Cianidanol

Base Information

• Chemical Name: Cianidanol
• CAS No.: 154-23-4
• Deprecated CAS: 16198-00-8,321-01-7,4211-28-3,5323-80-8,159761-73-6,29907-20-8,72690-97-2,159761-73-6,321-01-7,379227-23-3,4211-28-3,523994-21-0,5323-80-8
• Molecular Formula: C15H14O6
• Molecular Weight: 290.273
• Hs Code.: 29329990
• European Community (EC) Number: 205-825-1
• NSC Number: 755824,2819
• UNII: 8R1V1STN48,5J4Y243W61
• DSSTox Substance ID: DTXSID3022322,DTXSID001349029
• Nikkaji Number: J9.391B
• Wikidata: Q415007
• NCI Thesaurus Code: C63654
• Metabolomics Workbench ID: 21831
• ChEMBL ID: CHEMBL311498
• Mol file: 154-23-4.mol

Synonyms:(+)-Catechin;(+)-Cyanidanol;(+)-Cyanidanol-3;(-)-Epicatechin;(2R,3R)-2-(3,4-Dihydroxyphenyl)-3,5,7-chromanetriol;2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R-cis)-;3,3',4',5,7-Flavanpentol;Catechin;Catechinic Acid;Catechuic Acid;Catergen;Cianidanol;Cyanidanol 3;Cyanidanol-3;Epicatechin;KB 53;KB-53;KB53;Z 7300;Zyma

Chemical Property of Cianidanol

Chemical Property:

• Appearance/Colour: Tan solid
• Vapor Pressure: 9.29E-17mmHg at 25°C
• Melting Point: 175-177 °C (anhydrous)(lit.)
• Refractive Index: 1.741
• Boiling Point: 630.4 °C at 760 mmHg
• PKA: 9.54±0.10(Predicted)
• Flash Point: 335 °C
• PSA: 110.38000
• Density: 1.593 g/cm³
• LogP: 1.54610
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated, Heated)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 290.07903816
• Heavy Atom Count: 21
• Complexity: 364

Purity/Quality:

99% ^*data from raw suppliers

Catechin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O
• Isomeric SMILES: C1[C@@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O
• General Description: Cianidanol, also known as (+)-catechin, is a flavan-3-ol compound with antioxidant and bioactive properties. It serves as a key precursor in the synthesis of modified proanthocyanidins, where its structure can be regioselectively functionalized, such as through acylation at the C-8 position, to create derivatives for further chemical applications. Studies highlight its role in enhancing inhibitory activity against ribonuclease A (RNase A) when conjugated with resorcinol or phloroglucinol, emphasizing the importance of phenolic hydroxyl groups in bioactivity. Additionally, cianidanol is a constituent of naturally occurring proanthocyanidins in plants like *Cinnamomum sieboldii*, where it contributes to the formation of oligomeric structures with potential chemotaxonomic and sensory significance.

Technology Process of Cianidanol

There total 195 articles about Cianidanol 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: 89.0%

leucocyanidin (15963-96-9) → catechin (154-23-4,490-46-0,7295-85-4,17334-50-8,18829-70-4,35323-91-2,72690-97-2,13392-26-2)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In methanol; for 6h;

Reference yield: 65.0%

racemic 5,7,3',4'-tetra-O-benzyl-(+/-)-catechin (896121-49-6) → catechin (154-23-4,490-46-0,7295-85-4,17334-50-8,18829-70-4,35323-91-2,72690-97-2,13392-26-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; ethyl acetate; at 20 - 55 ℃;

Reference yield:

PZ-5 → pelargonidin (7690-51-9) + cyanidin (13306-05-3) + delphinidin (13270-61-6) + catechin (154-23-4)

Guidance literature:

Acid hydrolysis;

DOI:10.1023/A:1015773513717

upstream raw materials:

procyanidin B₂

procyanidin B₁

procyanidin B₃

sodium methylate

Downstream raw materials:

catechin

(2R)-2r-(3-methoxy-4-trimethylsilanyloxy-phenyl)-5,7-bis-trimethylsilanyloxy-chroman-3t-ol

