Wortmannin

Base Information Edit

Chemical Name:Wortmannin
CAS No.:19545-26-7
Molecular Formula:C23H24O8
Molecular Weight:428.439
Hs Code.:29322090
NSC Number:627609,221019
UNII:XVA4O219QW
DSSTox Substance ID:DTXSID8040642
Nikkaji Number:J13.549F
Wikipedia:Wortmannin
Wikidata:Q73401372
NCI Thesaurus Code:C1277
Pharos Ligand ID:L6DJFK5T3MYF
Metabolomics Workbench ID:58201
ChEMBL ID:CHEMBL428496
Mol file:19545-26-7.mol

Synonyms:MS 54;MS-54;MS54;wortmannin

Suppliers and Price of Wortmannin

Supply Marketing:Edit

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Usbiological
Wortmannin, Penicillium funiculosum
1mg
$ 297.00

Usbiological
Wortmannin
1mg
$ 283.00

TRC
Wortmannin
5mg
$ 50.00

TRC
Wortmannin
100mg
$ 495.00

Tocris
Wortmannin
5
$ 367.00

Tocris
Wortmannin
1
$ 95.00

TCI Chemical
Wortmannin >98.0%(HPLC)
20mg
$ 203.00

Sigma-Aldrich
Wortmannin from
1mg
$ 95.90

Sigma-Aldrich
Wortmannin, Ready Made Solution ≥95% (HPLC)
250ul
$ 107.00

Sigma-Aldrich
Wortmannin, Ready Made Solution from Penicillium funiculosum, ≥95% (HPLC)
250 μL
$ 111.00

Total 49 raw suppliers

Chemical Property of Wortmannin Edit

Chemical Property:

Appearance/Colour:White to pale yellow powder
Vapor Pressure:4.35E-15mmHg at 25°C
Melting Point:234-240 °C
Refractive Index:1.591
Boiling Point:615.6 °C at 760 mmHg
Flash Point:326.1 °C
PSA：109.11000
Density:1.39 g/cm³
LogP:2.53640
Storage Temp.:2-8°C
Sensitive.:Light Sensitive
Solubility.:DMSO: soluble
XLogP3:1.2
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:4
Exact Mass:428.14711772
Heavy Atom Count:31
Complexity:921

Purity/Quality:

98%,99%, ^*data from raw suppliers

Wortmannin, Penicillium funiculosum ^*data from reagent suppliers

Safty Information:

Pictogram(s): Xi,T+,T
Hazard Codes:T+,T,Xi,Xn,F
Statements: 26/27/28-36/37/38-36-20/21/22-11
Safety Statements: 28-36/37-45-37/39-26-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Canonical SMILES:CC(=O)OC1CC2(C(CCC2=O)C3=C1C4(C(OC(=O)C5=COC(=C54)C3=O)COC)C)C
Isomeric SMILES:CC(=O)O[C@@H]1C[C@]2([C@@H](CCC2=O)C3=C1[C@]4([C@H](OC(=O)C5=COC(=C54)C3=O)COC)C)C
Description Wortmannin (19545-26-7) is a potent and selective inhibitor of PI3-kinase which acts via covalent modification of Lys-802.2?Inhibits autophagy in rat hepatocytes.3?Inhibits adipocyte differentiation of 3T3-L1 cells.4?Wortmannin is useful tool for probing PI3-K-mediated cellular events.5
Uses Wortmannin is a steroidal metabolite belonging to the viridin group, isolated from Penicillium wortmannii in 1957. The structure was finally solved in 1968. Wortmannin exhibits broad spectrum antifungal activity, together with antitumour and antiinflammatory activity. Wortmannin is a potent inhibitor of phosphoinositide 3-kinase and myosin light chain kinase. Wortmannin also activates neutrophil and formyl-Met-Leu-Phe-mediated phospholipase D, inhibits autophagy, potentiates LPS-induced NO production and induces Alzheimer-like hyperphosphorylation in tau in vivo. Wortmannin is used as inhibitor of phosphatidylinositol 3-kinase, used cell biology reagent that has been used previously in research to inhibit DNA repair, receptor-mediated endocytosis and cell proliferation. It inhibits fMLP induced PIP3 and superoxide anion production in guinea pig neutrophils. It blocks insulin metabolic effects in rat adipocytes without affecting the insulin receptor tyrosine kinase activity. Wortmannin, Ready Made Solution has been used: as a phosphoinositide 3-kinase (PI3K) pathway inhibitoras an endoderm-inducing agent in stem cell selection and differentiation as a autophagy inhibitor

