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RUTOSIDE (rutin)

HCID 6728944
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Basic information

CAS
153-18-4
Standard SMILES
C[C@@H]1O[C@@H](OC[C@H]2OC(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-KUKMIBIMSA-N
Molecular formula
C27H30O16
Average molar mass
610.5 g/mol
Monoisotopic mass
610.15338487

Names & identifiers

Preferred name
RUTOSIDE (rutin)
IUPAC
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(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

RUTOSIDE (rutin)Rutoside (rutin)rutinaSpectrum2_000779Spectrum5_000637SPECTRUM300607SPBio_000858HMS2091A19Pharmakon1600-00300607NSC755835AKOS015960545CCG-213741
Show more names
RUTOSIDEQUERCETIN-3-RUTINOSIDERutinumRoutinebioflavonoidBIRUTANSOPHORINilixathinphytomelinRutin Standard
NSC-755835NCGC00263808-012-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(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-oneAC-20302AS-13340SBI-0206670.P002AB01563186_01SR-05000001990

Database identifiers

CAS
153-18-4
PubChem CID
6728944

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

Collision Cross Section230.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

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

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

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

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

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Compound notes

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

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

Additional notes

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