9-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one

• ChemBase ID: 127808
• Molecular Formular: C16H14O4
• Molecular Mass: 270.27996
• Monoisotopic Mass: 270.08920893
• SMILES: O=c1oc2c(OCC=C(C)C)c3occc3cc2cc1
• Canonical SMILES: CC(=CCOc1c2occc2cc2c1oc(=O)cc2)C
• InChI: InChI=1S/C16H14O4/c1-10(2)5-7-19-16-14-12(6-8-18-14)9-11-3-4-13(17)20-15(11)16/h3-6,8-9H,7H2,1-2H3
• InChIKey: OLOOJGVNMBJLLR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one
• IUPAC Traditional name: 9-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one; imperatorin
• Synonyms: 9-[(3-METHYL-2-BUTEN-1-YL)OXY]-7H-FURO[3,2-G][1]BENZOPYRAN-7-ONE; Marmelide; NSC 402949; Imperatorin; 9-[(3-Methyl-2-butenyl)-oxy]-7H-furo[3,2-g][1][benzopyran-7-one; Enoxypsoralen; Ammidin; Marmelosin; Pentosalen; 8-Isoamylenoxypsoralen; 8-Isopentenyloxypsoralene; Imperatorin

Database IDs

• CAS Number: 482-44-0
• EC Number: 207-581-1
• MDL Number: MFCD00016881
• PubChem SID: 162222126
• PubChem CID: 10212
• CHEMBL: 453805
• Chemspider ID: 9797
• KEGG ID: C09269
• Unique Ingredient Identifier: K713N25C78
• Wikipedia Title: Imperatorin

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.1460578
• LogD (pH = 7.4): 3.1460578
• Log P: 3.1460578
• Molar Refractivity: 75.9711 cm^3
• Polarizability: 29.721748 Å^3
• Polar Surface Area: 48.67 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Alcohol; Benzene; Chloroform; DMSO: ≥5 mg/mL; Ether
• Apperance: Cryst.; off-white to light brown powder; White Solid
• Melting Point: 90-92°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Cytokine release inhibitor

Product Information

• Purity: ≥98% (HPLC); 99.0
• Biological Source: Present in roots of Imperatoria ostruthium and Clausena dentata . Also in Aegle marmelos, Angelica spp., Ammi majus, Pastinaca spp., Seseli campestre and others
• Application(s): Anticonvulsant, antiinflammatory agent; Anti-HIV activity; Shows antimicrobial activity
• Empirical Formula (Hill Notation): C16H14O4

DETAILS

Sigma Aldrich - I6659

Biochem/physiol Actions
Imperatorin is a modulator of p38, ERK pathway. Imperatorin increases BMP-2 expression (mRNA) and increases bone density/volume and mineralization in vivo.

REFERENCES

• Spath, E. et al., Ber., 1933, 66, 1137, (struct)
• Govindachari, T.R. et al., Tetrahedron, 1968, 24, 753, (isol)
• Basa, S.C. et al., Chem. Ind. (London), 1970, 746, (isol, uv, ir, nmr)
• Booer, M. et al., Ghana J. Sci., 1970, 10, 82, (pharmacol)
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, no. 1377, (occur)
• Murray, R.D.H. et al., The Natural Coumarins, J. Wiley, 1982, (occur, tox)
• Murray, R.D.H. et al., Tetrahedron, 1984, 40, 5225, (struct)
• Masuda, T. et al., Phytochemistry, 1998, 47, 13-16, (isol, uv, pmr, cmr)
• Zhou, P. et al., Phytochemistry, 2000, 53, 689, (activity)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, IHR300