ChemicalBook > CAS DataBase List > Brefeldin A

Brefeldin A

Product Name
Brefeldin A
CAS No.
20350-15-6
Chemical Name
Brefeldin A
Synonyms
BFA;CS-766;CYANEIN;cyanaein;DECUMBIN;ASCOTOXIN;Brefeldin;NSC 89671;NSC 107456;NECTROLIDE
CBNumber
CB0689753
Molecular Formula
C16H24O4
Formula Weight
280.36
MOL File
20350-15-6.mol
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Brefeldin A Property

Melting point:
200-205 °C
alpha 
93 º (C=2 IN MEOH)
Boiling point:
492.7±45.0 °C(Predicted)
Density 
1.108±0.06 g/cm3(Predicted)
vapor pressure 
0.56 hPa ( 20 °C)
Flash point:
87 °C
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
methanol: 10 mg/mL, clear, colorless to faintly yellow
form 
Crystalline Powder
pka
12.92±0.60(Predicted)
color 
White to almost white
Water Solubility 
Soluble in dimethylsulfoxide, dichloromethane and ethanol. Slightly soluble in water.
Merck 
13,1355
BRN 
25191
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
InChIKey
QSECOIOBNZLGOD-OBCVZTHZSA-N
CAS DataBase Reference
20350-15-6
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Safety

Hazard Codes 
Xn,T
Risk Statements 
22-25-36/37/38-20/21/22
Safety Statements 
24/25-45-36-26
RIDADR 
UN 2811 6.1/PG 3
WGK Germany 
3
RTECS 
GY8410000
Autoignition Temperature
301 °C
HS Code 
29411090
Toxicity
LD50 i.p. in mice: >200 mg/kg (Haerri)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

Precautionary statements

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
B6542
Product name
Brefeldin A
Purity
≥99% (HPLC and TLC), BioXtra, for molecular biology
Packaging
5mg
Price
$210
Updated
2024/03/01
Sigma-Aldrich
Product number
B5936
Product name
Brefeldin A
Purity
from Penicillium brefeldianum, Ready Made Solution, 10?mg/mL in DMSO, 0.2 μm filtered
Packaging
200μL
Price
$161
Updated
2024/03/01
Sigma-Aldrich
Product number
5.00583
Product name
InSolution (+)-Brefeldin A, Eupenicillium brefeldianum - CAS 20350-15-6 - Calbiochem
Packaging
2mg
Price
$142
Updated
2024/03/01
TCI Chemical
Product number
B3820
Product name
Brefeldin A
Packaging
10MG
Price
$127
Updated
2024/03/01
TCI Chemical
Product number
B3820
Product name
Brefeldin A
Packaging
50MG
Price
$436
Updated
2024/03/01
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Brefeldin A Chemical Properties,Usage,Production

Description

Brefeldin A (20350-15-6) is a specific inhibitor of protein translocation from endoplasmic reticulum to Golgi. Induces apoptosis. Brefeldin A activates sphingomyelin metabolism. Cell permeable.

Chemical Properties

White Powder

Uses

A macrolide isolated from Penicillium brefeldianum. It affects the vesticular transport of the Golgi apparatus and induces DNA fragmentation which leads to apoptosis

Uses

Brefeldin A is a potent inhibitor of cell growth first described in 1958, then independently rediscovered by several groups as a potent active in a broad range of bioassays. Brefeldin has antiviral, antibiotic, antifungal, antitumour and herbicidal activity. Early studies on the mode of action of brefeldin identified inhibition of protein and nucleic acid synthesis by disruption of the Golgi apparatus. The precise molecular target is a subset of Sec7-type GTP exchange factors (GEFs) that activate a small GTPase, Arf1p, an integral component of protein trafficking and signalling.

Uses

Brefeldin A (BFA) is a natural fungal metabolite which has been used extensively to study intracellular transport by vesicles or endosomes. Early studies demonstrated that BFA reversibly interferes with protein trafficking and secretion mediated by the Golgi apparatus and endoplasmic reticulum. BFA directly and reversibly inhibits Sec7 domain-containing guanine-exchange factors which are necessary for ADP-ribosylation factor activation associated with vesicular transport (IC50 = ~10 μM). BFA is used to study endosomal trafficking and function in cells of plants as well as those of fungi, invertebrates, and vertebrates.

Definition

ChEBI: A metabolite from Penicillium brefeldianum that exhibits a wide range of antibiotic activity.

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. Blocks binding of ADP-ribosylation factor to the Golgi and inhibits the GDP-GTP exchange. Inhibits the activity of BIG1 and BIG2, the guanine-nucleotide exchange proteins for ADP-ribosylation factors. Also available as a 25 mM solution in DMSO (Cat. No. 500583).

Biological Activity

Reversible inhibitor of protein translocation from the endoplasmic reticulum (ER) to the Golgi apparatus. Blocks binding of ADP-ribosylation factor to the Golgi apparatus and inhibits GDP-GTP exchange.

Biochem/physiol Actions

Primary TargetBlocks translocation of proteins from the endoplasmic reticulum (ER) to the Golgi apparatus

storage

-20°C (desiccate)

Purification Methods

Brefeldin A was isolated from Penicillium brefeldianum and recrystallised from aqueous MeOH/EtOAc or MeOH. Its solubility in H2O is 0.6mg/mL, 10mg/mL in MeOH and 24.9mg/mL in EtOH. The O-acetate recrystallises from Et2O/pentane and has m 130-131o, [] D +17o (c 0.95, MeOH). [Sigg Helv Chim Acta 47 1401 1964, UV and IR: H.rri et al. Helv Chim Acta 46 1235 1963, total synthesis: Kitahara et al. Tetrahedron 3021 1979, X-ray : Weber et al. Helv Chim Acta 54 2763 1971, Beilstein 18 III/IV 1220.]

