2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4H-chromen-4-one

• ChemBase ID: 129255
• Molecular Formular: C16H12O7
• Molecular Mass: 316.26228
• Monoisotopic Mass: 316.05830272
• SMILES: COc1cc(c2c(c1)oc(c(c2=O)O)c1cc(c(cc1)O)O)O
• Canonical SMILES: COc1cc(O)c2c(c1)oc(c(c2=O)O)c1ccc(c(c1)O)O
• InChI: 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
• InChIKey: JGUZGNYPMHHYRK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4H-chromen-4-one
• IUPAC Traditional name: rhamnetin
• Synonyms: 7-Methylquercetin; 7-Methoxyquercetin; 7-O-Methylquercetin; beta-Rhamnocitrin; Quercetin 7-methyl ether; Rhamnetin; 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-y-methoxy-4H-1-benzopyran-4-one; Rhamnetin; 3,3',4',5-Tetrahydroxy-7-methoxyflavone; 3,5,3',4'-Tetrahydroxy-7-methoxyflavone; C.I. 75690; LY 805921; NSC 19802; β-Rhamnocitrin; 7-O-Methyl Quercetin; Rhamnetin; 鼠李亭

Database IDs

• CAS Number: 90-19-7
• EC Number: 201-974-1
• MDL Number: MFCD00016931
• Beilstein Number: 47741
• PubChem SID: 24850707; 162223549
• PubChem CID: 5281691
• Wikipedia Title: Rhamnetin

CALCULATED PROPERTIES

• H Donor: 4
• LogD (pH = 5.5): 2.3009005
• LogD (pH = 7.4): 2.2063975
• Log P: 2.3021934
• Molar Refractivity: 81.3445 cm^3
• Polarizability: 30.311293 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 8.023193
• H Acceptors: 7

PROPERTIES

Safety Information

• RTECS: LK8748000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ADORA3(140)mouse ... Hexa(15211)

Product Information

• Purity: ≥99.0% (HPLC)
• Grade: analytical standard
• Empirical Formula (Hill Notation): C16H12O7

DETAILS

Toronto Research Chemicals - M326555

O-Methylated metabolite of the flavanoid Quercertin (Q509500) with antioxidant activity.

REFERENCES

• Soobrattee, M.A. et al.: Mut. Res. Fund. Mol. Mech. Mutagen., 579, 200 (2005)
• Yamamoto, N. et al.: Arch. Biochem. Biophys., 372, 347 (2005)