beta-Eudesmol

Base Information

• Chemical Name: beta-Eudesmol
• CAS No.: 473-15-4
• Molecular Formula: C15H26O
• Molecular Weight: 222.371
• European Community (EC) Number: 610-334-4
• UNII: 6R61524P48
• DSSTox Substance ID: DTXSID60883391
• Nikkaji Number: J12.133I
• Wikidata: Q27108630
• Metabolomics Workbench ID: 53533
• ChEMBL ID: CHEMBL88244
• Mol file: 473-15-4.mol

Synonyms:beta-eudesmol;beta-eudesmol, (2s-(2alpha,4aalpha,8abeta))-isomer

Chemical Property of beta-Eudesmol

Chemical Property:

• Vapor Pressure: 0.000101mmHg at 25°C
• Melting Point: 72-74 ºC
• Refractive Index: 1.498
• Boiling Point: 301.7°Cat760mmHg
• PKA: 15.18±0.29(Predicted)
• Flash Point: 108.6°C
• PSA: 20.23000
• Density: 0.95g/cm³
• LogP: 3.92000
• Storage Temp.: 2-8°C
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 222.198365449
• Heavy Atom Count: 16
• Complexity: 292

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Beta-Eudesmol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCCC(=C)C1CC(CC2)C(C)(C)O
• Isomeric SMILES: C[C@]12CCCC(=C)[C@@H]1C[C@@H](CC2)C(C)(C)O
• General Description: Beta-Eudesmol is a sesquiterpene alcohol belonging to the eudesmane family, characterized by its decahydronaphthalene core structure with hydroxyl and methylene substituents. It is synthesized via a concise route involving key intermediates and intramolecular cyclization, demonstrating its structural significance in terpenoid chemistry. beta-Eudesmol and its derivatives are of interest due to their natural occurrence and potential biological activities.

Technology Process of beta-Eudesmol

There total 2 articles about beta-Eudesmol 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:

(+)-hedycaryol (157241-50-4) → cryptomeridiol (60132-35-6,92857-25-5,108006-39-9,122674-21-9,143004-65-3,4666-84-6,55353-16-7) + r-eudesmol (473-16-5,69686-15-3,69686-16-4,69686-18-6,70427-82-6,72173-99-0,75684-39-8,79254-46-9,94373-04-3,95529-68-3,123123-38-6,92480-60-9) + eudesm-4-en-11-ol (13902-07-3,15051-81-7,72173-98-9,98683-12-6,117066-77-0,1209-71-8,6710-66-3) + beta-eudesmol (473-15-4)

Guidance literature:

With sulfuric acid; In ethanol; acetone; Ambient temperature;

DOI:10.1016/0040-4020(94)00938-Q

Reference yield:

→ r-eudesmol (473-16-5,69686-15-3,69686-16-4,69686-18-6,70427-82-6,72173-99-0,75684-39-8,79254-46-9,94373-04-3,95529-68-3,123123-38-6,92480-60-9) + beta-eudesmol (473-15-4)

Guidance literature:

With calcium hydroxide; water; at 95 ℃;

DOI:10.1002/hlca.19310140523

Reference yield: 70.0%

beta-eudesmol (473-15-4) → dihydroeudesmol (6770-16-7)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethanol; for 6h;

DOI:10.1248/cpb.44.1603

upstream raw materials:

(+)-hedycaryol

Downstream raw materials:

dihydroeudesmol

((1R)-1-methyl-cyclohexane-1r,2t-diyl)-di-acetic acid

β-eudesmyl 3,5-dinitrobenzoate

beta-selinene

Refernces

A Short-Step Synthetic Approach to Eudesmane Skeleton. A Synthesis of (+/-)-β-Eudesmol and Related Eudesman Sesquiterpenes

10.1246/bcsj.61.3770

The research aims to develop an efficient and concise method for synthesizing the eudesmane skeleton, which is a significant structural motif in various sesquiterpenes, including (±)-β-eudesmol, cryptomeridiol, and neointermediol. The study employs a strategy based on the use of key intermediates like A or B, which undergo intramolecular cyclization via aldol condensation or Michael reaction. The synthesis starts from readily available 3-vinyl-2-cyclohexen-1-one, which is treated with dimethyl malonate in the presence of sodium methoxide to yield the Michael adduct. Subsequent steps involve acetalization, reduction with lithium aluminum hydride, selective benzylation, oxidation with pyridinium dichromate (PDC), and catalytic hydrogenation. The crucial step is the intramolecular aldol condensation, which constructs the desired α,β-unsaturated ketone. The final steps include oxidation, esterification, and selective reduction to obtain the target compounds. The research concludes that this approach provides a general method for constructing eudesmane sesquiterpenes, offering a formal total synthesis of (±)-β-eudesmol and its related compounds.