(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: 126224
• Molecular Formular: C16H24O4
• Molecular Mass: 280.35936
• Monoisotopic Mass: 280.16745925
• SMILES: O=C1O[C@H](CCC/C=C/[C@H]2[C@H]([C@H](O)/C=C\1)C[C@@H](O)C2)C
• 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/t11-,12+,13-,14+,15+/m0/s1
• InChIKey: KQNZDYYTLMIZCT-XPABHHOTSA-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; γ,4- Dihydroxy- 2-(6-hydroxy-1-heptenyl)- 4-cyclopentanecrotonic acid λ-lactone; Brefeldin A

Database IDs

• CAS Number: 20350-15-6
• MDL Number: MFCD12913297
• Beilstein Number: 25191
• PubChem SID: 162220564
• PubChem CID: 71308166; 5287620
• CHEBI ID: 48080
• CHEMBL: 19980
• Chemspider ID: 4449949
• DrugBank ID: DB07348
• Wikipedia Title: Brefeldin_A

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: methanol: soluble10 mg/mL, clear, colorless to faintly yellow
• Apperance: White to off-white crystalline powder
• Melting Point: 200-205 °C; 204–205 °C
• Flash Point: 188.6 °F; 87 °C

Safety Information

• RTECS: GY8410000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 2; 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; Eyeshields, Faceshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (TLC)
• Concentration: 10 mg/mL in DMSO
• Biological Source: from Penicillium brefeldianum
• Sterility: 0.2 μm filtered
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C16H24O4

DETAILS

Sigma Aldrich - B5936

Application
Brefeldin A is produced from Penicillium brefeldianum and is used to study protein transport.
Biochem/physiol Actions
Brefeldin A (BFA) is a fungal metabolite which disrupts the structure and function of the Golgi apparatus by inhibiting transport of proteins from ER to Golgi and inducing retrograde protein transport from the Golgi apparatus to the endoplasmic reticulum. 1 BFA is an activator of the sphingomyelin cycle. Brefeldin A-mediated apoptosis has been observed in human tumor cells.
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 - 15870

Other Notes
Effects a rapid increase of Golgi cisternae volume and subsequent loss of recognizable Golgi apparatus in treated cells1,2.
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.