancer drugs. Moreover, it also has anti-inflammatory, anti-oxidant as well as protein effect on the nervous system. 2. Luteolin is a kind of PDE4 inhibitors, phosphodiesterase inhibitors (2) and interleukin-6 inhibitor (3). It can significantly reverse the induction effect of anesthesia of mice xylazine/ ketamine induction of anesthesia. 4 Preclinical studies have shown that the pharmacological effects of luteolin might include anti-oxidant, anti-inflammatory, antibacterial and anti-cancer. Preliminary studies have found that luteolin can inhibit the apoptosis of the angiogenesis induced cell, affect the tumor growth in animal models, reduce the tumor growth and also improve the cytotoxicity of certain anti-cancer drugs on the tumor cell, indicating that luteolin could be potential cancer chemo-preventive drugs and chemotherapy drugs. 3. The mechanism of biological activity of luteolin may be regulating the level of ROS, inhibition of topoisomerase I and topoisomerase II, reducing the transcription factor NF-κB and AP-1, and stabilizing p53 and inhibition of phosphatidylinositol 3-kinase, signal transduction and activator of transcription 3 (STAT3), insulin-like growth factor 1 receptor (IGF1R) and human epidermal growth factor receptor II activity.

Pharmacological effects

1, anti-tumor: the inhibitory effect of luteolin on tumor cell proliferation is mainly through inhibiting certain intracellular kinase activity and causing cell cycle arrest. 2. Antioxidant: the antioxidant effect of luteolin itself mainly exhibits as a reducing agent involved in the oxidation reaction as well as enhancing the activity of the biological antioxidant system. 3, Anti-inflammatory: the anti-inflammatory activity of luteolin is mainly manifested that it can reduce the activity of inflammatory cytokine transcription factor and production of the pro-inflammatory cytokines and inflammatory mediators. 4, the neuro-protective effect: luteolin has protective effect on the learning and memory ability of the nervous system. 5, anti-fibrosis: luteolin can reduce the extent of liver fibrosis, reduce the hydroxyproline (HYP) in the liver tissue, the content of malondialdehyde (MDA) and the mRNA expression of type I pro-collagen mRNA. In vitro, it can inhibit the proliferation of hepatic star like cells (HSC) and collagen synthesis. It can also alleviate the bleomycin-induced pulmonary fibrosis and histopathological changes, reduce the lung weight index, significantly suppress the increase of MDA, HYP and inhibit the expression of transforming growth factor-β1 (TGF-β1) mRNA in the lung tissue. In vitro, it can inhibit the proliferation of human embryo lung fibroblasts, induce the apoptosis. 6, anti-fertility and hormonal effects: luteolin has a significant dose-dependent anti-implantation activity. After oral administration, it can significantly increase the weight, diameter of uterine, the thickness of endometrium and the height of epithelial cells. Single administration has estrogenic effect while its combination with ethinyloestradiol exhibits anti-estrogenic effect. 7, other functions: luteolin can inhibit various kinds of bacteria and viruses, such as Staphylococcus aureus, Escherichia coli, herpes simplex virus, polio virus, Coxsackie B3 virus. It can inhibit the activity of integrase of AIDS virus HIV-1 and therefore has potential anti-HIV effect. Luteolin is able to bind to the s2 protein of the severe acute respiratory syndrome (SARS) corona virus, thus inhibiting viral for entry into host cells. Luteolin also has inhibitory effect on the Leishmania donovani. Through inhibiting the action of the topoisomerase I and topoisomerase II of Leishmania donovani and inhibit their growth. Additionally, luteolin also has immunomodulatory effects and so on.

Pharmacokinetics

The pharmacokinetic experiment of rat has shown that after the oral administration of luteolin by rats, the in vivo plasma concentration is significantly higher than that after acid hydrolysis which demonstrating it is mostly presented in the glucuronic acid-bound form. The biliary study have found that the level of luteolin in the biliary sample is undetectable using HPLC method at each time after the administration if without the hydrolysis treatment, demonstrating that luteolin is mainly presented in the bound form in the bile.

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.

Side effects

Some patients may get dry mouth, upset stomach, dizziness, nausea and other side effects. After prolonged administration, the symptom may gradually disappear.

