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5.00583

(+)-Brefeldin A, Eupenicillium brefeldianum

Name: (+)-Brefeldin A, <i>Eupenicillium brefeldianum</i>
Brand: MM

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

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Properties

Quality Level

100

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

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

Description

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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Global Trade Item Number

SKU	GTIN
5005830001	04055977244984