Luteolin - Moligand™, ≥98%(HPLC) , CAS No.491-70-3

CAS: 491-70-3 Cat. No.: L107329 Formula: C₁₅H₁₀O₆ Peso molecolare: 286.24 Beilstein Registry Number: 292084 Numero EC: 207-741-0

GRADE & PURITY Moligand™, ≥98%(HPLC)

Synonyms

4dew | Cyanidenon 1470 | HMS3561N09 | 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one | C.I. Natural Yellow 2 | LUTEOLIN [WHO-DD] | BIDD:ER0122 | Flacitran | Luteolin, >=98% (TLC), powder | Luteolol | MLS006011917 | CCRIS 3790 | BCP9000865 | HMS335

Storage

Store at 2-8°C

Shipped In

Wet ice

Panoramica

Luteolin is an antioxidant flavonoid and a free radical scavenger. It inhibits rat liver cytosolic glutathione S-transferase activity and soybean and reticulocyte 15-LO (15-lipoxygenases). Luteolin also shows cytotoxic effects on Raji lymphoma cells. Incubation of the non-tumor cell line C3H10T?CL8 with luteolin results in induction of p53 accumulation and apoptosis, with apoptosis occurring at the G2/M phase of the cell cycle. Luteolin is an inhibitor of Cot, PDE1-5, c-Src, HDAC, Maltase-glucoamylase, Topo I, PKC ε, Fatty Acid Synthase, PPAR γ and MMP.
An inhibitor of glutathione S-transferase and 15-LO.

Specifications

Sinonimi

4dew | Cyanidenon 1470 | HMS3561N09 | 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one | C.I. Natural Yellow 2 | LUTEOLIN [WHO-DD] | BIDD:ER0122 | Flacitran | Luteolin, >=98% (TLC), powder | Luteolol | MLS006011917 | CCRIS 3790 | BCP9000865 | HMS335

Specifiche e purezza

Moligand™, ≥98%(HPLC)

Meccanismi biochimici e fisiologici

Anti-inflammatory, antioxidant and free radical scavenger. Inhibits LPS-induced TNF-α, IL-6 and inducible nitric oxide production and blocks NF-κB and AP-1 activation. Also inhibits TNF-α-induced COX-2 expression. Antiproliferative and chemopreventative;

Condizioni di conservazione di stoccaggio

Store at 2-8°C

Spedito in

Wet ice

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Grado

Moligand™

Purezza

≥98%(HPLC)

Nomi e identificatori

Pubchem Sid

488195204

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488195204

Sorrisi canonici

C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)O

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one

InChIKey

IQPNAANSBPBGFQ-UHFFFAOYSA-N

INCHI

1S/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

Isomeri SMILES

C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)O

WGK Germania

3

RTECS

LK9275210

Peso molecolare

286.24

Beilstein

292084

Reaxy-Rn

292084

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=292084&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Classe Flavonoids
      • Subclass Flavones

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Classe: Flavonoids
• Subclass: Flavones
• Intermediate Tree Nodes: Not available
• Direct Parent: Flavones
• Alternative Parents: 3'-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Chromones Catechols 1-hydroxy-2-unsubstituted benzenoids Pyranones and derivatives 1-hydroxy-4-unsubstituted benzenoids Benzene and substituted derivatives Heteroaromatic compounds Vinylogous acids Oxacyclic compounds Hydrocarbon derivatives Organooxygen compounds Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 3'-hydroxyflavonoid - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Flavone - Hydroxyflavonoid - Chromone - Benzopyran - 1-benzopyran - Catechol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Pyranone - Monocyclic benzene moiety - Pyran - Benzenoid - Vinylogous acid - Heteroaromatic compound - Organoheterocyclic compound - Oxacycle - Organooxygen compound - Hydrocarbon derivative - Organic oxygen compound - Organic oxide - Aromatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
• External Descriptors: Flavones and Flavonols

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Obiettivi associati (umani)

CYP1A2 Tchem Cytochrome P450 1A2 (1 Activities)

Discover Target: CYP1A2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CYP1B1 Tchem Cytochrome P450 1B1 (3 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

DPP4 Tclin Dipeptidyl peptidase 4 (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TTR Tclin Transthyretin (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MMP12 Tchem Macrophage metalloelastase (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CA4 Tclin Carbonic anhydrase 4 (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CA12 Tclin Carbonic anhydrase 12 (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CA7 Tclin Carbonic anhydrase 7 (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CYP1A1 Tchem Cytochrome P450 1A1 (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

XDH Tclin Xanthine dehydrogenase/oxidase (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

AKR1B1 Tclin Aldose reductase (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

NOX4 Tchem NADPH oxidase 4 (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PLG Tclin Plasminogen (2339 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA2 Tclin Carbonic anhydrase II (17698 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PRSS1 Tclin Trypsin I (2306 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AR Tclin Androgen Receptor (11781 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TOP1 Tclin DNA topoisomerase I (7553 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TOP2A Tclin DNA topoisomerase II alpha (6317 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACE Tclin Angiotensin-converting enzyme (1423 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TYR Tclin Tyrosinase (717 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOA Tclin Monoamine oxidase A (11911 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACHE Tclin Acetylcholinesterase (18204 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOB Tclin Monoamine oxidase B (8835 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