Description

Luteolin is a polyphenolic flavone found in many plants including soybeans and perilla leaves.1 Luteolin is one of the most potent flavanoid inhibitors of soybean and reticulocyte 15-lipoxygenases, with an IC50 of 0.6 μM.2 Luteolin has also been found to inhibit the release of TNFα from neutrophils, and to inhibit matrix metalloproteinases.3

Description

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.

Chemical Properties

Yellow Needles

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.

History

At present, luteolin does not have the application of the proprietary medicine, but as one of the main active ingredients of medicinal plants, there is a long history of application. In northern and southern dynasties, honeysuckle with sweet taste, nontoxic, can treat swelling, lose weight, and prolong life under long-term use. In Tang dynasty, honeysuckle was used for treatment of abdominal distension, hot toxic blood dysentery, and water dysentery. It was showed that the clinical application of honeysuckle had made significant progress. During the Song and Yuan dynasties, honeysuckle was widely used for the treatment of diseases such as sore and ulcer. To the Ming dynasty, there were many treatises about honeysuckle. For example, it is said in Compendium of Materia Medica: honeysuckle cure all rheumatism QI and all sorts of swollen poison, ulcer,scab, and heat dissipation detoxify. The prescription has also expanded its scope of application. Up to the Qing dynasty, the application of honeysuckle can not only inherit the theory of the predecessors but also put forward some original ideas and innovation in some respects. In recent years, through the in-depth study of pharmacological effects, it is found that luteolin has significant effects on antitumor, cardioprotection, neuroprotection,respiratory system, immune regulation, anti-inflammatory, spasmolysis, expectorant, anti-allergic, enzyme activities, antioxidant, diuretic, and other aspects.

Uses

Expectorant

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

Uses

Hydroxylated flavone derivative with strong anti-oxidant and radical scavenging properties. Suggested to play a role in cancer prevention

Indications

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.

General Description

Luteolin is a naturally occurring flavone, readily present in vegetables. It may possess many biological properties like anti-tumor activity against condition of skin papilloma.

Biological Activity

Anti-inflammatory, antioxidant and free radical scavenger. Inhibits LPS-induced TNF- α , IL-6 and inducible nitric oxide production and blocks NF- κ B and AP-1 activation. Antiproliferative; inhibits proliferation of Lewis lung carcinoma cells in vivo .

Biochem/physiol Actions

Hydroxylated flavone derivative, a strong antioxidant and radical scavenger. Suggested to play a role in prevention of cancer, possibly via the inhibition of fatty acid synthase activity.

Pharmacology

Luteolin can selectively inhibit the fatty acid synthase activity in prostate cancer and breast cancer cells, which is related to the inhibitory effect of luteolin on tumor cell growth and apoptosis. Luteolin can significantly reduce the incidence of colon cancer and the size of tumor caused by dimethylhydrazine, which may be related to the regulation of lipid peroxidation, antioxidation, and antiproliferative effect. The anti-inflammatory activity of luteolin is related to the inhibition of nitric oxide (NO) and other inflammatory cytokines such as tumor necrosis factor alpha (TNF-α) and interleukin-6 (IL-6) generation and inhibition of protein tyrosine phosphorylation and nuclear transcription factor KB (NF-KB)-mediated gene expression. Luteolin can enhance the transfer of synapses in the hippocampus dentate gyrus, causing long-term potentiation. Moreover, in chronic hypoperfusion injury caused by vascular occlusion, luteolin can still protect synapses, causing long-term potentiation, and reduce the escape latency in the Morris water maze test in rats. Luteolin can reduce the degree of hepatic fibrosis, hydroxyproline level in liver tissues (HYP), malondialdehyde (MDA) content, and mRNA expression of procollagen type I and inhibit hepatic stellate cell (HSC) proliferation and collagen synthesis in vitro. Luteolin can also improve the histological changes of pulmonary fibrosis induced by bleomycin, reduce the lung weight index, significantly reduce the increase in MDA and HYP, and inhibit the level of mRNA of transforming growth factor beta 1 (TGF-β1) in lung tissue. Luteolin in vitro can inhibit the proliferation of human embryonic lung fibroblast cells and promote apoptosis .

