Isoquercetin

HCID 5280804

Substructure search Find similar structures

Basic information

CAS: 21637-25-2
Standard SMILES: O=c1c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c(-c2ccc(O)c(O)c2)oc2cc(O)cc(O)c12
InChIKey: OVSQVDMCBVZWGM-QSOFNFLRSA-N
Molecular formula: C21H20O12
Average molar mass: 464.4 g/mol
Monoisotopic mass: 464.09547608

Overview

Quercetin 3-O-beta-D-glucopyranoside is a quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells. It has a role as a geroprotector, an antioxidant, an antineoplastic agent, a histamine antagonist, a bone density conservation agent, an antipruritic drug, an osteogenesis regulator and a plant metabolite. It is a beta-D-glucoside, a tetrahydroxyflavone, a monosaccharide derivative and a quercetin O-glucoside. It is functionally related to a beta-D-glucose. It is a conjugate acid of a quercetin 3-O-beta-D-glucopyranoside(1-).

Names & identifiers

Preferred name: Isoquercetin
IUPAC: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
English name: ISOQUERCITRIN
Molecular formula: C21H20O12
Molecular weight: 464.38

Names & synonyms

IsoquercetinHirsutrinQuercetin 3-o-glucopyranoside3-GlucosylquercetinQuercetin 3-D-glucosideQuercetol 3-monoglucosideCONTIGOSIDE BQuercetin-3-O-glucopyranosideQuercetol 3-glucosideQuercetin 3-monoglucosideQuercetin 3-beta-glucosidequercetin glucoside

Show more names

QUERCETIN-3-O-GLUCOSIDEQUERCETIN-3-GLUCOSIDEISOQUERCITROSIDEIsotrifoliinnaringenin-7-O-β-D-glucosideQUERCETIN-3-O-BETA-GLUCOPYRANOSIDEISOTRIFOLINQuercetin 3-Quercitin-3-beta-D-glucofuranoside

Quercetin-3-glucoseQuercetin 3-beta-O-glucosideRonacare isoquercetinGlucosyl-3-quercetinquercetin 3-O-beta-D-glucopyranosideIsoquercetin, (-)-6HN2PC637TUNII-6HN2PC637T

Database identifiers

CAS: 21637-25-2、482-35-9
PubChem CID: 5280804
DTXSID: DTXSID3041110
ChEMBL: CHEMBL250450
ChEBI: CHEBI:68352
UNII: 6HN2PC637T
EC Number: 483-280-0、640-533-1
Nikkaji: J263.910F

Properties

Computed structural properties

XLogP: 0.4
Topological polar surface area: 207 Å²
Hydrogen bond donors: 8
Hydrogen bond acceptors: 12
Rotatable bonds: 4
Heavy atoms: 33
Formal charge: 0
Complexity: 758

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]

LogP0.7

Melting Point238 - 242 °C

Physical DescriptionSolid

Physicochemical properties

Melting point: 225 · 225-227°
Boiling point: 916.3 · 916.3±65.0 °C(Predicted)
Density: 1.87 · 1.87±0.1 g/cm3(Predicted)
FEMA: 4225 · 4225 | ISOQUERCITRIN, ENZYMATICALLY MODIFIED
storage temp.: -20 °C · Inert atmosphere,Store in freezer, under -20°C
solubility: DMSO (Slightly, Heated), Ethyl Acetate (Slightly), Methanol (Slightly, Heated)
form: Solid
pka: 6.17 · 6.17±0.40(Predicted)
color: Yellow to Dark Yellow
Odor: odorless
Cosmetics Ingredients Functions: ANTIOXIDANT
InChIKey: OVSQVDMCBVZWGM-QSOFNFLRSA-N
SMILES: C1(OC2=C(C(O)=CC(O)=C2)C(=O)C=1O[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O)C1C=CC(O)=C(O)C=1 |&1:14,15,17,18,20,r|
LogP: 0.82 · 0.82
EWG's Food Scores: 1 · 1
FDA UNII: 0 YX10VRV6J · 0YX10VRV6J
NCI Drug Dictionary: isoquercetin
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P280-P301+P312-P302+P352-P305+P351+P338
Safety Statements: 24 · 24/25
RIDADR: 2811 · 2811
WGK Germany: 3 · 3
RTECS: 8960000 · LK8960000
F: 10 · 10-23
HS Code: 29389090 · 29389090

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.

Not Classified

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory InformationStatus: Cease Manufacture Update: 10-11-2008 https://echa.europa.eu/registration-dossier/-/registered-dossier/3865

Hazard Classes and Categories · 2 items

Skin Irrit. 2 (100%)

Not Classified

Safety data

F: 10-23
wgk: 3
rtecs: LK8960000
ridadr: 2811
hs_code: 29389090
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 24/25
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Applications

OccurrenceReported found in Gossypium spp.

UsesIsoquercitroside is a flavonoid compound that is within medicinal plants which displays various biological activity. This includes inhibition of adipocyte differentiation.