480-18-2

Basic information

• Product Name: Taxifolin
• Synonyms: 2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4h-1-benzopyran-4-on;2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4h-1-benzopyran-4-on(;2,3-dihydro-3,3’,4’,5,7-pentahydroxy-flavon;2theta-trans)-;3,3’,4’,5,7-pentahydroxy-flavanon;dihydro-querceti;distylin;taxifoliol
• CAS NO: 480-18-2
• Molecular Formula: C₁₅H₁₂O₇
• Molecular Weight: 304.25
• EINECS: 207-543-4
• Product Categories: Flavanones;Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 480-18-2.mol
• Article Data: 29

Chemical Properties

• Melting Point: 230-233°C (dec.)
• Boiling Point: 365.09°C (rough estimate)
• Flash Point: 264.1 °C
• Appearance: /
• Density: 1.3326 (rough estimate)
• Vapor Pressure: 7.51E-20mmHg at 25°C
• Refractive Index: 1.4790 (estimate)
• Storage Temp.: -20?C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 7.39±0.60(Predicted)
• BRN: 5299277
• CAS DataBase Reference: Taxifolin(CAS DataBase Reference)
• NIST Chemistry Reference: Taxifolin(480-18-2)
• EPA Substance Registry System: Taxifolin(480-18-2)

Safety Data

• Statements: 22
• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: LK6920000
• HazardClass: IRRITANT
• Hazardous Substances Data: 480-18-2(Hazardous Substances Data)

Usage

Structural chemistry

Taxifolin is a subclass of flavanonols, an isoflavanone in flavonoids family. The basic structure of two phenyl groups (ring A and ring B) which are joined together by a heterocyclic ring referred to as ring C . The structure contains 3-hydroxyl group at the C ring which is connected to the B ring at carbon-2. Taxifolin is a pentahydroxyflavone containing five hydroxyl groups at the 3-, 3'-, 4'-, 5- and 7-positions. It ?has two stereocenters on the C-ring and 4 stereoisomers. It with the configuration of (2R, 3R) is one of them and it comprises 2 pairs of enantiomers.

Description

Taxifolin, a chemical substance extracted from pine plants such as larch and Douglas fir. It belongs to the bioflavonoid pseudo-vitamin P, and its scientific name is dihydroquercetin. Japanese scholar Fukui first isolated it from the leaves of conifers (Chamaecyparis obtusa), and its biological activity was subsequently discovered and confirmed.

Chemical Properties

Yellow Solid

Uses

Reference Standard in the analysis of herbal medicinal products

Definition

ChEBI: A taxifolin that has (2R,3R)-configuration.

Application

Taxifolin is a flavonoid commonly found in onion, milk, French maritime pine bark and Douglas fir bark. It is also used in various commercial preparations like Legalon?, Pycnogenol?, and Venoruton?. This review focuses on taxifolin’s biological activities and related molecular mechanisms. It showed promising pharmacological activities in the management of inflammation, tumors, microbial infections, oxidative stress, cardiovascular, and liver disorders. The anti-cancer activity was more prominent than other activities evaluated using different in vitro and in vivo models. Further research on the pharmacokinetics, in-depth molecular mechanisms, and safety profile using well-designed randomized clinical studies are suggested to develop a drug for human use.

General Description

Taxifolin is a plant flavonoid, which may find applications in the treatment of coronary heart disease, angina pectoris, cerebral thrombosis, cerebral infarction and sequelae.

