2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オン

2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オン 化学構造式
491-70-3
CAS番号.
491-70-3
化学名:
2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オン
别名:
4',5,5',7-テトラヒドロキシフラボン;2-(3-ヒドロキシ-4-ヒドロキシフェニル)-5-ヒドロキシ-7-ヒドロキシ-4H-1-ベンゾピラン-4-オン;ルテオロール;ヤマカリヤス;ルテオリン;3',4',5,7-テトラヒドロキシフラボン;ジギトフラボン;クエルシチン;シアニデノン1470;5,7,3',4'-テトラヒドロキシフラボン;2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オン;クエルセトリン;フラシトラン;C.I.ナチュラルイエロー2;5,7,3′,4′-テトラヒドロキシフラボン;4′,5,5′,7-テトラヒドロキシフラボン;3′,4′,5,7-テトラヒドロキシフラボン;2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-4H-クロメン-4-オン;2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-2-クロメン-4-オン
英語名:
Luteolin
英語别名:
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4h-1-benzopyran-4-on;LUTEOLOL;luteoline;cyanidenon;digitoflavone;Rose extract P.E;uteoL;LUTEOLIN;weldlake;Luteloin
CBNumber:
CB7282616
化学式:
C15H10O6
分子量:
286.24
MOL File:
491-70-3.mol
MSDS File:
SDS

2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オン 物理性質

融点 :
~330 °C(lit.)
沸点 :
348.61°C (rough estimate)
比重(密度) :
1.2981 (rough estimate)
屈折率 :
1.4413 (estimate)
貯蔵温度 :
2-8°C
溶解性:
メタノール(わずかに加熱)
外見 :
酸解離定数(Pka):
6.50±0.40(Predicted)
色:
黄色
水溶解度 :
アルカリ水溶液 (1.4mg/ml)、エタノール (~5mg/ml)、ジメチルスルホキシド (7mg/ml)、1eq. 水酸化ナトリウム (5mM)、ジメチルホルムアミド (~20mg/ml) )、水 (1 mg/ml) に可溶ml) および 25°C のメタノール。
Merck :
14,5614
BRN :
292084
InChIKey:
IQPNAANSBPBGFQ-UHFFFAOYSA-N
LogP:
2.40
CAS データベース:
491-70-3(CAS DataBase Reference)
EPAの化学物質情報:
Luteolin (491-70-3)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  Xi
Rフレーズ  36/37/38
Sフレーズ  26-36-36/37/39
WGK Germany  3
RTECS 番号 LK9275210
HSコード  29329990
絵表示(GHS) GHS hazard pictograms
注意喚起語 警告
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H315 皮膚刺激 皮膚腐食性/刺激性 2 警告 GHS hazard pictograms P264, P280, P302+P352, P321,P332+P313, P362
H319 強い眼刺激 眼に対する重篤な損傷性/眼刺激 性 2A 警告 GHS hazard pictograms P264, P280, P305+P351+P338,P337+P313P
H335 呼吸器への刺激のおそれ 特定標的臓器毒性、単回暴露; 気道刺激性 3 警告 GHS hazard pictograms
注意書き
P261 粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。
P304+P340 吸入した場合:空気の新鮮な場所に移し、呼吸しやすい 姿勢で休息させること。
P305+P351+P338 眼に入った場合:水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。
P405 施錠して保管すること。

2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オン 価格 もっと(30)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01CAY10004161
Luteolin
491-70-3 10mg ¥7000 2024-03-01 購入
富士フイルム和光純薬株式会社(wako) W01CAY10004161
Luteolin
491-70-3 50mg ¥15400 2024-03-01 購入
東京化成工業 T2682 3',4',5,7-テトラヒドロキシフラボン >98.0%(HPLC)
3',4',5,7-Tetrahydroxyflavone >98.0%(HPLC)
491-70-3 1g ¥6500 2024-03-01 購入
東京化成工業 T2682 3',4',5,7-テトラヒドロキシフラボン >98.0%(HPLC)
3',4',5,7-Tetrahydroxyflavone >98.0%(HPLC)
491-70-3 5g ¥22800 2024-03-01 購入
関東化学株式会社(KANTO) 24288-96 ルテオリン
Luteolin
491-70-3 50mg ¥11500 2024-03-01 購入

