(1R,6S,11aS,13S,14aR)-1,13-dihydroxy-6-methyl-1H,4H,6H,7H,8H,9H,11aH,12H,13H,14H,14aH-cyclopenta[f]oxacyclotridecan-4-one

• ChemBase ID: 132479
• Molecular Formular: C16H24O4
• Molecular Mass: 280.35936
• Monoisotopic Mass: 280.16745925
• SMILES: C[C@H]1CCC/C=C\[C@@H]2C[C@@H](C[C@H]2[C@@H](/C=C\C(=O)O1)O)O
• Canonical SMILES: O[C@@H]1C[C@@H]2[C@@H](C1)/C=C\CCC[C@@H](OC(=O)/C=C\[C@H]2O)C
• InChI: InChI=1S/C16H24O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h4,6-8,11-15,17-18H,2-3,5,9-10H2,1H3/b6-4-,8-7-/t11-,12+,13-,14+,15+/m0/s1
• InChIKey: KQNZDYYTLMIZCT-QJNJASIYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,6S,11aS,13S,14aR)-1,13-dihydroxy-6-methyl-1H,4H,6H,7H,8H,9H,11aH,12H,13H,14H,14aH-cyclopenta[f]oxacyclotridecan-4-one
• IUPAC Traditional name: brefeldin A
• Synonyms: γ,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic acid λ-lactone; Ascotoxin; BFA; Cyanein; Decumbin; Brefeldin A

Database IDs

• CAS Number: 20350-15-6
• MDL Number: MFCD12913297
• Beilstein Number: 25191
• PubChem SID: 24891917; 162226756; 24278285
• PubChem CID: 24123450

CALCULATED PROPERTIES

• Acid pKa: 14.419293
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.007216
• LogD (pH = 7.4): 2.007216
• Log P: 2.007216
• Molar Refractivity: 78.7488 cm^3
• Polarizability: 30.270922 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: soluble1-5 mg/mL (Store stock solutions at -20 °C.); methanol: soluble10 mg/mL (Store stock solutions at -20 °C.)

Safety Information

• RTECS: GY8410000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99% (HPLC and TLC)
• Grade: for molecular biology
• Biological Source: from Penicillium brefeldianum
• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - B6542

Analysis Note
Tested for inhibition of interleukin export from Jurkat cells.
Biochem/physiol Actions
Brefeldin A (BFA) is a fungal metabolite which disrupts the structure and function of the Golgi apparatus. BFA is an activator of the sphingomyelin cycle. Brefeldin A-mediated apoptosis has been observed in human tumor cells.

Sigma Aldrich - B7651

Biochem/physiol Actions
Brefeldin A (BFA) is a fungal metabolite which disrupts the structure and function of the Golgi apparatus. BFA is an activator of the sphingomyelin cycle. Brefeldin A-mediated apoptosis has been observed in human tumor cells.