Anticancer Research

It is a flavone with yellow crystalline appearance. Dietary sources of luteolin includeoregano, celery, orange, broccoli, rosemary, green pepper, peppermint, parsley,olive oil, thyme, carrot, dandelion, chamomile tea, and perilla. It is found to obstructepithelial-mesenchymal transition (Singh et al. 2016b). It is inhibiting the cancercell proliferation, angiogenesis, and metastasis. In addition, it suppresses thepathways like PI3K/AKT, NF-κB, and X-linked inhibitor of apoptosis protein(XIAP) which enhances the cell growth and function. It also induces apoptosis andtumor suppressor p53. Hence, luteolin can be used as a potential antineoplasticagent in different cancers (Lin et al. 2008).

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.
InChI:InChI=1/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

491-70-3 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (T2682)  3',4',5,7-Tetrahydroxyflavone  >98.0%(HPLC) 491-70-3 1g 990.00CNY Detail
TCI America (T2682)  3',4',5,7-Tetrahydroxyflavone  >98.0%(HPLC) 491-70-3 5g 3,250.00CNY Detail
Alfa Aesar (L14186)  3',4',5,7-Tetrahydroxyflavone, 97%    491-70-3 100mg 719.0CNY Detail
Alfa Aesar (L14186)  3',4',5,7-Tetrahydroxyflavone, 97%    491-70-3 500mg 2670.0CNY Detail
Sigma-Aldrich (72511)  Luteolin  analytical standard 491-70-3 72511-10MG 3,278.34CNY Detail
Sigma-Aldrich (03880590)  Luteolin  primary pharmaceutical reference standard 491-70-3 03880590-25MG 4,031.82CNY Detail
Sigma (L9283)  Luteolin  ≥98% (TLC), powder 491-70-3 L9283-10MG 1,193.40CNY Detail
Sigma (L9283)  Luteolin  ≥98% (TLC), powder 491-70-3 L9283-50MG 4,139.46CNY Detail

491-70-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name luteolin

1.2 Other means of identification

Product number -
Other names 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:491-70-3 SDS

491-70-3Synthetic route

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
520-36-5

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With C9H8IO4Pol In dimethyl sulfoxide at 25℃; for 2h;95%
With cytochromes P450 in human liver microsomes Kinetics; Enzymatic reaction;
2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
855-97-0

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With pyridine hydrochloride at 190℃; for 6h; Inert atmosphere;89%
With pyridine hydrochloride at 180℃; for 6.5h; Inert atmosphere;88%
Stage #1: 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one With aluminum (III) chloride In toluene at 80 - 140℃;
Stage #2: With hydrogenchloride In water; toluene at 0℃; Reagent/catalyst; Solvent; Temperature; Time;
70.2%
2-(3,4-bis(benzyloxy)phenyl)-5,7-dihydroxy-4H-chromen-4-one
58124-13-3

2-(3,4-bis(benzyloxy)phenyl)-5,7-dihydroxy-4H-chromen-4-one

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In N,N-dimethyl-formamide Ambient temperature;80%
1-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-(2,4,6-trihydroxy-phenyl)-propane-1,3-dione

1-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-(2,4,6-trihydroxy-phenyl)-propane-1,3-dione

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With sulfuric acid In acetic acid at 95 - 100℃; for 1h;78%
2',3,4,4',6'-pentahydroxychalcone
14917-41-0

2',3,4,4',6'-pentahydroxychalcone

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With oxygen at 20℃; under 760.051 Torr; for 1h; Reagent/catalyst;72%
luteolin 7-O-glucoside
5373-11-5, 68321-11-9

luteolin 7-O-glucoside

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With sulfuric acid for 4h;68.2%
With acid
With sulfuric acid; water for 2h; Heating;70 mg
luteolin 7-O-glucoside
5373-11-5, 68321-11-9

luteolin 7-O-glucoside

A

D-glucose
50-99-7

D-glucose

B

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With water Acidic conditions;A n/a
B 66%
Acid hydrolysis;
Acidic aq. solution;
Acidic conditions;
4,6-bis(methoxymethyl)-2-(3,4-diacetoxybenzoyloxy)acetophenone

