Isoquercitrin

Names

[ CAS No. ]:
482-35-9

[ Name ]:
Isoquercitrin

[Synonym ]:
Quercetin 3-O-β-glucoside
trifoliin
quercetin 3-O-β-D-glucopyranoside
Quercetin 3β-O-glucoside
Quercetin 3-β-glucoside
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl β-D-glucopyranoside
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Quercetin 3-β-D-glucoside
3-O-β-D-Glucopyranosylquercetin
Quercetin glucoside
Quercetin-3-O-β-D-glucoside
Quercetin-3-O-β-glucopyranoside
Isoquercetrin
Quercetin 3-O-glucoside
Quercetin 3-D-glucoside
Isoquercitrin
isoquercetin
quercetin 3-O-β-D-glucoside
Hirsutrin
isotrifoliin
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-
Quercetin 3-glucoside
Quercetin-3-β-glucopyranoside
Quercetin-3-O-glucoside
Quercetin 3-β-O-glucoside
Quercetin 3-O-glucopyranoside

Biological Activity

[Description]:

Quercetin-3-glucoside is a naturally occurring polyphenol that has antioxidant, anti-proliferative, and anti-inflammatory properties.Quercetin-3-glucoside alleviates ethanol-induced hepatotoxicity, oxidative stress, and inflammatory responses via the Nrf2/ARE antioxidant signaling pathway[1].Quercetin-3-glucoside regulates the expression of nitric oxide synthase 2 (NO2) via modulating the nuclear factor-κB (NF-κB) transcription regulation system. Quercetin-3-glucoside has high bioavailability and low toxicity, is a promising candidate agent to prevent birth defects in diabetic pregnancies[2].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> NO Synthase

Research Areas >> Inflammation/Immunology

[In Vitro]

Quercetin-3-glucoside (5-20 μM; 24 hours) substantially reduces ethanol-induced cytotoxicity , protects hepatic cells against ethanol‐stimulated liver injury[1].Quercetin-3-glucoside (10 μM; pre-treat 1 hour) dramatically downregulates the levels of ethanol-induced iNOS protein expression in HepG2 cells[1]. Cell Viability Assay[1] Cell Line: HepG2 cells Concentration: 5 μM, 10 μM, 20 μM Incubation Time: 24 hours Result: Caused significantly enhanced cell viability as positive controls. Western Blot Analysis[1] Cell Line: HepG2 cells Concentration: 10 μM Incubation Time: 1 hour Result: Decreased ethanol‐ induced iNOS protein expression.

[References]

[1]. Lee S, et al. Relative protective activities of quercetin, quercetin-3-glucoside, and rutin in alcohol-induced liver injury. J Food Biochem. 2019 Aug 5:e13002.

[2]. Tan C, et al. Modulation of nuclear factor-κB signaling and reduction of neural tube defects by quercetin-3-glucoside in embryos of diabetic mice. Am J Obstet Gynecol. 2018 Aug;219(2):197.e1-197.e8.

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
872.6±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₁H₂₀O₁₂

[ Molecular Weight ]:
464.376

[ Flash Point ]:
307.5±27.8 °C

[ Exact Mass ]:
464.095490

[ PSA ]:
210.51000

[ LogP ]:
1.75

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.803

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DJ2982500

CHEMICAL NAME :: 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-3-(beta-D-gluco pyranosyloxy)-

CAS REGISTRY NUMBER :: 482-35-9

BEILSTEIN REFERENCE NO. :: 0100989

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C21-H20-O12

MOLECULAR WEIGHT :: 464.41

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 19,326,1985

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi: Irritant;

[ Safety Phrases ]:
24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
LK8960000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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