Rutoside, Rutin

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  • Molecular FormulaC27H30O16
  • Average mass610.518
  • рутозид [Russian] [INN]
    ルチン [Japanese]
    روتوسيد [Arabic] [INN]
    芦丁 [Chinese] [INN]

CAS 153-18-4

  • C.I. 75730
  • NSC-9220


Rutin trihydrate | CAS 250249-75-3 - Order from Adipogen

Rutin trihydrate | CAS 250249-75-3 - Order from Adipogen

Rutin trihydrate | CAS 250249-75-3 

CAS Registry Number: 153-18-4
CAS Name: 3-[[6-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
Additional Names: rutoside; quercetin-3-rutinoside; 3,3¢,4¢,5,7-pentahydroxyflavone-3-rutinoside; melin; phytomelin; eldrin; ilixathin; sophorin; globularicitrin; paliuroside; osyritrin; osyritin; myrticolorin; violaquercitrin
Trademarks: Birutan (Merck KGaA)
Molecular Formula: C27H30O16
Molecular Weight: 610.52
Percent Composition: C 53.12%, H 4.95%, O 41.93%
Literature References: Identity with ilixanthin: Schindler, Herb, Arch. Pharm. 288, 372 (1955). Found in many plants, especially the buckwheat plant (Fagopyrum esculentum Moench., Polygonaceae) which contains about 3% (dry basis): Couch et al., Science 103, 197 (1946). From tobacco (Nicotiana tabacum L., Solanaceae) Couch, Krewson, U.S. Dept. Agr., Eastern Regional Res. Lab. AIC-52 (1944).
In forsythia [Forsythia suspensa (Thunb.) Vahl. var. fortunei (Lindl.) Rehd., Oleaceae], in hydrangea (Hydrangea paniculata Sieb., Saxifragaceae), in pansies (Viola sp., Violaceae).
General extraction procedure: Beilstein XXXI, 376. From leaves of Eucalyptus macroryncha F. v. Muell., Myrtaceae: Attree, Perkin, J. Chem. Soc. 1927, 234.
Industrial production from Eucalyptus spp.: Humphreys, Econ. Bot. 18, 195 (1964).
Structure: Zemplén, Gerecs, Ber. 68B, 1318 (1935).
Synthesis: Shakhova et al., Zh. Obshch. Khim. 32, 390 (1962), C.A. 58, 1426e (1963). Rutin is hydrolyzed by rhamnodiastase from the seed of Rhamnus utilis Decne, Rhamnaceae (Chinese buckthorn); emulsin is not effective: Bridel, Charaux, Compt. Rend. 181, 925 (1925). Toxicity data: Harrison et al., J. Am. Pharm. Assoc. 39, 557 (1950). Book: J. Q. Griffith, Jr., Rutin and Related Flavonoids (Mack, Easton, Pa., 1955).
Comprehensive description: T. I. Khalifa et al., Anal. Profiles Drug Subs. 12, 623-681 (1983).
Properties: Pale yellow needles from water, gradual darkening on exposure to light. The crystals contain 3 H2O and become anhydr after 12 hrs at 110° and 10 mm Hg. Anhydr rutin browns at 125°, becomes plastic at 195-197°, and dec 214-215° (with effervescence). [a]D23 +13.82° (ethanol); [a]D23 -39.43° (pyridine). Anhydr rutin is hygroscopic. One gram dissolves in about 8 liters water, about 200 ml boiling water, 7 ml boiling methanol. Sol in pyridine, formamide and alkaline solns; slightly sol in alcohol, acetone, ethyl acetate. Practically insol in chloroform, carbon bisulfide, ether, benzene, petr solvents. Dil solns give green color with ferric chloride. Rutin is colored brown by tobacco enzyme under experimental conditions: Neuberg, Kobel, Naturwissenschaften 23, 800 (1935). LD50 i.v. in mice: 950 mg/kg (propylene glycol soln) (Harrison).
Optical Rotation: [a]D23 +13.82° (ethanol); [a]D23 -39.43° (pyridine)
Toxicity data: LD50 i.v. in mice: 950 mg/kg (propylene glycol soln) (Harrison)
Therap-Cat: Capillary protectant.
Keywords: Vasoprotectant.

