Record Information
Version1.0
Creation date2010-04-08 22:05:25 UTC
Update date2020-09-17 15:39:09 UTC
Primary IDFDB002536
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameQuercetin 3-rutinoside
DescriptionRutin, also known as rutoside or phytomelin, belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Rutin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Rutin is found, on average, in the highest concentration within a few different foods, such as parsley, common buckwheats, and sorrels and in a lower concentration in grape wines, italian sweet red peppers, and nectarines. Rutin has also been detected, but not quantified in, several different foods, such as summer grapes, peachs, broccoli, rosemaries, and tartary buckwheats. This could make rutin a potential biomarker for the consumption of these foods. A rutinoside that is quercetin with the hydroxy group at position C-3 substituted with glucose and rhamnose sugar groups.
CAS Number153-18-4
Structure
Thumb
Synonyms
SynonymSource
3-[[6-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-oneGenerator
3-[[6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-oneChEBI
3-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-oneGenerator
3-Rhamnoglucoside OF 3,3',4',5,7-pentahydroxyflavoneHMDB
3-Rhamnoglucosylquercetinbiospider
3-Rutinosyl quercetinbiospider
3,3',4',5,7-Pentahydroxyflavone-3-rutinosidebiospider
beta-Quercetin-3-rutinosideHMDB
BioflavonoidHMDB
BirutanHMDB
Birutan forteHMDB
Birutinbiospider
Eldrindb_source
Globulariacitrindb_source
Globularicitrinbiospider
Hydroxyethylrutosidebiospider
Ilixanthinbiospider
Melindb_source
Myrticolorindb_source
Neoisorutinbiospider
Osyritindb_source
Osyritrinbiospider
Oxyritinbiospider
Paliurosidedb_source
Phytomelinbiospider
Quercetin 3-b-D-rutinosidedb_source
Quercetin 3-O-[beta-L-rhamnosyl-(1->6)-beta-D-glucoside]biospider
Quercetin 3-O-beta-D-rutinosidebiospider
Quercetin 3-O-beta-delta-rutinosidebiospider
Quercetin 3-O-rutinosidebiospider
Quercetin 3-rhamnoglucosidebiospider
Quercetin 3-rutinosidebiospider
Quercetin rhamnoglucosinebiospider
Quercetin-3-rutinosidebiospider
Quercetin-3beta-rutinosidebiospider
Quercetol 3-rhamnoglucosidebiospider
Quercitin 3-rutinosidebiospider
RUTHMDB
Rutabionbiospider
Rutinmanual
Rutin trihydrateHMDB
RutineHMDB
Rutinic aciddb_source
Rutiniondb_source
Rutinion acidbiospider
RutinumHMDB
RutosidHMDB
RutosideChEBI
Rutoside, BAN, INNdb_source
RutosidoHMDB
RutosidumHMDB
RutozydHMDB
SophorinHMDB
Sophorin?db_source
Tanrutinbiospider
Venorutonbiospider
Violaquercitrindb_source
Vitamin P?db_source
Predicted PropertiesNot Available
Chemical FormulaC27H30O16
IUPAC name
InChI IdentifierInChI=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
InChI KeyIKGXIBQEEMLURG-NVPNHPEKSA-N
Isomeric SMILESC[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=CC(O)=CC(O)=C4C3=O)C3=CC(O)=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
Average Molecular Weight610.5175
Monoisotopic Molecular Weight610.153384912
Classification
ClassificationNot classified
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 53.12%; H 4.95%; O 41.93%DFC
Melting PointMp 214-215 dec. (anhyd.)DFC
Boiling PointNot Available
Experimental Water Solubility0.125 mg/mLMERCK INDEX (1989)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]23D +13.82 (EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID4444362
ChEMBL IDCHEMBL226335
KEGG Compound IDC05625
Pubchem Compound ID5280805
Pubchem Substance IDNot Available
ChEBI ID28527
Phenol-Explorer ID296
DrugBank IDDB01698
HMDB IDHMDB03249
CRC / DFC (Dictionary of Food Compounds) IDCMH35-W:CMH35-W
EAFUS ID3346
Dr. Duke IDQUERCETIN-3-RHAMNOGLUCOSIDE|QUERCETIN-3-O-BETA-D-RUTOSIDE|QUERCETIN-3-O-RUTINOSIDE|QUERCETIN-3-0-RUTINOSIDE| QUERCITIN-3-RUTINOSIDE|RUTIN|RUTOSIDE
BIGG IDNot Available
KNApSAcK ID3346
HET IDRUT
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDRutin
Phenol-Explorer Metabolite ID296
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
5-hydroxytryptamine inhibitor48279 Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.DUKE
aldehyde-oxidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
allelochemicDUKE
anti aggregantDUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti apoplectic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti atherogenic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti atherosclerotic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti capillary-fragilityDUKE
anti cataract52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti clastogenDUKE
anti convulsant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti CVIDUKE
anti dementia52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti dermatitic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti edemicDUKE
anti erythemic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti feedantDUKE
anti glaucomicDUKE
anti hematuricDUKE
anti hemorrhoidal52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti hypertensive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti metastatic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti mutagenicDUKE
anti nephritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti nociceptive35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti peroxidantDUKE
anti plateletDUKE
anti proliferantDUKE
anti protozoal33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti purpuric50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti radicularDUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti sunburn52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti thrombogenic50248 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.DUKE
anti thyroidDUKE
anti trypanosomic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
anti varicose52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
apoptoticDUKE
cAMP-phosphodiesterase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
capillariprotectiveDUKE
catabolicDUKE
catechol O-methyltransferase inhibitor48406 An EC 2.1.1.* (methyltransferase) inhibitor that interferes with the action of catechol O-methyltransferase (EC 2.1.1.6).DUKE
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cholereticDUKE
cytoprotectiveDUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
estrogenicDUKE
hemostatDUKE
hepatomagenicDUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hypocholesterolemicDUKE
hypotensiveDUKE
immunomodulator50846 Biologically active substance whose activity affects or plays a role in the functioning of the immune system.DUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
Insectiphile24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
juvabionalDUKE
larvistatDUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
mutagenicDUKE
myoprotectiveDUKE
myorelaxantDUKE
oviposition stimulantDUKE
platelet aggregation factor inhibitor50427 A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
protisticideDUKE
radioprotective35232 Any pharmaceutical compound containing a radioisotope.DUKE
sunscreen52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
topoisomerase-II inhibitor50750 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.DUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
vasopressorDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.