3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one

• ChemBase ID: 127918
• Molecular Formular: C16H12O7
• Molecular Mass: 316.26228
• Monoisotopic Mass: 316.05830272
• SMILES: COc1c(ccc(c1)c1c(c(=O)c2c(cc(cc2o1)O)O)O)O
• Canonical SMILES: COc1cc(ccc1O)c1oc2cc(O)cc(c2c(=O)c1O)O
• InChI: InChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
• InChIKey: IZQSVPBOUDKVDZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one
• IUPAC Traditional name: isorhamnetin
• Synonyms: 3′-Methoxy-3,4′,5,7-tetrahydroxyflavone; Isorhamnetin; 3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one; 3,3',5,7-Tetrahydroxy-3'-methoxyflavone; 3'-Methylquercetin; C.I. 75680; Isorhamnetin; Quercetin 3'-Methyl Ether; 3'-O-Methyl Quercetin; 3-methylquercetin; Isorhamnetol; isorhamentin; isorhamnetine; iso-rhamnetin; 3'-Methoxyquercetin; Tamarixetin; Isorhamnetin

Database IDs

• CAS Number: 480-19-3
• EC Number: 207-545-5
• MDL Number: MFCD00017310
• Beilstein Number: 44723
• PubChem SID: 162222235; 24850701
• PubChem CID: 5281654
• CHEMBL: 379064
• Unique Ingredient Identifier: 73WRA8Z8M8
• Wikipedia Title: Isorhamnetin

CALCULATED PROPERTIES

• Molar Refractivity: 81.3445 cm^3
• Polarizability: 30.311304 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 6.381414
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 2.2488089
• LogD (pH = 7.4): 1.1663433
• Log P: 2.3021934

PROPERTIES

Physical Property

• Apperance: Yellow powder
• Melting Point: 307 °C

Safety Information

• RTECS: LK9275450
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• Safety Statements: 36/37
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (HPLC); ≥99% (HPLC)
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C16H12O7

DETAILS

Sigma Aldrich - 17794

Biochem/physiol Actions
Isorhamnetin inhibits adipogenesis by interfering with differentiation of adipose stem cells, by a mechanism involving stabilization of β-catenin and up-regulating the Wnt signaling pathway.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 17794.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Protocols & Applications
Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references

Sigma Aldrich - 38907

Biochem/physiol Actions
Isorhamnetin inhibits adipogenesis by interfering with differentiation of adipose stem cells, by a mechanism involving stabilization of β-catenin and up-regulating the Wnt signaling pathway.1

Toronto Research Chemicals - M326575

A metabolite of the flavanoid Quercetin (Q509500) with antioxidant properties. It helps to protect H9c2 cardiomyoblasts against H2O2-induced oxidative stress via the modulation of PI3K/Akt and ERK1/2 signaling pathways.

REFERENCES

• Duenas, M. et al.: Eur. Food Res. Technol., 232, 103 (2011)
• Ameho, C.K. et al.: J. Nutrit. Biochem., 19, 467 (2011)
• Angeloni, C. et al.: Biochimie, 89, 73 (2011)