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Rutin

HCID 5280805
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
153-18-4
Standard SMILES
C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3c(-c4ccc(O)c(O)c4)oc4cc(O)cc(O)c4c3=O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
InChIKey
IKGXIBQEEMLURG-NVPNHPEKSA-N
Molecular formula
C27H30O16
Average molar mass
610.5 g/mol
Monoisotopic mass
610.15338488

Overview

Rutin is a rutinoside that is quercetin with the hydroxy group at position C-3 substituted with glucose and rhamnose sugar groups. It has a role as an antioxidant and a metabolite. It is a rutinoside, a tetrahydroxyflavone, a disaccharide derivative and a quercetin O-glucoside.

Names & identifiers

Preferred name
Rutin
IUPAC
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
English name
Rutin
Molecular formula
C27H30O16
Molecular weight
610.52

Names & synonyms

RUTIN153-18-4rutosideQuercetin 3-rutinosideBirutanPhytomelinSophorinIlixanthinMyrticolorinGlobulariacitrinOsyritrinPaliuroside
Show more names
RutinumRoutinebioflavonoidilixathinRutin Standard
Tanrutin3-Rutinosyl quercetinQuercetin-3-rutinosideQuercetin 3-O-rutinosideYunxiangganRutosidoRutine3-Rhamnoglucosylquercetin

Database identifiers

CAS
153-18-4、207671-50-9
PubChem CID
5280805
DTXSID
DTXSID3022326
ChEMBL
CHEMBL226335
ChEBI
CHEBI:28527
UNII
5G06TVY3R7
EC Number
205-814-1、683-619-4
Nikkaji
J818D

Properties

Computed structural properties

XLogP
-1.3
Topological polar surface area
266 Ų
Hydrogen bond donors
10
Hydrogen bond acceptors
16
Rotatable bonds
6
Heavy atoms
43
Formal charge
0
Complexity
1,020

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
CosmeticsHair conditioning; Skin conditioning; Antioxidant
Food AdditivesUse unspecified -> FDA Substance added to food
Solubility · 2 items

0.125 mg/mL

Poorly soluble in water whereas readily soluble in pyridine.

Melting Point125 °C
Physical Description · 2 items

Solid

Yellowish powder

Collision Cross Section · 4 items

251.61 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

232.6 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

245.04 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

234.7 Ų [M-H]-

Physicochemical properties

Melting point
195 °C · 195 °C (dec.)(lit.)
alpha
23 · D23 +13.82° (ethanol); D23 -39.43° (pyridine)
Boiling point
576.13 °C · 576.13°C (rough estimate)
Density
1.3881 · 1.3881 (rough estimate)
refractive index
1.765 · 1.7650 (estimate)
storage temp.
2 · Keep in dark place,Sealed in dry,2-8°C
solubility
50 mg/mL · pyridine: 50 mg/mL
Colour Index
75730 · 75730
form
powder
pka
6.17 · 6.17±0.40(Predicted)
color
yellow to green
Odor
Odorless
Water Solubility
12.5 g/100 · 12.5 g/100 mL
Merck
8304 · 8304
Stability
Hygroscopic
Major Application
pharmaceutical
Cosmetics Ingredients Functions
ANTIOXIDANTHAIR CONDITIONINGSKIN CONDITIONING
LogP
-2.02 · -2.020 (est)
CAS DataBase Reference
153 · 153-18-4(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS)
RUTIN
EWG's Food Scores
1 · 1
FDA UNII
5 G06TVY3R7 · 5G06TVY3R7
ATC code
5 CA01,C05CA51 · C05CA01,C05CA51
NIST Chemistry Reference
-3 · Flavone-3-rutinoside, 3,3',4',5,7-pentahydroxy(153-18-4)
EPA Substance Registry System
Rutin (153-18-4)
UNSPSC Code
41116107 · 41116107
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319
Precautionary statements
261 · P261-P305+P351+P338
Hazard Codes
Xn,Xi
Risk Statements
22 · 22-36/37/38
Safety Statements
24 · 24/25-36-26
WGK Germany
3 · 3
RTECS
2975000 · VM2975000
F
8 · 8
TSCA
TSCA listed
HS Code
29381000 · 29381000
Toxicity
50 i.v · LD50 i.v. in mice: 950 mg/kg (propylene glycol soln) (Harrison)
REACH Registrations
Active

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 143 reports by companies from 1 notifications to the ECHA C&L Inventory.

