Quercitrin

Names

[ CAS No. ]:
522-12-3

[ Name ]:
Quercitrin

[Synonym ]:
quercetin 3-O-α-L-rhamnopyranoside
quercetin-3-L-rhamnoside
3-O-α-rhamnosylquercetine
Quercetin 3-O-L-rhamnoside
Quercitroside
QUERCETIN 3-L-RHAMNOSIDE
EINECS 208-322-5
Thujin
3,3',4',5,7-Pentahydroxyflavone 3-(6-deoxy-a-L-mannopyranoside)
4H-1-Benzopyran-4-one, 3-((6-deoxy-α-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4H-chromen-4-on
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4H-chromen-4-one
Quercetin 3-O-α-L-rhamnoside
2-(3,4-Dihydroxyphényl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-méthyltétrahydro-2H-pyran-2-yl]oxy}-4H-chromén-4-one
Quercetin-3-O-α-L-rhamnopyranoside
3-[(6-Deoxy-α-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyran-4-one
Quercimelin
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl-6-deoxy-α-L-mannopyranoside
Quercetin-3-rhamnoside
4H-1-Benzopyran-4-one, 3-[(6-deoxy-α-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
Quercetrin
FLAVIN
Quercetin-3-O-rhamnoside
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-deoxy-α-L-mannopyranoside
usafcf-2
quercetin 3-O-rhamnoside
MFCD00016932
3-[(6-Deoxy-a-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
Quercitrin
quercetin 3-rhamnoside

Biological Activity

[Description]:

Quercitrin is a natural compound found in Tartary buckwheat with a potential anti-inflammation effect that is used to treat heart and vascular conditions.IC50 value:Target:In vitro: There were significant increases in caspase-3 activity, loss of MMP, and increases in the apoptotic cell population in response to quercitrin in DLD-1 colon cancer cells in a time- and dose-dependent manner. [1] In vivo: ICR mice received CCl4 intraperitoneally with or without quercitrin co-administration for 4 weeks. Data showed that quercitrin significantly suppressed the elevation of reactive oxygen species (ROS) production and malondialdehyde (MDA) content, reduced tissue plasminogen activator (t-PA) activity, enhanced the antioxidant enzyme activities and abrogated cytochrome P450 2E1 (CYP2E1) induction in mouse brains. [2]

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> MAPK/ERK Pathway >> Ribosomal S6 Kinase (RSK)

Natural Products >> Flavonoids

Research Areas >> Inflammation/Immunology

[References]

[1]. Cincin ZB, et al. Apoptotic Effects of Quercitrin on DLD-1 Colon Cancer Cell Line. Pathol Oncol Res. 2015 Apr;21(2):333-8.

[2]. Ma JQ, et al. Quercitrin offers protection against brain injury in mice by inhibiting oxidative stress and inflammation. Food Funct. 2016 Jan 20;7(1):549-56.

[3]. Li W, et al. Quercitrin ameliorates the development of systemic lupus erythematosus-like disease in a chronic graft-versus-host murine model. Am J Physiol Renal Physiol. 2016 Feb 24:ajprenal.00249.2015.

[Related Small Molecules]

BI-D1870 | CMK | PF-4708671 | LY-2584702 tosylate salt | BIX 02565 | AT7867 | Pluripotin | A-196 | LJI308 | LJH-685 | AT13148 | Carnosol

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
814.0±65.0 °C at 760 mmHg

[ Melting Point ]:
174-183ºC

[ Molecular Formula ]:
C₂₁H₂₀O₁₁

[ Molecular Weight ]:
448.377

[ Flash Point ]:
288.3±27.8 °C

[ Exact Mass ]:
448.100555

[ PSA ]:
190.28000

[ LogP ]:
2.17

[ Vapour Pressure ]:
0.0±3.1 mmHg at 25°C

[ Index of Refraction ]:
1.776

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UZ5950000

CHEMICAL NAME :: Quercitrin

CAS REGISTRY NUMBER :: 522-12-3

BEILSTEIN REFERENCE NO. :: 0068135

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C21-H20-O11

MOLECULAR WEIGHT :: 448.41

WISWESSER LINE NOTATION :: T66 BO EVJ CR CQ DQ& GQ IQ DO- BT6OTJ CQ DQ EQ F1

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 :: 200 mg/kg

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

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >150 mg/kg

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

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 166 nmol/plate

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 54,297,1978

Safety Information

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UZ5950000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Separation of the antioxidant compound quercitrin from Lindera obtusiloba Blume and its antimelanogenic effect on B16F10 melanoma cells.

Biosci. Biotechnol. Biochem. 77(1) , 58-64, (2013)

Considering the growing evidence of the presence of antioxidant compounds in plant extracts, the objectives of this study were to identify antioxidant compounds in Lindera obtusiloba Blume (Lauraceae)...

[Chemical constituents from Commelina communis].

Zhongguo Zhong Yao Za Zhi 38(19) , 3304-8, (2013)

To investigate the chemical constituents from Commelina communis, fifteen compounds were separated and purified by silica gel, Sephadex LH-20, and ODS column chromatography, and semi-preparative HPLC....

Analysis of different European hazelnut (Corylus avellana L.) cultivars: authentication, phenotypic features, and phenolic profiles.

J. Agric. Food Chem. 62(26) , 6236-46, (2014)

Hazelnuts exhibit functional properties due to their content in fatty acids and phenolic compounds that could positively affect human health. The food industry requires precise traits for morphologica...