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

• ChemBase ID: 154140
• Molecular Formular: C21H21ClO10
• Molecular Mass: 468.83844
• Monoisotopic Mass: 468.08232455
• SMILES: c1cc(ccc1c1c(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.[Cl-]
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc3c(O)cc(cc3[o+]c2c2ccc(cc2)O)O)[C@@H]([C@H]([C@H]1O)O)O.[Cl-]
• InChI: InChI=1S/C21H20O10.ClH/c22-8-16-17(26)18(27)19(28)21(31-16)30-15-7-12-13(25)5-11(24)6-14(12)29-20(15)9-1-3-10(23)4-2-9;/h1-7,16-19,21-22,26-28H,8H2,(H2-,23,24,25);1H/t16-,17+,18+,19-,21-;/m1./s1
• InChIKey: CAHGSEFWVUVGGL-QSLGVYCOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-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: 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ^4-chromen-1-ylium chloride
• Synonyms: 3-(Glucosyloxy)-4′,5,7-trihydroxyflavylium chloride; Pelargonidin 3-O-glucoside chloride; Callistephin chloride

Database IDs

• CAS Number: 18466-51-8
• MDL Number: MFCD00017578
• PubChem SID: 24887475; 162248279
• PubChem CID: 16218556

CALCULATED PROPERTIES

• Acid pKa: 6.396818
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): 0.6192396
• LogD (pH = 7.4): -0.59826374
• Log P: 0.6714
• Molar Refractivity: 114.2766 cm^3
• Polarizability: 43.362774 Å^3
• Polar Surface Area: 173.21 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: ≥97.0% (HPLC)
• Empirical Formula (Hill Notation): C21H21ClO10

DETAILS

Sigma Aldrich - 79576

Biochem/physiol Actions
Anthocyanin found in berries.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 79576.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.