522-12-3

Basic information

• Product Name: 3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyran-4-one
• Synonyms: 3,3’,4’,5,7-pentahydroxy-flavon3-(6-deoxy-alpha-l-mannopyranoside);3,3’,4’,5,7-pentahydroxy-flavon3-rhamnoside;3,3’,4’,5,7-pentahydroxyflavone-3-l-rhamnoside;3-[(6-deoxy-alpha-l-mannopyranosyl)-oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy;-4h-1-benzopyran-4-one;4h-1-benzopyran-4-one,3-((6-deoxy-alpha-l-mannopyranosyl)oxy)-2-(3,4-dihydroxy;7-dihydroxy-phenyl)-;c.i.75720
• CAS NO: 522-12-3
• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.38
• EINECS: 208-322-5
• Product Categories: Flavanols;Biochemistry;Flavonoids;Biochemicals Found in Plants;Bioflavonoids;Nutrition Research;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 522-12-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 174-183°C
• Boiling Point: 477.14°C (rough estimate)
• Flash Point: 288.3 °C
• Appearance: /
• Density: 1.3943 (rough estimate)
• Vapor Pressure: 5.22E-28mmHg at 25°C
• Refractive Index: 1.5376 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
• PKA: 6.17±0.40(Predicted)
• Stability: Hygroscopic
• Merck: 8125
• BRN: 68135
• CAS DataBase Reference: 3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyran-4-one(522-12-3)
• EPA Substance Registry System: 3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyran-4-one(522-12-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: UZ5950000
• F: 10-23
• Hazardous Substances Data: 522-12-3(Hazardous Substances Data)

Usage

Chemical Properties

Yellow solid

Uses

Different sources of media describe the Uses of 522-12-3 differently. You can refer to the following data:
1. antiinflammatory, antioxidant, antihemmorrhagic
2. Quercitrin is known as an bio flavonoid antioxidant and was investigated extensively in its antioxidant potential in streptrozotocin (STZ)-induced diabetic rats. Quercitrin is also a constituent of th e dye quercitron. Quercitrin can be found in Tartary buckwheat and in oaks species such as white oak or European red oak.
3. Quercitrin has been used as textile dye. Flavine yellow shade is prepared by extracting quercitron bark with high pressure steam and consists mainly of quercitrin: Tisdale, Can. Text. J. 57, 44 (1941).

Definition

ChEBI: A quercetin O-glycoside that is quercetin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage.

General Description

Produced and qualified by HWI pharma services GmbH.Exact content by quantitative NMR can be found on the certificate.

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

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

Downstream Products

• 7400-08-0 p-Coumaric Acid 
• 3615-41-6 L-Rhamnose 
• 117-39-5 quercetol 
• 19229-45-9 quercitrin heptaacetate 
• 73-34-7 L-rhamnose 
• 6014-42-2 L-rhamnose 
• 69711-90-6 2''',3'''-isopropylidenequercitrin 
• 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 

Relevant articles and documents

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.

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.