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

Colour Index 

75730

form 

powder

pka

6.17±0.40(Predicted)

color 

yellow to green

Water Solubility 

12.5 g/100 mL

Merck 

8304

Stability:

Hygroscopic

LogP

-2.020 (est)

CAS DataBase Reference

153-18-4(CAS DataBase Reference)

NIST Chemistry Reference

Flavone-3-rutinoside, 3,3',4',5,7-pentahydroxy(153-18-4)

EPA Substance Registry System

Rutin (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

F 

8

HS Code 

29381000

Toxicity

LD50 i.v. in mice: 950 mg/kg (propylene glycol soln) (Harrison)

MSDS

• Language:English Provider:Rutin sulfate
• Language:English Provider:ACROS

Rutin Usage And Synthesis

Description

Rutin 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 Properties

Pale-Yellow Crystalline Solid

Physical properties

Appearance: 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.

History

In 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.

Uses

Found in many plants, especially the buckwheat plant. Identity with Ilixanthin. Capillary protectant. Rutin is colored brown by tobacco enzyme under experimental conditions.

Uses

antidiabetic, dipeptidyl peptidase–4 inhibitor

Uses

For nutritional product

Uses

rutin 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.

Definition

ChEBI: A rutinoside that is quercetin with the hydroxy group at position C-3 substituted with glucose and rhamnose sugar groups.

Pharmacology

As 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 Use

Rutin 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 .

Side effects

Rutin is usually well tolerated. And since rutin is mostly derived from fruits and vegetables, it has mostly no adverse effects when taken orally, and rutin supplements may be safe when taken in doses of up to 600 mg per day for up to 12 weeks. Side effects may include headache or stomach upset.

target

COX | NOS | p38MAPK | JNK | AP-1 | TGF-β/Smad | NF-kB | ERK | Nrf2 | HO-1 | p53 | IL Receptor

Purification Methods

The 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.]

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