Herbacetin supplier | CasNO.527-95-7

Name
Herbacetin
EINECS
CAS No. 527-95-7
Article Data18
CAS DataBase
Density 1.799 g/cm³
Solubility
Melting Point 284oC
Formula C₁₅H₁₀O₇
Boiling Point 618.7 °C at 760 mmHg
Molecular Weight 302.24
Flash Point 239 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 3,5,7,8,4'-Pentahydroxyflavone;8-Hydroxykaempferol;Herbacetin;Isoarticulatidin;Flavone,3,4',5,7,8-pentahydroxy- (8CI);
PSA 131.36000
LogP 1.98800

Synthetic route

: 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3,8-dihydroxy-4H-chromen-4-one

: 527-95-7
herbacetin

Conditions

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

: 527-95-7
herbacetin

Conditions

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

: C22H24O10

: 527-95-7
herbacetin

Conditions

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

A: 527-95-7
herbacetin

B: herbacetin 8-O-β-D-glucopyranoside

Conditions

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

: 85734-53-8
7-hydroxy-3,4',5,8-tetramethoxyflavone

: 527-95-7
herbacetin

Conditions

Conditions	Yield
With hydrogen iodide Erwaermen des erhaltenen Jodids;

: 71468-54-7
3-hydroxy-5,7,8-trimethoxy-2-(4-methoxy-phenyl)-chromen-4-one

: 527-95-7
herbacetin

Conditions

Conditions	Yield
With hydrogen iodide; acetic anhydride

: 571-72-2
4'-Hydroxywogonin

: 527-95-7
herbacetin

Conditions

Conditions	Yield
With hydrogen iodide; acetic anhydride

: 74137-44-3
Litvinolin

: 527-95-7
herbacetin

Conditions

Conditions	Yield
With hydrogenchloride In water Further byproducts given;

: 68385-35-3
herbacetin 8-(3''-O-acetylxyloside)

: 527-95-7
herbacetin

Conditions

Conditions	Yield
With hydrogenchloride In water Further byproducts given;

: 68385-35-3
herbacetin 8-(3''-O-acetylxyloside)

A: 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
D-Xylose

B: 527-95-7
herbacetin

Conditions

Conditions	Yield
With hydrogen cation

: 90193-30-9
herbacetin 8-O-β-D-xylopyranoside 4'-O-β-D-xylopyranoside

: 527-95-7
herbacetin

Conditions

Conditions	Yield
With hydrogenchloride In water Further byproducts given;

: 72055-94-8, 90193-30-9
rhodolide

: 527-95-7
herbacetin

Conditions

Conditions	Yield
With hydrogenchloride In water Further byproducts given;

: herbacetin 7-O-(6''-quinylglucoside)

A: 77-95-2
D-(-)-quinic acid

B: 527-95-7
herbacetin

Conditions

Conditions	Yield
With hydrogenchloride In water

: 35815-07-7
herbacetin 7-O-β-D-glucopyranoside

: 527-95-7
herbacetin

Conditions

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

: 35815-07-7
herbacetin 7-O-β-D-glucopyranoside

A: 2280-44-6
D-Glucose

B: 527-95-7
herbacetin

Conditions

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

: 527-95-7
herbacetin

Conditions

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

herbacitrin: herbacitrin

: 527-95-7
herbacetin

Conditions

Conditions	Yield
With sulfuric acid

: 42923-40-0
2,4-dihydroxy-ω,3,6-trimethoxyacetophenone

: 527-95-7
herbacetin

Conditions

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

: 794-94-5
p-Methoxybenzoic anhydride

: 527-95-7
herbacetin

Conditions

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

: 1104525-48-5
herbacetin 3-O-glucuronide

A: 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
D-glucuronic acid

B: 17353-48-9
glucurono-6,3-lactone

C: 527-95-7
herbacetin

Conditions

Conditions	Yield
With hydrogenchloride; water Heating;

...Expand

: 909803-26-5
herbacetin 3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside

