10-(acetyloxy)-8,8-dimethyl-2-oxo-2H,8H,9H,10H-pyrano[2,3-h]chromen-9-yl 3-methylbutanoate

• ChemBase ID: 167709
• Molecular Formular: C21H24O7
• Molecular Mass: 388.41106
• Monoisotopic Mass: 388.15220311
• SMILES: c1(=O)ccc2c(o1)c1c(cc2)OC(C(C1OC(=O)C)OC(=O)CC(C)C)(C)C
• Canonical SMILES: CC(CC(=O)OC1C(OC(=O)C)c2c(OC1(C)C)ccc1c2oc(=O)cc1)C
• InChI: InChI=1S/C21H24O7/c1-11(2)10-16(24)27-20-19(25-12(3)22)17-14(28-21(20,4)5)8-6-13-7-9-15(23)26-18(13)17/h6-9,11,19-20H,10H2,1-5H3
• InChIKey: ALKTVPFKDYZFGA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 10-(acetyloxy)-8,8-dimethyl-2-oxo-2H,8H,9H,10H-pyrano[2,3-h]chromen-9-yl 3-methylbutanoate
• IUPAC Traditional name: 10-(acetyloxy)-8,8-dimethyl-2-oxo-9H,10H-pyrano[2,3-h]chromen-9-yl 3-methylbutanoate
• Synonyms: Butanoic Acid 3-Methyl-10-(acetyloxy)-9,10-dihydro-8,8-dimethyl-2-oxo-2H,8H-benzo[1,2-b:3,4-b']dipyran-9-yl Ester; (+/-)-3,4,5-Trihydroxy-2,2-dimethyl-6-chromanacrylic Acid δ-Lactone 4-Acetate 3-Isovalerate; rac Dihydro Samidin

Database IDs

• CAS Number: 21311-66-0
• PubChem SID: 162261842
• PubChem CID: 2841560

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.1277719
• LogD (pH = 7.4): 3.1277719
• Log P: 3.1277719
• Molar Refractivity: 99.6279 cm^3
• Polarizability: 39.329464 Å^3
• Polar Surface Area: 88.13 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D449525

A derivative of Samidin (S110500). A potent vasodilatory agent isolated from Ammi visnaga. Used in the synthesis of (+/-)-Praeruptorin A.

REFERENCES

• Mathur, S.B., et al.: Tetrahedron, 21, 3575 (1965)
• Schneider, G., et al.: Arch. Pharm., 300, 913 (1965)