Robinin

Names

[ CAS No. ]:
301-19-9

[ Name ]:
Robinin

[Synonym ]:
4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-galactopyranosyl]-oxy]-7-[(6-deoxy-α-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-
5-Hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}methyl)tetrahydro-2H-pyran-2-yl]oxy}-4H-chromen-4-one
3-[[6-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-galactopyranosyl]oxy]-7-[(6-deoxy-a-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
7-[(6-Deoxy-α-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl-6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-galactopyranoside
kaempherol-3-O-robinoside-7-O-rhamnoside
Kaempferol-3-O-gal-rham-7-O-rham
7-[(6-Deoxy-α-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-galactopyranoside
Robinin
5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
Kaempferol 3-Robinoside 7-Rhamnoside
kaempherol-3-O-gal-rha-7-O-rha
4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-galactopyranosyl]oxy]-7-[(6-deoxy-α-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-
5-Hydroxy-2-(4-hydroxyphényl)-7-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-méthyltétrahydro-2H-pyran-2-yl]oxy}-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-méthyltétrahydro-2H-pyran-2-yl]oxy}méthyl)tétrahydro-2H-pyran-2-yl]oxy}-4H-chromén-4-one
4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-galactopyranosyl)oxy)-7-((6-deoxy-α-L-mannopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl
5-Hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}methyl)tetrahydro-2H-pyran-2-yl]oxy}-4H-chromen-4-on
Kaempferol-3-O-robinoside-7-O-rhamnoside
4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-galactopyranosyl)oxy)-7-((6-deoxy-α-L-mannopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-
EINECS 206-113-3

Biological Activity

[Description]:

Robinin is present in flavonoid fraction of Vigna unguiculata leaf. Robinin inhibits upregulated expression of TLR2 and TLR4. Robinin ameliorates oxidized low density lipoprotein (Ox-LDL) induced inflammatory insult through TLR4/NF-κB pathway[1].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> Toll-like Receptor (TLR)

Research Areas >> Inflammation/Immunology

[Target]

TLR2

TLR4

[References]

[1]. Janeesh PA, et al. Robinin modulates TLR/NF-κB signaling pathway in oxidized LDL induced human peripheral blood mononuclear cells. Int Immunopharmacol. 2014 Jan;18(1):191-7.

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
1064.4±65.0 °C at 760 mmHg

[ Melting Point ]:
194-195ºC

[ Molecular Formula ]:
C₃₃H₄₀O₁₉

[ Molecular Weight ]:
740.659

[ Flash Point ]:
335.7±27.8 °C

[ Exact Mass ]:
740.216370

[ PSA ]:
308.12000

[ LogP ]:
0.89

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

[ Index of Refraction ]:
1.728

[ Storage condition ]:
?20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DJ2979380

CHEMICAL NAME :: 4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-galac topyranosyl) oxy)-7-((6-deoxy-alpha-L-mannopyranosyl)oxy)-5-hydrox y-2-(4-hydroxyphenyl)-

CAS REGISTRY NUMBER :: 301-19-9

LAST UPDATED :: 199410

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C33-H40-O19

MOLECULAR WEIGHT :: 740.73

WISWESSER LINE NOTATION :: T66 BO EVT&J GQ IO- BT6OTJ CQ DQ EQ F1& DO- BT6OTJ CQ DQ EQ F1O- BT6OTJ CQ DQ EQ F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 100 ug/plate

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 66,223,1979

Safety Information

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

Precursor & DownStream

Precursor

DownStream

Articles

Roles of flavonoids in plant resistance to insects.

Prog. Clin. Biol. Res. 213 , 87-100, (1986)

Simultaneous determination of the flavonoids robinin and kaempferol in human breast cancer cells by liquid chromatography-tandem mass spectrometry.

J. Pharm. Biomed. Anal. 55 , 109-113, (2011)

An accurate, precise and sensitive method was developed and validated for the simultaneous quantification of the flavonoid glycoside robinin, and its algycone kaempferol in human breast cancer MCF-7 c...

Effects of selected flavonoids and carotenoids on drug accumulation and apoptosis induction in multidrug-resistant colon cancer cells expressing MDR1/LRP.

In Vivo 19 , 433-8., (2005)

The effects of various flavonoids and carotenoids on Rhodamine 123 accumulation in multidrug-resistant Colo 320 human colon cancer cells expressing MDR1/LRP were studied. The Colo 205 cell line was us...