527-95-7

Basic information

• Product Name: Herbacetin
• Synonyms: 3,4',5,7,8-Pentahydroxyflavone;HERBACETIN(P)(PLEASE CALL);3,5,7,8-Tetrahydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;Isoarticulatidin;4',5,7,8-Tetrahydroxyflavonol;4H-1-Benzopyran-4-one,3,5,7,8-tetrahydroxy-2-(4-hydroxyphenyl)-;Herbacetin 8-Hydroxykaempferol;3,5,7,8-Tetrahydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• CAS NO: 527-95-7
• Molecular Formula: C₁₅H₁₀O₇
• Molecular Weight: 302.237
• Product Categories: Penta-substituted Flavones;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 527-95-7.mol
• Article Data: 13

Chemical Properties

• Melting Point: 284℃
• Boiling Point: 618.7 °C at 760 mmHg
• Flash Point: 239 °C
• Appearance: /
• Density: 1.799
• Vapor Pressure: 6.68E-16mmHg at 25°C
• Refractive Index: 1.823
• PKA: 6.49±0.40(Predicted)
• CAS DataBase Reference: Herbacetin(CAS DataBase Reference)
• NIST Chemistry Reference: Herbacetin(527-95-7)
• EPA Substance Registry System: Herbacetin(527-95-7)

Safety Data

• Hazardous Substances Data: 527-95-7(Hazardous Substances Data)

Usage

General Description

Herbacetin is a naturally occurring flavonoid found in several plant species such as flax seeds and ramose scouring rush. It is recognized for its potential health benefits, including anti-inflammatory, antioxidant, and anticancer properties. Studies have suggested that it can inhibit the growth of certain types of cancer cells and can protect against oxidative stress and inflammation, which contribute to various chronic diseases. As a flavonoid, herbacetin also displays other biological activities such as antiviral and antibacterial effects. Furthermore, research is ongoing to explore other potential therapeutic uses of this chemical compound.

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

Synthetic route

5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3,8-dihydroxy-4H-chromen-4-one → herbacetin (527-95-7)

Conditions	Yield
With boron trichloride In dichloromethane at 0℃; for 1h; Inert atmosphere;	95%
With boron trichloride In dichloromethane at 15 - 25℃; for 2h; Inert atmosphere; Cooling with ice;	93%
With boron trichloride In dichloromethane at 20℃; for 2h; Inert atmosphere; Cooling with ice;	93%

C21H22O10 → herbacetin (527-95-7)

Conditions	Yield
With sulfuric acid In methanol at 60℃; for 2h;	76%

C22H24O10 → herbacetin (527-95-7)

Conditions	Yield
With sulfuric acid In methanol at 60℃; for 2h;	76%

Herbacetin-3-β-D-(2-O-β-D-glucopyranosidoglucopyranosid)-8-β-D-glucopyranosid → herbacetin (527-95-7) + herbacetin 8-O-β-D-glucopyranoside

Conditions	Yield
With hydrogenchloride In ethanol at 70℃; for 1h;	A n/a B 50%

7-hydroxy-3,4',5,8-tetramethoxyflavone (85734-53-8) → herbacetin (527-95-7)

Conditions	Yield
With hydrogen iodide Erwaermen des erhaltenen Jodids;

3-hydroxy-5,7,8-trimethoxy-2-(4-methoxy-phenyl)-chromen-4-one (71468-54-7) → herbacetin (527-95-7)

Conditions	Yield
With hydrogen iodide; acetic anhydride

4'-Hydroxywogonin (571-72-2) → herbacetin (527-95-7)

Conditions	Yield
With hydrogen iodide; acetic anhydride

Litvinolin (74137-44-3) → herbacetin (527-95-7)

Conditions	Yield
With hydrogenchloride In water Further byproducts given;

herbacetin 8-(3''-O-acetylxyloside) (68385-35-3) → herbacetin (527-95-7)

Conditions	Yield
With hydrogenchloride In water Further byproducts given;

herbacetin 8-(3''-O-acetylxyloside) (68385-35-3) → D-Xylose (87-72-9, 608-45-7, 608-46-8, 608-47-9, 2460-44-8, 6748-95-4, 6763-34-4, 7261-26-9, 7283-06-9, 7283-07-0, 7296-55-1, 7296-56-2, 7296-58-4, 7296-59-5, 7296-60-8, 7296-61-9, 7296-62-0, 7322-30-7, 10257-31-5, 10257-32-6, 10257-33-7, 10257-34-8, 10257-35-9, 19982-83-3, 20242-88-0, 28697-53-2, 36562-42-2, 41546-41-2, 89299-64-9, 107655-34-5, 115794-06-4, 115794-07-5, 130550-15-1, 130606-21-2) + herbacetin (527-95-7)

