3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

• ChemBase ID: 172038
• Molecular Formular: C16H10O8
• Molecular Mass: 330.2458
• Monoisotopic Mass: 330.03756728
• SMILES: c1(cc(c2c(c1O)C(=O)c1c(C2=O)c(c(c(c1)O)C(=O)O)C)O)O
• Canonical SMILES: OC(=O)c1c(O)cc2c(c1C)C(=O)c1c(C2=O)c(O)c(cc1O)O
• InChI: InChI=1S/C16H10O8/c1-4-9-5(2-6(17)10(4)16(23)24)13(20)12-11(15(9)22)7(18)3-8(19)14(12)21/h2-3,17-19,21H,1H3,(H,23,24)
• InChIKey: CXORMDKZEUMQHX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
• IUPAC Traditional name: 3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxoanthracene-2-carboxylic acid
• Synonyms: 9,10-Dihydro-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-2-anthracenecarboxylic Acid; 1-Methyl-2-carboxy-3,5,6,8-tetrahydroxyanthraquinone; C.I. Natural Red 3; Kermes; Kermes (dye); Kermesic Acid

Database IDs

• CAS Number: 18499-92-8
• PubChem SID: 164227948
• PubChem CID: 11727234

CALCULATED PROPERTIES

• Acid pKa: 2.216366
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 0.7337714
• LogD (pH = 7.4): 0.109560736
• Log P: 3.825449
• Molar Refractivity: 81.372 cm^3
• Polarizability: 30.015625 Å^3
• Polar Surface Area: 152.36 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K163500

Principle constituent of kermes, one of the oldest known insect dyes. Used as brilliant scarlet dye.

REFERENCES

• Tanoue, Y., et al.: Fisheries Sci., 67, 726 (2001)
• Dhananjeyan, M., et al.: J. Med. Chem., 48, 2822 (2001)
• Kouloumpi, E., et al.: Anal. Bioanal. Chem., 387, 803 (2001)