Rutin, also called rutosidequercetin-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.

Rutin, also called rutoside, is the glycoside flavonoid found in a certain fruits and vegetables. Most rutine-rich foods are capers, olives, buckwheat (whole grain flour), asparagus, raspberry.In a clinical trial, rutin was found to aid control of intraocular pressure in patients with primary open angle glaucoma. As a component of dietary supplement Phlogenzym, rutin is used for treatment of osteoarthritis. Rutin is also used for treatment of post-surgical swelling of the arm after breast cancer surgery. Traditionally, rutin is used to prevent mucositis due to cancer treatment, to treat blood vessel disease such as varicose veins, bleeding, hemorrhoids.


Rutin is one of the phenolic compounds found in the invasive plant species Carpobrotus edulis and contributes to the antibacterial[3] properties of the plant.

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

Various citrus fruit peels contain 32 to 49 mg/g of flavonoids expressed as rutin equivalents.[4]

Citrus leaves contain rutin at concentrations of 11 and 7 g/kg in orange and lime trees respectively.[5]


The enzyme quercitrinase can be found in Aspergillus flavus.[6] It is an enzyme in the rutin catabolic pathway.[7]

In food

Rutin is a citrus flavonoid glycoside found in many plants including buckwheat,[8] the leaves and petioles of Rheum species, and asparagusTartary buckwheat seeds have been found to contain more rutin (about 0.8–1.7% dry weight) than common buckwheat seeds (0.01% dry weight).[8] Rutin is one of the primary flavonols found in ‘clingstone’ peaches.[9] It is also found in green tea infusions.[10]

Approximate rutin content per 100g of selected foods, in milligrams per 100 milliliters:[11]

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


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 syndromevenous insufficiency, or endothelial dysfunction, but there was no high-quality evidence for their safe and effective uses as of 2018.[12][13][14][needs update] 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.[12]


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 pcoumaroyl-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.[15]

Rutin Biosynthesis.svg


The compound 2 was synthesized for the first time by highly selective esterification reaction and fully characterized. The by-products of the reaction were complex, which brought out many considerable difficulties in separation and purification of the target product. Our work was the first in using the improved pyrogallol autoxidation method to test the antioxidant activities of these two flavonoids compounds in vitro and discovered that the compound 2 was much more effective as a free radical scavenger than the compound 1.


Synthesis of Rutin

The synthesis of rutin can be achieved according to the following three schemes. These schemes differ in the synthesis of ouercetin (the aglycone moiety of rutin).

Scheme 1: Kostanecki — et al. 1904 (33 ). Based upon the Claisen reaction between 2-hydroxy4, 6-dimethoxyacetophenone [l] and 3, 4-dimethoxybenzaldehyde [2] to give the intermediate [3] which upon treatment with HC1, cyclization occurs to give 5, 7, 3 , which upon treatment with F2SO4 enolisation occurs to give 5, 7, 1’3 ,’4 -tetramethoxyflavonol [6]. tion with HI affords quercetin [7].

Scheme 2: Robinson et al. 1926 (34 ). , ‘4 -tetramethoxyflavonone [4]. Oximination affords [5] Demethyla- — Condensation ofw-methoxypholoroacetophenone [I] with veratric acid anhydride [2] in the presence of the potassium salt of veratric acid to give the diarylester [3]. On hydrolysis with alcoholic KOH affords 5, 7-dihydroxy-3, /3 , ‘4 -trimethoxyf lavone [ 41 , which on demethylation with HI gives quercetin [5].