InChI:InChI=1/C15H12O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,14-19,21H/t14-,15+/m1/s1

Synthetic route

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-4-one (574749-31-8) → taxifolin (480-18-2)

Conditions	Yield
With hydrogen; palladium on activated charcoal In tetrahydrofuran; methanol at 20℃; for 24h;	90%
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; methanol for 48h; Inert atmosphere;	85%

catechin (154-23-4) → taxifolin (480-18-2)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: K2CO3 / dimethylformamide / 3 h / 130 °C 1.2: 81 percent / NaH / dimethylformamide / 3 h / 20 °C 2.1: 85 percent / Pb3O4 / benzene / 3 h / 75 - 80 °C 3.1: 90 percent / K2CO3 / methanol; tetrahydrofuran / 2 h / 20 °C 4.1: 85 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; MgSO4 / CH2Cl2 / 3 h / 20 °C 5.1: 90 percent / H2 / Pd/C / methanol; tetrahydrofuran / 24 h / 20 °C View Scheme
With extract of Burkholderia oxyphila OX-01, Japan, Tsukuba, acidic forest soil In aq. phosphate buffer at 28℃; for 3h; pH=7;
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere 3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; 1,4-dioxane; water / 8 h / 0 - 20 °C / Inert atmosphere 4.1: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran / 48 h / Inert atmosphere View Scheme

(2R,3R)-5,7,3',4'-tetrahydroxyflavanonol 2"-acetylrhamnoside (1298135-47-3) → taxifolin (480-18-2)

Conditions	Yield
With sulfuric acid In 1,4-dioxane at 100℃; for 1h;

C17H16O8 → taxifolin (480-18-2)

Conditions	Yield
With hydrogenchloride at 55℃; for 0.5h; pH=< 1;	55%

taxifolin O-α-D-glucoside (1235442-81-5) → taxifolin (480-18-2)

Conditions	Yield
With water; Saccharomyces cerevisiae α-glucosidase at 30℃; for 18h; pH=7.3; Enzymatic reaction; Potassium phosphate buffer;

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol (490-46-0) → taxifolin (480-18-2)

Conditions	Yield
With extract of Burkholderia oxyphila OX-01, Japan, Tsukuba, acidic forest soil In aq. phosphate buffer at 30℃; for 3h; pH=7;

1-(3,4-dihydroxy)phenyl-2-(2,4,6-trihydroxy)phenylethylene oxide → taxifolin (480-18-2)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 0 - 5℃; for 5h; Large scale;	41.3 kg

1-(2',4',6'-trihydroxyphenyl)-2-hydroxyethanone (55313-03-6) + 3,4-dihydroxybenzaldehyde (139-85-5) → taxifolin (480-18-2)

Conditions	Yield
Stage #1: 1-(2',4',6'-trihydroxyphenyl)-2-hydroxyethanone; 3,4-dihydroxybenzaldehyde With rac-Pro-OH In tetrahydrofuran at 85 - 100℃; for 6h; Stage #2: With acetic acid In tetrahydrofuran at 20℃; for 2h; Solvent; Temperature;	36.7 g

(-)-chalcone epoxide (36804-13-4, 91318-14-8, 115523-95-0, 115523-96-1) → taxifolin (480-18-2)

Conditions	Yield
With hydrogenchloride In methanol at 50℃; for 0.333333h;	82%

astilbin (29838-67-3, 54081-47-9, 54081-48-0, 54141-72-9) → taxifolin (480-18-2)

Conditions	Yield
With sulfuric acid; water for 2h; Hydrolysis; Heating;	70%
With hesperidinase In water at 37℃; for 36h;	37 mg
With hydrogenchloride; water In methanol at 80℃; for 0.75h; Kinetics; Activation energy; Temperature; Concentration;

3,3',4',5,7-pentahydroxy flavanone (215257-15-1) → (2S,3S)-taxifolin 3-O-β-D-glucoside (480-18-2, 24198-97-8, 98006-93-0, 114761-89-6, 111003-33-9) + taxifolin (480-18-2)

Conditions	Yield
With DAICEL CHIRALPAK IA In ethanol; hexane Resolution of racemate;

trans-taxifolin 3-O-α-L-arabinofuranoside → L-arabinose (5328-37-0) + taxifolin (480-18-2)

Conditions	Yield
With hesperidase In water at 37℃; for 456h; enzimatic hydrolysis;	A 23 mg B 48 mg
With hydrogenchloride In water at 50℃; for 16h;	A 15 mg B 32 mg

