522-12-3

Usage

Uses

1. Used in Pharmaceutical Applications:
Quercitrin is employed as an anti-inflammatory, antioxidant, and anti-hemorrhagic agent. Its antioxidant properties have been extensively investigated, particularly in streptozotocin (STZ)-induced diabetic rats. 3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyran-4-one has shown potential in modulating various biological pathways and providing therapeutic benefits in various conditions.
2. Used in Textile Industry:
Quercitrin has been used as a textile dye, specifically in the preparation of the flavine yellow shade. It is extracted from quercitron bark using high-pressure steam, and its presence in the dye is primarily responsible for its color properties.
3. Used in Food Industry:
Quercitrin can be found in various food sources, such as Tartary buckwheat and oak species like white oak or European red oak. Its presence in these food items contributes to their antioxidant and anti-inflammatory properties, making it a valuable component in the human diet.
4. Used in Research and Development:
Produced and qualified by HWI Pharma Services GmbH, Quercitrin is used in research and development for its exact content determination through quantitative NMR analysis. This allows for a better understanding of its chemical properties and potential applications in various industries.

Biochem/physiol Actions

Quercitrin is a glycoside flavonoid with antioxidant properties. Quercitrin has been reported to have anti-viral and anti-inflammatory effects.

InChI:InChI=1/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7?,15-,17+,18+,21-/m0/s1

Synthetic route

3-O-(2′′-O-galloyl-α-L-rhamnopyranosyl) quercetin (80229-08-9) → quercitrin (522-12-3)

Conditions	Yield
With ammonium hydroxide In methanol for 24h; Ambient temperature;

myricitrin (17912-87-7) → quercitrin (522-12-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogen; sodium hydroxide; 5%-palladium/activated carbon / 28 h / 40 °C / 15001.5 Torr 2.1: sodium hydroxide / 1 h / Reflux 2.2: 1 h / Reflux 3.1: N,N-dimethyl-formamide 3.2: 5 h / 80 - 100 °C View Scheme

C14H18O9 + 3,4-dihydroxybenzaldehyde (139-85-5) → quercitrin (522-12-3)

Conditions	Yield
Stage #1: C14H18O9; 3,4-dihydroxybenzaldehyde In N,N-dimethyl-formamide Stage #2: With L-proline In N,N-dimethyl-formamide at 80 - 100℃; for 5h; Solvent; Temperature;	28.9 g

acetone (67-64-1) + quercitrin (522-12-3) → 2''',3'''-isopropylidenequercitrin (69711-90-6)

Conditions	Yield
With hydrogenchloride In methanol

quercitrin (522-12-3) → L-rhamnose (73-34-7)

Conditions	Yield
With ethanol; sulfuric acid for 3h; Heating;
With α-L-rhamnosidase from Pichia angusta X349 In acetate buffer at 30℃; for 18h; pH=6.5; Enzymatic reaction;
Stage #1: quercitrin With sulfuric acid In 1,4-dioxane at 100℃; for 1h; Stage #2: With pyridine; D-cysteine In water at 60℃; for 1h; Stage #3: With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane at 60℃; for 0.5h;

quercitrin (522-12-3) → quercetol (117-39-5)

Conditions	Yield
With hydrogenchloride; ethanol for 1h; Heating;	122 mg
With naringinase In acetate buffer at 20℃; for 3h; pH=5.5; Enzymatic reaction;
Stage #1: quercitrin With sodium hydroxide; ascorbic acid at 20℃; for 2h; Darkness; Stage #2: With hydrogenchloride; water In methanol at 100℃; for 2h;
With flavonol 3-O-rhamnosyltransferase UGT78D1 from arabidopsis thaliana; UDP

quercitrin (522-12-3) → L-rhamnose (6014-42-2) + quercetol (117-39-5)

Conditions	Yield
With sulfuric acid In water at 100℃; for 1h; Product distribution;
Product distribution; acid hydrolysis;

quercitrin (522-12-3) → L-rhamnose (73-34-7) + quercetol (117-39-5)