2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オン 化学特性,用途語,生産方法

外観

淡黄色~黄褐色の結晶性の粉末

溶解性

メタノール又はエタノール(99.5)に溶けにくく、水にほとんど溶けない。

解説

C15H10O6(286.23).ルテオリンは,フラボンの一種.モクセイソウReseda luteola L.の全草中,マメ科Genista tinctoria,ジギタリスDigitalis purpurea L.の種子や葉に配糖体のガルテオリンとして存在する.黄色の針状晶.分解点327~329 ℃.λmax 253,267,349 nm(メタノール).塩化鉄(Ⅲ)で緑色を呈する.エタノール,メタノール,アルカリ溶液に可溶,水,エーテルに不溶.森北出版「化学辞典(第2版)

用途

薬理、生理作用研究用。

説明

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.

化学的特性

Yellow Needles

物理的性質

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.

来歴

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.

使用

Luteolin has been used:
  • to induce and elucidate the apoptotic pathway in renal cell carcinoma 786-O cells
  • as an additive in M9 minimal medium to induce nodF gene expression
  • as 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 assay
  • to 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

適応症

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.

定義

ChEBI: 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 luteolin-7-olate.

一般的な説明

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. 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.

生物活性

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 .

薬理学

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 .

抗がん研究

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).

臨床応用

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.

2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オン 上流と下流の製品情報

原材料

準備製品


2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オン 生産企業

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491-70-3(2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オン)キーワード:


  • 491-70-3
  • 3',4',5,7-TETRAHYDROXYFLAVONE,FLACITRAN,LUTEOLOL
  • 2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4H-1-BENZOPYRAN-4-ONE
  • 2-(3,4-DIHYDROXY-PHENYL)-5,7-DIHYDROXY-CHROMEN-4-ONE
  • 5,7,3',4'-TETRAHYDROXYFLAVONE
  • LUTEOLIN
  • LUTEOLIN-3',7-O-DIGLUCURONIDE
  • FLACITRAN
  • cyanidenon digitoflavone 3',4',5,7-Tetrahydroxyflavone 5,7,3',4'-Tetrahydroxyflavone
  • peannt shell extract
  • 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
  • Luteolin Synonyms : 3`,4`,5,7-Tetrahydroxyflavone
  • Luteolin, >=98%(HPLC)
  • Flavopurpol
  • Daphneflavonol
  • 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chroMen-4-one
  • YaMa Kariyasu
  • Salifazide
  • 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyran-4-one
  • RARECHEM AB DU K001
  • weldlake
  • cyanidenon1470
  • c.i.naturalyellow2
  • c.i.75590
  • 3’,4’,5,7-tetrahydroxy-flavon
  • LUTEOLIN MONOHYDRATE
  • LUTEOLIN(P)
  • Luteolin,3′,4′,5,7-Tetrahydroxyflavone
  • Luteolin ,96%
  • 5,7-dihydroxy-
  • 3’,4’,5,7-tetrahydroxyflavone Digitoflavone Cyanidenon
  • 4',5,5',7-テトラヒドロキシフラボン
  • 2-(3-ヒドロキシ-4-ヒドロキシフェニル)-5-ヒドロキシ-7-ヒドロキシ-4H-1-ベンゾピラン-4-オン
  • ルテオロール
  • ヤマカリヤス
  • ルテオリン
  • 3',4',5,7-テトラヒドロキシフラボン
  • ジギトフラボン
  • クエルシチン
  • シアニデノン1470
  • 5,7,3',4'-テトラヒドロキシフラボン
  • 2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オン
  • クエルセトリン
  • フラシトラン
  • C.I.ナチュラルイエロー2
  • 5,7,3′,4′-テトラヒドロキシフラボン
  • 4′,5,5′,7-テトラヒドロキシフラボン
  • 3′,4′,5,7-テトラヒドロキシフラボン
  • 2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-4H-クロメン-4-オン
  • 2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-2-クロメン-4-オン
  • その他の有機分析用の標準物質
  • 有機標準物質
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