(2R,3S)-3,5,7-tris(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)chroman (85443-49-8) → taxifolin (480-18-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: 85 percent / Pb3O4 / benzene / 3 h / 75 - 80 °C 2: 90 percent / K2CO3 / methanol; tetrahydrofuran / 2 h / 20 °C 3: 85 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; MgSO4 / CH2Cl2 / 3 h / 20 °C 4: 90 percent / H2 / Pd/C / methanol; tetrahydrofuran / 24 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; 1,4-dioxane; water / 8 h / 0 - 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran / 48 h / Inert atmosphere View Scheme

(+)-3',4',3,5,7-penta-O-benzyl-(4S)-hydroxycatechine (574749-29-4) → taxifolin (480-18-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; MgSO4 / CH2Cl2 / 3 h / 20 °C 2: 90 percent / H2 / Pd/C / methanol; tetrahydrofuran / 24 h / 20 °C View Scheme

(+)-(4S)-acetoxy-3',4',3,5,7-penta-O-benzylcatechine (478241-14-4) → taxifolin (480-18-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / K2CO3 / methanol; tetrahydrofuran / 2 h / 20 °C 2: 85 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; MgSO4 / CH2Cl2 / 3 h / 20 °C 3: 90 percent / H2 / Pd/C / methanol; tetrahydrofuran / 24 h / 20 °C View Scheme

3,5-dihydroxyphenol (108-73-6) → taxifolin (480-18-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / dichloromethane / 2 h / 5 - 10 °C / Large scale 1.2: 4 h / 10 - 20 °C / Large scale 2.1: 3-chloro-benzenecarboperoxoic acid / methanol / 4 h / 5 - 15 °C / Large scale 3.1: trifluoroacetic acid / dichloromethane / 5 h / 0 - 5 °C / Large scale View Scheme
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere 1.2: 5 h / -5 °C / Inert atmosphere 2.1: trifluoromethylsulfonic anhydride / dichloromethane / 0.08 h / -5 °C / Inert atmosphere 2.2: -5 °C / Inert atmosphere 3.1: sodium hydroxide; dihydrogen peroxide / methanol / 5 h / 20 °C / Inert atmosphere 4.1: hydrogenchloride / methanol; water; tetrahydrofuran / 2 h / 55 °C / Inert atmosphere 5.1: Resolution of racemate View Scheme

(2R,3R)-taxifolin 3-β-D-glucopyranoside 6''-gallate → 3,4,5-trihydroxybenzoic acid (149-91-7) + taxifolin (480-18-2)

Conditions	Yield
With sulfuric acid In ethanol; water for 3h; Heating;	A 12 mg B 32 mg

(E)-3-(3,4-bis(methoxymethoxy)phenyl)-1-(2,4,6-tris(methoxymethoxy)phenyl)-prop-2-en-1-one (36804-12-3) → taxifolin (480-18-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; dihydrogen peroxide / methanol / 5 h / 20 °C / Inert atmosphere 2: hydrogenchloride / methanol; water; tetrahydrofuran / 2 h / 55 °C / Inert atmosphere 3: Resolution of racemate View Scheme

(+/-)-2,3-trans-2,3-epoxy-1-2",4",6"-tris(methoxymethoxy)phenyl-3-3',4'-bis(methoxymethoxy)phenylpropanone → taxifolin (480-18-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / methanol; water; tetrahydrofuran / 2 h / 55 °C / Inert atmosphere 2: Resolution of racemate View Scheme

caffeic acid (331-39-5) → taxifolin (480-18-2)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: sulfuric acid / methanol / 1 h / 20 °C / Inert atmosphere 1.2: 0 °C / Inert atmosphere 2.1: sodium hydroxide / methanol; tetrahydrofuran / Inert atmosphere 3.1: trifluoromethylsulfonic anhydride / dichloromethane / 0.08 h / -5 °C / Inert atmosphere 3.2: -5 °C / Inert atmosphere 4.1: sodium hydroxide; dihydrogen peroxide / methanol / 5 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride / methanol; water; tetrahydrofuran / 2 h / 55 °C / Inert atmosphere 6.1: Resolution of racemate View Scheme

