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

• ChemBase ID: 156744
• Molecular Formular: C22H20O13
• Molecular Mass: 492.3864
• Monoisotopic Mass: 492.0903907
• SMILES: Cc1c2c(cc(c1C(=O)O)O)C(=O)c1c(c(c(c(c1O)O)[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)C2=O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)c1c(O)c2c(c(c1O)O)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)16(28)12(18(30)17(10)29)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: DGQLVPJVXFOQEV-JNVSTXMASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-7-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9,10-dihydroanthracene-2-carboxylic acid
• IUPAC Traditional name: 3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-7-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracene-2-carboxylic acid
• Synonyms: Carminic acid; Natural Red 4; Carminic acid; 中性红 4; 胭脂红酸

Database IDs

• CAS Number: 1260-17-9
• EC Number: 215-023-3
• MDL Number: MFCD00167028
• Beilstein Number: 71651
• PubChem SID: 162250881; 24853740
• PubChem CID: 10255083
• Color Index Number: 75470
• E Number: E120

CALCULATED PROPERTIES

• Acid pKa: 2.2163415
• H Acceptors: 13
• H Donor: 9
• LogD (pH = 5.5): -2.0285447
• LogD (pH = 7.4): -2.8462205
• 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

• Optical Rotation: [α]20/D +3.1°, c = 1 in H2O
• Absorption Wavelength: λmax 495 nm

Safety Information

• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥96.0% (HPLC); 95+%
• Grade: analytical standard; for microscopy (Hist.); indicator (pH 4.8-6.2)
• Ignition Residue: ~5%
• Loss on Drying: ~3% loss on drying
• Empirical Formula (Hill Notation): C22H20O13

DETAILS

Sigma Aldrich - 22010

Application
for spectrophotometric determination of B

Sigma Aldrich - 229253

Packaging
1, 5 g in glass bottle