Rutin

Rutin
Rutin
Rutin
Names
IUPAC name
3′,4′,5,7-Tetrahydroxy-3-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]flavone
Systematic IUPAC name
(42S,43R,44S,45S,46R,72R,73R,74R,75R,76S)-13,14,25,27,43,44,45,73,74,75-Decahydroxy-76-methyl-24H-3,6-dioxa-2(2,3)-[1]benzopyrana-4(2,6),7(2)-bis(oxana)-1(1)-benzenaheptaphane-24-one
Other names
Rutoside (INN)
Phytomelin
Sophorin
Birutan
Eldrin
Birutan Forte
Rutin trihydrate
Globularicitrin
Violaquercitrin
Quercetin rutinoside
IdentifiersCategory:Articles without EBI source
3D model (JSmol)
ChemSpider
DrugBank
ECHA InfoCardCategory:ECHA InfoCard ID from Wikidata 100.005.287 Edit this at Wikidata
KEGG
RTECS number
  • VM2975000
UNII
  • 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
  • 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
C27H30O16
Molar mass 610.521 g·mol−1
Appearance Solid
Melting point 242 °C (468 °F; 515 K)
12.5 mg/100 mL[1]
13 mg/100mL[2]
Pharmacology
C05CA01 (WHO)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Category:Articles containing unverified chemical infoboxesCategory:Chembox image size set

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

Occurrences

Rutin is one of the phenolic compounds found in the plant species Carpobrotus edulis. Its name comes from the name of Ruta graveolens, a plant that also contains rutin. Various citrus fruit peels contain 32 to 49 mg per g of flavonoids expressed as rutin equivalents.[3] Citrus leaves contain rutin at concentrations of 11 mg per g in orange trees and 7 mg per g in lime trees.[4] In 2021, Samoan researchers identified rutin in the native plant matalafi (Psychotria insularum).[5]

Metabolism

The enzyme quercitrinase found in Aspergillus flavus is in the rutin catabolic pathway.[6]

In food

Rutin is a citrus flavonoid glycoside found in many plants, including buckwheat,[7] 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).[7] Rutin is one of the primary flavonols found in 'clingstone' peaches.[8] It is also found in green tea infusions.[9]

Approximate rutin content of selected foods, in milligrams per 100 grams or milliliters:[10]

Sortable table
Numeric Alphabetic
389[11]Tartary buckwheat, roasted bran
332Capers, spice
68[11]Tartary buckwheat, roasted grain
45Olive (black), raw
36Buckwheat, whole grain flour
32Green tea, infusion
23Asparagus, raw
19Black raspberry, raw
17Black tea, infusion
11Red raspberry, raw
9Buckwheat, groats, thermally treated
6Buckwheat, refined flour
6Greencurrant
6Plum, fresh
5Blackcurrant, raw
4Blackberry, raw
3Tomato (cherry), whole, raw
2Prune
2Fenugreek
2Marjoram, dried
1Grape, raisin
1Zucchini, raw
1Apricot, raw
0Apple
0Redcurrant
0Grape (green)
0Tomato, whole, raw

Research

Rutin (rutoside or rutinoside)[12] 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 remains no high-quality evidence for their safe and effective uses, as of 2018.[12][13][14] A 2020 review indicated that oral rutosides may reduce leg edema by a small amount in people with post-thrombotic syndrome, but the risk of adverse effects was higher.[15]

As a flavonol among similar flavonoids, rutin has low bioavailability due to poor absorption, high metabolism, and rapid excretion that collectively make its biological properties in vivo difficult to study, and its potential for use as a therapeutic agent limited.[12]

Biosynthesis

The biosynthesis pathway of rutin in mulberry (Morus alba L.) leaves begins with phenylalanine, which produces cinnamic acid under the action of phenylalanine ammonia lyase (PAL). Cinnamic acid is catalyzed by cinnamic acid-4-hydroxylase (C4H) and 4-coumarate-CoA ligase (4CL) to form p-coumaroyl-CoA. Subsequently, chalcone synthase (CHS) catalyzes the condensation of p-coumaroyl-CoA and three molecules of malonyl-CoA to produce naringenin chalcone, which is eventually converted into naringenin flavanone with the participation of chalcone isomerase (CHI). With the action of flavanone 3-hydroxylas (F3H), dihydrokaempferol (DHK) is generated. DHK can be further hydroxylated by flavonoid 3´-hydroxylase (F3'H) to produce dihydroquercetin (DHQ), which is then catalyzed by flavonol synthase (FLS) to form quercetin. After quercetin is catalyzed by UDP-glucose flavonoid 3-O-glucosyltransferase (UFGT) to form isoquercitrin, finally, the formation of rutin from isoquercitrin is catalyzed by flavonoid 3-O-glucoside L-rhamnosyltransferase.[16]