2H-1-benzopyran,3,4-dihydro-2-[3,4 bis[(trimethylsilyl)oxy]phenyl]

3-(3,4-dihydroxy-phenyl)-2-(2,4,6-trihydroxy-benzyl)-2,3-dihydro-benzofuran-4,6-diol

Refernces

Synthesis of modified proanthocyanidins: Introduction of acyl substituents at C-8 of catechin. Selective synthesis of a C-4 → O → C-3 ether-linked procyanidin-like dimer

10.1016/j.bmcl.2004.11.046

The study focuses on the regioselective synthesis of modified proanthocyanidins by introducing acyl substituents at the C-8 position of (+)-catechin, leading to the creation of various catechin derivatives. These derivatives were utilized for further synthesis of modified proanthocyanidins, with a particular emphasis on the synthesis of a new 3-O-4 ether-linked procyanidin-like derivative. Key chemicals used in the study include tetra-O-benzyl catechin, penta-O-benzyl catechin, trifluoroacetic anhydride, and titanium tetrachloride (TiCl4) as a catalyst. These chemicals served various purposes, such as starting materials for the synthesis, reagents for acylation and electrophilic addition reactions, and a catalyst for the selective condensation reaction that led to the formation of the ether-linked procyanidin-like derivative. The study aimed to investigate the influence of substitution patterns on the behavior of these compounds in Lewis acid-catalyzed synthesis of naturally occurring procyanidins and to develop a new methodology for managing regiochemical features related to the dimerization reaction of flavan-3-ol monomers.

Synthesis and ribonuclease A inhibition activity of resorcinol and phloroglucinol derivatives of catechin and epicatechin: Importance of hydroxyl groups

10.1016/j.bmc.2010.06.077

The research discusses the synthesis and inhibitory activity of resorcinol and phloroglucinol derivatives of catechin and epicatechin against ribonuclease A (RNase A), with the aim of increasing the number of phenolic hydroxyl groups to enhance inhibition. The study concluded that these novel conjugates were more effective inhibitors of RNase A than catechin and epicatechin, highlighting the importance of phenolic hydroxyl groups in inhibiting ribonucleolytic activity. The research also explored the compounds' anti-angiogenic activity through the chorioallantoic membrane (CAM) assay, finding that the epicatechin-based polyphenols showed inhibition of angiogenin-induced angiogenesis. Chemicals used in the synthesis process included (+)-catechin, (-)-epicatechin, phloroglucinol, resorcinol, LiBr, and various protecting groups such as benzyl ether. The study employed techniques like fluorescence studies, protein-ligand docking, and CD spectroscopic studies to evaluate binding parameters and interactions.

Tannins and related compounds. XXXV. Proanthocyanidins with a doubly linked unit from the root bark of Cinnamomum sieboldii Meisner

10.1248/cpb.33.4338

The research focused on the isolation and structural elucidation of proanthocyanidins from the root bark of Cinnamomum sieboldii Meisner, a plant belonging to the Lauraceae family. The purpose of the study was to determine the structures of proanthocyanidin trimers and to clarify the composition of higher oligomeric proanthocyanidins in this plant. The researchers used acid-catalyzed thiolytic degradation, proton and carbon-13 nuclear magnetic resonance analyses to establish the structures of the compounds. They isolated a trimer, two tetramers, and a pentamer, and demonstrated the presence of (-)-epicatechin, (+)-catechin, and known proanthocyanidins B-1, B-2, and B-5, among others. The conclusions highlighted that the root bark of C. sieboldii contains large amounts of proanthocyanidins with a doubly linked bisflavanoid (A-type) unit, accompanied by minor singly linked procyanidins, and that the composition of proanthocyanidins in C. sieboldii is similar to that in C. zeylanicum, which is of chemotaxonomical interest. The study also noted that proanthocyanidin trimers 1 and 9 have a sweet taste, contrasting with the astringent taste of other oligomeric proanthocyanidins.