Conditions	Yield
With hydrogen cation

herbacetin 8-O-β-D-xylopyranoside 4'-O-β-D-xylopyranoside (90193-30-9) → herbacetin (527-95-7)

Conditions	Yield
With hydrogenchloride In water Further byproducts given;

rhodolide (72055-94-8, 90193-30-9) → herbacetin (527-95-7)

Conditions	Yield
With hydrogenchloride In water Further byproducts given;

herbacetin 7-O-(6''-quinylglucoside) → D-(-)-quinic acid (77-95-2) + herbacetin (527-95-7)

Conditions	Yield
With hydrogenchloride In water

herbacetin 7-O-β-D-glucopyranoside (35815-07-7) → herbacetin (527-95-7)

Conditions	Yield
With hydrogenchloride In water at 100℃; for 2h;

herbacetin 7-O-β-D-glucopyranoside (35815-07-7) → D-Glucose (2280-44-6) + herbacetin (527-95-7)

Conditions	Yield
With water

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-8-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-chromen-4-one → herbacetin (527-95-7)

Conditions	Yield
With hydrogenchloride at 100℃; for 2h;

herbacitrin → herbacetin (527-95-7)

Conditions	Yield
With sulfuric acid

2,4-dihydroxy-ω,3,6-trimethoxyacetophenone (42923-40-0) → herbacetin (527-95-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium-<4-methoxy benzoate> / 180 °C / unter vermindertem Druck und Erwaermen des Reaktionsprodukts mit wss.-aethanol. Kalilauge 2: aqueous hydriodic acid / Erwaermen des erhaltenen Jodids View Scheme

p-Methoxybenzoic anhydride (794-94-5) → herbacetin (527-95-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium-<4-methoxy benzoate> / 180 °C / unter vermindertem Druck und Erwaermen des Reaktionsprodukts mit wss.-aethanol. Kalilauge 2: aqueous hydriodic acid / Erwaermen des erhaltenen Jodids View Scheme

herbacetin 3-O-glucuronide (1104525-48-5) → D-glucuronic acid (6556-12-3, 489-91-8, 528-16-5, 552-12-5, 577-46-8, 643-33-4, 2240-07-5, 6294-16-2, 10133-02-5, 18402-78-3, 18968-14-4, 21179-08-8, 23018-83-9, 33599-45-0, 33599-46-1, 46171-67-9, 46171-69-1, 46172-26-3, 70021-34-0, 71031-08-8, 104195-06-4, 106499-29-0, 124817-72-7) + glucurono-6,3-lactone (17353-48-9) + herbacetin (527-95-7)

Conditions	Yield
With hydrogenchloride; water Heating;

herbacetin 3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside (909803-26-5) → L-Rhamnose (3615-41-6) + D-glucose (50-99-7) + herbacetin (527-95-7)

Conditions	Yield
With hydrogenchloride; water for 3h; Reflux;

1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone (18065-05-9) → herbacetin (527-95-7)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C 1.2: 10.5 h / 2 - 20 °C 2.1: iodine; dimethyl sulfoxide / 110 °C 3.1: iodine; silver trifluoromethanesulfonate / dichloromethane / 2 h / 0 °C 4.1: palladium diacetate; tris-(o-tolyl)phosphine / tetrahydrofuran / 5 h / 5 - 60 °C / Inert atmosphere 5.1: oxone; sodium hydrogencarbonate; sodium carbonate; acetone / dichloromethane; water / 29 h / 0 °C / pH 9 6.1: toluene-4-sulfonic acid / dichloromethane / 0.5 h / 20 °C 7.1: boron trichloride / dichloromethane / 1 h / 0 °C / Inert atmosphere View Scheme

p-benzyloxybenzaldehyde (4397-53-9) → herbacetin (527-95-7)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C 1.2: 10.5 h / 2 - 20 °C 2.1: iodine; dimethyl sulfoxide / 110 °C 3.1: iodine; silver trifluoromethanesulfonate / dichloromethane / 2 h / 0 °C 4.1: palladium diacetate; tris-(o-tolyl)phosphine / tetrahydrofuran / 5 h / 5 - 60 °C / Inert atmosphere 5.1: oxone; sodium hydrogencarbonate; sodium carbonate; acetone / dichloromethane; water / 29 h / 0 °C / pH 9 6.1: toluene-4-sulfonic acid / dichloromethane / 0.5 h / 20 °C 7.1: boron trichloride / dichloromethane / 1 h / 0 °C / Inert atmosphere View Scheme

