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

Luteolin

HCID 5280445CAS 491-70-3

基本情報

標準SMILES
O=c1cc(-c2ccc(O)c(O)c2)oc2cc(O)cc(O)c12
InChIKey
IQPNAANSBPBGFQ-UHFFFAOYSA-N
分子式
C15H10O6
平均分子量
286.24 g/mol
単同位体質量
286.04773803

名称と識別子

優先名称
Luteolin
IUPAC
2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
現地名
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
英語名
Luteolin
分子式
C15H10O6
分子量
286.24

名称と別名

luteolin491-70-33',4',5,7-TetrahydroxyflavoneDigitoflavoneLuteolol2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-oneFlacitranLuteolineSalifazideYama kariyasuWeld Lake5,7,3',4'-Tetrahydroxyflavone
名称をさらに表示
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14705,7,3',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25,7,3′,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cyanidenon2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4h-1-benzopyran-4-onRose extract P.ELuteolin Synonyms : 3`,4`,5,7-Tetrahydroxyflavone
Cyanidenon-14702-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-benzopyrone4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-KUX1ZNC9J2DTXSID4074988CHEBI:158643',4',5,7-Tetrahydroxy-Flavone

データベース識別子

CAS
491-70-3
PubChem CID
5280445
DTXSID
DTXSID4074988
ChEMBL
CHEMBL151
ChEBI
CHEBI:15864
UNII
KUX1ZNC9J2
EC Number
207-741-0
Nikkaji
J1.554G

物性

構造計算による物性

XLogP
1.4
極性表面積
107 Ų
水素結合供与体数
4
水素結合受容体数
6
回転可能結合数
1
重原子数
21

実験および物理化学的性質

LogP2.53
Melting Point329.5 °C
Physical DescriptionSolid
Collision Cross Section158.43 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点
330 °C · ~330 °C(lit.)
沸点
348.61 °C · 348.61°C (rough estimate)
比重(密度)
1.2981 · 1.2981 (rough estimate)
屈折率
1.4413 · 1.4413 (estimate)
貯蔵温度
2 · 2-8°C
溶解性
メタノール(わずかに加熱)

化学的性質

化学的特性Yellow Needles

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 1.9% (1 of 54) of reports.

Warning

H315 (98.1%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (98.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (96.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 54 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 54 reports by companies.;There are 9 notifications provided by 53 of 54 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Hazard Classes and CategoriesSkin Irrit. 2 (98.1%);Eye Irrit. 2 (98.1%);STOT SE 3 (96.3%)

安全データ

wgk
3
rtecs
LK9275210
hs_code
29329990
risk_code
36/37/38
hazard_code
Xi
safety_code
26-36-36/37/39

化学と産業

薬理情報

Metabolism/MetabolitesLuteolin 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.
Cellular LocationsMembrane
応用分野 · 6 件

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.[3] 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.Fig 2 Source of Luteolin[4]

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 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

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.

上流・下流製品情報

サプライヤー50 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
济南诚汇双达生物有限公司053158897070 15550412551
補足説明 · 1 件

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.

関連反応

4 件

関連ノート

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