5,7,3',4'-tetra-O-benzyl-(+)-catechin (20728-73-8) → taxifolin (480-18-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; 1,4-dioxane; water / 8 h / 0 - 20 °C / Inert atmosphere 3.1: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran / 48 h / Inert atmosphere View Scheme

1,3,5-tris(methoxymethoxy)benzene (120677-47-6) → taxifolin (480-18-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: trifluoromethylsulfonic anhydride / dichloromethane / 0.08 h / -5 °C / Inert atmosphere 1.2: -5 °C / Inert atmosphere 2.1: sodium hydroxide; dihydrogen peroxide / methanol / 5 h / 20 °C / Inert atmosphere 3.1: hydrogenchloride / methanol; water; tetrahydrofuran / 2 h / 55 °C / Inert atmosphere 4.1: Resolution of racemate View Scheme

(E)-3-(3,4-bis(methoxymethoxy)phenyl)acrylic acid (850177-05-8) → taxifolin (480-18-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: trifluoromethylsulfonic anhydride / dichloromethane / 0.08 h / -5 °C / Inert atmosphere 1.2: -5 °C / Inert atmosphere 2.1: sodium hydroxide; dihydrogen peroxide / methanol / 5 h / 20 °C / Inert atmosphere 3.1: hydrogenchloride / methanol; water; tetrahydrofuran / 2 h / 55 °C / Inert atmosphere 4.1: Resolution of racemate View Scheme

C15H20O7 → taxifolin (480-18-2)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: sodium hydroxide / methanol; tetrahydrofuran / Inert atmosphere 2.1: trifluoromethylsulfonic anhydride / dichloromethane / 0.08 h / -5 °C / Inert atmosphere 2.2: -5 °C / Inert atmosphere 3.1: sodium hydroxide; dihydrogen peroxide / methanol / 5 h / 20 °C / Inert atmosphere 4.1: hydrogenchloride / methanol; water; tetrahydrofuran / 2 h / 55 °C / Inert atmosphere 5.1: Resolution of racemate View Scheme

(R)-3,5,7-Trihydroxy-2-[4-hydroxy-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-chroman-4-one → D-glucose (50-99-7) + (-)-epitaxifolin (480-18-2, 24198-97-8, 98006-93-0, 111003-33-9, 114761-89-6) + taxifolin (480-18-2)

Conditions	Yield
With pectinase In water Ambient temperature;	A n/a B 20 mg C 3 g

(+/-)-taxifolin (480-18-2, 24198-97-8, 98006-93-0, 111003-33-9, 114761-89-6) → (2S,3S)-taxifolin 3-O-β-D-glucoside (480-18-2, 24198-97-8, 98006-93-0, 114761-89-6, 111003-33-9) + taxifolin (480-18-2)

Conditions	Yield
With acetic acid In water; acetonitrile Resolution of racemate;
Resolution of racemate;

(+)-taxifolin 3-O-β-D-xylopyranoside (40672-47-7) → D-xylose (58-86-6) + taxifolin (480-18-2)

Conditions	Yield
In water at 37℃; for 1h; hesperidinase; Yield given. Yields of byproduct given;

(2R,3R)-(+)-dihydroquercetin-3-β-D-glucopyranoside (27297-45-6) → D-glucose (50-99-7) + taxifolin (480-18-2)

Conditions	Yield
With sulfuric acid In ethanol for 2h; Heating;	A n/a B 48 mg

caffeic acid chloride (23416-69-5) → taxifolin (480-18-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / dichloromethane / 2 h / 5 - 10 °C / Large scale 1.2: 4 h / 10 - 20 °C / Large scale 2.1: 3-chloro-benzenecarboperoxoic acid / methanol / 4 h / 5 - 15 °C / Large scale 3.1: trifluoroacetic acid / dichloromethane / 5 h / 0 - 5 °C / Large scale View Scheme

