3-(3-hydroxy-4-methoxyphenyl)-1-(2-hydroxy-6-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one

• ChemBase ID: 140158
• Molecular Formular: C29H36O15
• Molecular Mass: 624.58714
• Monoisotopic Mass: 624.20542045
• SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)Oc1cc(c(c(c1)OC)C(=O)/C=C/c1ccc(c(c1)O)OC)O)O)O)O)O)O)O
• Canonical SMILES: COc1cc(O[C@@H]2O[C@H](CO[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O)O)[C@H]([C@@H]([C@H]2O)O)O)cc(c1C(=O)/C=C/c1ccc(c(c1)O)OC)O
• InChI: InChI=1S/C29H36O15/c1-12-22(33)24(35)26(37)28(42-12)41-11-20-23(34)25(36)27(38)29(44-20)43-14-9-17(32)21(19(10-14)40-3)15(30)6-4-13-5-7-18(39-2)16(31)8-13/h4-10,12,20,22-29,31-38H,11H2,1-3H3/t12-,20+,22-,23+,24+,25-,26+,27+,28+,29+/m0/s1
• InChIKey: FDHNLHLOJLLXDH-YQKWYTHGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(3-hydroxy-4-methoxyphenyl)-1-(2-hydroxy-6-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one
• IUPAC Traditional name: 3-(3-hydroxy-4-methoxyphenyl)-1-(2-hydroxy-6-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one
• Synonyms: (E)-1-[4-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2-hydroxy-6-methoxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)-2-propen-1-one; Hesperidin methyl chalcone; 甲基橙皮甙查尔酮

Database IDs

• CAS Number: 24292-52-2
• EC Number: 246-128-2
• MDL Number: MFCD00010438
• PubChem SID: 162234402; 24895666
• PubChem CID: 6436550

CALCULATED PROPERTIES

• Acid pKa: 8.129467
• H Acceptors: 15
• H Donor: 8
• LogD (pH = 5.5): 0.32128292
• LogD (pH = 7.4): 0.24843974
• Log P: 0.32229304
• Molar Refractivity: 148.7601 cm^3
• Polarizability: 59.020145 Å^3
• Polar Surface Area: 234.29 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 120 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -71°, c = 1 in ethanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Empirical Formula (Hill Notation): C29H36O15

DETAILS

Sigma Aldrich - H5006

Packaging
25 g in glass bottle
Application
Involved in pharmacological studies of:
• The effects on adhesion molecules in vascular endothelium1
• Thymidine monophosphate kinase inhibitors as antitubercular agents2