irigenin
5,7,3'-trimethoxy-6,4',5'-trimethoxyisoflavone
Identification
| Name | irigenin |
| IUPAC | 5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxychromen-4-one |
| CAS Number | 548-76-5 |
| EINECS | 208-958-3 |
| FDA UNII | 6O4NX37350 |
| Molecular Formula | C18 H16 O8 |
| Molecular Weight | 360.31912000 |
| Nikkaji Number | J6.451C |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 93.68 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| 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 irigenin usage levels up to | not for fragrance use. |
| Recommendation for irigenin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
4H-1-
benzopyran-4-one, 5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-
5,7-
dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4-benzopyrone
5,7-
dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one
5,7-
dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxychromen-4-one
5,7,3'-
trimethoxy-6,4',5'-trimethoxyisoflavone
PubMed:
Ionic-liquid-based ultrasound-assisted extraction of isoflavones from Belamcanda chinensis and subsequent screening and isolation of potential α-glucosidase inhibitors by ultrafiltration and semipreparative high-performance liquid chromatography.
PubMed:
8-Hydroxyirilone 5-methyl ether and 8-hydroxyirilone, new antioxidant and α-amylase inhibitors isoflavonoids from Iris germanica rhizomes.
PubMed:
Irigenin, a novel lead from Western Himalayan chemiome inhibits Fibronectin-Extra Domain A induced metastasis in Lung cancer cells.
PubMed:
Ultrafiltration-LC-MS combined with semi-preparative HPLC for the simultaneous screening and isolation of lactate dehydrogenase inhibitors from Belamcanda chinensis.
PubMed:
LC-MS Guided Isolation of Bioactive Principles from Iris hookeriana and Bioevaluation of Isolates for Antimicrobial and Antioxidant Activities.
PubMed:
Belamcanda chinensis (L.) DC-An ethnopharmacological, phytochemical and pharmacological review.
PubMed:
Characterization of in vitro metabolites of irisflorentin by rat liver microsomes using high-performance liquid chromatography coupled with tandem mass spectrometry.
PubMed:
Belamcandae chinensis rhizome--a review of phytochemistry and bioactivity.
PubMed:
[Chemical constituents from rhizomes of Iris germanica].
PubMed:
Dynamic changes of flavonoids contents in the different parts of rhizome of Belamcanda chinensis during the thermal drying process.
PubMed:
Chemical constituents of the ethyl acetate extract of Belamcanda chinensis (L.) DC roots and their antitumor activities.
PubMed:
New constituents from the rhizomes of Egyptian Iris germanica L.
PubMed:
Characterisation and quantification of flavonoids in Iris germanica L. and Iris pallida Lam. resinoids from Morocco.
PubMed:
Simultaneous determination of tectorigenin, irigenin and irisflorentin in rat plasma and urine by UHPLC-MS/MS: application to pharmacokinetics.
PubMed:
Characterization and determination of the major constituents in Belamcandae Rhizoma by HPLC-DAD-ESI-MS(n).
PubMed:
Preparative isolation and purification of seven isoflavones from Belamcanda chinensis.
PubMed:
Application of complexation high-speed counter-current chromatography in the separation of 5-hydroxyisoflavone isomers from Belamcanda chinensis (L.) DC.
PubMed:
Antimutagenic and anti-oxidant activities of isoflavonoids from Belamcanda chinensis (L.) DC.
PubMed:
Preparative isolation and purification of flavonoids from the Chinese medicinal herb Belamcanda by high-speed countercurrent chromatography.
PubMed:
Antiproliferative activity on human cancer cell lines after treatment with polyphenolic compounds isolated from Iris pseudopumila flowers and rhizomes.
PubMed:
Isolation and purification of isoflavonoids from Rhizoma Belamcandae by two-dimensional preparative high-performance liquid chromatography with column switch technology.
PubMed:
The rapid identification of isoflavonoids from Belamcanda chinensis by LC-NMR and LC-MS.
PubMed:
Quality evaluation of Rhizoma Belamcandae (Belamcanda chinensis (L.) DC.) by using high-performance liquid chromatography coupled with diode array detector and mass spectrometry.
PubMed:
Inhibitory effects of Irigenin from the rhizomes of Belamcanda chinensis on nitric oxide and prostaglandin E(2) production in murine macrophage RAW 264.7 cells.
PubMed:
Analysis of DNA in endometrial cancer cells treated with phyto-estrogenic compounds using comparative genomic hybridisation microarrays.
PubMed:
Phenolic constituents of the rhizomes of the Thai medicinal plant Belamcanda chinensis with proliferative activity for two breast cancer cell lines.
PubMed:
[Study on the fingerprints of Belamcanda chinensis (L.) DC by capillary electrophoresis].
PubMed:
Phytoestrogens derived from Belamcanda chinensis have an antiproliferative effect on prostate cancer cells in vitro.
PubMed:
Cancer chemopreventive in vitro activities of isoflavones isolated from Iris germanica.
PubMed:
Alkylated benzoquinones from Iris kumaonensis.
PubMed:
Isoflavonoids from the rhizomes of Belamcanda chinensis and their effects on aldose reductase and sorbitol accumulation in streptozotocin induced diabetic rat tissues.
PubMed:
[Determination of five isoflavones in Belamcanda Chinensis by RP-HPLC].
PubMed:
[Analysis of isoflavones in Belamcanda chinensis (L.)DC. and Iris tectorum Maxim by square wave voltammetry].
PubMed:
Synthesis of isoflavones. V. Irigenin and tectorigenin.