PROCYANIDIN A2

Base Information

• Chemical Name: PROCYANIDIN A2
• CAS No.: 41743-41-3
• Molecular Formula: C30H24O12
• Molecular Weight: 576.513
• UNII: UQN6668Q4R
• DSSTox Substance ID: DTXSID00904175
• Nikkaji Number: J575.384H
• Wikipedia: Procyanidin_A2
• Wikidata: Q7247550
• Metabolomics Workbench ID: 51729
• ChEMBL ID: CHEMBL286933
• Mol file: 41743-41-3.mol

Synonyms:Proanthocyanidin A2;Procyanidoepicatechin;Epicatechin-(2beta->7,4beta->8)-epicatechin;Proanthocyanidin A-2;Epicatechin-(2β→7,4β→8)-epicatechin;(2R,3R,8S,14R,15R)-2,8-Bis(3,4-dihydroxyphenyl)-2,3,4,14-tetrahydro-8,14-methanobenzo[7,8][1,3]dioxocino[4,5-h]chromene-3,5,11,13,15-pentaol;(+)-Epicatechin-(4.beta.-8,2.beta.-O-7)-epicatechin;(2R,3R,8S,14R,15R)-2,8-Bis(3,4-dihydroxyphenyl)-3,4-dihydro-2H,14H-8,14-methanobenzo[7,8][1,3]dioxocino[4,5-h]chromene-3,5,11,13,15-pentaol;(+)-Proanthocyanidin A2;Dimeric catechin;Procyanidin dimer A2;Procyanidol A2;(2R,3R,8S,14R,15R)-2,8-Bis(3,4-dihydroxyphenyl)-3,4-dihydro-2H,14H-8,14-methanochromeno[7,8-d][1,3]benzodioxocine-3,5,11,13,15-pentol;Procyanidin A2;

Chemical Property of PROCYANIDIN A2

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 300℃
• Boiling Point: 946°C at 760 mmHg
• PKA: 8.77±0.70(Predicted)
• Flash Point: 525.9°C
• PSA: 209.76000
• Density: 1.766±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 2.79350
• Storage Temp.: 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 2
• Exact Mass: 576.12677620
• Heavy Atom Count: 42
• Complexity: 986

Purity/Quality:

95%-98% ^*data from raw suppliers

Procyanidin A2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC2=C1C(=CC3=C2C4C(C(O3)(OC5=CC(=CC(=C45)O)O)C6=CC(=C(C=C6)O)O)O)O)C7=CC(=C(C=C7)O)O)O
• Isomeric SMILES: C1[C@H]([C@H](OC2=C1C(=CC3=C2[C@@H]4[C@H]([C@](O3)(OC5=CC(=CC(=C45)O)O)C6=CC(=C(C=C6)O)O)O)O)C7=CC(=C(C=C7)O)O)O
• Uses: Procyanidin A2 is a type of procyanidin and is found in avocado, nuts and berries and may provide antioxidant activity as well as antiviral activity.

Technology Process of PROCYANIDIN A2

There total 15 articles about PROCYANIDIN A2 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%

C51H41BrO12 → procyanidin A2 (41743-41-3)

Guidance literature:

With 5% Pd(OH)₂/C; hydrogen; In tetrahydrofuran; methanol; water; at 20 ℃; for 1h; under 760.051 Torr;

DOI:10.1002/anie.201405600

Reference yield: 99.0%

C79H65BrO12 → procyanidin A2 (41743-41-3)

Guidance literature:

With 5% Pd(OH)₂/C; hydrogen; In tetrahydrofuran; methanol; water; at 20 ℃; for 1.5h; under 760.051 Torr;

DOI:10.1002/anie.201405600

Reference yield: 93.0%

C86H74O13 → procyanidin A2 (41743-41-3)

Guidance literature:

With 10 wt% Pd(OH)2 on carbon; hydrogen; In water; ethyl acetate; at 20 ℃; for 3h;

DOI:10.1021/acs.orglett.5b00646

upstream raw materials:

proanthocyanidin A-2 4'-benzylthioether

4-benzylthioproanthocyanidin-A₂

aesculitannin G

phenylmethanethiol

Downstream raw materials:

(-)-epicatechin-(2β→O→7,4β→8)-(-)-catechin

proanthocyanidin A-2 nona-acetate

Proanthocyanidin A-2-heptamethylaether

Refernces

• 1、 Yu, Ru-Jian,Liu, Hai-Bin,Yu, Yang,Liang, Lu,Xu, Rui,Liang, Chun,Tang, Jin-Shan,Yao, Xin-Sheng. "Anticancer activities of proanthocyanidins from the plant Urceola huaitingii and their synergistic effects in combination with chemotherapeutics". . p. 175 - 182. Retrieved 2016/07/06.
• 2、 Ito, Yuji,Ohmori, Ken,Suzuki, Keisuke. "Annulation approach to doubly linked (A-type) oligocatechins: Syntheses of (+)-procyanidin A2 and (+)-cinnamtannin B1". supporting information. p. 10129 - 10133. Retrieved 2015/03/31.