2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-benzopyron

Luteolin

HCID 5280445CAS 491-70-3

Grundinformationen

Standard-SMILES
O=c1cc(-c2ccc(O)c(O)c2)oc2cc(O)cc(O)c12
InChIKey
IQPNAANSBPBGFQ-UHFFFAOYSA-N
Summenformel
C15H10O6
Durchschnittliche Molmasse
286,24 g/mol
Monoisotopische Masse
286,04773803

Namen und Bezeichner

Bevorzugter Name
Luteolin
IUPAC
2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
Lokaler Name
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-benzopyron
Englischer Name
Luteolin
Summenformel
C15H10O6
Molmasse
286.24

Namen und Synonyme

luteolin491-70-33',4',5,7-TetrahydroxyflavoneDigitoflavoneLuteolol2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-oneFlacitranLuteolineSalifazideYama kariyasuWeld Lake5,7,3',4'-Tetrahydroxyflavone
Weitere Namen anzeigen
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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,4
Polarare Oberfläche (TPSA)
107 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
1
Schwere Atome
21

Experimentelle und physikochemische Eigenschaften

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]

Physikochemische Eigenschaften

Schmelzpunkt
330 °C · ~330 °C(lit.)
Siedepunkt
348.61 °C · 348.61°C (rough estimate)
Dichte
1.2981 · 1.2981 (rough estimate)
Brechungsindex
1.4413 · 1.4413 (estimate)
storage temp.
2 · 2-8°C
Löslichkeit
Methanol (Slightly, Heated)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

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.

Gefahrenhinweise

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

Sicherheitsdaten

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

Chemie und Industrie

Pharmakologische Informationen

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
Anwendungen · 3 Einträge

BeschreibungLuteolin 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]

HistoryAt 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.

VerwendenLuteolin 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

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

Anbieter50 Anbieter

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
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 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.

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