(E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one (88607-79-8) → herbacetin (527-95-7)

Conditions

Yield

Multi-step reaction with 6 steps 1: iodine; dimethyl sulfoxide / 110 °C 2: iodine; silver trifluoromethanesulfonate / dichloromethane / 2 h / 0 °C 3: palladium diacetate; tris-(o-tolyl)phosphine / tetrahydrofuran / 5 h / 5 - 60 °C / Inert atmosphere 4: oxone; sodium hydrogencarbonate; sodium carbonate; acetone / dichloromethane; water / 29 h / 0 °C / pH 9 5: toluene-4-sulfonic acid / dichloromethane / 0.5 h / 20 °C 6: boron trichloride / dichloromethane / 1 h / 0 °C / Inert atmosphere View Scheme

5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one (96333-59-4) → herbacetin (527-95-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: iodine; silver trifluoromethanesulfonate / dichloromethane / 2 h / 0 °C 2: palladium diacetate; tris-(o-tolyl)phosphine / tetrahydrofuran / 5 h / 5 - 60 °C / Inert atmosphere 3: oxone; sodium hydrogencarbonate; sodium carbonate; acetone / dichloromethane; water / 29 h / 0 °C / pH 9 4: toluene-4-sulfonic acid / dichloromethane / 0.5 h / 20 °C 5: boron trichloride / dichloromethane / 1 h / 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: silver trifluoromethanesulfonate; iodine / dichloromethane / 2 h / 0 °C 2: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere 3: sodium carbonate; sodium hydrogencarbonate; Oxone / dichloromethane; acetone / 0 - 25 °C 4: boron trichloride / dichloromethane / 2 h / 15 - 25 °C / Inert atmosphere; Cooling with ice View Scheme
Multi-step reaction with 4 steps 1: silver trifluoromethanesulfonate; iodine / dichloromethane / 2 h / 0 °C 2: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere 3: Oxone / dichloromethane; acetone / 0 - 20 °C 4: boron trichloride / dichloromethane / 2 h / 20 °C / Inert atmosphere; Cooling with ice View Scheme

5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-8-iodo-4H-chromen-4-one (97828-25-6) → herbacetin (527-95-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: palladium diacetate; tris-(o-tolyl)phosphine / tetrahydrofuran / 5 h / 5 - 60 °C / Inert atmosphere 2: oxone; sodium hydrogencarbonate; sodium carbonate; acetone / dichloromethane; water / 29 h / 0 °C / pH 9 3: toluene-4-sulfonic acid / dichloromethane / 0.5 h / 20 °C 4: boron trichloride / dichloromethane / 1 h / 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere 2: sodium carbonate; sodium hydrogencarbonate; Oxone / dichloromethane; acetone / 0 - 25 °C 3: boron trichloride / dichloromethane / 2 h / 15 - 25 °C / Inert atmosphere; Cooling with ice View Scheme
Multi-step reaction with 3 steps 1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere 2: Oxone / dichloromethane; acetone / 0 - 20 °C 3: boron trichloride / dichloromethane / 2 h / 20 °C / Inert atmosphere; Cooling with ice View Scheme

5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4H-chromen-4-one → herbacetin (527-95-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: oxone; sodium hydrogencarbonate; sodium carbonate; acetone / dichloromethane; water / 29 h / 0 °C / pH 9 2: toluene-4-sulfonic acid / dichloromethane / 0.5 h / 20 °C 3: boron trichloride / dichloromethane / 1 h / 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: sodium carbonate; sodium hydrogencarbonate; Oxone / dichloromethane; acetone / 0 - 25 °C 2: boron trichloride / dichloromethane / 2 h / 15 - 25 °C / Inert atmosphere; Cooling with ice View Scheme

C36H28O7 → herbacetin (527-95-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / dichloromethane / 0.5 h / 20 °C 2: boron trichloride / dichloromethane / 1 h / 0 °C / Inert atmosphere View Scheme

herbacetin 3-O-β-xylopyranosyl-(1'''→2'')-β-O-glucopyranoside → D-xylose (58-86-6) + D-glucose (50-99-7) + herbacetin (527-95-7)