References

1) Fujiwara et al. (1988) Brefeldin A causes disassembly of the Golgi complex and accumulation of secretory proteins in the endoplasmic reticulum; J. Biol. Chem., 263 18545 2) Shao et al. (1996), Brefeldin A is a potent inducer of apoptosis in human cancer cells independently of p53; Exp. Cell Res., 227 190 3) Linardic et al. (1996), Brefeldin A promotes hydrolysis of sphingomyelin; Cell Growth Differ., 7 765

Brefeldin A Preparation Products And Raw materials

Raw materials

Preparation Products

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Brefeldin A Suppliers

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View Lastest Price from Brefeldin A manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
Brefeldin A 20350-15-6
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-10-28
Hebei Yanxi Chemical Co., Ltd.
Product
Brefeldin A 20350-15-6
Price
US $10.00-1.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20 tons
Release date
2023-09-20
airuikechemical co., ltd.
Product
brefeldin 20350-15-6
Price
US $0.00-0.00/Kg
Min. Order
1Kg
Purity
99.9%
Supply Ability
200tons
Release date
2024-04-09

20350-15-6, Brefeldin ARelated Search:

Kresoxim-methyl Methyl acrylate Thiophanate-methyl Tylosin tartrate Methyl acetate Doramectin Bensulfuron methyl Methylparaben Abamectin Ivermectin Nystatin Methyl ETHYL TRANS-2-OCTENOATE Parathion-methyl Methyl bromide ETHYL TRANS-2-DECENOATE BREFELDIN A, [3H],BREFELDIN-A, [7-3H] FEMA 2194 Brefeldin

  • NSC 107456
  • (1R,2E,6S,10E,11aS,13S,14aR)-1,13-dihydroxy-6-Methyl-6,7,8,9,12,13,14,14a-octahydro-1H-cyclopenta[f][1]oxacyclotridecin-4(11aH)-one
  • Ascotoxin, Cyanein, DecuMbin
  • Brefeldin A, FroM EupenicilliuM brefeldianuM
  • Brefeldin A, 98%, from Eupenicillium brefeldianum
  • NECTROLIDE
  • SYNERGISIDIN
  • 4h-cyclopent(f)oxacyclotridecin-4-one,1,6,7,8,9,11a-beta,12,13,14,14a-alpha-de
  • cahydro-1-beta-13-alpha-dihydroxy-6-beta-methyl-
  • cyanaein
  • CYANEIN
  • DECUMBIN
  • GAMMA-4-DIHDYROXY-2-(6-HYDROXY-1-HEPTENYL)-4-CYCLOPENTANECROTONIC ACID LAMBDA-LACTONE
  • GAMMA,4-DIHYDROXY-2-[6-HYDROXY-1-HEPTENYL]-4-CYCLOPENTANECROTONIC ACID LAMBDA-LACTONE
  • BFA
  • (+)-BREFELDIN A, EUPENICILLIUM BREFELDIANUM
  • BREFELDIN A, EUPENICILLIUM BREFELDIANUM
  • (+)-BREFELDIN A
  • BREFELDIN A
  • ASCOTOXIN
  • 1,6,7,8,9,11A,12,13,14,14A-DECAHYDRO-1,13-DIHYDROXY-6-METHYL-4H-CYCLOPENT[F]OXACYCLOTRIDECIN-4-ONE
  • Brefeldin A Cyanein Ascotoxin
  • Brefeldin A, from Penicillium brefeldianum, ≥98% (HPLC)
  • CS-766
  • (+)-Brefeldin A, Eupenicillium brefeldianum - CAS 20350-15-6 - Calbiochem
  • (1R,2E,6S,10E,11aS,13S,14aR)-1,13-Dihydroxy-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f][1]oxacyclotridecin-4-one
  • 1,6,7,8,9,11AB,12,13,14,14AA-DECAHYDRO-1B,13A-DIHYDROXY-6B-METHYL-4H-CYCLOPENT(F)OXACYCLOTRIDECIN-4-ONE
  • BREFELDIN A, MOLECULAR BIOLOGY REAGENT
  • BREFELDIN A FROM PENICILLIUM BREFELDIANUM
  • Brefeldin A, >=99%
  • (1R,2E,6S,10E,13S)-1,13-Dihydroxy-6-methyl-6,7,8,9,12,13,14,14a-octahydro-1H-cyclopenta[f][1]o
  • Brefeldin A, natural
  • g-4-Dihdyroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic Acid, Lactone, BFA, Cyanein, Ascotoxin, Decumbin
  • Brefeldin
  • 4H-Cyclopentfoxacyclotridecin-4-one, 1,6,7,8,9,11a,12,13,14,14a-decahydro-1,13-dihydroxy-6-methyl-, (1R,2E,6S,10E,11aS,13S,14aR)-
  • (+)-Brefeldin A, Ascotoxin, Cyanein, Decumbin, Nectrolide, Synergisidin
  • -4-Dihdyroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic Acid, -Lactone, BFA, Cyanein, Ascotoxin, Decumbin
  • Ascotoxin, BFA, Cyanein, Decumbin, γ,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic acid λ-lactone
  • 4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic acid λ-lactone
  • BFA / Ascotoxin / Cyanein / Decumbin
  • BREFELDIN ARESEARCH GRADE
  • BrefeldinA,γ,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic acid λ-lactone, Ascotoxin, BFA, Cyanein, Decumbin
  • Brefeldin A(BFA,Ascotoxin,Cyanein)
  • NSC 244390
  • NSC 89671
  • Brefeldin A(BFA)
  • Brefeldin A USP/EP/BP
  • 20350-15-6
  • 20350-16-6
  • C16H24O4
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