This chemical does not meet GHS hazard criteria for 58.9% (63 of 107) of all reports.

Warning

Hazard information

Regulatory Information · 3 items

Chemical: 4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-

Status: Active Update: 31-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26165

4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazard Classes and Categories · 2 items

Skin Irrit. 2 (38.3%)

Acute Tox. 4 (100%)

Toxicology

Toxicity SummaryA 2021 review notes that Rutin can be considered safe for clinical use, and that no toxic signs were observed in acute and chronic toxicity studies of rats, guinea pigs and rabbits.

Safety data

F
8
wgk
3
tsca
TSCA listed
rtecs
VM2975000
hs_code
29381000
Toxicity
LD50 i.v. in mice: 950 mg/kg (propylene glycol soln) (Harrison)
risk_code
22-36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn,Xi
safety_code
24/25-36-26
Hazard statements
H302-H315-H319
REACH Registrations
Active
Precautionary statements
P261-P305+P351+P338

Chemistry & industry

Pharmacology

ATC Code · 3 items

C05CA01

C - Cardiovascular system

QC - Cardiovascular system

Mechanism of Action · 1 item

A 2022 review of Rutin focused on its protective effects on the heart, liver, and kidneys against various chemical and natural toxins. The antioxidant effects involve enhancement of various antioxidant enzymes, Nrf2/HO-1 pathway activation, Glutathione (GSH) elevation, and malondialdehyde (MDA) reduction. The anti-inflammatory effects involve inhibition of IL-1β, IL-6, TGF-β1, COX-2, iNOS, TLR4, and XO. The antiapoptotic effects involve inhibition of free radicals, caspase-3/-7/-9, hsp70, HMGB1, and p53, and elevation of antiapoptotic protein Bcl-2.

Absorption, Distribution and Excretion · 1 item

A 2021 review notes that poor water solubility of Rutin is a major drawback, and that efforts have been made to improve its solubility by introducing a new functional group, e.g., a carboxylate group on its sugar moiety. Also, drug delivery systems have been developed to improve Rutin's pharmacokinetic properties and therapeutic potential, e.g., using liposomes, polymeric micelles and nanoparticles as carriers for rutin.

Cellular LocationsCytoplasm

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >25000
Household ProductsInformation on 1 consumer products that contain Rutin in the following categories is provided:
Use ClassificationCosmetics -> Hair conditioning; Skin conditioning; Antioxidant
General Manufacturing Information4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-: ACTIVE
Applications · 6 items

DescriptionRutin is widely found in nature and is almost contained in all of the Rutaceae and Sectaceae plants, especially abundant in Rutaceae, Rutaceae, Epacridaceae of leguminous, buckwheat of Polygonaceae, Eulali of Hypericum, Berchemia polyphylla var. leioclada of Tetranychidae, and wild wutong leaves of thistle, which are also used as raw materials in rutin extraction. In addition, it also exists in the Ilex pubescens of Aquifoliaceae, Forsythia of Oleaceae, pagoda tree pod of Leguminosae, tobacco, jujube, apricots, flavedo, tomatoes, and other plants.At present, rutin in China mainly extracted from the Sophora japonica Linn of leguminous, which is listed in top grade of Shen Nong’s Classic Materia Medica. In addition, tartary buckwheat, which is rich in rutin and flavonoids, is native to India and now produced in China’s northwest, southwest, north, south, and other places.

