eupatorin
3',5-dihydroxy-4',6,7-trimethoxyflavone
Identification
| Name | eupatorin |
| IUPAC | 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxychromen-4-one |
| CAS Number | 855-96-9 |
| FDA UNII | 3J474AV6MY |
| Molecular Formula | C18 H16 O7 |
| Molecular Weight | 344.31992000 |
| MDL Number | MFCD00016929 |
| Nikkaji Number | J7.145E |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 587.00 °C. @ 760.00 mm Hg (est) |
| Flash Point | 421.00 °F. TCC ( 216.00 °C. ) (est) |
| logP (o/w) | 2.960 (est) |
| Soluble in | water, 45.53 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for eupatorin usage levels up to | not for fragrance use. |
| Recommendation for eupatorin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
4H-1-
benzopyran-4-one, 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy- (9CI)
3',5-
dihydroxy-4',6,7-trimethoxyflavone
5,3'-
dihydroxy-6,7,4'-trimethoxyflavone
eupatorine
flavone, 3',5-dihydroxy-4',6,7-trimethoxy- (8CI)
5-
hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxychromen-4-one
PubMed:
Eupatorin-induced cell death in human leukemia cells is dependent on caspases and activates the mitogen-activated protein kinase pathway.
PubMed:
Orthosiphon stamineus protects Caenorhabditis elegans against Staphylococcus aureus infection through immunomodulation.
PubMed:
Preparation and characterization of nano liposomes of Orthosiphon stamineus ethanolic extract in soybean phospholipids.
PubMed:
Antioxidant and enzyme inhibitory activities of Plebeian herba (Salvia plebeia R. Br.) under different cultivation conditions.
PubMed:
Benzo[a]pyrene sensitizes MCF7 breast cancer cells to induction of G1 arrest by the natural flavonoid eupatorin-5-methyl ether, via activation of cell signaling proteins and CYP1-mediated metabolism.
PubMed:
Characterization of the Interaction between Eupatorin and Bovine Serum Albumin by Spectroscopic and Molecular Modeling Methods.
PubMed:
A simple isocratic HPLC method for the simultaneous determination of sinensetin, eupatorin, and 3'-hydroxy-5,6,7,4'-tetramethoxyflavone in Orthosiphon stamineus extracts.
PubMed:
Antiproliferative and antiangiogenic effects of flavone eupatorin, an active constituent of chloroform extract of Orthosiphon stamineus leaves.
PubMed:
Bioactivity-guided isolation of antiproliferative compounds from Centaurea jacea L.
PubMed:
Flavonoids eupatorin and sinensetin present in Orthosiphon stamineus leaves inhibit inflammatory gene expression and STAT1 activation.
PubMed:
The flavonoid eupatorin inactivates the mitotic checkpoint leading to polyploidy and apoptosis.
PubMed:
Comparative CYP1A1 and CYP1B1 substrate and inhibitor profile of dietary flavonoids.
PubMed:
In vitro effects of active constituents and extracts of Orthosiphon stamineus on the activities of three major human cDNA-expressed cytochrome P450 enzymes.
PubMed:
Flavones and rosmarinic acid from Salvia limbata.
PubMed:
In vitro modulatory effects of Andrographis paniculata, Centella asiatica and Orthosiphon stamineus on cytochrome P450 2C19 (CYP2C19).
PubMed:
Evaluation of the genotoxicity of Orthosiphon stamineus aqueous extract.
PubMed:
Bioactivity-guided isolation of antiproliferative compounds from Centaurea arenaria.
PubMed:
HPLC and anti-inflammatory studies of the flavonoid rich chloroform extract fraction of Orthosiphon stamineus leaves.
PubMed:
The methoxylated flavones eupatorin and cirsiliol induce CYP1 enzyme expression in MCF7 cells.
PubMed:
Evaluation of the anti-pyretic potential of Orthosiphon stamineus Benth standardized extract.
PubMed:
Antiproliferative and cytostatic effects of the natural product eupatorin on MDA-MB-468 human breast cancer cells due to CYP1-mediated metabolism.
PubMed:
Diterpenoids and flavonoids from the fruits of Vitex agnus-castus and antioxidant activity of the fruit extracts and their constituents.
PubMed:
New Bisabolane-Type Sesquiterpenes from the Aerial Parts of Lippia dulcis.
PubMed:
Determination of flavonoids from Orthosiphon stamineus in plasma using a simple HPLC method with ultraviolet detection.
PubMed:
Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship.
PubMed:
Constituents of the Vietnamese medicinal plant Orthosiphon stamineus.
PubMed:
Analysis of vervain flavonoids by HPLC/Diode array detector method. Its application to quality control.
PubMed:
Anti-inflammatory effects of South American Tanacetum vulgare.
PubMed:
Lipophilic flavonoids from Orthosiphon spicatus prevent oxidative inactivation of 15-lipoxygenase.
PubMed:
Inhibition of mitochondrial respiration and cyanide-stimulated generation of reactive oxygen species by selected flavonoids.
PubMed:
Methylated Flavones from Teucrium polium.
PubMed:
Plant anticancer agents. IX. Constituents of Hyptis tomentosa.
PubMed:
Eupatorin, a constituent of Merrillia caloxylon.
PubMed:
Flavonoid constituents from Eupatorium altissimum L. (Compositae).
PubMed:
Tumor inhibitors. 8. Eupatorin, new cytotoxic flavone from Eupatorium semiserratum.