(+)-Protolichesterinic acid

Base Information

• Chemical Name: (+)-Protolichesterinic acid
• CAS No.: 493-46-9
• Molecular Formula: C19H32 O4
• Molecular Weight: 324.461
• DSSTox Substance ID: DTXSID601154975
• Nikkaji Number: J15.185H
• Wikidata: Q104251078
• Metabolomics Workbench ID: 138782
• ChEMBL ID: CHEMBL490329
• Mol file: 493-46-9.mol

Synonyms:3-Furancarboxylicacid, tetrahydro-4-methylene-5-oxo-2-tridecyl-, (2S-trans)-; 3-Furoic acid,tetrahydro-4-methylene-5-oxo-2-tridecyl-, (2S,3R)-(-)- (8CI); Succinic acid,(1-hydroxytetradecyl)methylene-, g-lactone (6CI,7CI); (-)-Protolichesterinic acid; Protolichesteric acid;Protolichesteric acid, (-)-; Protolichesterinic acid; Protolichesterinic acid,(-)-

Chemical Property of (+)-Protolichesterinic acid

Chemical Property:

• Boiling Point: 488.4°Cat760mmHg
• Flash Point: 166.7°C
• PSA: 63.60000
• Density: 1.02g/cm³
• LogP: 4.86990
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 13
• Exact Mass: 324.23005950
• Heavy Atom Count: 23
• Complexity: 389

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC1C(C(=C)C(=O)O1)C(=O)O
• Isomeric SMILES: CCCCCCCCCCCCC[C@H]1[C@@H](C(=C)C(=O)O1)C(=O)O

Technology Process of (+)-Protolichesterinic acid

There total 58 articles about (+)-Protolichesterinic acid 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: 85.0%

(2R,3S,4R)-4-Benzenesulfinyl-4-methyl-5-oxo-2-tridecyl-tetrahydro-furan-3-carboxylic acid → (+)-protolichesterinic acid (493-46-9,1448-96-0,17002-28-7,22800-27-7,51260-32-3,58845-78-6,58845-79-7,60478-54-8)

Guidance literature:

In toluene; at 110 ℃; for 1h;

DOI:10.1021/jo9606970

Reference yield: 72.0%

magnesium methyl carbonate (4861-79-4) + (2R,3S)-5-oxo-2-tridecyl-tetrahydrofuran-3-carboxylic acid (244612-58-6) → (+)-protolichesterinic acid (493-46-9,1448-96-0,17002-28-7,22800-27-7,51260-32-3,58845-78-6,58845-79-7,60478-54-8)

Guidance literature:

magnesium methyl carbonate; (2R,3S)-5-oxo-2-tridecyl-tetrahydrofuran-3-carboxylic acid; In N,N-dimethyl-formamide; at 135 - 140 ℃; for 70h;

With formaldehyd; sodium acetate; acetic acid; In water; at 20 ℃; for 2h;

DOI:10.1002/ejoc.200500961

Reference yield: 72.0%

(+)-Protolichesterinsaeuremethylester (144071-11-4) → (+)-protolichesterinic acid (493-46-9,1448-96-0,17002-28-7,22800-27-7,51260-32-3,58845-78-6,58845-79-7,60478-54-8)

Guidance literature:

With hydrogenchloride; In water; butanone; for 2h; Heating;

DOI:10.1016/S0957-4166(01)00345-7

upstream raw materials:

(+)-Protolichesterinsaeuremethylester

magnesium methyl carbonate

(2R,3S)-5-oxo-2-tridecyl-tetrahydrofuran-3-carboxylic acid

(4S,5R)-5-tridecyl-4-[tris(methylsulfanyl)methyl]-4,5-dihydro-3H-furan-2-one

Downstream raw materials:

(-)-lichesterinic acid

(+)-lichesterinic acid

(2R,3S,4S)-5-Oxo-4-(N'-phenyl-hydrazinomethyl)-2-tridecyl-tetrahydro-furan-3-carboxylic acid

(+)-Dibromprotolichesterinsaeure

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