References

  1. ↑ Merck Index, 12th Edition, 8456
  2. ↑ Krewson CF, Naghski J (November 1952). "Some physical properties of rutin". Journal of the American Pharmaceutical Association. 41 (11): 582–587. doi:10.1002/jps.3030411106. PMID 12999623.
  3. ↑ Wang, Yuan-Chuen; Chuang, Yueh-Chueh; Hsu, Hsing-Wen (2008). "The flavonoid, carotenoid and pectin content in peels of citrus cultivated in Taiwan". Food Chemistry. 106 (1): 277–284. Bibcode:2008FoodC.106..277W. doi:10.1016/j.foodchem.2007.05.086. ISSN 0308-8146.
  4. ↑ Soares, Márcio Santos; da Silva, Danielle Fernandes; Forim, Moacir Rossi; et al. (2015). "Quantification and localization of hesperidin and rutin in Citrus sinensis grafted on C. limonia after Xylella fastidiosa infection by HPLC-UV and MALDI imaging mass spectrometry". Phytochemistry. 115: 161–170. Bibcode:2015PChem.115..161S. doi:10.1016/j.phytochem.2015.02.011. ISSN 0031-9422. PMID 25749617.
  5. ↑ Molimau-Samasoni S, Woolner VH, Foliga ST, et al. (November 2021). "Functional genomics and metabolomics advance the ethnobotany of the Samoan traditional medicine "matalafi"". Proceedings of the National Academy of Sciences of the United States of America. 118 (45) e2100880118. Bibcode:2021PNAS..11800880M. doi:10.1073/pnas.2100880118. PMC 8609454. PMID 34725148. S2CID 240423413.
  6. ↑ Tranchimand S, Brouant P, Iacazio G (November 2010). "The rutin catabolic pathway with special emphasis on quercetinase". Biodegradation. 21 (6): 833–859. doi:10.1007/s10532-010-9359-7. PMID 20419500. S2CID 30101803.
  7. 1 2 Kreft S, Knapp M, Kreft I (November 1999). "Extraction of rutin from buckwheat (Fagopyrum esculentumMoench) seeds and determination by capillary electrophoresis". Journal of Agricultural and Food Chemistry. 47 (11): 4649–4652. Bibcode:1999JAFC...47.4649K. doi:10.1021/jf990186p. PMID 10552865.
  8. ↑ Chang S, Tan C, Frankel EN, Barrett DM (February 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): 147–151. Bibcode:2000JAFC...48..147C. doi:10.1021/jf9904564. PMID 10691607.
  9. ↑ 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.
  10. ↑ "foods in which the polyphenol Quercetin 3-O-rutinoside is found". Phenol-Explorer v 3.6. June 2015.
  11. 1 2 Noda, T.; Ishiguro, K.; Suzuki, T.; Morishita, T. (2021). "Roasted Tartary Buckwheat Bran as a Material for Producing Rutin-Rich Tea Beverages". Plants. 10 (12): 2662. Bibcode:2021Plnts..10.2662N. doi:10.3390/plants10122662. PMC 8704535. PMID 34961131.
  12. 1 2 3 "Flavonoids". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis, Oregon. 2025. Retrieved 15 September 2025.
  13. ↑ Morling JR, Broderick C, Yeoh SE, Kolbach DN (November 2018). "Rutosides for treatment of post-thrombotic syndrome". The Cochrane Database of Systematic Reviews. 2018 (11) CD005625. doi:10.1002/14651858.CD005625.pub4. PMC 6517027. PMID 30406640.
  14. ↑ Martinez-Zapata, Maria José; Vernooij, Robin Wm; Simancas-Racines, Daniel; et al. (2020-11-03). "Phlebotonics for venous insufficiency". The Cochrane Database of Systematic Reviews. 2020 (11) CD003229. doi:10.1002/14651858.CD003229.pub4. ISSN 1469-493X. PMC 8094625. PMID 33141449.
  15. ↑ Martinez-Zapata, Maria José; Vernooij, Robin Wm; Simancas-Racines, Daniel; et al. (3 November 2020). "Phlebotonics for venous insufficiency". The Cochrane Database of Systematic Reviews. 2020 (11) CD003229. doi:10.1002/14651858.CD003229.pub4. ISSN 1469-493X. PMC 8094625. PMID 33141449.
  16. ↑ Yu X, Liu J, Wan J, et al. (2020). "Cloning, prokaryotic expression, and enzyme activity of a UDP-glucose flavonoid 3-o-glycosyltransferase from mulberry (Morus alba L.) leaves" (PDF). Pharmacognosy Magazine. 16 (69): 441–7. doi:10.4103/pm.pm_396_19 (inactive 7 December 2025).{{cite journal}}: CS1 maint: DOI inactive as of December 2025 (link)Category:CS1 maint: DOI inactive as of December 2025
Category:CYP3A4 inhibitors Category:Quercetin glycosides Category:Flavonol rutinosides Category:Flavonoid antioxidants Category:Polyphenols
Category:Articles containing unverified chemical infoboxes Category:Articles with changed ChemSpider identifier Category:Articles with changed KEGG identifier Category:Articles with short description Category:Articles without EBI source Category:CS1 maint: DOI inactive as of December 2025 Category:CYP3A4 inhibitors Category:Chembox image size set Category:Commons category link from Wikidata Category:ECHA InfoCard ID from Wikidata Category:Flavonoid antioxidants Category:Flavonol rutinosides Category:Polyphenols Category:Quercetin glycosides Category:Short description is different from Wikidata