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153-18-4

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Identification

Name
Rutin
CAS
153-18-4
Synonyms
3,3',4',5,7-PENTAHYDROXYFLAVONE-3-RHAMNOGLUCOSIDE
3,3',4',5,7-PENTAHYDROXYFLAVONE-3-RUTINOSIDE
3-[[6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4h-1-benzopyran-4-one
BIRUTAN
c.i. 75730
ELDRIN
GLOBULARIACITRIN
MELIN
OSYRITIN
QUERCETIN-3-RUTINOSIDE
(+)-RUTIN
RUTIN
RUTOSIDE
SOPHORIN
TANRUTIN
VITAMIN P
3,3’,4’,5,7-pentahydroxy-flavon3-(o-rhamnosylglucoside)
3-[[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,74H-1-Benzopyran-4-one
3-[[6-O-(-Deoxy-L-mannopyranosyl)-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
4-dihydroxyphenyl)-5,7-dihydroxy-yranosyl]oxy]-2-(
EINECS(EC#)
205-814-1
Molecular Formula
C27H30O16
MDL Number
MFCD00006830
Molecular Weight
610.52
MOL File
153-18-4.mol

Chemical Properties

Appearance
Pale-Yellow Crystalline Solid
Melting point 
195 °C (dec.)(lit.)

mp 
195 °C (dec.)(lit.)

Boiling point 
576.13°C (rough estimate)
alpha 
D23 +13.82° (ethanol); D23 -39.43° (pyridine)
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

pka
6.17±0.40(Predicted)
Colour Index 
75730
color 
yellow to green

Water Solubility 
12.5 g/100 mL
Usage
Found in many plants, especially the buckwheat plant. Identity with ilixanthin. Capillary protectant
Detection Methods
HPLC,NMR
Merck 
8304
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.
CAS DataBase Reference
153-18-4(CAS DataBase Reference)
Storage Precautions
Light sensitive
NIST Chemistry Reference
Flavone-3-rutinoside, 3,3',4',5,7-pentahydroxy(153-18-4)
EPA Substance Registry System
153-18-4(EPA Substance)

Safety Data

Hazard Codes 
Xn,Xi
Risk Statements 
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
Safety Statements 
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
WGK Germany 
3

RTECS 
VM2975000

8
HS Code 
29329900
Toxicity
LD50 i.v. in mice: 950 mg/kg (propylene glycol soln) (Harrison)

Raw materials And Preparation Products

Material Safety Data Sheet(MSDS)

Hazard Information

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.
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 .
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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