Conditions	Yield
With hydrogenchloride In hydrogenchloride for 1h; Product distribution; Heating;

acetic anhydride (108-24-7) + quercitrin (522-12-3) → quercitrin heptaacetate (19229-45-9)

Conditions	Yield
With pyridine at 25℃; for 24h;

quercitrin (522-12-3) → L-Rhamnose (3615-41-6) + quercetol (117-39-5)

Conditions	Yield
With hydrogenchloride; water In methanol for 2h; Reflux;

quercitrin (522-12-3) → C21H18(2)H2O11

Conditions	Yield
With water-d2; ammonium formate In aq. buffer at 90℃; pH=3; Temperature; Time; pH-value; Darkness; regioselective reaction;

quercitrin (522-12-3) → p-Coumaric Acid (7400-08-0)

Conditions	Yield
With sodium hydroxide; ascorbic acid at 20℃; for 2h; Darkness;

quercitrin (522-12-3) → quercetin-3-rhamnoside oxide

Conditions	Yield
With UPLC columns (Waters BEH C18 column (2.1 × 50 mm,1.7 μm), Waters HSS T3 (2.1 × 100 mm, 1.8 μm)

Upstream product

• 80229-08-9 3-O-(2′′-O-galloyl-α-L-rhamnopyranosyl) quercetin 
• 17912-87-7 myricitrin 
• 139-85-5 3,4-dihydroxybenzaldehyde 

Downstream Products

• 69711-90-6 2''',3'''-isopropylidenequercitrin 
• 117-39-5 quercetol 
• 6014-42-2 L-rhamnose 
• 73-34-7 L-rhamnose 
• 3615-41-6 L-Rhamnose 
• 7400-08-0 p-Coumaric Acid 
• 19229-45-9 Acetic acid 2-acetoxy-5-[5,7-diacetoxy-4-oxo-3-((3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-4H-chromen-2-yl]-phenyl ester 
• 19229-45-9 quercitrin heptaacetate 

Relevant academic research and scientific papers

Flavonoids of Polygonum sieboldi and P. filiforme

Five flavonoids containing a new flavonol glycoside were isolated from Polygonum sieboldi and P. filiforme.The structure of the new compound was determined as quercetin 3-rhamnoside 2"-gallate by chemical and spectroscopic data.

A new method for preparing engelhardtia leaves fall (by machine translation)

The invention relates to a raw material synthesis method of medicine, in particular to a new method for preparing engelhardtia leaves off. In order to solve the problems of the prior art fall bride extracted from plants [...], because the content of the new engelhardtia leaves drop lower, using the extraction method is very difficult to obtain a good yield of the product, and the plant waste of resources and solvent is large the technical problem, the present invention provides a method of synthesizing new engelhardtia leaves fall, to [...] as the starting material, first hydrogenation to obtain the dihydro [...], then in certain alkaline conditions, hydrolysis reaction, generating hydroxy acetophenone intermediate (2 - (3, 4, 5 - trihydroxy - 6 - methyl four hydrogenation - 2 - chromene) - 1 - (2, 4, 6 - trihydroxy phenyl) - acetyl), with 3, 4 - dihydroxy benzaldehyde catalytic cyclization, generating fall bride [...], final refining receive quality content of 98% or more of the new woman [...]. Prepared by the method of the new engelhardtia leaves falling, raw materials are easy, simple operation, low cost, and is suitable for industrial production. (by machine translation)

QUERCETIN-3-O-α-, AN AGLYCONE-LIKE FLAVONOL GLYCOSIDE FROM LIBOCEDRUS BIDWILLII

Quercetin-3-O-α-, a new natural product with unusual mixed acylation, has been found accompanying the biflavonoids in L. bidwillii.Aglycone-like chromatographic properties resulted in this compound being missed in the initial chemotaxonomic screening of flavonoid glycosides in Libocedrus, Key Word Index - Libocedrus bidwillii; Cupressaceae; leaf; quercetin 3-O-rhamnoside; mixed acylation; p-coumaroyl; p-hydroxybenzoyl; aglycon-like.