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Rutin

Names
IUPAC name 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one
Preferred IUPAC name 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3--4H-chromen-4-one
Other names Rutoside Phytomelin Sophorin Birutan Eldrin Birutan Forte Rutin trihydrate Globularicitrin Violaquercitrin Quercetin rutinoside
Identifiers
CAS Number	153-18-4
3D model (JSmol)	Interactive image
ChemSpider	4444362
DrugBank	DB01698
ECHA InfoCard	100.005.287
KEGG	C05625
PubChem CID	5280805
RTECS number	VM2975000
UNII	5G06TVY3R7
CompTox Dashboard (EPA)	DTXSID3022326
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	610.521 g·mol
Appearance	Solid
Melting point	242 °C (468 °F; 515 K)
Solubility in water	12.5 mg/100 mL 13 mg/100mL
Pharmacology
ATC code	C05CA01 (WHO)
Hazards
NFPA 704 (fire diamond)	2 0 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

Rutin, also called rutoside, quercetin-3-O-rutinoside and sophorin, is the glycoside combining the flavonol quercetin and the disaccharide rutinose (α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranose). It is a citrus flavonoid found in a wide variety of plants including citrus fruit.

Occurrences

Rutin is one of the phenolic compounds found in the invasive plant species Carpobrotus edulis and contributes to the antibacterial 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 one of the primary flavonols found in 'clingstone' peaches. It is also found in green tea infusions.

Approximate rutin content per 100g of selected foods, based on the Phenol-Explorer database:

332 mg Capers, spice
45 mg Olive , raw
36 mg Buckwheat, whole grain flour
23 mg Asparagus, raw
19 mg Black raspberry, raw
11 mg Red raspberry, raw
9 mg Buckwheat, groats, thermally treated
6 mg Buckwheat, refined flour
6 mg Greencurrant
6 mg Plum, fresh
5 mg Blackcurrant, raw
4 mg Blackberry, raw
3 mg Tomato , whole, raw
2 mg prune
2 mg Fenugreek, fresh
2 mg Marjoram, dried
2 mg Tea , infusion
1 mg Grape, raisin
1 mg Zucchini, raw
1 mg Apricot, raw
1 mg Tea , infusion
0 mg apple
0 mg redcurrant
0 mg Grape
0 mg Tomato, whole, raw

Research

Rutin (rutoside or rutinoside) and other dietary flavonols are under preliminary clinical research for their potential biological effects, such as in reducing post-thrombotic syndrome, venous insufficiency, or endothelial dysfunction, but there was no high-quality evidence for their safe and effective uses as of 2016. As a flavonol among similar flavonoids, rutin has low bioavailability due to poor absorption, high metabolism, and rapid excretion that collectively make its potential for use as a therapeutic agent limited.

In mouse brain tissue, rutin appears to upregulate CB₁ receptors, peroxisome proliferator-activated receptor-α coactivator (PGC-1α) and sirtuin 1 (SIRT1).

Metabolism

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

References

1. Merck Index, 12th Edition, 8456
2. Krewson CF, Naghski J (Nov 1952). "Some physical properties of rutin". Journal of the American Pharmaceutical Association. American Pharmaceutical Association. 41 (11): 582–7. doi:10.1002/jps.3030411106. PMID 12999623.
3. van der Watt E, Pretorius JC (2001). "Purification and identification of active antibacterial components in Carpobrotusedulis L.". Journal of Ethnopharmacology. 76 (1): 87–91. doi:10.1016/S0378-8741(01)00197-0. PMID 11378287.
4. ^ Kreft S, Knapp M, Kreft I (Nov 1999). "Extraction of rutin from buckwheat (Fagopyrum esculentumMoench) seeds and determination by capillary electrophoresis". Journal of Agricultural and Food Chemistry. 47 (11): 4649–52. doi:10.1021/jf990186p. PMID 10552865.
5. Chang S, Tan C, Frankel EN, Barrett DM (Feb 2000). "Low-density lipoprotein antioxidant activity of phenolic compounds and polyphenol oxidase activity in selected clingstone peach cultivars". Journal of Agricultural and Food Chemistry. 48 (2): 147–51. doi:10.1021/jf9904564. PMID 10691607.
6. Malagutti AR, Zuin V, Cavalheiro ÉT, Henrique Mazo L (2006). "Determination of Rutin in Green Tea Infusions Using Square‐Wave Voltammetry with a Rigid Carbon‐Polyurethane Composite Electrode". Electroanalysis. 18 (10): 1028–1034. doi:10.1002/elan.200603496.
7. foods in which the polyphenol Quercetin 3-O-rutinoside is found
8. ^ "Flavonoids". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis, Oregon. November 2015. Retrieved 25 February 2018.
9. Morling, J. R; Yeoh, S. E; Kolbach, D. N (2015). "Rutosides for treatment of post-thrombotic syndrome". Cochrane Database of Systematic Reviews (9): CD005625. doi:10.1002/14651858.CD005625.pub3. PMID 26376212.
10. Martinez-Zapata, M. J; Vernooij, R. W; Uriona Tuma, S. M; Stein, A. T; Moreno, R. M; Vargas, E; Capellà, D; Bonfill Cosp, X (2016). "Phlebotonics for venous insufficiency". Cochrane Database of Systematic Reviews. 4: CD003229. doi:10.1002/14651858.CD003229.pub3. PMID 27048768.
11. Sharma, Charu; Sadek, Bassem; Goyal, Sameer N.; Sinha, Satyesh; Kamal, Mohammad Amjad; Ojha, Shreesh (2015-01-01). "Small Molecules from Nature Targeting G-Protein Coupled Cannabinoid Receptors: Potential Leads for Drug Discovery and Development". Evidence-based Complementary and Alternative Medicine : eCAM. 2015. doi:10.1155/2015/238482. ISSN 1741-427X. PMC 4664820. PMID 26664449.{{cite journal}}: CS1 maint: unflagged free DOI (link)
12. quercitrinase on www.brenda-enzymes.org
13. Tranchimand S, Brouant P, Iacazio G (Nov 2010). "The rutin catabolic pathway with special emphasis on quercetinase". Biodegradation. 21 (6): 833–59. doi:10.1007/s10532-010-9359-7. PMID 20419500.

External links

• Media related to Rutin at Wikimedia Commons

• Quercetin glycosides
• Flavonol rutinosides
• Flavonoid antioxidants
• Polyphenols