Galanolactone

Base Information

• Chemical Name: Galanolactone
• CAS No.: 115753-79-2
• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.456
• UNII: 4FX4852TYQ
• Nikkaji Number: J1.719.400C,J393.485C
• Wikipedia: Galanolactone
• Wikidata: Q754392
• ChEMBL ID: CHEMBL4520851
• Mol file: 115753-79-2.mol

Synonyms:galanolactone

Chemical Property of Galanolactone

Chemical Property:

• Vapor Pressure: 1.24E-08mmHg at 25°C
• Boiling Point: 459.6°C at 760 mmHg
• Flash Point: 197.3°C
• PSA: 38.83000
• Density: 1.1g/cm³
• LogP: 4.26140
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 318.21949481
• Heavy Atom Count: 23
• Complexity: 549

Purity/Quality:

98%min ^*data from raw suppliers

Galanolactone 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCC2(C1CCC3(C2CC=C4CCOC4=O)CO3)C)C
• Isomeric SMILES: C[C@]12CCCC([C@@H]1CC[C@]3([C@@H]2C/C=C/4\CCOC4=O)CO3)(C)C

Technology Process of Galanolactone

There total 25 articles about Galanolactone 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: 20.0%

(3E)-3-{2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}oxolan-2-one (189239-51-8) → galanolactone (115753-79-2) + (3E)-3-{2-[(1R,2R,8aS)-5,5,8a-trimethyl-octahydro-1H-spiro[naphthalene-2,2'-oxiran]-1-yl]ethylidene}oxolan-2-one

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 2h;

DOI:10.1016/j.ejmech.2019.04.023

Reference yield:

3-(diethylphosphonio)tetrahydrofuran-2-one + C16H26O2 (123522-42-9) → C20H30O3 (115753-79-2,123619-18-1,123619-23-8) + (+/-)-galanolactone (115753-79-2,123619-18-1,123619-23-8)

Guidance literature:

With sodium hydride; In toluene; at 0 - 80 ℃; for 1h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)95251-1

Reference yield:

3-(diethylphosphonio)tetrahydrofuran-2-one + C16H26O2 (123522-42-9) → C20H30O3 (115753-79-2,123619-18-1,123619-23-8) + (+/-)-galanolactone (115753-79-2,123619-18-1,123619-23-8)

Guidance literature:

With sodium hydride; In toluene; at 0 - 80 ℃; for 1h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)95251-1

upstream raw materials:

(3E)-3-{2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}oxolan-2-one

sclareol

(1R,2R,8aS)-2,5,5,8a-tetramethyl-1-(2-oxoethyl)decahydronaphthalen-2-yl acetate

Acetic acid (1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-{2-[2-oxo-dihydro-furan-(3E)-ylidene]-ethyl}-decahydro-naphthalen-2-yl ester

Refernces

• 1、 Tran, Quy T.N.,Wong, W.S. Fred,Chai, Christina L.L.. "The identification of naturally occurring labdane diterpenoid calcaratarin D as a potential anti-inflammatory agent". . p. 33 - 44. Retrieved 2019.