2,4,6-trihydroxyacetophenone (480-66-0) → taxifolin (480-18-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 2 h / 5 °C 1.2: 4 h / 25 °C 2.1: dihydrogen peroxide / tetrahydrofuran; water / 4 h / 25 °C 3.1: hydrogenchloride / 0.5 h / 55 °C / pH < 1 View Scheme

n-octanoic acid chloride (111-64-8) + taxifolin (480-18-2) → taxifolin tetra-octanoate

Conditions	Yield
Stage #1: n-octanoic acid chloride; taxifolin In 1,4-dioxane at 20℃; for 0.166667h; Stage #2: With pyridine In 1,4-dioxane at 20℃; for 16h;	86%
Stage #1: n-octanoic acid chloride; taxifolin In 1,4-dioxane at 20℃; for 0.166667h; Stage #2: With pyridine In 1,4-dioxane for 16h;	79%

taxifolin (480-18-2) → taxifolin 4'-O-sulfate

Conditions	Yield
With p-nitrophenyl sulfate; arylsulfate sulfotransferase from Desulfitobacterium hafniense In acetone at 30℃; for 4h; pH=8.9; Inert atmosphere; Enzymatic reaction;	75%

1-deoxy-1-fluoro-α-D-glucose (2106-10-7) + taxifolin (480-18-2) → taxifolin 7-α-O-glucoside

Conditions	Yield
With α-glucosidase from sulfolobus solfataricus In dimethyl sulfoxide at 45℃; for 2h; pH=9; Enzymatic reaction;	99%

water (7732-18-5) + copper(II) sulfate (7758-99-8) + taxifolin (480-18-2) → C15H14CuO9

Conditions	Yield
With ammonia In ethanol at 20℃; for 1h; pH=5 - 7; Temperature;	86.3%

catechin (154-23-4) + taxifolin (480-18-2) → procyanidin B3 (23567-23-9)

Conditions	Yield
With sodium tetrahydroborate; acetic acid In ethanol; water for 0.5h; pH=4.5; Inert atmosphere;	22%
With sodium tetrahydroborate; water; acetic acid 1.) EtOH, 30 min, 2.) EtOH; Multistep reaction;
With sodium tetrahydroborate In ethanol Inert atmosphere;
Stage #1: taxifolin With sodium tetrahydroborate; ethanol at 20℃; for 0.75h; Stage #2: catechin With hydrogenchloride In water for 1h;	200 mg

taxifolin (480-18-2) → 2,3-trans-flavan-3,4-diol (480-17-1)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20℃; for 1h;
Stage #1: taxifolin With sodium tetrahydroborate In ethanol at 20℃; for 1h; Stage #2: for 0.5h;

taxifolin (480-18-2) → (+)-(2R,3S,4S)-3,4,5,7,3',4'-hexahydroxyflavan (93527-39-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / ethanol / 2 h / Ambient temperature 2: 0.05 M citrate-Pi buffer, pH 2.6 / 0.5 h / 40 °C View Scheme
With NADPH In aq. buffer at 45℃; for 0.5h; pH=6; Enzymatic reaction;

taxifolin (480-18-2) → (2R,3S,4R)-(+)-3,4,5,7,3',4'-hexahydroxyflavan (69256-15-1)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20℃; for 2h;	75%
With sodium tetrahydroborate In ethanol for 2h; Ambient temperature;
With sodium tetrahydroborate In ethanol for 2h;

water (7732-18-5) + copper diacetate (142-71-2) + taxifolin (480-18-2) → C15H14CuO9

Conditions	Yield
In ethanol at 20℃; for 1h;	86.3%

6-[(2-aminopropyl)amino]-6-deoxy-β-cyclodextrin (131991-59-8) + taxifolin (480-18-2) → C15H12O7*C45H78N2O34

Conditions	Yield
In ethanol at 45℃; for 72h;	64%

zinc(II) acetate dihydrate (5970-45-6) + taxifolin (480-18-2) → Zn(2+)*2C15H11O7(1-)*2H2O

