(3S,3aR,9aR)-3-hexanoyl-9a-methyl-6-(prop-1-en-1-yl)-2H,3H,3aH,4H,8H,9H,9aH-furo[3,2-g]isochromene-2,9-dione

• ChemBase ID: 156056
• Molecular Formular: C21H26O5
• Molecular Mass: 358.42814
• Monoisotopic Mass: 358.17802393
• SMILES: CCCCCC(=O)[C@@H]1[C@H]2CC3=C(COC(=C3)/C=C/C)C(=O)[C@@]2(OC1=O)C
• Canonical SMILES: CCCCCC(=O)[C@H]1C(=O)O[C@@]2([C@@H]1CC1=C(C2=O)COC(=C1)/C=C/C)C
• InChI: InChI=1S/C21H26O5/c1-4-6-7-9-17(22)18-16-11-13-10-14(8-5-2)25-12-15(13)19(23)21(16,3)26-20(18)24/h5,8,10,16,18H,4,6-7,9,11-12H2,1-3H3/t16-,18+,21-/m1/s1
• InChIKey: XXKNHBAFFJINCK-PLMTUMEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,3aR,9aR)-3-hexanoyl-9a-methyl-6-(prop-1-en-1-yl)-2H,3H,3aH,4H,8H,9H,9aH-furo[3,2-g]isochromene-2,9-dione
• IUPAC Traditional name: (3S,3aR,9aR)-3-hexanoyl-9a-methyl-6-(prop-1-en-1-yl)-3H,3aH,4H,8H-furo[3,2-g]isochromene-2,9-dione
• Synonyms: (3S,3aR,9aR)-3-Hexanoyl-9a-methyl-6-((E)-propenyl)-3a,4,8,9a-tetrahydro-3H-furo[3,2-g]isochromene-2,9-dione; (3S,3aR,9aR)-3a,4,8,9a-Tetrahydro-9a-methyl-3-(1-oxohexyl)-6-(1E)-1-propenyl-2H-furo[3,2-g][2]benzopyran-2,9(3H)-dione; Monascoflavin; Monascin

Database IDs

• CAS Number: 21516-68-7
• MDL Number: MFCD09260177
• Beilstein Number: 51355
• PubChem SID: 162250194
• PubChem CID: 12118082

CALCULATED PROPERTIES

• Acid pKa: 10.165562
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.9064884
• LogD (pH = 7.4): 3.905759
• Log P: 3.6731644
• Molar Refractivity: 100.4979 cm^3
• Polarizability: 38.113415 Å^3
• Polar Surface Area: 69.67 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (HPLC)
• Empirical Formula (Hill Notation): C21H26O5

DETAILS

Sigma Aldrich - 52442

Biochem/physiol Actions
Monascin is one of the azaphilonoid pigments in extracts of Monascus pilosus-fermented rice (red-mold rice). It is a potent inhibitor of carcinogenesis measured against chemical or UV initiated, phorbol-promoted mouse skin tumors.1