2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ4-chromen-1-ylium chloride

• ChemBase ID: 154142
• Molecular Formular: C21H21ClO11
• Molecular Mass: 484.83784
• Monoisotopic Mass: 484.07723917
• SMILES: c1cc(c(cc1c1c(cc2c(cc(cc2[o+]1)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)O)O.[Cl-]
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc3c(O)cc(cc3[o+]c2c2ccc(c(c2)O)O)O)[C@@H]([C@H]([C@H]1O)O)O.[Cl-]
• InChI: InChI=1S/C21H20O11.ClH/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8;/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26);1H/t16-,17+,18+,19-,21-;/m1./s1
• InChIKey: YTMNONATNXDQJF-QSLGVYCOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ^4-chromen-1-ylium chloride
• IUPAC Traditional name: cyanidin 3-O-β-D-galactoside chloride
• Synonyms: 3-(Galactosyloxy)-3′,4′,5,7-tetrahydroxyflavylium chloride; Cyanidin 3-O-galactoside chloride; Idein chloride; Idaein chloride

Database IDs

• CAS Number: 27661-36-5
• MDL Number: MFCD00270387
• PubChem SID: 162248281; 24851441
• PubChem CID: 176457

CALCULATED PROPERTIES

• Acid pKa: 6.3883295
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): 0.33378032
• LogD (pH = 7.4): -0.9419018
• Log P: 0.387
• Molar Refractivity: 116.2575 cm^3
• Polarizability: 44.011936 Å^3
• Polar Surface Area: 193.44 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)
• Empirical Formula (Hill Notation): C21H21ClO11

DETAILS

Sigma Aldrich - 19050

Biochem/physiol Actions
Anthocyanin.
Application
Idaein chloride (Cyanidin 3-O-galactoside) is a glycoside derivative of cyanidin, a potent inhibitor of the epidermal growth-factor receptor, used in comparative analysis of anti-EGF activity in cancer cells.