Conditions	Yield
In water at 92℃; for 0.4h; Time; Industrial scale;	84%

acetic anhydride (108-24-7) + taxifolin (480-18-2) → 2-(3,4-diacetoxyphenyl)-4-oxochroman-3,5,7-triyl triacetate (6685-67-2, 70497-17-5, 132487-23-1)

Conditions	Yield
With pyridine for 18h; Ambient temperature;	88%
With pyridine at 90℃; for 3h; Acetylation;	47%
In pyridine

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol (490-46-0) + taxifolin (480-18-2) → procyanidin B4 (29106-51-2)

Conditions	Yield
With sodium tetrahydroborate
Stage #1: taxifolin With sodium tetrahydroborate; ethanol at 20℃; for 0.75h; Stage #2: (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol With hydrogenchloride In water for 1h;	200 mg

D-Glucose (2280-44-6) + taxifolin (480-18-2) → (2R,3R)-(+)-3',4',5,7-tetrahydroxydihydroflavonol-6-C-β-D-glucopyranoside (112494-39-0)

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In water; acetonitrile for 48h; Reagent/catalyst; Solvent; Inert atmosphere; Reflux; stereoselective reaction;	35%

taxifolin (480-18-2) → 6,8-dibromodihydroquercetin

Conditions	Yield
With N-Bromosuccinimide In acetone at 25℃; for 0.716667h; regiospecific reaction;	94%
With 2,3-dibromo-3-phenylpropanoic acid; potassium carbonate In N,N-dimethyl-formamide at 60℃; for 16h; Inert atmosphere;	46%
With hypobromous acid In ethanol; water at 20℃; aq. phosphate buffer;

taxifolin (480-18-2) + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) → C26H30O7

Conditions	Yield
With sodium hydrogencarbonate In ethanol at 120 - 130℃; for 10h; Temperature;	70 g

α-lipoic acid chloride (387358-39-6) + taxifolin (480-18-2) → 2-(3,4-bis(5-(1,2-dithiolan-3-yl)pentanoyloxy)phenyl)-4-oxochroman-3,5,7-triyl tris(5-(1,2-dithiolan-3-yl)pentanoate)

Conditions	Yield
Stage #1: α-lipoic acid chloride; taxifolin In 1,4-dioxane at 20℃; for 0.116667h; Stage #2: With pyridine In 1,4-dioxane at 20℃; for 4h;	1.8 g

5-((3R)-1,2-dithiolan-3-yl)pentanoyl chloride (13880-12-1) + taxifolin (480-18-2) → 2-(3,4-bis(5-(1,2-dithiolan-3-yl)pentanoyloxy)phenyl)-4-oxochroman-3,5,7-triyl tris(5-(1,2-dithiolan-3-yl)pentanoate)

Conditions	Yield
Stage #1: 5-((3R)-1,2-dithiolan-3-yl)pentanoyl chloride; taxifolin In 1,4-dioxane at 20℃; for 0.116667h; Stage #2: With pyridine In 1,4-dioxane at 20℃; for 19h;	1.8 g

taxifolin (480-18-2) + epigallocatechin (970-73-0, 1617-55-6, 3371-27-5, 13425-13-3, 136892-45-0, 970-74-1) → C29H22O13

Conditions	Yield
With apple polyphenol oxidase In aq. phosphate buffer at 35℃; for 1h; pH=4; Enzymatic reaction;

