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
• Uses: procollagen production inhibitoe, hepatoprotectant (+)-Catechin is a flavonoid found primarily in higher woody plants as (+)-Catechin along with (-)-Epicatechin (cis form). Antidiarrheal. Labelled (+)-Catechin (C217500). (+)-Catechin is a flavonoid found primarily in higher woody plants as (+)-Catechin along with (-)-Epicatechin (cis form). Antidiarrheal. Cianidanol, also known as (+)-catechin; (+)-3,3′4′,5,7-flavanepentol; 3,3′,4′, 5,7-pentahydroxyflavane, [R,3S]-2-[3,4-dihydroxyphenyl]-3,4-dihydro-1[2H]- benzopyran-3,4,7-triol, or 2-(3,4-dihydroxyphenyl)-3,4-dihydro-(2r-trans)-2h- 1-benzopyran-7-triol, is a flavonoid associated with a variety of blood disorders. An association of cianidanol and immune hemolytic anemia and thrombocytopenia has been suggested in numerous case reports. In several reports, the presence of flavonoid-dependent antibodies against red blood cells is evident with cianidanol combining with erythrocyte membranes and inducing development of autoantibodies and antibodies.Several patients had platelet antibodies with increased serum-bindable IgG values without the presence of cianidanol and several with high platelet-associated IgG levels.Antibodies against cianidanol were not detectable in certain cases.The hemolytic anemia caused acute renal failure in some patients and can be life threatening, leading to fatalities. Upon cessation of treatment with cianidanol, hematology appears to return to normal over time.These side effects do not appear to be specific to cianidanol as the formation of IgE and IgG antibodies to troxerutin (Venoruton) and silymarin (Kegalon) was also evident with patients presenting with fever, skin eruptions, and intravascular hemolysis often demonstrating high IgG titers.Furthermore, cianidanol-induced hemolysis might also occur after sensitization by other flavonoids including rutin.

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:

ent-catechin 3',4',5,7-tetra-O-methyl ether

catechin

catechin

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

Refernces

• 1、 Foo, Lai Yeap,Hrstich, Liana,Vilain, Christian. "PHYLLOFLAVAN, A CHARACTERISTIC CONSTITUENT OF PHYLLOCLADUS SPECIES". . p. 1495 - 1498. Retrieved 1985.
• 2、 Zhong, Cheng,Hu, Deng,Hou, Lian-Bing,Song, Lu-Yao,Zhang, Ying-Jun,Xie, Yang,Tian, Li-Wen. "Phenolic compounds from the rhizomes of Smilax China L. & their anti-inflammatory activity". . . Retrieved 2017.
• 3、 Kiatgrajai, Preecha,Wellons, J. D.,Gollob, Lawrence,White, James D.. "Kinetics of Epimerization of (+)-Catechin and Its Rearrangement to Catechinic Acid". . p. 2910 - 2912. Retrieved 1982.
• 4、 Manguro, Lawrence Onyango Arot,Wagai, Samuel Otieno,Onyango, Joab Otieno. "Terpenoids of Boswellia neglecta oleo-gum resin". . p. 317 - 323. Retrieved 2016.
• 5、 A. Stafford, Helen,H. Lester, Hope,J. Porter, Lawrence. "Chemical and enzymatic synthesis of monomeric procyanidins (leucocyanidins or 3′,4′,5,7-tetrahydroxyflavan-3,4-diols) from (2R,3R)-dihydroquercetin". . p. 333 - 338. Retrieved 1985.
• 6、 Pashinina, L. T.,Abil'kaeva, S. A.,Sheichenko, B. I.. "DIMERIC FLAVANOLS OF Juniperus sabina. I.". . p. 282 - 287. Retrieved 1982.
• 7、 Shi, Meng,Nie, Ying,Zheng, Xin-Qiang,Lu, Jian-Liang,Liang, Yue-Rong,Ye, Jian-Hui. "Ultraviolet B (UVB) photosensitivities of tea catechins and the relevant chemical conversions". . . Retrieved 2016.
• 8、 He, Rui-Jie,Huang, Yong-Lin,Li, Dian-Peng,Liu, Zhang-Bin,Wang, Ya-Feng,Yang, Bing-Yuan,Zou, Bi-Qun. "Structural Characterization and Assessment of Anti-Inflammatory Activities of Polyphenols and Depsidone Derivatives from Melastoma malabathricum subsp. normale". . . Retrieved 2022/03/01.
• 9、 Chen, Yang,Gao, Liping,Gui, Lin,Guo, Lina,Lei, Ting,Li, Yan,Ma, Xiubing,Ruan, Haixiang,Wang, Longji,Wang, Yunsheng,Xia, Tao. "Optimization of the biosynthesis of b-ring ortho-hydroxy lated flavonoids using the 4-hydroxyphenylacetate 3-hydroxylase complex (Hpabc) of escherichia coli". . . Retrieved 2021/05/31.