Technology Process of Wortmannin

There total 51 articles about Wortmannin 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: 85.0%

: 58053-83-1,108740-89-2
17-beta-Hydroxywortmannin

: 19545-26-7
wortmannin

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 2.5h;
DOI:10.1021/jacs.7b02515

Reference yield: 84.0%

: 51819-63-7
11-O-desacetyl-wortmannin

: 108-24-7
acetic anhydride

: 19545-26-7
wortmannin

Guidance literature:: In pyridine; at 20 ℃; for 12h;
DOI:10.1021/jacs.7b02515

Reference yield:

: 22614-34-2
9α,11α-epoxy-4-androstene-3,17-dione

: 19545-26-7
wortmannin

Guidance literature:: Multi-step reaction with 28 steps

1: iPr₂NEt / CH₂Cl₂ / 0.5 h / -78 °C

2: 1) mCPBA, KHCO₃, 2) citric acid / 1) CH₂Cl₂, -30 to -20 deg C, 1 h, 2) MeOH, 0 deg C to RT

3: NaIO₄ / methanol; H₂O / 0 deg C, 12 h; RT, 3 h

4: CHCl₃ / Ambient temperature

5: 71 percent / LTBA / tetrahydrofuran / -78 to -40 deg C; -35 deg C, 4 h

6: 89 percent / nBu₃P / tetrahydrofuran / 1 h / 0 - 20 °C

7: 85 percent / 30percent H₂O₂ / tetrahydrofuran / 18 h / 0 - 20 °C

8: I₂, NaHCO₃ / CH₂Cl₂ / 48 h / Ambient temperature

9: 90 percent / methanol / 4 h / 0 - 20 °C

10: LTBA / tetrahydrofuran / 3 h / 0 °C

11: pyridine / 2 h / 0 - 20 °C

12: 56 percent / CSA, dihydroquinone / benzene / 3 h / Heating

13: 1) mCPBA, 2) 2N HCl / 1) CH₂Cl₂, -30 to -25 deg C, 20 h, 2) THF, RT, 16 h

14: Me₄NBH(OAc)3 / acetic acid; acetonitrile / 2 h / 0 °C

15: DDQ / dioxane / 4 h / 80 °C

16: 94 percent / Ag₂O / acetonitrile / 24 h / Ambient temperature

17: 92 percent / MsCl, Et₃N / CH₂Cl₂ / Ambient temperature

18: 47 percent / OsO₄, DABCO / tetrahydrofuran / 24 h / -40 °C

19: 92 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 16 h / Ambient temperature

20: CH(NMe₂)3 / 1 h / 100 °C

21: 2N HCl / tetrahydrofuran / 20 h / Ambient temperature

22: PCC / CH₂Cl₂ / 5 h / Ambient temperature

23: CH₂Cl₂ / 0.33 h / Ambient temperature

24: DBN / CH₂Cl₂ / 6 h / Ambient temperature

25: K₂CO₃, MeOH / 5 h / Ambient temperature

26: 1N HCl / tetrahydrofuran / 12 h / Ambient temperature

27: 49 percent / pyridine / 12 h / -20 °C

28: 73 percent / PCC / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; methanol; sodium periodate; osmium(VIII) oxide; tributylphosphine; tris(dimethylamino)methane; 2,6-dichloro-benzonitrile; camphor-10-sulfonic acid; dihydrogen peroxide; iodine; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; potassium hydrogencarbonate; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; hydroquinone; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; citric acid; silver(l) oxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water; acetic acid; acetonitrile; benzene;
DOI:10.1016/0040-4039(96)01332-9