HistoryIn the mid-1930s, Hungarian scientist Szent Gyorgy firstly separated the flavonoid mixture. After the German pharmacy firstly made it into ranosine in 1942, the concept of vitamin P has been established worldwide. Further study proved that rutin was the most important flavonoids of vitamin P. These compounds were certified to have effects on many diseases in medical.Recently, the research of rutin mainly focuses on the extraction process improvement, pharmacological effects, and pharmacodynamics research, aiming at improvement of its bioavailability through the development of different dosage forms. As for the extraction process, new extraction and purification methods have been developed since the original alkali extraction acid precipitation method. These methods greatly improve its extraction efficiency and reduce cost, including hot water precipitation, hot water extraction with macroporous resin adsorbing purification, ultrasonic radiation, hot water extraction with alcohol precipitation, cold alkali percolation extraction with acid precipitation, continuous reflux extraction, ethanol extraction, supercritical CO2 extraction, and enzymatic hydrolysis .In recent years, advanced rutin dosage forms, such as rutin cyclodextrin saturation, HPMC controlled release tablets, solid dispersion tablets, coprecipitate, and rutin effervescent particles, greatly improve the rutin dissolution rate and its bioavailability.

UsesFound in many plants, especially the buckwheat plant. Identity with Ilixanthin. Capillary protectant. Rutin is colored brown by tobacco enzyme under experimental conditions.

Usesantidiabetic, dipeptidyl peptidase–4 inhibitor

UsesFor nutritional product

Usesrutin is described as helping to tighten and strengthen skin capillaries, and as such it could help prevent a couperose condition. It also demonstrates anti-oxidant properties. Rutin is a flavonoid found in rue leaves, buckwheat, and other plants.

Upstream & downstream products

Downstream products

Enzymaticallv modified rutinQuercetinEnzymaticallydecomposedrutin3,4'-Dimethoxy-3',5,7-trihydroxyflavoneTAMARIXETINKERACYANIN CHLORIDEβ-D-Glucopyranoside, (2E)-3-(4-hydroxyphenyl)-2-propen-1-yl

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
南京道尔医药科技有限公司025-82232968 15250951870 · [email protected]
西安天朗源生物科技有限公司17749038280 17749038280 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
Shaanxi Huike Botanical Development Co., Ltd+86-29-62663046 · [email protected]
Jai Radhe Sales+(91)-(79)-26431096/65255722 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
天津万象恒远科技有限公司15722085254 · [email protected]
成都普菲德生物技术有限公司028-82610909 13388174823 · [email protected]
上海融禾医药科技发展有限公司17301719108 13341702378 · [email protected]
嘉兴市艾森化工有限公司0573-85285100 18627885956 · [email protected]
TransMIT GmbH PlantMetaChem+49-172-1024293 · [email protected]
上海泰坦科技股份有限公司400-6009262 15618770481 · [email protected]
深圳虹彩祥根生物科技有限公司+86-0755-89668383 · [email protected]
上海瀚香生物科技有限公司177-54423994 17754423994 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
武汉科美沃化工有限公司027-85736489 · [email protected]
成都健腾生物技术有限公司86-28-85159085 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
成都锦然生物科技有限公司028-83311324 1278112614 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
西安康培基生物科技有限公司86-029-85456576 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
南京杜莱生物技术有限公司025-84699383-8003;025-846993838003-8003 18013301590 · [email protected]
山东博洛达生物科技有限公司0531-68659041 · [email protected]
深圳市石金谷科技有限公司(0086)755-61930359 (0086)18038192047 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
上海湄水化工科技有限公司021-60549325 18616193163
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
上海笛柏生物科技有限公司400-008-9730,021-54359730 400-008-9730 · [email protected]
上海石洋化工有限公司021-56795766 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海卓因生物科技有限公司021-61317773 · [email protected]

Additional notes

DefinitionChEBI: A rutinoside that is quercetin with the hydroxy group at position C-3 substituted with glucose and rhamnose sugar groups.

Related reactions

9 records
New reaction record
HRID 83468 reaction equation
HRID 83468As reactantuspto-grants-2014_09
HRID 638761 reaction equation
HRID 638761As reactantuspto-grants-2010_04
HRID 638762 reaction equation
HRID 638762As reactantuspto-grants-2010_04
HRID 638763 reaction equation
HRID 638763As reactantuspto-grants-2010_04
HRID 1601419 reaction equation
HRID 1601419As reactantuspto-grants-1999_11
HRID 1862501 reaction equation
HRID 1862501As reactantuspto-grants-2003_03
HRID 2057567 reaction equation
HRID 2057567As reactantuspto-grants-1980_07
HRID 2230905 reaction equation
HRID 2230905As reactantuspto-grants-2002_07
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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes