Rutin

Rutin Basic information
Product Name:Rutin
Synonyms:4-dihydroxyphenyl)-5,7-dihydroxy-yranosyl]oxy]-2-(;myrticalorin;myrticolorin;myticolorin;paliuroside;phytomelin;quercetin,3-(6-0-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranoside);quercetin,3-(6-o-alpha-l-rhamnopyranosyl-beta-d-glucopyranoside)
CAS:153-18-4
MF:C27H30O16
MW:610.52
EINECS:205-814-1
Product Categories:Inhibitors;Natural Plant Extract;Intermediates & Fine Chemicals;Pharmaceuticals;Biochemistry;Disaccharides;Flavonoids;Glycosides;Sugars;Flavanols;ONGLYZA;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Plant extracts;Herb extract;Aromatics;Heterocycles;Oligosaccharides;reference substance;TROXEPURE;153-18-4
Mol File:153-18-4.mol
Rutin Structure
Rutin Chemical Properties
Melting point 195 °C (dec.)(lit.)
alpha D23 +13.82° (ethanol); D23 -39.43° (pyridine)
Boiling point 576.13°C (rough estimate)
density 1.3881 (rough estimate)
refractive index 1.7650 (estimate)
storage temp. Keep in dark place,Sealed in dry,2-8°C
solubility pyridine: 50 mg/mL
form powder
pka6.17±0.40(Predicted)
Colour Index 75730
color yellow to green
Water Solubility 12.5 g/100 mL
Merck 8304
Stability:Hygroscopic
LogP-2.020 (est)
CAS DataBase Reference153-18-4(CAS DataBase Reference)
NIST Chemistry ReferenceFlavone-3-rutinoside, 3,3',4',5,7-pentahydroxy(153-18-4)
EPA Substance Registry SystemRutin (153-18-4)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38
Safety Statements 24/25-36-26
WGK Germany 3
RTECS VM2975000
8
HS Code 29381000
ToxicityLD50 i.v. in mice: 950 mg/kg (propylene glycol soln) (Harrison)
MSDS Information
ProviderLanguage
Rutin sulfate English
ACROS English
Rutin Usage And Synthesis
DescriptionRutin is widely found in nature and is almost contained in all of the Rutaceae and Sectaceae plants, especially abundant in Rutaceae, Rutaceae, Epacridaceae of leguminous, buckwheat of Polygonaceae, Eulali of Hypericum, Berchemia polyphylla var. leioclada of Tetranychidae, and wild wutong leaves of thistle, which are also used as raw materials in rutin extraction. In addition, it also exists in the Ilex pubescens of Aquifoliaceae, Forsythia of Oleaceae, pagoda tree pod of Leguminosae, tobacco, jujube, apricots, flavedo, tomatoes, and other plants.
At present, rutin in China mainly extracted from the Sophora japonica Linn of leguminous, which is listed in top grade of Shen Nong’s Classic Materia Medica. In addition, tartary buckwheat, which is rich in rutin and flavonoids, is native to India and now produced in China’s northwest, southwest, north, south, and other places.
Chemical PropertiesPale-Yellow Crystalline Solid
Physical propertiesAppearance: light yellow or yellow-green needle crystal or crystalline powder, tastes slightly bitter, usually contains three crystal water, melting point at 176– 178 °C. Solubility: Rutin is soluble in methanol, pyridine, alkaline solution, and boiling water and hardly soluble in cold water, chloroform, carbon disulfide, ether, benzene, and petroleum ether.
HistoryIn the mid-1930s, Hungarian scientist Szent Gyorgy firstly separated the flavonoid mixture. After the German pharmacy firstly made it into ranosine in 1942, the concept of vitamin P has been established worldwide. Further study proved that rutin was the most important flavonoids of vitamin P. These compounds were certified to have effects on many diseases in medical.
Recently, the research of rutin mainly focuses on the extraction process improvement, pharmacological effects, and pharmacodynamics research, aiming at improvement of its bioavailability through the development of different dosage forms. As for the extraction process, new extraction and purification methods have been developed since the original alkali extraction acid precipitation method. These methods greatly improve its extraction efficiency and reduce cost, including hot water precipitation, hot water extraction with macroporous resin adsorbing purification, ultrasonic radiation, hot water extraction with alcohol precipitation, cold alkali percolation extraction with acid precipitation, continuous reflux extraction, ethanol extraction, supercritical CO2 extraction, and enzymatic hydrolysis .
In recent years, advanced rutin dosage forms, such as rutin cyclodextrin saturation, HPMC controlled release tablets, solid dispersion tablets, coprecipitate, and rutin effervescent particles, greatly improve the rutin dissolution rate and its bioavailability.

UsesFound in many plants, especially the buckwheat plant. Identity with Ilixanthin. Capillary protectant. Rutin is colored brown by tobacco enzyme under experimental conditions.
UsesFor nutritional product
Usesantidiabetic, dipeptidyl peptidase–4 inhibitor
Usesrutin is described as helping to tighten and strengthen skin capillaries, and as such it could help prevent a couperose condition. It also demonstrates anti-oxidant properties. Rutin is a flavonoid found in rue leaves, buckwheat, and other plants.
DefinitionChEBI: A rutinoside that is quercetin with the hydroxy group at position C-3 substituted with glucose and rhamnose sugar groups.
PharmacologyAs a flavonoid substance, rutin has a significant protective effect on the cardiovascular system, including the endothelium-dependent vasodilation through NO-guanylate cyclase pathway, antagonization on platelet-activating factor (PAF), inhibition on subsequent reactions induced by PAF binding to its specific membrane receptor, and protection of myocardial cells .
Rutin also has good free radical scavenging effects. Studies showed that rutin and its derivatives had a strong free radical scavenging effect, of which rutin possessed the strongest antioxidant activity. Rutin removed superoxide anion and hydroxyl radicals, exerted a strong anti-lipid peroxidation, protected mitochondria, and enhanced the activity of superoxide dismutase (SOD).
Clinical UseRutin is mainly used for the adjuvant treatment of hypertension and treatment for the prevention of other bleedings due to lack of rutin, such as cerebral hemorrhage, retinal hemorrhage, purpura, acute hemorrhagic nephritis, chronic bronchitis, and abnormal blood osmolality, restoration of capillary elastic embolism, and also for the prevention and treatment of diabetes and hyperlipidemia . Troxerutin, the most important active ingredient in hydroxy rutin, is used in the treatment of varicose veins/venous disorders, hemorrhoids, lymphedema, and postoperative edema, treatment of thrombosis and cerebrovascular disease, and also in the treatment of diabetes and liver disease. Since rutin has a mild effect with low cost and less adverse reactions, especially its remarkable effect on acute cerebral infarction, it is of great worth on promotion and application of rutin .
targetCOX | NOS | p38MAPK | JNK | AP-1 | TGF-β/Smad | NF-kB | ERK | Nrf2 | HO-1 | p53 | IL Receptor
Purification MethodsThe vitamin crystallises from MeOH or water/EtOH, dry it in air, then dry it further for several hours at 110o or in high vacuum at 120o. It forms yellow crystals from EtOH/Me2CO/H2O (2:1:1). It has also been purified by passing (0.5g) through a Kieselgel column (30 x 5cm) with EtOAc/MeOH/H2O (100:20:15), and after 750mL have passed through, the yellow fraction of 250mL gives the glycoside (0.3g) on evaporation. [H.rhammer et al. Chem Ber 101 1183 1968, Marini-Bettòlo Gazz Chim Ital 80 631 1950, Beilstein 18/5 V 519.]
Rutin Preparation Products And Raw materials
Preparation ProductsENZYMATICALLYDECOMPOSEDRUTIN-->Quercetin-->Enzymaticallv modified rutin-->3,4'-DIMETHOXY-3',5,7-TRIHYDROXYFLAVONE-->TAMARIXETIN-->KERACYANIN CHLORIDE-->β-D-Glucopyranoside, (2E)-3-(4-hydroxyphenyl)-2-propen-1-yl
RUTIN (FOR BIOCHEMISTRY) α-D-Glucosyl rutin Rutin NF11,DAB10 Rutin DAB9 Ombuoside RUTIN, WATER SOLUBLE rutin-N-mustard Vitamin A B12 VITAMIN B12 rutin sulfate 3-[[6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one, tetrakis(2-hydroxyethyl) ether Vitamin B series ALPHAG-RUTIN Cocarboxylase Venalot (+)-RUTIN HYDRATE,RUTIN HYDRATE,(+)-RUTIN TRIHYDRATE,RUTIN TRIHYDRATE SODIUM RUTIN SULFATE Typhaneoside

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