A: 3615-41-6
L-Rhamnose

B: 50-99-7
D-glucose

C: 527-95-7
herbacetin

Conditions

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

...Expand

: 18065-05-9
1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone

: 527-95-7
herbacetin

Conditions

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

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

: 4397-53-9
p-benzyloxybenzaldehyde

: 527-95-7
herbacetin

Conditions

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

Yield

: 88607-79-8
(E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one

: 527-95-7
herbacetin

Conditions

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

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

: 96333-59-4
5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one

: 527-95-7
herbacetin

Conditions

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

: 97828-25-6
5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-8-iodo-4H-chromen-4-one

: 527-95-7
herbacetin

Conditions

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

: 527-95-7
herbacetin

Conditions

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

: 527-95-7
herbacetin

Conditions

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

A: 58-86-6
D-xylose

B: 50-99-7
D-glucose

C: 527-95-7
herbacetin

Conditions

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

...Expand

: 3690-05-9
para-coumaryl alcohol

: 527-95-7
herbacetin

: 134070-57-8
demethoxyrhodiolin

Conditions

Conditions	Yield
horseradish peroxidase;

: 458-35-5
coniferol

: 527-95-7
herbacetin

: 86831-53-0
rhodiolinin

Conditions

Conditions	Yield
horseradish peroxidase;

: 20675-96-1, 104330-63-4, 537-33-7
Syringenin

: 527-95-7
herbacetin

: 134070-58-9
methoxyrhodiolin

Conditions

Conditions	Yield
horseradish peroxidase;

Herbacetin Specification

The 4H-1-Benzopyran-4-one, 3, 5, 7, 8-tetrahydroxy-2-(4-hydroxyphenyl)-, with the CAS registry number 527-95-7, is also known as Herbacetin. It belongs to the product categories of Penta-substituted Flavones. This chemical's molecular formula is C₁₅H₁₀O₇ and molecular weight is 302.237. What's more, its IUPAC name is 3, 5, 7, 8-Tetrahydroxy-2-(4-hydroxyphenyl)chromen-4-one.

Physical properties about 4H-1-Benzopyran-4-one, 3, 5, 7, 8-tetrahydroxy-2-(4-hydroxyphenyl)- are: (1)ACD/LogP: 1.14; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 1.09; (4)ACD/LogD (pH 7.4): 0.06; (5)ACD/BCF (pH 5.5): 3.88; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 89.22; (8)ACD/KOC (pH 7.4): 8.19; (9)#H bond acceptors: 7; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 72.45 Å²; (13)Index of Refraction: 1.823; (14)Molar Refractivity: 73.31 cm³; (15)Molar Volume: 167.9 cm³; (16)Polarizability: 29.06×10^-24 cm³; (17)Surface Tension: 114.8 dyne/cm; (18)Density: 1.799 g/cm³; (19)Flash Point: 239 °C; (20)Enthalpy of Vaporization: 95.09 kJ/mol; (21)Boiling Point: 618.7 °C at 760 mmHg; (22)Vapour Pressure: 6.68E-16 mmHg at 25 °C.

Preparation of 4H-1-Benzopyran-4-one, 3, 5, 7, 8-tetrahydroxy-2-(4-hydroxyphenyl)-: this chemical is prepared by Herbacetin-3-β-D-(2-O-β-D-glucopyranosidoglucopyranosid)-8-β-D-glucopyranosid. The reaction needs reagent 1 % HCl and solvent Ethanol. The reaction time is 1 hour with reaction temperature of 70 °C. The yield is about 50 %.

The 4H-1-Benzopyran-4-one, 3, 5, 7, 8-tetrahydroxy-2-(4-hydroxyphenyl)- can be obtained by Herbacetin-3-β-D-(2-O-β-D-glucopyranosidoglucopyranosid)-8-β-D-glucopyranosid.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C1c3c(O/C(=C1/O)c2ccc(O)cc2)c(O)c(O)cc3O
(2) 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
(3) InChIKey: ZDOTZEDNGNPOEW-UHFFFAOYAP

Product Name

Herbacetin

Synthetic route

Herbacetin Specification

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