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Details

Stereochemistry ACHIRAL
Molecular Formula C16H12O7
Molecular Weight 316.2623
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RHAMNETIN

SMILES

COC1=CC2=C(C(=O)C(O)=C(O2)C3=CC(O)=C(O)C=C3)C(O)=C1

InChI

InChIKey=JGUZGNYPMHHYRK-UHFFFAOYSA-N
InChI=1S/C16H12O7/c1-22-8-5-11(19)13-12(6-8)23-16(15(21)14(13)20)7-2-3-9(17)10(18)4-7/h2-6,17-19,21H,1H3

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28858248 | https://www.ncbi.nlm.nih.gov/pubmed/27091611 | https://www.ncbi.nlm.nih.gov/pubmed/26155182

Rhamnetin is phenolic flavonoid compound and methylated derivatives of quercetin commonly found in fruits and vegetables that possess antioxidant and anti-inflammatory properties. Rhamnetin can be found in cloves, sweet wormwood, and green vegetables such as coriander leaves and seeds Cloves and coriander are common elements in many types of cuisine. Similar amounts of rhamnetin are found in apple pomace, peanuts, sour cherries, and radishes.8 It is generally considered that a regular intake of small amounts of the above-mentioned fruits and vegetables, which are commonly available, serves a protective role in preventing various diseases. Rhamnetin suppressed the mouse macrophage inflammatory protein (MIP-1, MIP-2), and mouse TNF-α cytokine production in LPS-stimulated macrophages. A nontoxic dose of rhamnetin also suppressed NO production. Rhamnetin acts as a promising sensitizer to chemotherapy and may be a novel approach to overcome the multi-drug resistance process of hepatocellular carcinoma.

Originator

Sources: Justus Liebig's Annalen der Chemie 196, 299, 338. From: J. Am. Chem. Soc. 2(1), 62-5 1880.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Application of the electrotopological state index to QSAR analysis of flavone derivatives as HIV-1 integrase inhibitors.
1996 Dec
Characterization of flavonoid--biomembrane interactions.
2002 Mar 1
Comparative study on the free flavonoid aglycones in herbs of different species of Polygonum L.
2002 Mar-Apr
Detection of isorhamnetin glycosides in extracts of apples (Malus domestica cv. "Brettacher") by HPLC-PDA and HPLC-APCI-MS/MS.
2002 Mar-Apr
Sesquiterpene lactones from Anthemis altissima and their anti-Helicobacter pylori activity.
2003 May
Structural requirements of flavonoids for increment of ocular blood flow in the rabbit and retinal function recovery in rat eyes.
2004 Jun
Allelochemicals of Polygonella myriophylla: chemistry and soil degradation.
2004 May
Effects of naturally occurring compounds on fibril formation and oxidative stress of beta-amyloid.
2005 Nov 2
Evaluation of behavioural and antioxidant activity of Cytisus scoparius Link in rats exposed to chronic unpredictable mild stress.
2008 Apr 24
Interaction of flavonoids, the naturally occurring antioxidants with different media: a UV-visible spectroscopic study.
2010 Apr
Patents

Sample Use Guides

Mice: 200 mkg/kg/day for 20 days
Route of Administration: Intraperitoneal
To determine cell viability, a 2,3-bis [2-methyloxy-4-nitro-5-sulfophenyl]-2H-tetrazolium-5-carboxanilide (XTT) assay was employed using the WelCountTM cell proliferation assay kit (WELLGENE, Daegu, South Korea). H9c2 cells were harvested with trypsin-EDTA and resuspended in culture medium. H9c2 cells (5 × 103 cells/well) were then seeded in 96-well plates and cultivated in DMEM containing 10% FBS for 24 h. Cells were then cultivated in serum-free DMEM for 6 h, followed by incubation in serum-free medium containing rhamnetin or miconazole for 24 h. XTT dye was added to each well and incubated for 3 h. Formazan dye formation was quantitated with an enzymelinked immunosorbent assay reader at 450 nm. Morphological changes in the cells were observed, and images were captured under an inverted microscope connected to a digital camera
Name Type Language
RHAMNETIN
MI  
Common Name English
QUERCETIN 7-METHYL ETHER
Common Name English
2-(3,4-DIHYDROXYPHENYL)-3,5-DIHYDROXY-7-METHOXY-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
RHAMNETIN [MI]
Common Name English
3,5,3',4'-TETRAHYDROXY-7-METHOXYFLAONE
Common Name English
FLAVONE, 3,3',4',5-TETRAHYDROXY-7-METHOXY-
Systematic Name English
3,3',4',5-TETRAHYDROXY-7-METHOXYFLAVONE
Systematic Name English
7-METHYLQUERCETIN
Common Name English
7-METHOXYQUERCETIN
Common Name English
7-O-METHYLQUERCETIN
Common Name English
FLAVONE, 7-METHOXY-3,3',4',5-TETRAHYDROXY-
Systematic Name English
NSC-19802
Code English
.BETA.-RHAMNOCITRIN
Common Name English
4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-3,5-DIHYDROXY-7-METHOXY-
Systematic Name English
Code System Code Type Description
WIKIPEDIA
RHAMNETIN
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
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MERCK INDEX
m9564
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
PRIMARY Merck Index
CAS
90-19-7
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
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PUBCHEM
5281691
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
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ECHA (EC/EINECS)
201-974-1
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
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NSC
19802
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
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CHEBI
74992
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
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EPA CompTox
DTXSID40237979
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
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MESH
C063423
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
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FDA UNII
71803L5F4S
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
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