brefeldin A

Base Information

• Chemical Name: brefeldin A
• CAS No.: 20350-15-6
• Deprecated CAS: 11006-23-8,11039-44-4,19022-59-4,27740-36-9,31874-13-2,3459-16-3,60132-23-2,78206-62-9,11039-44-4,19022-59-4,27740-36-9,31874-13-2,60132-23-2,78206-62-9
• Molecular Formula: C16H24O4
• Molecular Weight: 280.364
• Hs Code.: 29411090
• NSC Number: 107456,89671,244390,56310
• UNII: XG0D35F9K6
• DSSTox Substance ID: DTXSID00880041
• Wikipedia: Brefeldin_A
• Wikidata: Q168790
• Metabolomics Workbench ID: 56895
• ChEMBL ID: CHEMBL19980
• Mol file: 20350-15-6.mol

Synonyms:Ascotoxin;Brefeldin A;Cyanein;Decumbin;NSC 89671;NSC-89671;NSC89671;Synergisidin

Chemical Property of brefeldin A

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 200-205 °C
• Refractive Index: 1.513
• Boiling Point: 492.7 °C at 760 mmHg
• PKA: 12.92±0.60(Predicted)
• Flash Point: 180.8 °C
• PSA: 66.76000
• Density: 1.108 g/cm³
• LogP: 1.96240
• Storage Temp.: 2-8°C
• Solubility.: methanol: 10 mg/mL, clear, colorless to faintly yellow
• Water Solubility.: Soluble in dimethylsulfoxide, dichloromethane and ethanol. Slightly soluble in water.
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 280.16745924
• Heavy Atom Count: 20
• Complexity: 388

Purity/Quality:

99% ^*data from raw suppliers

Brefeldin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn; T
• Hazard Codes: Xn,T
• Statements: 22-25-36/37/38-20/21/22
• Safety Statements: 24/25-45-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCCC=CC2CC(CC2C(C=CC(=O)O1)O)O
• Isomeric 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
• 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.
• Uses: A macrolide isolated from Penicillium brefeldianum. It affects the vesticular transport of the Golgi apparatus and induces DNA fragmentation which leads to apoptosis 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. 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.

Technology Process of brefeldin A

There total 271 articles about brefeldin A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(-)-(2E,4S,5R,7S,9S,10E,15S)-4-<(p-Methoxybenzyl)oxy>-7-<(2-methoxyethoxy)methoxy>brefeldin → (+)-brefeldin A (20350-15-6)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1021/jo00069a013

Reference yield: 95.0%

4-oxo-brefeldin-A (54202-13-0) → (+)-brefeldin A (20350-15-6)

Guidance literature:

With sodium tetrahydroborate; In methanol; at -78 ℃;

DOI:10.1016/S0040-4039(00)02278-4

Reference yield: 95.0%

(5E,13E)-(2S,3aR,4R,9S,14aS)-4-Hydroxy-2-methoxymethoxy-9-methyl-1,2,3,3a,4,9,10,11,12,14a-decahydro-8-oxa-cyclopentacyclotridecen-7-one → (+)-brefeldin A (20350-15-6)

Guidance literature:

With boron trifluoride diethyl etherate; thiophenol; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/jo010743i

upstream raw materials:

brefeldin A 4,7-O-diacetate

(E)-4-[(1R,2S,4S)-2-((E)-(S)-6-Hydroxy-hept-1-enyl)-4-(2-methoxy-ethoxymethoxy)-cyclopentyl]-4-(2-methoxy-ethoxymethoxy)-but-2-enoic acid

(1R,6S,11aS,13S,14aR)-1,13-bis[(2-methoxyethoxy)methoxy]-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

(+)-Brefeldin A 7-methoxyethoxymethylether

Refernces

• 1、 Seo, Seung-Yong,Jung, Jae-Kyung,Paek, Seung-Mann,Lee, Yong-Sil,Kim, Seok-Ho,Suh, Young-Ger. "An olefin disconnection strategy for the practical synthesis of (+)-brefeldin A: olefin cross metathesis and intramolecular Horner-Wadsworth-Emmons olefination". . p. 6527 - 6530. Retrieved 2006.
• 2、 Xiong, Ziyue,Hale, Karl J.. "Total synthesis of the antitumor macrolides, (+)-brefeldin A and 4-epi-brefeldin A from d-glucose: Use of the Padwa anionic allenylsulfone [3 + 2]-cycloadditive elimination to construct trans-configured chiral cyclopentane systems". . p. 4254 - 4257. Retrieved 2016.
• 3、 Zhu, Ji-Wen,Nagasawa, Hideko,Nagura, Fumi,Mohamad, Saharuddin B.,Uto, Yoshihiro,Ohkura, Kazuto,Hori, Hitoshi. "Elucidation of strict structural requirements of Brefeldin A as an inducer of differentiation and apoptosis". . p. 455 - 463. Retrieved 2000.
• 4、 Mabuni,Garlaschelli,Ellison,Hutchinson. "Biosynthetic origin of the oxygen atoms in the C15 macrolide antibiotic brefeldin A". . p. 7718 - 7720. Retrieved 1977.