7-[(3,7-dimethylocta-2,6-dien-1-yl)oxy]-2H-chromen-2-one

• ChemBase ID: 125980
• Molecular Formular: C19H22O3
• Molecular Mass: 298.37618
• Monoisotopic Mass: 298.15689456
• SMILES: O=c1oc2cc(OC/C=C(\C)/CCC=C(C)C)ccc2cc1
• Canonical SMILES: C/C(=C\COc1ccc2c(c1)oc(=O)cc2)/CCC=C(C)C
• InChI: InChI=1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3
• InChIKey: RSDDHGSKLOSQFK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(3,7-dimethylocta-2,6-dien-1-yl)oxy]-2H-chromen-2-one; 7-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-2H-chromen-2-one
• IUPAC Traditional name: 7-[(3,7-dimethylocta-2,6-dien-1-yl)oxy]chromen-2-one; 7-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-2H-chromen-2-one; auraptene
• Synonyms: 7-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-2H-1-benzopyran-2-one; Auraptene; Aurapten; 7-Geranyloxycoumarin; Auraptene; O-Geranylumbelliferone; Feronialactone

Database IDs

• CAS Number: 495-02-3
• MDL Number: MFCD00075948
• PubChem SID: 162220323
• PubChem CID: 1550607
• CHEMBL: 307341
• Chemspider ID: 1267148
• Wikipedia Title: Auraptene

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.646649
• LogD (pH = 7.4): 4.646649
• Log P: 4.646649
• Molar Refractivity: 90.9326 cm^3
• Polarizability: 34.31586 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: Powder; white to off-white powder

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Pharmacology Properties

• Mechanism of Action: Thromboxane A2 inhibitor

Product Information

• Purity: ≥98% (HPLC); 98.5
• Biological Source: Isol. from Citrus aurantium, Feronia elephantum, Aegle marmelos, Libanotis intermedia and others
• Application(s): Antiaggregant; Antifungal agent; Spasmolytic
• Empirical Formula (Hill Notation): C19H22O3

DETAILS

Sigma Aldrich - A9861

Biochem/physiol Actions
Auraptene is an estrogen receptor modulator that also acts as an ACAT inhibitor. It displays anti-tumor effects in several xenograft and chemically-induced murine tumor models. Auraptene induces apoptosis and is anti-proliferative in cancer cell lines. It has agonistic properties against PPARs, and interferes with lipid and cholesterol production by inhibiting ACAT (IC50 = 4 uM).