18003-33-3

Basic information

• Product Name: 6-hydroxyluteolin
• Synonyms: 6-hydroxyluteolin
• CAS NO: 18003-33-3
• Molecular Formula: C₁₅H₁₀O₇
• Molecular Weight: 302.24
• Mol File: 18003-33-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 275 °C
• Boiling Point: 706.4°Cat760mmHg
• Flash Point: 272.3°C
• Appearance: /
• Density: 1.763g/cm³
• Vapor Pressure: 1.28E-20mmHg at 25°C
• Refractive Index: 1.804
• PKA: 6.31±0.40(Predicted)
• CAS DataBase Reference: 6-hydroxyluteolin(CAS DataBase Reference)
• NIST Chemistry Reference: 6-hydroxyluteolin(18003-33-3)
• EPA Substance Registry System: 6-hydroxyluteolin(18003-33-3)

Safety Data

• Hazardous Substances Data: 18003-33-3(Hazardous Substances Data)

Usage

Uses

6-Hydroxyluteolin was used to enhance uptake of MNPs with an associated therapeutic agent to a target sites (such as a tumor. It was also used in the analysis of Oroxylum indicum, a popluar chinese herbal medicine for hyperactivty and sore throat

Definition

ChEBI: A pentahydroxyflavone that is luteolin with an additional hydroxy group at position 6.

InChI:InChI=1/C15H10O7/c16-7-2-1-6(3-8(7)17)11-4-9(18)13-12(22-11)5-10(19)14(20)15(13)21/h1-5,16-17,19-21H

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Relevant articles and documents

FLAVONE GLYCOSIDES OF SALVIA TRILOBA

From Salvia triloba, 13 flavonids were isolated and identified.The 7-glucosides and 7-glucoronides of apigenin, luteolin, 6-methoxyapigenin and 6-methoxyluteolin and chrysoeriol 7-glucuronide were identified.Also present were 6,8-di-C-glucosylapigenin, luteolin 7-diglucoside, luteolin 7-glucuronide-3'-glucoside and 6-hydroxy-luteolin 6,3'-dimethyl ether.Key Word Index-Salvia triloba; Labiatae; 6-methoxyflavones; flavone glucosides; chemosystematics.

Phytochemical Characterization of Low Molecular Weight Constituents from Marshmallow Roots (Althaea officinalis) and Inhibiting Effects of the Aqueous Extract on Human Hyaluronidase-1

Extract RE was obtained from the roots of Althaea officinalis in a yield of 8.1%, related to the dried plant material, by extraction with MeOH-H2O (1:1), followed by precipitation with EtOH to remove high molecular weight constituents. Phytochemical investigation of RE revealed the presence of N-phenylpropenoyl-l-amino acid amides 1-5, 8% glycine betaine 6, about 9% total amino acids with proline as the main compound, and about 61% mono- and oligomeric carbohydrates with sucrose as the main compound. Further fractionation revealed the presence of a hypolaetin diglycoside (12) and four hypolaetin glycosides (7-9 and 11) with O-sulfocarbohydrate moieties; additionally, 4′-O-methylisoscutellarein-8-O-β-d-(3-O-sulfo)glucuronopyranoside (10) and the diglycosylated coumarin haploperoside D (13) were identified. The hypolaetin-O-sulfoglycosides 7-10 are new natural products. RE inhibited the enzymatic activity of surface-displayed human hyaluronidase-1 on Escherichia coli F470 cells with an IC50 of 7.7 mg/mL. RE downregulated mRNA expression of hyal-1 in HaCaT keratinocytes at 125 and 250 μg/mL, respectively. These data contribute to a deeper phytochemical understanding of marshmallow root extracts and to the positive influence of extracts used for therapy of irritated and inflamed buccal tissue and cough.

Regioselective hydroxylation of diverse flavonoids by an aromatic peroxygenase

Aromatic peroxygenases are extracellular fungal biocatalysts that selectively oxidize a variety of organic compounds. We found that the peroxygenase of the fungus Agrocybe aegerita (AaeAPO) catalyzes the H 2O2-dependent hydroxylation of diverse flavonoids. The reactions proceeded rapidly and regioselectively yielding preferentially monohydroxylated products, e.g., from flavanone, apigenin, luteolin, flavone as well as daidzein, quercetin, kaempferol, and genistein. In addition to hydroxylation, O-demethylation of fully methoxylated tangeretin was catalyzed by AaeAPO. The enzyme was merely lacking activity on the quercetin glycoside rutin, maybe due to sterical hindrance by the bulky sugar substituents. Mechanistic studies indicated the presence of epoxide intermediates during hydroxylation and incorporation of H2O2-derived oxygen into the reaction products. Our results raise the possibility that fungal peroxygenases may be useful for versatile, cost-effective, and scalable syntheses of flavonoid metabolites.