Ebelactone a

Base Information

• Chemical Name: Ebelactone a
• CAS No.: 76808-16-7
• Molecular Formula: C₂₀H₃₄O₄
• Molecular Weight: 338.488
• DSSTox Substance ID: DTXSID501318085
• Nikkaji Number: J34.507E
• Wikidata: Q76386368
• Metabolomics Workbench ID: 98870
• Mol file: 76808-16-7.mol

Synonyms:3,11-dihydroxy-2,4,6,8,10,12-hexamethyl-9-oxo-6-tetradecenoic 1,3-lactone;ebelactone A

Chemical Property of Ebelactone a

Chemical Property:

• Vapor Pressure: 1.64E-10mmHg at 25°C
• Boiling Point: 462.8°C at 760 mmHg
• Flash Point: 152.8°C
• PSA: 63.60000
• Density: 1.011g/cm³
• LogP: 3.76870
• Storage Temp.: 2-8°C
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 338.24570956
• Heavy Atom Count: 24
• Complexity: 482

Purity/Quality:

99%min ^*data from raw suppliers

Ebelactone A microbial esterase inhibitor ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(C)C(C(C)C(=O)C(C)C=C(C)CC(C)C1C(C(=O)O1)C)O
• Isomeric SMILES: CC[C@@H](C)[C@H]([C@H](C)C(=O)[C@H](C)/C=C(\C)/C[C@H](C)[C@H]1[C@@H](C(=O)O1)C)O
• Description: Ebelactone A is a β-lactone enzyme inhibitor that was first isolated from a cultured strain of soil actinomycetes. It can inhibit esterases, lipases, and N-formylmethionine aminopeptidases (IC50s = 0.056, 0.003, and 0.08 μg/ml, respectively) found on cell surfaces, which has been shown to stimulate host defense in immune cells. Ebelactone A is also reported to inhibit cutinases produced by fungal pathogens, thus demonstrating a plant-protective function.

Technology Process of Ebelactone a

There total 26 articles about Ebelactone 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:

(3R,4R)-4-((E)-(1R,5S,7R,8R)-8-Hydroxy-1,3,5,7-tetramethyl-9-methylene-6-oxo-undec-3-enyl)-3-methyl-oxetan-2-one (132950-85-7) → (3R,4R)-4-((E)-(1R,5S,7R,8S,9R)-8-Hydroxy-1,3,5,7,9-pentamethyl-6-oxo-undec-3-enyl)-3-methyl-oxetan-2-one (76808-16-7,133006-98-1,133006-99-2) + (+/-)-Ebelactone A (76808-16-7,133006-98-1,133006-99-2)

Guidance literature:

With hydrogen; Wilkinson's catalyst; In benzene; at 20 ℃; for 2h; under 760 Torr; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)88532-9

Reference yield:

(3R,4R)-4-((E)-(1R,5S,7R,8R)-8-Hydroxy-1,3,5,7-tetramethyl-9-methylene-6-oxo-undec-3-enyl)-3-methyl-oxetan-2-one (132950-85-7) → (3R,4R)-4-((E)-(1R,5S,7R,8S,9R)-8-Hydroxy-1,3,5,7,9-pentamethyl-6-oxo-undec-3-enyl)-3-methyl-oxetan-2-one (76808-16-7,133006-98-1,133006-99-2) + (+/-)-Ebelactone A (76808-16-7,133006-98-1,133006-99-2)

Guidance literature:

With hydrogen; Wilkinson's catalyst; In benzene; at 20 ℃; for 2h; under 760 Torr; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)88532-9

Reference yield:

ethylacrolein (922-63-4) → (3R,4R)-4-((E)-(1R,5S,7R,8S,9R)-8-Hydroxy-1,3,5,7,9-pentamethyl-6-oxo-undec-3-enyl)-3-methyl-oxetan-2-one (76808-16-7,133006-98-1,133006-99-2)

Guidance literature:

Multi-step reaction with 12 steps

2: 92 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

4: 94 percent / DMAP, NEt₃ / CH₂Cl₂ / 2 h / 20 °C

5: 1) Me₃SiCl, NEt₃, LDA, 2) aq. HCl / 1) THF, -78 deg C, 1 h, then 20 deg C, 1 h, then 60 deg C, 2 h

6: diethyl ether / 0 °C

7: 80 percent / DIBAL / diethyl ether / 0.33 h / -98 °C

9: 99 percent / H₂O₂, LiOH / tetrahydrofuran; H₂O / 20 h / 20 °C

10: 87 percent / PhSO₂Cl, pyridine / 16 h / -20 °C

11: 100 percent / aq. HF / acetonitrile / 2 h / 20 °C

12: H₂ / (Ph₃P)3RhCl / benzene / 2 h / 20 °C / 760 Torr

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; dmap; lithium hydroxide; chloro-trimethyl-silane; hydrogen fluoride; hydrogen; dihydrogen peroxide; diisobutylaluminium hydride; triethylamine; benzenesulfonyl chloride; lithium diisopropyl amide; Wilkinson's catalyst; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)88532-9

upstream raw materials:

(3R,4R)-4-((E)-(1R,5S,7R,8R)-8-Hydroxy-1,3,5,7-tetramethyl-9-methylene-6-oxo-undec-3-enyl)-3-methyl-oxetan-2-one

ethylacrolein

(4S,5S)-5-Hydroxy-4-methyl-6-methylene-octan-3-one

(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-6-methylene-octan-3-one

Refernces