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Rutoside, Rutin

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Rutin
Rutin.png

Rutoside

RUTIN

  • 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

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

Rutin trihydrate | CAS 250249-75-3 - Order from Adipogen
Rutin trihydrate | CAS 250249-75-3 - Order from Adipogen
Structure of RUTOSIDE TRIHYDRATE

Rutin trihydrate | CAS 250249-75-3 RutinCAS 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: C27H30O16Molecular Weight: 610.52Percent 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.,Science103, 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: BeilsteinXXXI, 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).UV

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, Naturwissenschaften23, 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. 
C13

MASS 

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.

Occurrences

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]

Metabolism

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]

NumericAlphabetic
332Capers, spice
45Olive [Black], raw
36Buckwheat, whole grain flour
23Asparagus, raw
19Black raspberry, raw
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
2Tea (Black), infusion
1Grape, raisin
1Zucchini, raw
1Apricot, raw
1Tea (Green), infusion
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 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]

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 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

SYN

https://www.sciencedirect.com/science/article/abs/pii/S100184171300017X

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.

SYN

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. 

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References

  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 www.brenda-enzymes.org
  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
Names
IUPAC name3′,4′,5,7-Tetrahydroxy-3-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]flavone
Preferred 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 namesRutoside (INN)
Phytomelin
Sophorin
Birutan
Eldrin
Birutan Forte
Rutin trihydrate
Globularicitrin
Violaquercitrin
Quercetin rutinoside
Identifiers
CAS Number153-18-4 
3D model (JSmol)Interactive image
ChemSpider4444362 
DrugBankDB01698 
ECHA InfoCard100.005.287 
KEGGC05625 
PubChem CID5280805
RTECS numberVM2975000
UNII5G06TVY3R7 
CompTox Dashboard (EPA)DTXSID3022326 
showInChI
showSMILES
Properties
Chemical formulaC27H30O16
Molar mass610.521 g·mol−1
AppearanceSolid
Melting point242 °C (468 °F; 515 K)
Solubility in water12.5 mg/100 mL[1]
13 mg/100mL[2]
Pharmacology
ATC codeC05CA01 (WHO)
Hazards
NFPA 704 (fire diamond)NFPA 704 four-colored diamond200
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒ verify (what is  ?)
Infobox references

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

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

wdt-2

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DR ANTHONY CRASTO

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK LIFE SCIENCES LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 30 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, Dr T.V. Radhakrishnan and Dr B. K. Kulkarni, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 30 PLUS year tenure till date June 2021, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 90 Lakh plus views on dozen plus blogs, 233 countries, 7 continents, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 33 lakh plus views on New Drug Approvals Blog in 233 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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