Ionomycin

Base Information

• Chemical Name: Ionomycin
• CAS No.: 56092-81-0
• Molecular Formula: C₄₁H₇₂O₉
• Molecular Weight: 709.017
• Hs Code.: 29419090
• European Community (EC) Number: 611-356-7
• UNII: 54V905V6AT
• DSSTox Substance ID: DTXSID2040521
• Nikkaji Number: J81.906I
• Wikipedia: Ionomycin
• Wikidata: Q73403125
• NCI Thesaurus Code: C596
• Metabolomics Workbench ID: 63068
• ChEMBL ID: CHEMBL501617
• Mol file: 56092-81-0.mol

Synonyms:Ionomycin;SQ 23377;SQ-23377;SQ23377

Chemical Property of Ionomycin

Chemical Property:

• Appearance/Colour: Pale Yellow Oil
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.512
• Boiling Point: 817.2 °C at 760 mmHg
• PKA: 4.77±0.10(Predicted)
• Flash Point: 235.2 °C
• PSA: 153.75000
• Density: 1.072 g/cm³
• LogP: 7.79960
• Storage Temp.: −20°C
• Solubility.: Soluble to 10 mM in Ethanol and to 10 mM in DMSO.
• XLogP3: 7.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 22
• Exact Mass: 708.51763387
• Heavy Atom Count: 50
• Complexity: 1120

Purity/Quality:

98%Min ^*data from raw suppliers

Ionomycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 36-36/37/39-27-26-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CCC(=O)O)CC(C)CC(C)C(=O)C=C(C(C)CC(C)CC=CC(C)C(C(C)C(CC1CCC(O1)(C)C2CCC(O2)(C)C(C)O)O)O)O
• Isomeric SMILES: C[C@H](CCC(=O)O)C[C@H](C)C[C@H](C)C(=O)/C=C(/[C@H](C)C[C@H](C)C/C=C/[C@@H](C)[C@H]([C@@H](C)[C@H](C[C@@H]1CC[C@@](O1)(C)[C@H]2CC[C@@](O2)(C)[C@@H](C)O)O)O)\O
• Description: Ionomycin (56092-81-0) is a highly selective nonfluorescent calcium (Ca2+) ionophore.1 Induces a rapid rise in cytosolic Ca2+ in human neutrophils which is due to both release from cytosolic Ca2+ stores as well as Ca2+ influx.2 It activates (2 μM) and primes (20-200 nM) neutrophil NADPH oxidase2. Down regulates beta-catenin/Tcf signaling in a colon cancer cell line via suppressing the binding of Tcf to its specific DNA-binding site.3 In rat hepatoma cells, sub-lethal ionomycin activates the stress response by activating SAPK/JNK and HSF/HSE interaction leading to upregulation of HSP70 biosynthesis.4
• Uses: Ionomycin was isolated from Streptomyces conglobatus as a potent Gram positive antibiotic . During isolation, it was recognised that ionomycin exhibits a very high affinity and selectivity for calcium ions, suggesting the metabolite acts as a calcium ionophore. More recently, ionomycin has been used in cell biology as a universal calcium ionophore to explore the role of calcium regulation in the cell. Ionomycin is more effective than A23187 as a Ca++ionophore. Ionomycin is used in research on Ca++ transport across biological membranes; Ionomycin induces apoptotic degeneration of embryonic cortical neurons Ionomycin free acid is a beneficial tool in research to raise intracellular calcium levels. Also this antibiotic can be used to study the calcium transport across the plasma membrane. It has been shown to induce central demyelination , inhibit adrenal bovine TREK-1 channels , and to regulate cell division of mature human B cells . It is used to study the effects of calcium flux on endoplasmic reticulum (ER) stress, mitochondrial stress and intrinsic apoptosis mechanisms. It is also used to stimulate the intracellular production of the cytokines, interferon, perforin, IL-2, and IL-4 usually in conjunction with PMA.

Technology Process of Ionomycin

There total 113 articles about Ionomycin 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:

ionomycin methyl ester (110497-18-2) → ionomycin (56092-81-0)

Guidance literature:

With lithium hydroxide; In 1,2-dimethoxyethane; at 25 ℃; for 0.75h;

DOI:10.1021/ja00169a042

Reference yield:

(2R,3R,4S)-1-(benzyloxy)-2,4-dimethyl-3,5,6-hexanetriol (128329-68-0,128440-44-8) → ionomycin (56092-81-0)

Guidance literature:

Multi-step reaction with 19 steps

1: 2.01 g / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / 25 °C

2: 2.13 g / 2,2-dimethoxypropane, d,l-camphorsulfonic acid / 2 h / 25 °C

3: 1 N Bu₄NF / tetrahydrofuran / 10 h / 25 °C

4: 95 percent / triethylamine, SO₃*pyridine / dimethylsulfoxide / 0.75 h / 25 °C

5: 1.) sodium bis(trimethylsilyl)amide / 1.) toluene, 20 deg C, 15 min, 2a.) -78 deg C, 15 min, 2b.) 20 deg C, 30 min

