Bisabolangelone

Base Information

• Chemical Name: Bisabolangelone
• CAS No.: 30557-81-4
• Deprecated CAS: 1408-30-6,10208-69-2
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• ChEMBL ID: CHEMBL2016934
• Metabolomics Workbench ID: 126166
• Nikkaji Number: J1.533.034A,J346.569A
• Wikidata: Q105013407
• Mol file: 30557-81-4.mol

Synonyms:bisabolangelone

Chemical Property of Bisabolangelone

Chemical Property:

• Melting Point: 157-158 °C
• Boiling Point: 396.0±42.0 °C(Predicted)
• PKA: 14.54±0.40(Predicted)
• PSA: 46.53000
• Density: 1.154±0.06 g/cm3(Predicted)
• LogP: 2.52160
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 248.14124450
• Heavy Atom Count: 18
• Complexity: 466

Purity/Quality:

98% ^*data from raw suppliers

Bisabolangelone 98.22% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)C2C(C1)OC(=CC=C(C)C)C2(C)O
• Isomeric SMILES: CC1=CC(=O)[C@H]2[C@@H](C1)O/C(=C\C=C(C)C)/[C@@]2(C)O
• General Description: (+)-Bisabolangelone is a sesquiterpenoid isolated from *Angelica bisecta* seeds, recognized for its strong insect antifeeding activity. Its synthetic production was achieved to address the instability of the natural compound, employing a cyclization strategy involving a γ-acetylenic alcohol and utilizing protective groups and reagents like lithium acetylide, PPTS, and t-BuOK. The synthesized product matched the natural compound in spectral and chromatographic properties, confirming its structural and functional equivalence.

Technology Process of Bisabolangelone

There total 26 articles about Bisabolangelone 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: 92.0%

EE-bisabolangelone (124456-86-6,124456-87-7) → (+)-bisabolangelone (30557-81-4,110269-60-8)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; for 2.5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80090-9

Reference yield: 62.0%

(+/-) TES-bisabolangelone (110211-75-1,124511-42-8) → (+/-) bisabolangelone (30557-81-4,110269-60-8)

Guidance literature:

With pyridine; hydrogen fluoride; In dichloromethane; at 30 ℃; for 72h;

DOI:10.1016/S0040-4039(00)85112-6

Reference yield: 62.0%

TES-bisabolangelone (124511-42-8) → (+)-bisabolangelone (30557-81-4,110269-60-8)

Guidance literature:

With pyridine; hydrogen fluoride; In dichloromethane; -78 deg C; 30 deg C, 4 d;

DOI:10.1016/S0040-4020(01)80090-9

upstream raw materials:

EE-bisabolangelone

TES-bisabolangelone

(+/-) TES-bisabolangelone

5-methylcyclohex-2-en-1-one

Downstream raw materials:

3-methyl-phenol

Refernces

TOTAL SYNTHESIS OF (+/-)-BISABOLANGELONE

10.1016/S0040-4039(00)85112-6

The research focuses on the total synthesis of the sesquiterpenoid (+)-bisabolangelone, a compound isolated from the seeds of Angelica bisecta, known for its potent insect antifeeding properties. The purpose of the study was to overcome the limitations posed by the unstable nature of the natural product and to create a synthetic approach to form the heterocyclic ring by cyclization of a γ-acetylenic alcohol, a procedure already known in the field. The synthesis process involved a series of chemical reactions using various reagents such as lithium acetylide of Z-methylpent-2-ene-4-yne, MeI/KOH/DMSO for methylation, PPTS for deprotection, t-BuOK for cyclization, and protective groups like tetrahydropyranyl ether (THP), methylthiomethyl ether (MTM), and [2(trimethylsilyl)ethoxy]methyl ether (SEM). The successful synthesis of (+)-bisabolangelone was confirmed by comparing its spectral data (NMR, IR, MS, UV) and TLC behavior with that of the natural product, yielding a final product identical to the naturally occurring bisabolangelone.

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