27696-41-9

Usage

Uses

Used in Pharmaceutical Industry:
HYPOLAETIN is used as a pharmaceutical compound for its potential therapeutic properties. The expression is: HYPOLAETIN is used as a therapeutic agent for its unique chemical structure and potential medicinal applications.
Used in Chemical Research:
HYPOLAETIN is used as a research compound for studying its chemical properties and interactions with other molecules. The expression is: HYPOLAETIN is used as a research compound for understanding its chemical behavior and potential applications in various fields.
Used in Drug Development:
HYPOLAETIN may be used as a starting point for the development of new drugs, leveraging its unique structure and properties. The expression is: HYPOLAETIN is used as a starting compound for drug development due to its distinct chemical characteristics and potential therapeutic benefits.

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

Upstream product

• 17290-70-9 isosinensetin 
• 71847-58-0 5,8-dihydroxy-7-methoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone 
• 102273-91-6 3',4',5,7,8-pentahydroxyflavone 7-O-β-D-glucoside 
• 89456-37-1 8-Hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-5,7-dimethoxy-chromen-4-one 
• 491-70-3 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on 
• 1486-52-8 3-methoxy-4-benzyloxybenzoyl chloride 
• 32455-43-9 hypolaetin 7-O-β-D-glucopyranoside 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 91856-18-7 2'-hydroxy-3,4,3',4',6'-pentamethoxychalcone 
• 89456-24-6 4-Benzyloxy-3-methoxy-benzoic acid 2-acetyl-6-benzyloxy-3,5-dimethoxy-phenyl ester 
• 89456-17-7 1-(3-Benzyloxy-2-hydroxy-4,6-dimethoxy-phenyl)-3-(4-benzyloxy-3-methoxy-phenyl)-propane-1,3-dione 
• 89456-31-5 8-Benzyloxy-2-(4-benzyloxy-3-methoxy-phenyl)-5,7-dimethoxy-chromen-4-one 
• 54299-57-9 3-benzyloxy-2-hydroxy-4,6-dimethoxyacetophenone 
• 21919-66-4 2,30dihydroxy-4,6-dimethoxyacetophenone 

Downstream Products

• 137231-85-7 Scutellaprostin C 
• 17290-70-9 isosinensetin 
• 18003-33-3 3',4',5,6,7-pentahydroxyflavone 
• 89473-36-9 5,7,8-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one 

Relevant academic research and scientific papers

An NADPH and FAD dependent enzyme catalyzes hydroxylation of flavonoids in position 8

Yellow flavonols contribute to flower pigmentation in Asteraceae. In contrast to common flavonols, they show additional hydroxyl groups in position 6 and/or 8 of the aromatic A-ring in addition to the basic 5,7-hydroxylation pattern. An enzyme introducing a hydroxyl group in position 8 of flavonols and flavones was demonstrated for the first time with enzyme preparations from petals of Chrysanthemum segetum. Flavanones, dihydroflavonols and glucosylated flavonols and flavones were not accepted as substrates. The enzyme was localized in the microsomal fraction and uses NADPH and FAD as cofactors. Experiments with carbon monoxide/blue light and with antibodies specific for cytochrome P450 reductase did not indicate the involvement of a classical cytochrome P450 dependent monooxygenase in the reaction. Thus, the flavonoid 8-hydroxylase represents a novel type of hydroxylating enzyme in the flavonoid pathway. Apart from flavonoid 8-hydroxylase activity, the presence of all enzymes involved in the formation of flavonoid 7-O-glucosides in C. segetum was demonstrated. The pathway leading to 8-hydroxyflavonoids in C. segetum has been derived from enzyme activities and substrate specificities observed.

Preparation of Synthetic and Natural Derivatives of Flavonoids Using Suzuki–Miyaura Cross-Coupling Reaction

Herein, we report the use of the Suzuki–Miyaura cross-coupling reaction for the preparation of a library of synthetic derivatives of flavonoids for biological activity assays. We have investigated the reactivity of halogenated flavonoids with aryl boronates and with boronyl flavonoids. This reaction was used to prepare new synthetic derivatives of flavonoids substituted at C-8 with aryl, heteroaryl, alkyl, and boronate substituents. The formation of flavonoid boronate enabled a cross-coupling reaction with halogenated flavones yielding biflavonoids connected at C-8. This method was used for the preparation of natural compounds including C-8 prenylated compounds, such as sinoflavonoid NB. Flavonoid boronates were used for the preparation of rare C-8 hy-droxyflavonoids (natural flavonoids gossypetin and hypolaetin). A series of previously unknown derivatives of quercetin and luteolin were prepared and fully characterized.

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.

Studies on nepalese crude drugs. XIV. New flavonoids from the root of Scutellaria prostrata Jacq. ex Benth.

Six flavonoids, named scutellaprostins A, B, C, D, E and F, were isolated from the root of Scutellaria prostrata Jacq. ex Benth. (Labiatae). Their structures were established to be (2R*,3R*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9- pheny

Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. VI. Demethylation of 8-Hydroxy-5,7-dimethoxyflavones with Anhydrous Aluminum Chloride or Bromide in Acetonitrile

The demethylation of seven 8-hydroxy-5,7-dimethoxyflavones with anhydrous aluminum chloride or bromide in acetonitrile was studied and the following results were obtained. (1) Anhydrous aluminum chloride in acetonitrile selectively split the 5-methoxyl group without cleavage of the 7-methoxyl group, and seven 5,8-dihydroxy-7-methoxy-flavones were quantitatively synthesized by the demethylation. (2) In the demethylation with anhydrous aluminum bromide, the 5- and 7-methoxyl groups on 4',5,7-trimethoxy- and 3',4',5,7-tetramethoxy-8-hydroxyflavone were selectively split to give the corresponding 5,7,8-trihydroxyflavones in good yield.However, the demethylation was not accessible to the synthesis of 5,7,8-trihydroxy-3',4',5'-trimethoxyflavone, 4',5,7,8-tetrahydroxy-3'-methoxy-, and 3',5,7,8-tetrahydroxy-4'-methoxyflavone, because of the cleavage of the methoxyl groups on the B ring.The synthesized flavones were employed for the identification of the two natural flavones, which were proposed to be 4',5,8-trihydroxy-7-methoxyflavone and 4',5,8-trihydroxy-3',7-dimethoxyflavone.The former, salvitin, was revised to 4',5,7-trihydroxy-6-methoxyflavone and the latter seemed to be 4',5,7-trihydroxy-3',8-dimethoxyflavone.

PHYTOCHEMICAL STUDIES ON FLAVONOIDS AND OTHER COMPOUNDS OF JUNIPER FRUITS (JUNIPERUS COMMUNIS L.)

From methanolic extract of juniper fruits (Juniperus communis L.) 7-O-glycosides of: hypolaetin, scutellarein, 7-hydroxy-4',5,6-trimethoxy-flavone, apigenin, as well as 3-O-arabinosyl-glucoside of quercetin were isolated.The presence of rutin, isoquercitrin, 6-O-xylosides of scutellarein and 6-OH luteolin, biflavonoids such as amentoflavone, cupressoflavone were stated too, as described earlier for the compounds isolated from leaves of juniper.The petrol and chloroform extracts from drug were initially analyzed, too.