Isoquercitrin
Basic information
- CAS
21637-25-2- Standard SMILES
O=c1c(O[C@@H]2O[C@H]([C@H](O)CO)[C@H](O)[C@H]2O)c(-c2ccc(O)c(O)c2)oc2cc(O)cc(O)c12- InChIKey
OPJZLUXFQFQYAI-GNPVFZCLSA-N- Molecular formula
- C21H20O12
- Average molar mass
- 464.4 g/mol
- Monoisotopic mass
- 464.09547607
Overview
Quercetin 3-O-beta-D-glucofuranoside is a quercetin O-glucoside in which a glucofuranosyl residue is attached at position 3 of quercetin via a beta-glycosidic linkage. It has a role as a metabolite. It is a beta-D-glucoside, a tetrahydroxyflavone, a monosaccharide derivative and a quercetin O-glucoside.
Names & identifiers
- Preferred name
- Isoquercitrin
- IUPAC
- 3-[(2S,3R,4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
- English name
- ISOQUERCITRIN
- Molecular formula
- C21H20O12
- Molecular weight
- 464.38
Names & synonyms
21637-25-2IsoquercitrosideIsotrifolin0YX10VRV6Jquercetin 3-O-beta-D-glucofuranoside3,3',4',5,7-Pentahydroxyflavone 3-beta-D-glucofuranoside2-(3,4-Dihydroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-oneCHEBI:28299DTXSID809049764H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy-Flavone, 3,3',4',5,7-pentahydroxy-, 3-beta-D-glucofuranoside2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl beta-D-glucofuranoside
Show more names
ISOQUERCETINQUERCETIN-3-O-GLUCOSIDEQUERCETIN-3-GLUCOSIDEIsotrifoliinnaringenin-7-O-β-D-glucosideQUERCETIN-3-O-BETA-GLUCOPYRANOSIDEQuercetin 3-Quercitin-3-beta-D-glucofuranoside
RefChem:5924DTXCID101334095quercetin 3-(beta-D-glucofuranoside)ISOQUERCETIN ENZYMATICALLY MODIFIED4H-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-((2S,4R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxychromen-4-one244-488-5Isoquercitrin
Properties
Computed structural properties
- XLogP
- 0.4
- Topological polar surface area
- 207 Ų
- Hydrogen bond donors
- 8
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 5
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 758
Experimental & physicochemical properties
CosmeticsAntioxidant
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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
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.
Hazard information
Hazard Classes and CategoriesNot Classified
Toxicology
Toxicity Summary
A 2014 review notes an Acceptable Aaily Intake of about 5 mg/kg/day for 95% pure Isoquercitrin although higher doses in rats have included mostly (benign) chromaturia, and that some drug interactions may occur due to modulation of the activity and/or expression of drug metabolizing/transporting systems.
A 2022 review describes animal research demonstrating that Enzymatically Modified Isoquercitrin (EMIQ is a safe product with cardioprotective, anti-allergic, chemopreventive, neuroprotective, and musculotropic properties. The studies found EMIQ does not induce severe adverse effects, and does not exhibit cytotoxic, genotoxic, embryotoxic, or allergenic effects. Also, EMIQ was well tolerated and no adverse effects were reported in human subjects (42 mg EMIQ/day/6-times a week for 4 months).
Safety data
- F
- 10-23
- wgk
- 3
- rtecs
- LK8960000
- ridadr
- 2811
- hs_code
- 29389090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
Chemistry & industry
Pharmacology
Absorption, Distribution and Excretion
A 2014 review notes that Isoquercitrin can be found in plasma and tissues after oral administration, and that it is extensively metabolized in the intestine and the liver. Also, it has a higher bioavailability than Quercetin.
A 2022 review notes that enzymatically modified Isoquercitrin (EMIQ) is an Isoquercitrin derivative obtained from Rutin that has greatly enhanced bioavailability compared to Isoquercitrin.
Uses & manufacturing
Use ClassificationCosmetics -> Antioxidant
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.
Additional notes
DefinitionChEBI: A quercetin O-glucoside in which a glucofuranosyl residue is attached at position 3 of quercetin via a beta-glycosidic linkage.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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