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Merck

5.00583

(+)-Brefeldin A, Eupenicillium brefeldianum

InSolution, ≥95%, 25 mM in DMSO

Synonym(s):

InSolution (+)-Brefeldin A, Eupenicillium brefeldianum, 1,6,7,8,9,11a,12,13,14,14a-Decahydro-1,13-dihydroxy-6-methyl-4H-cyclopent[f]oxacyclotridecin-4-one, (1 S,2 E,7 S,10 E,12 R,13 R,15 S)-12,15-dihydroxy-7-methyl-8-oxabicyclo[11.3.0]hexadeca-2,10-dien-9-one,

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About This Item

Empirical Formula (Hill Notation):
C16H24O4
CAS Number:
20350-15-6
Molecular Weight:
280.36
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD12913297
Assay:
≥95% (HPLC)
Form:
liquid
Quality level:
100
Storage condition:
OK to freeze, avoid repeated freeze/thaw cycles, desiccated (hygroscopic), protect from light

Key Documents

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SMILES string

O1[C@H](CCC\C=C\[C@H]2[C@H]([C@H](\C=C\C1=O)O)C[C@H](C2)O)C

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

InChI key

KQNZDYYTLMIZCT-PNFJWZTBSA-N

assay

≥95% (HPLC)

form

liquid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, avoid repeated freeze/thaw cycles, desiccated (hygroscopic), protect from light

storage temp.

−70°C

Quality Level

100

General description

Specifically and reversibly blocks translocation of proteins from the endoplasmic reticulum (ER) to the Golgi apparatus without affecting endocytosis or lysosome function. Inhibitor of HDL-mediated cholesterol efflux. Causes disassembly of the Golgi complex and ER swelling in a variety of mammalian cell lines at <40 ng/ml. Inhibits the activity of BIG1 and BIG2, the guanine-nucleotide exchange proteins for ADP-ribosylation factors. Blocks binding of ADP-ribosylation factor to the Golgi and inhibits the GDP-GTP exchange.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
ADP-ribosylation factor (ARF)
Reversible: yes

Packaging

Packaged under inert gas

Preparation Note

Following initial thaw, aliquot and freeze (-70°C). Aliquots are stable for up to 6 months at -70°C. Use only fresh DMSO for further dilutions prior to use.

Other Notes

Yamagi, R., et al. 2000. Proc. Natl. Acad. Sci. USA97, 2567.
Moriango, N., et al. 1996. Proc. Natl. Acad. Sci. USA93, 12856.
Mendez, A.J. 1995. J. Biol. Chem.270, 5891.
Ridgway, N.D., et al. 1995. J. Biol. Chem. 270, 8023.
Tsai, S.C., et al. 1994. Proc. Natl. Acad. Sci. USA91, 3063.
Ktistakis, N.Y., et al. 1992. Nature356, 344.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Irritant (B)

Storage Class

10 - Combustible liquids

wgk

WGK 2

flash_point_f

188.6 °F - (refers to pure substance)

flash_point_c

87 °C - (refers to pure substance)

Certificates of Analysis (COA)

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