6: 94 percent / Bu₄NF / tetrahydrofuran / 36 h / 80 °C

7: 1.) mercuric acetate, 2.) NaBH₄, 15percent aq. NaOH / 1.) CH₂Cl₂, 20 deg C, 7 h, 2.) MeOH, 20 deg C, 30 min

8: 100 percent / triethylamine / CH₂Cl₂ / 1.5 h / 0 °C

9: 94 percent / H₂ / 10percent Pd/C / acetone / 3 h / 20 °C / 760 Torr

10: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

11: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1 h

12: tetrahydrofuran; hexane / 1.5 h / 25 °C

13: sodium amalgam / methanol; ethyl acetate / 20 h / -30 °C

14: 94 percent / Bu₄NF / tetrahydrofuran / 21 h / 25 °C

15: oxalyl chloride, DMSO / CH₂Cl₂ / 0.42 h / -60 °C

16: 1.) di-n-butylboryl triflate, diisopropylethylamine / 1.) CH₂Cl₂, -78 deg C, 30 min, 2a.) -78 deg C, 1 h, 2b.) 0 deg C, 1.5 h

17: 72 percent / pyridine, CrO₃ / CH₂Cl₂ / 0.25 h

18: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C

19: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C

With pyridine; chromium(VI) oxide; dmap; lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; sodium amalgam; n-butyllithium; oxalyl dichloride; pyridine-SO₃ complex; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen fluoride; mercury(II) diacetate; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,2-dimethoxy-propane; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; acetone; acetonitrile;

DOI:10.1021/ja00169a042

Reference yield:

(3R,4S)-1-(benzyloxy)-3-hydroxy-4-(hydroxymethyl)-2-methyl-5-hexene (73814-77-4,108814-34-2) → ionomycin (56092-81-0)

Guidance literature:

Multi-step reaction with 22 steps

1: 0.908 g / pyridine / 18 h / 5 °C

2: 0.468 g / lithium triethylborohydride / tetrahydrofuran / 24 h / 25 °C

3: 1.30 g / N-methylmorpholine N-oxide monohydrate, 0.16 M aq. osmium tetraoxide / acetone / 10 h / 25 °C

4: 2.01 g / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / 25 °C

5: 2.13 g / 2,2-dimethoxypropane, d,l-camphorsulfonic acid / 2 h / 25 °C

6: 1 N Bu₄NF / tetrahydrofuran / 10 h / 25 °C

7: 95 percent / triethylamine, SO₃*pyridine / dimethylsulfoxide / 0.75 h / 25 °C

8: 1.) sodium bis(trimethylsilyl)amide / 1.) toluene, 20 deg C, 15 min, 2a.) -78 deg C, 15 min, 2b.) 20 deg C, 30 min

9: 94 percent / Bu₄NF / tetrahydrofuran / 36 h / 80 °C

10: 1.) mercuric acetate, 2.) NaBH₄, 15percent aq. NaOH / 1.) CH₂Cl₂, 20 deg C, 7 h, 2.) MeOH, 20 deg C, 30 min

11: 100 percent / triethylamine / CH₂Cl₂ / 1.5 h / 0 °C

12: 94 percent / H₂ / 10percent Pd/C / acetone / 3 h / 20 °C / 760 Torr

13: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

14: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1 h

15: tetrahydrofuran; hexane / 1.5 h / 25 °C

16: sodium amalgam / methanol; ethyl acetate / 20 h / -30 °C

17: 94 percent / Bu₄NF / tetrahydrofuran / 21 h / 25 °C

18: oxalyl chloride, DMSO / CH₂Cl₂ / 0.42 h / -60 °C

19: 1.) di-n-butylboryl triflate, diisopropylethylamine / 1.) CH₂Cl₂, -78 deg C, 30 min, 2a.) -78 deg C, 1 h, 2b.) 0 deg C, 1.5 h

20: 72 percent / pyridine, CrO₃ / CH₂Cl₂ / 0.25 h

21: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C

22: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C

With pyridine; chromium(VI) oxide; dmap; lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; sodium amalgam; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; pyridine-SO₃ complex; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen fluoride; mercury(II) diacetate; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; lithium triethylborohydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,2-dimethoxy-propane; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; acetone; acetonitrile;

DOI:10.1021/ja00169a042

upstream raw materials:

ionomycin methyl ester

benzoic acid 3-hydroxy-1-[5'-(1-hydroxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-20-methoxycarbonyl-2,4,8,10,14,16,18-heptamethyl-11,13-dioxo-eicos-5-enyl ester

[3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanal

[3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanenitrile

Refernces

• 1、 Evans,Dow,Shih,Takacs,Zahler. "Total synthesis of the polyether antibiotic ionomycin". . p. 5290 - 5313. Retrieved 2007/10/02.