Conditions	Yield
With hydrogenchloride In water at 100℃; for 2h;

para-coumaryl alcohol (3690-05-9) + herbacetin (527-95-7) → demethoxyrhodiolin (134070-57-8)

Conditions	Yield
horseradish peroxidase;

coniferol (458-35-5) + herbacetin (527-95-7) → rhodiolinin (86831-53-0)

Conditions	Yield
horseradish peroxidase;

Syringenin (20675-96-1, 104330-63-4, 537-33-7) + herbacetin (527-95-7) → methoxyrhodiolin (134070-58-9)

Conditions	Yield
horseradish peroxidase;

Upstream product

• 1104525-48-5 herbacetin 3-O-glucuronide 
• 97828-25-6 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-8-iodo-4H-chromen-4-one 
• 96333-59-4 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one 
• 88607-79-8 (E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 909803-26-5 herbacetin 3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside 
• 794-94-5 p-Methoxybenzoic anhydride 
• 42923-40-0 2,4-dihydroxy-3,6,ω-trimethoxyacetophenone 
• 35815-07-7 herbacetin 7-O-β-D-glucopyranoside 
• 72055-94-8 rhodolide 
• 90193-30-9 herbacetin 8-O-β-D-xylopyranoside 4'-O-β-D-xylopyranoside 
• 68385-35-3 herbacetin 8-(3''-O-acetylxyloside) 
• 74137-44-3 Litvinolin 

Downstream Products

• 86831-53-0 rhodiolin 

Relevant articles and documents

CONFIRMATION OF STRUCTURE OF THE FLAVONOL GLUCOSIDE TAMBULETIN

The structure of tambuletin, present in seeds of Xanthoxylum species has been confirmed as the 8-glucoside of gossypetin 7,4'-dimethyl ether. - Key Word Index - Zanthoxylum alatum; Rutaceae; tambuletin; 3,5,3'-trihydroxy-7,4'-dimethoxy-8-O-β-D-glucopyranosylflavone; structure determination.

Preparation method of flavonoids

The invention discloses a preparation method of flavonoids. The method comprises the following step: in a solvent, in the presence of iodine and a silver salt or in the presence of iodine and a copper salt, performing an iodination reaction on a compound 1 to obtain a compound 2. Raw materials used in the method are easy to acquire, and the method has high yields and simple post processes, and does not need column chromatography.

Beta vulgaris subspecies cicla var. flavescens (Swiss chard): Flavonoids, hepatoprotective and hypolipidemic activities

The novel flavonoids, 2″,2″′-di-O-α-rhamnopyranosyl-vicenin II, a di-C-glycosyl flavone, and herbacetin 3-O-β-xylopyranosyl- (1″′→2″)-O-β-glucopyranoside, were isolated from the leaves of Beta vulgaris subspecies cicla L. var. flavescens, an edible plant which is consumed in the Mediterranean areas, additional to the known flavonoids, 6-C-glucosyl isoscutellarein, vitexin-(1″′→2″)-O-β-xylopyranosyl, vitexin-(1″′→2″)-O-α-rhamnopyranosyl and vitexin. All metabolites were established by conventional methods of analysis and their structures were confirmed by spectroscopic analysis, including 1D and 2D-NMR and by HR-ESIMS, as well. The extract of the plant leaves shows hepatoprotective effects in rats intoxicated by administration of acetaminophen and exhibits hypolipidemic activity in rats with high-fat-diet induced hypercholesterolemia. The evaluation was done through measuring the liver function enzymes (aspartate and alanine aminotransferases and alkaline phosphatase, the lipid profile (total cholesterol, high density lipoprotein cholesterol, low density lipoprotein cholesterol and triglycerides) and histopathological analysis of liver slides.

Bioactive constituents from chinese natural medicines. XXXII.1 aminopeptidase N and aldose reductase inhibitors from sinocrassula indica: Structures of sinocrassosides B4, B5, C1, and D1-D3

From the methanolic extract of the whole plant of Sinocrassula indica (Crassulaceae), six new flavonol glycosides, sinocrassosides B4 (1), B5 (2), C1 (3), D1 (4), D2 (5), and D3 (6), were isolated together with 30 compounds. The structures of 1-6 were elucidated on the basis of chemical and physicochemical evidence. In addition, several constituents were found to show inhibitory effects on aminopeptidase N and aldose reductase.