Scheme 3: Shakhova et al. 1962 (35), complete synthesis of rutin. W-methoxyphloroacetophenone [2] was condensed with 0-benzylvanillinic acid, anhydride [ 13 in triethylamine to give 5 , 7-dihydroxy-4 -benzyloxy-3, /3 -dimethoxyf lavone [3]. On treatment with AcOH-HC1 mixture gave 5, 7, ‘4 -trihydroxy-3,’3 -dimethoxyflavone [4]. Demethylation of the latter with HI yielded (about 802) quercetin [5]. Ouercetin potassium salt [6] was produced upon treating [5] with AcOK in ethanol. Levoglucosan [7] was acetylated with Ac20 in the presence of AcONa to give 2, 3, 4-triacetyllevoglucosan [8] which with TIC14 gave 1-chloro-2, 3, 4-triacetyl Dglucose [9]. L-rhamnose tetraacetate [lo] treated with TiBr4 in CHC13 gave 1-bromo-2, 3, I-triacetyl-L-rhamnose [ll]. [lo] + [11] heated with Hg (OAC)~ in C6H6 gave (53x) CC – acetochloro-f3-l-L-rhamnosido-6-D-glucose [12]. [12] was treated with AgOAc and acetylated with Ac20 to prodilce (68.703 B-heptaacet yl-f3-1-L-rhamnos ido-6-D-glucose [13]. This with 33% HBr in AcOH gave (61%) d – acetobromo-~-l-L-rhamnosido-6-D-glucose [14]. [14] and quercetin potassium salt [6] were dissolved in NH40H which was evaporated and treated with methanol andpurified over a chromatographic column packed with polycaprolactum resin to give rutin [151.




  1. ^ Merck Index, 12th Edition, 8456
  2. ^ Krewson CF, Naghski J (Nov 1952). “Some physical properties of rutin”. Journal of the American Pharmaceutical Association41 (11): 582–7. doi:10.1002/jps.3030411106PMID 12999623.
  3. ^ van der Watt E, Pretorius JC (2001). “Purification and identification of active antibacterial components in Carpobrotusedulis L.”. Journal of Ethnopharmacology76 (1): 87–91. doi:10.1016/S0378-8741(01)00197-0PMID 11378287.
  4. ^ [1] p. 280 Table 1
  5. ^ [2] p.8 fig. 7
  6. ^ quercitrinase on
  7. ^ Tranchimand S, Brouant P, Iacazio G (Nov 2010). “The rutin catabolic pathway with special emphasis on quercetinase”. Biodegradation21 (6): 833–59. doi:10.1007/s10532-010-9359-7PMID 20419500S2CID 30101803.
  8. Jump up to:a b 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 Chemistry47 (11): 4649–52. doi:10.1021/jf990186pPMID 10552865.
  9. ^ 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 Chemistry48 (2): 147–51. doi:10.1021/jf9904564PMID 10691607.
  10. ^ 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”. Electroanalysis18 (10): 1028–1034. doi:10.1002/elan.200603496.
  11. ^ “foods in which the polyphenol Quercetin 3-O-rutinoside is found”. Phenol-Explorer v 3.6. June 2015.
  12. Jump up to:a b c “Flavonoids”. Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis, Oregon. November 2015. Retrieved 25 February 2018.
  13. ^ Morling, J. R; Yeoh, S. E; Kolbach, D. N (November 2018). “Rutosides for treatment of post-thrombotic syndrome”Cochrane Database of Systematic Reviews11 (11): CD005625. doi:10.1002/14651858.CD005625.pub4PMC 6517027PMID 30406640.
  14. ^ 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 Reviews4: CD003229. doi:10.1002/14651858.CD003229.pub3PMC 7173720PMID 27048768.
  15. ^ Yu X, Liu J, Wan J, Zhao L, Liu Y, Wei Y, Ouyang Z. Cloning, prokaryotic expression, and enzyme activity of a UDP-glucose flavonoid 3-o-glycosyltransferase from mulberry (Morus alba L.) leaves. Phcog Mag 2020;16:441-7
IUPAC name

Preferred IUPAC name

Other names

Rutoside (INN)
Birutan Forte
Rutin trihydrate
Quercetin rutinoside
3D model (JSmol)
ECHA InfoCard 100.005.287 Edit this at Wikidata
PubChem CID
RTECS number
  • VM2975000
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]
C05CA01 (WHO)
NFPA 704 (fire diamond)
Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform Flammability code 0: Will not burn. E.g. water Instability code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazards (white): no code

NFPA 704 four-colored diamond

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

/////////Rutoside, RUTIN, рутозид ルチン , روتوسيد 芦丁 C.I. 75730, NSC 9220,


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