3D Mol Similar

Rutin

: Iupac Name：2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one; CAS No.: 153-18-4; Molecular Weight：610.5175; Modify Date.: 2022-11-12 07:05; Introduction: Found in many plants, especially the buckwheat plant. Identity with Ilixanthin. Capillary protectant. Rutin is colored brown by tobacco enzyme under experimental conditions. View more+

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1. Names and Identifiers

: 1.1 Name; Rutin; 1.2 Synonyms; 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}methyl)tetrahydro-2H-pyran-2-yl]oxy}-4H-chromen-4-one 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-α-L-mannopyranosyl)-Β-D-glucopyranoside 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-α-L-mannopyranosyl)-Β-D-mannopyranoside 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl-6-O-(6-deoxy-α-L-mannopyranosyl)-Β-D-glucopyranoside 3-((6-O-(6-Deoxy-α-L-mannopyranosyl)-Β-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one 3,3',4',5,7-Pentahydroxyflavone 3-(O-rhamnosylglucoside) 3,3',4',5,7-Pentahydroxyflavone-3-rutinoside 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-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-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-( 4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-α-L-mannopyranosyl)-Β-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy- 4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-α-L-mannopyranosyl)-Β-D-glucopyranosyl]-oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy- 4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-α-L-mannopyranosyl)-Β-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy- 4h-1-benzopyran-4-one,3-[[6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucop 5-18-05-00519 bioflavonoid Birutan Eldrin globularicitrin ilixathin Melin MFCD00006830 Myrticolorin Osyritin Osyritrin Oxyritin Paliuroside Quercetin 3-O-rutinoside Quercetin 3-O-Β-D-rutinoside Quercetin 3-O-Β-rutinoside Quercetin 3-Β-rutinoside Quercetin-3-O-rutinoside Rutabion Rutin hydrate Rutin trihydrate Rutinic acid Rutinion acid Rutoside Rutozyd Tanrutin Violaquercitrin Vitamin P trihydrate; View all

1.3 CAS No.: 153-18-4

1.4 CID: 5280805

1.5 EINECS(EC#): 205-814-1

1.6 Molecular Formula: C27H30O16 (isomer)

1.7 Inchi: InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1

1.8 InChIkey: IKGXIBQEEMLURG-NVPNHPEKSA-N

1.9 Canonical Smiles: CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O

1.10 Isomers Smiles: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O

2. Properties

2.1 Density: 1.82

2.1 Melting point: 195℃

2.1 Boiling point: 983.1 °C at 760 mmHg

2.1 Refractive index: 1.765

2.1 Flash Point: 325.4 °C

2.1 Precise Quality: 610.15300

2.1 PSA: 269.43000

2.1 logP: -1.68710

2.1 Solubility: pyridine: 50?mg/mL

2.2 Appearance: Pale-Yellow Crystalline Solid

2.3 Chemical Properties: Pale-Yellow Crystalline Solid

2.4 Color/Form: yellow to green

2.5 pKa: 6.17±0.40(Predicted)

2.6 Water Solubility: 12.5 g/100 mL

2.7 Stability: Stable at room temperature in closed containers under normal storage and handling conditions.

2.8 StorageTemp: Keep in dark place,Sealed in dry,2-8°C

3. Use and Manufacturing

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

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

4. Safety and Handling

4.1 Hazard Codes: Xn; Xi

4.1 Risk Statements: R22

4.1 Safety Statements: S24/25

4.1 RIDADR: 20kgs

4.1 WGK Germany: 3

4.1 RTECS: VM2975000

4.1 Safety: Hazard Codes of Rutin (CAS NO.153-18-4):?Xn,Xi
Risk Statements: 22-36/37/38
R22: Harmful if swallowed.?
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26
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

4.2 Specification: ?Rutin , its cas register number is 153-18-4. the other name is rutoside , quercetin-3-rutinoside and sophorin , is a citrus flavonoid glycoside found in buckwheat, the leaves and asparagus,and petioles of Rheum species, . Rutin is also found in the fruit of the Fava D'Anta tree ,fruits and fruit rinds and berries such as mulberry and cranberries. Its name comes from the name of Ruta graveolens, a plant that also contains rutin.
The Health effects information of Rutin (CAS NO.153-18-4):
1. It has anti-inflammatory activity.
2. It?inhibits platelet aggregation, making the blood thinner and improves circulation.?
3. It inhibits aldose reductase activity. Aldose reductase is an enzyme normally present in the eye and elsewhere in the body.

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

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : in DMSO-d6

Predict 1H proton NMR

IR : KBr disc

IR : nujol mull

7. Other Information

7.0 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.

7.1 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.

7.2 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.; View all

7.3 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).

7.4 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 .

7.5 Merck: 8304

7.6 Chemical Properties: Pale-Yellow Crystalline Solid

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

7.8 Uses: antidiabetic, dipeptidyl peptidase–4 inhibitor

7.9 Uses: For nutritional product

7.10 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.

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

7.12 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.]

8. Computational chemical data

Molecular Weight: 610.5175g/mol
Molecular Formula: C₂₇H₃₀O₁₆
Compound Is Canonicalized: True
XLogP3-AA: -1.3
Exact Mass: 610.15338487
Monoisotopic Mass: 610.15338487
Complexity: 1020
Rotatable Bond Count: 6
Hydrogen Bond Donor Count: 10
Hydrogen Bond Acceptor Count: 16
Topological Polar Surface Area: 266
Heavy Atom Count: 43
Defined Atom Stereocenter Count: 10
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB4PgAAAAAAAAAAAAAAAAAAAAAAAAA0aIECAAAAAACBQAAAGgAACAAADBSwmAMyDoAABgCIAqBSAAICCAAkIAAIiAFGiMgdNzaGNR6ieWGl4BUPuQfI7LzOIAABCAAIQABAAAIQABCAAAAAAAAAAA==

9. Question & Answer

What is the significance of rutin in cardiovascular health and its potential applications? Jun 19 2022
Introduction Rutin, a flavonoid substance, is widely found in nature and is present in various plants of the Rutaceae and Sectaceae families. It has been recognized for its significant protective effe..

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