3,5,7,8-tetrahydroxy-1-methyl-9,10-dioxo-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9,10-dihydroanthracene-2-carboxylic acid

• ChemBase ID: 163818
• Molecular Formular: C22H20O13
• Molecular Mass: 492.3864
• Monoisotopic Mass: 492.0903907
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)c1c(c2c(c(c1O)O)C(=O)c1c(C2=O)cc(c(c1C)C(=O)O)O)O)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@H]([C@H]([C@H]([C@@H]1O)O)O)c1c(O)c(O)c2c(c1O)C(=O)c1c(C2=O)c(C)c(c(c1)O)C(=O)O
• InChI: InChI=1S/C22H20O13/c1-4-8-5(2-6(24)9(4)22(33)34)13(25)10-11(15(8)27)17(29)18(30)12(16(10)28)21-20(32)19(31)14(26)7(3-23)35-21/h2,7,14,19-21,23-24,26,28-32H,3H2,1H3,(H,33,34)/t7-,14-,19+,20-,21+/m1/s1
• InChIKey: CHPYRYUXLCQPRS-JNVSTXMASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5,7,8-tetrahydroxy-1-methyl-9,10-dioxo-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9,10-dihydroanthracene-2-carboxylic acid
• IUPAC Traditional name: 3,5,7,8-tetrahydroxy-1-methyl-9,10-dioxo-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracene-2-carboxylic acid
• Synonyms: 7-β-D-Glucopyranosyl-9,10-dihydro-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-2-anthracenecarboxylic Acid; NSC 326224; Carminic Acid, >70%

Database IDs

• CAS Number: 1260-17-9
• PubChem SID: 162257953
• PubChem CID: 71314565

CALCULATED PROPERTIES

• Acid pKa: 2.217335
• H Acceptors: 13
• H Donor: 9
• LogD (pH = 5.5): -2.028007
• LogD (pH = 7.4): -2.8492968
• Log P: 1.0681282
• Molar Refractivity: 114.4903 cm^3
• Polarizability: 43.73635 Å^3
• Polar Surface Area: 242.51 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Dark Red Solid
• Melting Point: >200°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C183620

A red glucosidal hydroxyanthrapurin, it is produced naturally within some insects as a defense mechanism.

REFERENCES

• Enoch, S., et al.: Chem. Res. Toxicol., 23, 1547 (2010)
• Valianou, L., et al.: Anal. Bioanal. Chem., 396, 3115 (2010)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010)