| Identification | More | [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 | Back Directory | [Appearance]
Pale-Yellow Crystalline Solid | [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 | [Usage]
Found in many plants, especially the buckwheat plant. Identity with ilixanthin. Capillary protectant | [Detection Methods]
HPLC,NMR | [Merck ]
8304 | [Stability:]
Hygroscopic | [LogP]
-2.020 (est) | [Uses]
rutin(153-18-4) 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) | [NIST Chemistry Reference]
Flavone-3-rutinoside, 3,3',4',5,7-pentahydroxy(153-18-4) | [Storage Precautions]
Light sensitive | [EPA Substance Registry System]
153-18-4(EPA Substance) |
| Safety Data | Back Directory | [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 | [F ]
8 | [HS Code ]
29329900 | [Toxicity]
LD50 i.v. in mice: 950 mg/kg (propylene glycol soln) (Harrison) |
| Hazard Information | Back Directory | [Description]
Rutin(153-18-4) 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(153-18-4) 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(153-18-4) 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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