Rutin

Template:Chembox E numberTemplate:Chembox RTECSTemplate:Chembox AppearanceTemplate:Chembox MeltingPtTemplate:Chembox SolubilityInWaterTemplate:Chembox NFPA

Rutin

Names
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]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one
Preferred IUPAC name 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]-4H-chromen-4-one
Other names Rutoside Phytomelin Sophorin Birutan Eldrin Birutan Forte Rutin trihydrate Globularicitrin Violaquercitrin
Identifiers
CAS Number	153-18-4 Y
3D model (JSmol)	Interactive image
ChemSpider	4444362 N
DrugBank	DB01698 Y
ECHA InfoCard
KEGG	C05625 N
PubChem CID	5280805
UNII	5G06TVY3R7 Y
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
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
Properties
Chemical formula	C27H30O16
Molar mass	610.52 g·mol−1
Hazards
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]Associate Editor(s)-in-Chief: Sheng Shi, M.D. [2]

Rutin, also called rutoside, quercetin-3-O-rutinoside and sophorin, is the glycoside between the flavonol quercetin and the disaccharide rutinose (α-L-rhamnopyranosyl-(1→6))-β-D-glucopyranose). In the fava d'anta tree, the synthesis is done via a rutin synthase activity.

Occurrences

Rutin is one of the phenolic compounds found in the invasive plant species Carpobrotus edulis and contributes to the antibacterial and antioxidant properties of the plant.

Its name comes from the name of Ruta graveolens, a plant that also contains rutin.

In food

Rutin is a citrus flavonoid glycoside found in many plants including buckwheat, the leaves and petioles of Rheum species, and asparagus. Tartary buckwheat seeds have been found to contain more rutin (about 0.8-1.7% dry weight) than common buckwheat seeds (0.01% dry weight). Rutin is also found in the fruit of the fava d'anta tree (from Brazil), fruits and flowers of the pagoda tree, fruits and fruit rinds (especially the citrus fruits orange, grapefruit, lemon, and lime) and apple; berries such as mulberry, ash tree fruits, aronia berries and cranberries.

Rutin is one of the primary flavonols found in 'clingstone' peaches.

Chemical relatives

Rutin (quercetin rutinoside), like quercitrin, is a glycoside of the flavonoid quercetin. As such, the chemical structures of both are very similar, with the difference existing in the hydroxyl functional group. Both quercetin and rutin are used in many countries as medications for blood vessel protection, and are ingredients of numerous multivitamin preparations and herbal remedies.

Role as ligand

It can combine with cations,Template:Which supplying nutrients from the soil to the cells in plants. In humans, it attaches to the iron ion Fe²⁺, preventing it from binding to hydrogen peroxide, which would otherwise create a highly reactive free radical that may damage cells. It is also an antioxidant.

Furthermore, it has been shown to inhibit in vitro the vascular endothelial growth factor in subtoxic concentrations, so acts as an inhibitor of angiogenesis. This finding may have potential relevance for the control of some cancers.

Health effects

While a body of evidence for the effects of rutin and quercetin is available in mice, rats, hamsters, and rabbits, as well as in vitro studies, no clinical studies directly demonstrate significant, positive effects of rutin as dietary supplement in humans.

• Rutin inhibits platelet aggregation, as well as decreases capillary permeability, making the blood thinner and improving circulation.
• Rutin shows anti-inflammatory activity in some animal and in vitro models.
• Rutin inhibits aldose reductase activity. Aldose reductase is an enzyme normally present in the eye and elsewhere in the body. It helps change glucose into the sugar alcohol sorbitol.
• Recent studies show rutin could help prevent blood clots, so could be used to treat patients at risk of heart attacks and strokes.
• Some evidence also shows rutin can be used to treat hemorrhoids, varicosis, and microangiopathy.
• Rutin increases thyroid iodide uptake in rats without raising serum T3 or T4.
• Rutin is also an antioxidant; compared to quercetin, acacetin, morin, hispidulin, hesperidin, and naringin, it was found to be the strongest.Template:Verify credibility However, in other trials, the effects of rutin were lower or negligible compared to those of quercetin.

Hydroxyethylrutosides, synthetic hydroxyethyl acetylations of rutin, are used in the treatment of chronic venous insufficiency.

In veterinary medicine

Rutin may have a veterinary use in the management of chylothorax in dogs and cats.

Metabolism

The enzyme quercitrinase can be found in Aspergillus flavus. It is an enzyme in the rutin catabolic pathway.

References

Template:Chembox header| Rutin
Rutin
Systematic name	2-(3,4-dihydroxyphenyl)- 4,5-dihydroxy-3-[3,4,5- trihydroxy-6-[(3,4,5- trihydroxy-6-methyl- oxan-2-yl)oxymethyl] oxan-2-yl]oxy-chromen- 7-one
Chemical formula	C27H30O16
Molecular mass	610.52 g/mol
Density	x.xxx g/cm3
Melting point	xx.x °C
Boiling point	xx.x °C
CAS number	[153-18-4]
SMILES	xxxxx
Template:Chembox header | Disclaimer and references

Rutin, also called rutoside, quercetin-3-rutinoside and sophorin, is a citrus flavonoid glycoside found in buckwheat, the leaves and petioles of Rheum species, and the fruit of the Fava D'Anta tree (from Brazil), as well as other sources. Rutin is the glycoside between the flavonol quercetin and the disaccharide rutinose.

It can combine with cations, supplying nutrients from the soil to the cells in plants. In humans, it attaches to the iron ion Fe²⁺, preventing it from binding to hydrogen peroxide which would otherwise create a highly reactive free radical that may damage cells. It is also an antioxidant, and therefore plays a role in inhibiting some cancers.

Rutin also strengthens the capillaries, and therefore can reduce the symptoms of haemophilia. It also may help to prevent a common unpleasant-looking venous edema of the legs. Rutin, as ferulic acid, can reduce the cytotoxicity of oxidized LDL cholesterol and lower the risk of heart disease.