4,6-bis(methoxymethyl)-2-(3,4-diacetoxybenzoyloxy)acetophenone

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
Stage #1: 4,6-bis(methoxymethyl)-2-(3,4-diacetoxybenzoyloxy)acetophenone With potassium hydroxide In pyridine at 50℃; for 0.333333h;
Stage #2: With acetic acid In pyridine; water for 0.5h;
Stage #3: With hydrogenchloride In methanol Reflux;
55%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With sulfuric acid; water for 2h; Heating;50%
5,7-dihydroxy-2-phenyl-chromen-4-one
480-40-0

5,7-dihydroxy-2-phenyl-chromen-4-one

A

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
520-36-5

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

B

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

C

luteolin 3'-monosulphate

luteolin 3'-monosulphate

Conditions
ConditionsYield
With Mucore ramannianus (ATCC 9628) In N,N-dimethyl-formamide for 336h; Microbiological reaction;A 3%
B 10.2%
C 10.2%
6-bromo-2-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-chromen-4-one

6-bromo-2-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-chromen-4-one

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With water; hydrogen iodide; acetic anhydride
diosmetin
520-34-3

diosmetin

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With pyridine hydrochloride at 170℃; for 2h;
luteolin 7-O-<β-D-glucuronosyl(1-2)β-D-glucuronide>-4'-O-β-D-glucuronide

luteolin 7-O-<β-D-glucuronosyl(1-2)β-D-glucuronide>-4'-O-β-D-glucuronide

B

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

C

luteolin 7-O-<β-D-glucuronosyl(1<*>2)β-D-glucuronide>

luteolin 7-O-<β-D-glucuronosyl(1<*>2)β-D-glucuronide>

Conditions
ConditionsYield
With formic acid In water at 100℃; for 3h; Product distribution; also enzymatic hydrolysis;
luteolin 7-O-glucoside
5373-11-5, 68321-11-9

luteolin 7-O-glucoside

A

D-Glucose
2280-44-6

D-Glucose

B

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With hydrogenchloride
With sulfuric acid for 6h;
luteolin 7-O-glucoside
5373-11-5, 68321-11-9

luteolin 7-O-glucoside

A

β-D-glucose
492-61-5

β-D-glucose

B

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
Product distribution; Acid hydrolysis;
luteolin-5-O-β-D-glucopyranoside
20344-46-1

luteolin-5-O-β-D-glucopyranoside

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With malic acid at 60℃; other object of study: half-lives; other reagent : acetic acid, oxalic acid, HCl; other temperature;
7-O-lactoyl-luteolin
126394-95-4

7-O-lactoyl-luteolin

A

LACTIC ACID
849585-22-4

LACTIC ACID

B

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With hydrogenchloride In methanol at 100℃; for 7h; Product distribution;
luteolin 7-O-<2-O-β-glucopyranosyl-lactate>

luteolin 7-O-<2-O-β-glucopyranosyl-lactate>

A

LACTIC ACID
849585-22-4

LACTIC ACID

B

D-Glucose
2280-44-6

D-Glucose

C

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With hydrogenchloride at 100℃; for 7h; Product distribution; other time; reaction in the presence of catalyst;
Conditions
ConditionsYield
With hydrogenchloride at 100℃; for 7h; Product distribution; other time; reaction in the presence of catalyst;
(3',4'-dibenzyloxy-5,7-dimethoxymethyl)flavone
169132-97-2

(3',4'-dibenzyloxy-5,7-dimethoxymethyl)flavone

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With hydrogenchloride In methanol
Multi-step reaction with 3 steps
1: 75 percent / HCl / ethanol; hexane / 1 h / Ambient temperature
2: 18percent HCl / ethanol / 0.5 h / Heating
3: 80 percent / H2 / Pd/C / dimethylformamide / Ambient temperature
View Scheme
3-<3,4-di(tert-butyldimethylsilyloxy)phenyl>-5-(2,4,6-trihydroxyphenyl)isoxazole

3-<3,4-di(tert-butyldimethylsilyloxy)phenyl>-5-(2,4,6-trihydroxyphenyl)isoxazole

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; boric acid; acetic acid; nickel 1.) dioxane-water, 2.) 2 h, reflux; Yield given. Multistep reaction;
2.4.6-trimethoxy-ω-<3.4-dimethoxy-benzoyl>-acetophenone