XDH Tclin Xanthine dehydrogenase (1038 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A3 Tclin Dopamine transporter (10535 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ELANE Tclin Leukocyte elastase (8173 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AKR1B1 Tclin Aldose reductase (1404 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LCK Tclin Tyrosine-protein kinase LCK (9212 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP1B1 Tchem Cytochrome P450 1B1 (1148 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PON1 Tbio Serum paraoxonase/arylesterase 1 (96 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA1 Tclin Carbonic anhydrase I (13240 Activities)

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GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)

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POLB Tchem DNA polymerase beta (23632 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CDK6 Tclin Cyclin-dependent kinase 6 (1724 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BCHE Tclin Butyrylcholinesterase (7174 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

APP Tclin Amyloid-beta A4 protein (8510 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NEU2 Tbio Sialidase 2 (382 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GLA Tclin Alpha-galactosidase A (5444 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AMY1A Salivary alpha-amylase (100 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GBA1 Tclin Beta-glucocerebrosidase (14647 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PIM1 Tchem Serine/threonine-protein kinase PIM1 (9629 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SYK Tclin Tyrosine-protein kinase SYK (7372 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX15B Tchem Arachidonate 15-lipoxygenase, type II (7244 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GAA Tclin Lysosomal alpha-glucosidase (35701 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MMP3 Tchem Matrix metalloproteinase 3 (3433 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP1A1 Tchem Cytochrome P450 1A1 (1169 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX12 Tchem Arachidonate 12-lipoxygenase (3262 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DAPK1 Tchem Death-associated protein kinase 1 (1664 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR1H3 Tchem LXR-alpha (2891 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FBP1 Tchem Fructose-1,6-bisphosphatase (1199 Activities)

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FASN Tchem Fatty acid synthase (3390 Activities)

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Obiettivi associati (non umani)

NA Neuraminidase (1107 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

fabI Enoyl-[acyl-carrier-protein] reductase (206 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ca7 Carbonic anhydrase VII (3 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Glo1 Glyoxalase I (4 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ttr Transthyretin (14 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mmp13 Matrix metalloproteinase 13 (19 Activities)

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Cruzipain (33337 Activities)

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Gusb Beta-glucuronidase (17 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DPP4 Dipeptidyl peptidase IV (11 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Abcb1b P-glycoprotein 1 (174 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA4 Carbonic anhydrase IV (1713 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mmp2 Matrix metalloproteinase-2 (12 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Hdac6 Histone deacetylase 6 (222 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mmp9 Matrix metalloproteinase 9 (38 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

pol Human immunodeficiency virus type 1 integrase (9041 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

M1AAP Zinc aminopeptidase (902 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAL62 Alpha-glucosidase MAL62 (106 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trichophyton benhamiae (1686 Activities)

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Streptococcus pneumoniae (31063 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Pseudomonas fluorescens (1630 Activities)

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Enterobacter cloacae (7976 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Proteus vulgaris (5823 Activities)

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Salmonella typhimurium (15756 Activities)

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Micrococcus luteus (7463 Activities)

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Staphylococcus aureus (210822 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Neisseria gonorrhoeae (1461 Activities)

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Escherichia coli (133304 Activities)

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Bacillus subtilis (32866 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Enterococcus faecalis (29875 Activities)

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Pichia kudriavzevii (7448 Activities)

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Aspergillus fumigatus (16427 Activities)

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Trypanosoma brucei brucei (13300 Activities)

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Entamoeba histolytica (2676 Activities)

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Plasmodium falciparum (966862 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Nakaseomyces glabratus (9108 Activities)

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Candida parapsilosis (8521 Activities)

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Candida tropicalis (8381 Activities)

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Trichophyton rubrum (3646 Activities)

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Leishmania donovani (89745 Activities)

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Trypanosoma cruzi (99888 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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Human alphaherpesvirus 1 (11089 Activities)

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Meccanismi d'azione

Proprietà chimiche e fisiche

• Solubilità: Solvent:1eq. NaOH, Max Conc. mg/mL: 1.43, Max Conc. mM: 5; Solvent:DMSO, Max Conc. mg/mL: 14.31, Max Conc. mM: 50
• Sensibilità: Heat Sensitive
• Punto di fusione (°C): 330°C
• Peso molecolare: 286.240 g/mol
• XLogP3: 1.400
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 286.048 Da
• Monoisotopic Mass: 286.048 Da
• Topological Polar Surface Area: 107.000 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 447.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Domande frequenti

What is the purity of this product, and how is it determined?

This product is supplied at ≥98% purity, determined by HPLC. Lot-specific values are stated on the Certificate of Analysis.

What is Moligand??

Moligand? is one of Aladdin Scientific's premium product lines, formulated for high-purity applications across multiple workflows. Compared to standard grades in the same workflow, Moligand? products typically offer tighter specifications, more rigorous QC, and stronger lot-to-lot consistency.

How should this product be stored?

Store at 2–8 °C. Refrigerated storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 491-70-3, the molecular formula is C15H10O6, and the molecular weight is 286.24 g/mol. InChIKey IQPNAANSBPBGFQ-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.