Ginnol

Base Information

• Chemical Name: Ginnol
• CAS No.: 2606-50-0
• Molecular Formula: C29H60 O
• Molecular Weight: 424.795
• UNII: 4O3O05K5Q3
• Metabolomics Workbench ID: 3179
• Wikidata: Q27115158
• Mol file: 2606-50-0.mol

Synonyms:Ginnol;(S)-nonacosan-10-ol;2606-50-0;Celidoniol;(10S)-nonacosan-10-ol;(10S)-10-Nonacosanol;10-Nonacosanol, (10S)-;(S)-(+)-Ginnol;nonacosan-10S-ol;4O3O05K5Q3;UNII-4O3O05K5Q3;GINNOL, (+)-;CHEBI:32948;10-NONACOSANOL, (S)-;CPGCVOVWHCWVTP-LJAQVGFWSA-N;10-NONACOSANOL, (+)-;HY-N7200;LMFA05000088;AKOS040760847;CS-0105216;C08385;Q27115158

Chemical Property of Ginnol

Chemical Property:

• Vapor Pressure: 1.61E-10mmHg at 25°C
• Melting Point: 81-82℃
• Boiling Point: 463°Cat760mmHg
• PKA: 15.23±0.20(Predicted)
• Flash Point: 136.5°C
• PSA: 20.23000
• Density: 0.84g/cm³
• LogP: 10.52970
• XLogP3: 14
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 26
• Exact Mass: 424.464416533
• Heavy Atom Count: 30
• Complexity: 288

Purity/Quality:

≥98% ^*data from raw suppliers

(10S)-NONACOSAN-10-OL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCCCCC(CCCCCCCCC)O
• Isomeric SMILES: CCCCCCCCCCCCCCCCCCC[C@H](CCCCCCCCC)O

Technology Process of Ginnol

There total 16 articles about Ginnol 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: 100.0%

(10S)-13-nonacosen-10-ol (214214-04-7) → (S)-nonacosan-10-ol (2606-50-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 60h; under 3000.24 Torr;

DOI:10.1016/S0040-4020(98)00688-7

Reference yield: 81.0%

1-Chlorononane (2473-01-0) + icosanal (2400-66-0) → (S)-nonacosan-10-ol (2606-50-0)

Guidance literature:

1-Chlorononane; With zinc dimethoxide; magnesium; lithium chloride; In diethyl ether; at 20 ℃; Inert atmosphere;

With 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-bis-diphenylphosphine oxide; In diethyl ether; at 20 ℃;

icosanal; In tetrahydrofuran; toluene; at 20 ℃; for 12h; optical yield given as %ee; enantioselective reaction;

DOI:10.1055/s-0030-1258129

Reference yield: 75.0%

nonacosan-10-yl 2-methoxy-2-phenylacetate (950665-38-0) → (S)-nonacosan-10-ol (2606-50-0)

Guidance literature:

With potassium hydroxide; water; In ethanol; for 2h; Heating;

DOI:10.1002/ejoc.200700262

upstream raw materials:

(10S)-13-nonacosen-10-ol

icosanal

nonacosan-10-yl 2-methoxy-2-phenylacetate

(S)-tridec-1-en-4-yl (2R)-2-methoxy-2-phenylacetate

Downstream raw materials:

optically active 10-acetoxy-nonacosane

Ginnon

Refernces

• 1、 Hatano, Manabu,Mizuno, Tomokazu,Ishihara, Kazuaki. "A concise synthesis of (S)-(+)-ginnol based on catalytic enantioselective addition of commercially unavailable Di(n -alkyl)zinc to aldehydes and ketones". experimental part. p. 2024 - 2028. Retrieved 2010/10/04.
• 2、 Berkenbusch, Thilo,Brueckner, Reinhard. "Synthesis of (+)-ginnol, a type R(long)-CH(OH)-R'(long) alcohol, by an asymmetric β,γ-unsaturated ester→γ-butyrolactone conversion". . p. 11471 - 11480. Retrieved 2007/10/03.