2.4.6-trimethoxy-ω-<3.4-dimethoxy-benzoyl>-acetophenone

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With hydrogen iodide
2.4.6-trimethoxy-ω-<3.4-methylenedioxy-benzoyl>-acetophenone

2.4.6-trimethoxy-ω-<3.4-methylenedioxy-benzoyl>-acetophenone

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With hydrogen iodide
diosmetin
520-34-3

diosmetin

hydrogen iodide
10034-85-2

hydrogen iodide

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

2-(3,4-dimethoxy-phenyl)-7-hydroxy-5-methoxy-chromen-4-one
10544-05-5

2-(3,4-dimethoxy-phenyl)-7-hydroxy-5-methoxy-chromen-4-one

hydrogen iodide
10034-85-2

hydrogen iodide

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

3',4'-methylenedioxy-5,7-dimethoxyflavone
89029-12-9

3',4'-methylenedioxy-5,7-dimethoxyflavone

hydrogen iodide
10034-85-2

hydrogen iodide

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

6,8-dibromo-2-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-chromen-4-one

6,8-dibromo-2-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-chromen-4-one

hydrogen iodide
10034-85-2

hydrogen iodide

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

5,7-diethoxy-2-(3,4-diethoxy-phenyl)-chromen-4-one
6169-14-8

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

hydrogen iodide
10034-85-2

hydrogen iodide

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

hydrogen iodide
10034-85-2

hydrogen iodide

chrysoeriol tri-O-acetate
3162-04-7

chrysoeriol tri-O-acetate

acetic acid
64-19-7

acetic acid

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

chlorosulfuric acid 2,2,2-trichloroethyl ester
764-09-0

chlorosulfuric acid 2,2,2-trichloroethyl ester

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

C23H14Cl12O18S4

C23H14Cl12O18S4

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 20℃;95%
furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

C20H13NO7

C20H13NO7

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water pH=9.2; Reflux;95%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

acetic anhydride
108-24-7

acetic anhydride

luteolin tetraacetate
1061-93-4

luteolin tetraacetate

Conditions
ConditionsYield
With pyridine Reflux;92%
With sodium acetate
In pyridine Ambient temperature;49 mg
TFE*OTf
1269657-45-5

TFE*OTf

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

C23H18Cl12O18S4
1313434-36-4

C23H18Cl12O18S4

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 0.366667h;92%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

2-(2-Aminoethoxy)ethanol
929-06-6

2-(2-Aminoethoxy)ethanol

C19H17NO8

C19H17NO8

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 65℃; pH=9.2;92%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

diethyl chlorophosphate
814-49-3

diethyl chlorophosphate

C31H46O18P4
1266147-86-7

C31H46O18P4

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 20℃; for 24.5h; Inert atmosphere; Cooling with ice;91%
With dmap; triethylamine In tetrahydrofuran at 70℃; for 3.5h; Cooling with ice; Inert atmosphere;
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

dimethyl sulfate
77-78-1

dimethyl sulfate

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
855-97-0

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one

Conditions
ConditionsYield
With potassium carbonate In acetone for 10h; Reflux;90.7%
With potassium carbonate; acetone
2,2,2-trichloroethoxysulfuryl 2-methyl-3-methylimidazolium triflate
1185733-70-3

2,2,2-trichloroethoxysulfuryl 2-methyl-3-methylimidazolium triflate

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

C23H18Cl12O18S4
1313434-36-4

C23H18Cl12O18S4

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 0.366667h;90%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

(1S,2R,4aS,6aR,6bR,8aR,12aR,12bR,14bS)-6a-Hydroxymethyl-1,2,6b,9,9,12a-hexamethyl-10-oxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid methyl ester

(1S,2R,4aS,6aR,6bR,8aR,12aR,12bR,14bS)-6a-Hydroxymethyl-1,2,6b,9,9,12a-hexamethyl-10-oxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid methyl ester

Conditions
ConditionsYield
In methanol for 0.5h; Ambient temperature;88%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

L-proline
147-85-3

L-proline

luteolin L-proline cocrystals (1:1)

luteolin L-proline cocrystals (1:1)

