(6R)-3,5,6-trihydroxy-2,6-bis(3-methylbut-2-en-1-yl)-4-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one

• ChemBase ID: 153171
• Molecular Formular: C21H30O5
• Molecular Mass: 362.4599
• Monoisotopic Mass: 362.20932406
• SMILES: CC(C)CC(=O)C1=C([C@@](C(=O)C(=C1O)CC=C(C)C)(CC=C(C)C)O)O
• Canonical SMILES: CC(=CCC1=C(O)C(=C([C@](C1=O)(O)CC=C(C)C)O)C(=O)CC(C)C)C
• InChI: InChI=1S/C21H30O5/c1-12(2)7-8-15-18(23)17(16(22)11-14(5)6)20(25)21(26,19(15)24)10-9-13(3)4/h7,9,14,23,25-26H,8,10-11H2,1-6H3/t21-/m0/s1
• InChIKey: VZMXLSLKOHIKTQ-NRFANRHFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R)-3,5,6-trihydroxy-2,6-bis(3-methylbut-2-en-1-yl)-4-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one
• IUPAC Traditional name: (6R)-3,5,6-trihydroxy-2,6-bis(3-methylbut-2-en-1-yl)-4-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one
• Synonyms: α-Bitter acid; α-Lupulic acid; Humulone, mixture of homologues

Database IDs

• CAS Number: 26472-41-3
• MDL Number: MFCD00076002
• PubChem SID: 24873348; 162247310
• PubChem CID: 72625

CALCULATED PROPERTIES

• Acid pKa: 5.078746
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.0400949
• LogD (pH = 7.4): 1.3029729
• Log P: 3.600608
• Molar Refractivity: 106.3035 cm^3
• Polarizability: 39.718803 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

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: ≥90.0% (HPLC)

DETAILS

Sigma Aldrich - 50247

Analysis Note
predominantly humulone and cohumulone