Upstream product

• 36804-12-3 (E)-3-(3,4-bis(methoxymethoxy)phenyl)-1-(2,4,6-tris(methoxymethoxy)phenyl)-prop-2-en-1-one 
• 331-39-5 caffeic acid 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 120677-47-6 1,3,5-tris(methoxymethoxy)benzene 
• 850177-05-8 (E)-3-[3,4-bis(methoxymethoxy)phenyl]acrylic acid 
• 108-73-6 3,5-dihydroxyphenol 
• 109430-52-6 (-)-taxifolin 3-O-β-D-xylopyranoside 
• 109430-54-8 (-)-epitaxifolin 3-O-β-D-xylopyranoside 
• 27297-45-6 (2R,3R)-(+)-dihydroquercetin-3-β-D-glucopyranoside 
• 40672-47-7 (+)-taxifolin 3-O-β-D-xylopyranoside 
• 29838-67-3 astilbin 
• 69256-15-1 (2R,3S,4R)-(+)-3,4,5,7,3',4'-hexahydroxyflavan 
• 36804-11-2 2,4,6-tri-MOM phloracetophenone 
• 215257-15-1 3,3',4',5,7-pentahydroxy flavanone 

Downstream Products

• 480-18-2 (2S,3S)-taxifolin 3-O-β-D-glucoside 
• 3162-26-3 (2R,3R)-3,7-bis(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-2,3-dihydro-5-hydroxy-4H-1-benzopyran-4-one 
• 6685-67-2 2-(3,4-diacetoxyphenyl)-4-oxochroman-3,5,7-triyl triacetate 
• 174589-51-6 catechin-(4α->8)-ent-epicatechin 
• 78128-76-4 (2R,3R)-3,5,3'-trihydroxy-7,4'-dimethoxyflavanone 
• 37971-67-8 (2R,3R)-dihydro-quercetin-7,3′-dimethyl ether 
• 491-51-0 (2R,3R)-(+)-7-O-methyldihydroquercetin 
• 74628-44-7 7,3′,4′-O-trimethyltaxifolin 
• 480-18-2 taxifolin 

Relevant articles and documents

Acidic hydrolysis of astilbin and its application for the preparation of taxifolin from Rhizoma Smilacis Glabrae

The acidic hydrolysis of astilbin to produce its aglycone, taxifolin, was investigated in this study. The effects of aq. HCl concentration and temperature on the reaction were studied, and the kinetic parameters were calculated. The results showed that with higher aq. HCl concentration and temperature, the hydrolysis of astilbin became faster. The activation energy of the hydrolysis reaction under 1 mol L?1 aq. HCl was calculated with a value of 148.6 kJ mol?1. The reaction was successfully applied to produce taxifolin from a sample of Rhizoma Smilacis Glabrae. A simple method for the purification of taxifolin from Rhizoma Smilacis Glabrae was developed with purity of 97.5%.

Total Synthesis of the Natural Products Ulmoside A and (2 R,3 R)-Taxifolin-6- C -β- d -glucopyranoside

An efficient first total synthesis of highly polar ulmoside A and (2 R,3 R)-taxifolin-6- C -β- d -glucopyranoside, useful for the prevention of metabolic disorders, has been described. Key elements of the synthesis include a Sc(OTf) 3-catalyzed regio- and stereoselective C -glycosidation on taxifolin in 35percent yield with d -glucose and chiral semipreparative reverse-phase high-performance liquid chromatography (HPLC) for the separation of both taxifolins and the diastereomeric mixture of taxifolin-6- C -β- d -glucopyranosides. Correlation of the analytical data of synthetic ulmoside A and its diastereomer with a natural ulmoside A sample confirmed the assigned absolute stereochemistry of the natural products.

Taxifolin preparation method

The invention relates to a method for synthesizing a raw material medicine, in particular to a taxifolin preparation method, aiming to solve the technical problems that waste of plant resources and solvents is great during separation and purification of taxifolin from plants, complete synthesis methods of the taxifolin have long synthetic routes, many complicated raw ingredients are involved, theoverall yield is low and the methods are not suitable for industrial production in the prior art. The taxifolin preparation method has the advantages that dihydromyricetin is selected as a starting material, a crude taxifolin product is obtained by hydrolysis and catalysis closed-loop two-step reactions, and a qualified refined taxifolin product is obtained through purification and refining; the raw material is easy to obtain, the operation is simple, the cost is low, environment friendliness and small pollution are realized, and the taxifolin preparation method is suitable for industrial production.