Conditions
ConditionsYield
In ethanol; acetonitrile at 50℃;86.3%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Hexanoyl chloride
142-61-0

Hexanoyl chloride

5,7,3',4'-tetra-O-hexanoyl-luteolin

5,7,3',4'-tetra-O-hexanoyl-luteolin

Conditions
ConditionsYield
With dmap; triethylamine In N,N-dimethyl-formamide at 20℃; for 4.5h; Cooling with ice;85%
With dmap; triethylamine In N,N-dimethyl-formamide
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

methyl iodide
74-88-4

methyl iodide

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
855-97-0

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 12h;84%
Dichlorodiphenylmethane
2051-90-3

Dichlorodiphenylmethane

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

2-(2,2-diphenyl-1,3-benzodioxol-5-yl)-5,7-dihydroxy-4H-1-benzopyran-4-one
1201808-21-0

2-(2,2-diphenyl-1,3-benzodioxol-5-yl)-5,7-dihydroxy-4H-1-benzopyran-4-one

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane; 1-methyl-pyrrolidin-2-one at 180℃; for 1h; Inert atmosphere; Sealed tube; Microwave irradiation;83%
In diphenylether at 165℃; for 2.5h;70%
In diphenylether at 165℃; for 2.5h;70%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

A

C15H9O9S(1-)*K(1+)
120537-30-6

C15H9O9S(1-)*K(1+)

B

C15H8O12S2(2-)*2K(1+)
116097-10-0

C15H8O12S2(2-)*2K(1+)

Conditions
ConditionsYield
With potassium acetate; tetra(n-butyl)ammonium hydrogensulfate; dicyclohexyl-carbodiimide In pyridine at 4℃; for 72h; Yields of byproduct given;A n/a
B 78%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

5,7-dihydroxy-2-(3,4-dihydroxyphenyl-2,5,6-D3)-4H-1-benzopyran-4-one-3,6,8-D3

5,7-dihydroxy-2-(3,4-dihydroxyphenyl-2,5,6-D3)-4H-1-benzopyran-4-one-3,6,8-D3

Conditions
ConditionsYield
With boron trifluoride; [D3]phosphoric acid In water-d2 at 55℃; for 48h; deuteration;78%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

ethylene dibromide
106-93-4

ethylene dibromide

2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5,7-dihydroxy-4H-chromen-4-one
445408-53-7

2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5,7-dihydroxy-4H-chromen-4-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 0.5h;78%
With potassium carbonate In dimethyl sulfoxide at 70℃; for 1h;32.4%
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 0.5h;28.1%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

ethanolamine
141-43-5

ethanolamine

C17H13NO7

C17H13NO7

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 65℃; pH=9.2;78%
propylamine
107-10-8

propylamine

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

C18H15NO6

C18H15NO6

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 50℃; pH=9.2;76%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

dimethyl sulfate
77-78-1

dimethyl sulfate

pilloin
32174-62-2

pilloin

Conditions
ConditionsYield
With potassium carbonate In acetone for 1h; Reflux;73%
With potassium carbonate In N,N-dimethyl-formamide at 60 - 65℃; for 3h;20.9%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

ethylamine
75-04-7

ethylamine

C17H13NO6

C17H13NO6

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 50℃; pH=9.2-9.3;72%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

benzyl bromide
100-39-0

benzyl bromide

7-(benzyloxy)-2-(3',4'-bis(benzyloxy)phenyl)-5-hydroxy-4H-chromen-4-one
1201807-92-2

7-(benzyloxy)-2-(3',4'-bis(benzyloxy)phenyl)-5-hydroxy-4H-chromen-4-one

Conditions
ConditionsYield
Stage #1: 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere;
71%
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃;56%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

benzylamine
100-46-9

benzylamine

C22H15NO6

C22H15NO6

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 50℃; pH=9.2; Sonication;70.1%
SEC-BUTYLAMINE
33966-50-6

SEC-BUTYLAMINE

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

C19H17NO6

C19H17NO6

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 50℃; pH=9.2;68%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

allyl bromide
106-95-6

allyl bromide

C27H26O6

C27H26O6

Conditions
ConditionsYield
With potassium carbonate In acetone for 10h; Reflux;67.6%
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