Leucocianidol

Base Information

• Chemical Name: Leucocianidol
• CAS No.: 93527-39-0
• Molecular Formula: C15H14O7
• Molecular Weight: 306.272
• DSSTox Substance ID: DTXSID70331530
• Nikkaji Number: J862.804A
• Wikipedia: Leucocyanidin
• Wikidata: Q8085718
• NCI Thesaurus Code: C81117
• Metabolomics Workbench ID: 22033
• ChEMBL ID: CHEMBL124022
• Mol file: 93527-39-0.mol

Synonyms:3,3',4,4',5,7-flavanhexanol;3,3',4,4',5,7-hexahydroflavane;5,7,3,4-tetrahydroxyflavan-3',4'-diol;flavanhexanol;leucocyanidin;leucodyanidol;Resivit;Venen Tabs

Chemical Property of Leucocianidol

Chemical Property:

• XLogP3: -0.8
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 306.07395278
• Heavy Atom Count: 22
• Complexity: 392

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C2C(C(C3=C(C=C(C=C3O2)O)O)O)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1[C@@H]2[C@H]([C@H](C3=C(C=C(C=C3O2)O)O)O)O)O)O

Technology Process of Leucocianidol

There total 5 articles about Leucocianidol 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: 45.0%

catechin (154-23-4) → (+)-(2R,3S,4S)-3,4,5,7,3',4'-hexahydroxyflavan (93527-39-0)

Guidance literature:

With Diaporthe sp; In methanol; for 24h;

DOI:10.1248/cpb.53.866

Reference yield:

→ 2r-(3,4-dihydroxy-phenyl)-chroman-3t,43ξ,5,7-tetraol (480-17-1,15963-96-9,17277-70-2,17912-82-2,69256-15-1,93527-39-0,104371-01-9)

Guidance literature:

With tetrahydrofuran; lithium aluminium tetrahydride; Hydrogenation_.an Palladium/Bariumsulfat in DMF;

Reference yield:

taxifolin (480-18-2,17654-26-1,5117-01-1) → (+)-leucocyanidin (480-17-1,15963-96-9,17277-70-2,17912-82-2,69256-15-1,93527-39-0,104371-01-9)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 1h; Ambient temperature;

DOI:10.1039/P19810001213

upstream raw materials:

taxifolin

(2R,3S,4R)-(+)-3,4,5,7,3',4'-hexahydroxyflavan

catechin

Downstream raw materials:

(2R,3S,4R)-2,3-trans-3,4-trans-4-(2,4-Dihydroxyphenyl)-3',4',5,7-tetrahydroxyflavan-3-ol

3’,4’,5,7-tetra-O-methyl-4β-hydroxycatechin

quercetol

[4,6]-2,3-trans-3,4-trans-(+)-catechin-(+)-catechin

Refernces

• 1、 Zhang, Jia-Rong,Tolchard, James,Bathany, Katell,Langlois D'Estaintot, Béatrice,Chaudiere, Jean. "Production of 3,4-cis- and 3,4-trans-Leucocyanidin and Their Distinct MS/MS Fragmentation Patterns". . p. 351 - 358. Retrieved 2018/01/17.
• 2、 Agusta, Andria,Maehara, Shoji,Ohashi, Kazuyoshi,Simanjuntak, Partomuan,Shibuya, Hirotaka. "Stereoselective oxidation at C-4 of flavans by the endophytic fungus Diaporthe sp. isolated from a tea plant". . p. 1565 - 1569. Retrieved 2007/10/03.