Procyanidin C1

Procyanidin C1

Names
IUPAC name (2R,2ʼR,2ʼʼR,3R,3ʼR,3ʼʼR,4R,4ʼS)-2,2ʼ,2ʼʼ-tris(3,4-dihydroxyphenyl)-3,3ʼ,3ʼʼ,4,4ʼ,4ʼʼ-hexahydro-2H,2ʼH,2ʼʼH-4,8ʼ:4ʼ,8ʼʼ-terchromene-3,3ʼ,3ʼʼ,5,5ʼ,5ʼʼ,7,7ʼ,7ʼʼ-nonol
Other names Procyanidin C1 Procyanidol C1 Epicatechin-(4.beta.-->8)epicatechin-(4.beta.-->8)epicatechin Epicatechin-(4β→8)-epicatechin--(4β→8)-epicatechin
Identifiers
CAS Number	37064-30-5=
3D model (Jmol)	Interactive image
ChEBI	CHEBI:75643
ChEMBL	ChEMBL290632
ChemSpider	148540
KEGG	C17624
PubChem	169853
InChI InChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41-,42-,43-/m1/s1 Key: MOJZMWJRUKIQGL-XILRTYJMSA-N InChI=1/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41-,42-,43-/m1/s1 Key: MOJZMWJRUKIQGL-XILRTYJMBW
SMILES c1cc(c(cc1[C@@H]2[C@@H](Cc3c(cc(c(c3O2)[C@H]4c5c(cc(c(c5O[C@@H]([C@@H]4O)c6ccc(c(c6)O)O)[C@H]7c8c(cc(cc8O[C@@H]([C@@H]7O)c9ccc(c(c9)O)O)O)O)O)O)O)O)O)O)O
Properties
Chemical formula	C45H38O18
Molar mass	866.77 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
verify (what is  ?)
Infobox references

Procyanidin C1 is a B type proanthocyanidin. It is an epicatechin trimer found in grape (Vitis vinifera).^[1]

Chemical synthesis

The stereoselective synthesis of seven benzylated proanthocyanidin trimers (epicatechin-(4β-8)-epicatechin-(4β-8)-epicatechin trimer (procyanidin C1), catechin-(4α-8)-catechin-(4α-8)-catechin trimer (procyanidin C2), epicatechin-(4β-8)-epicatechin-(4β-8)-catechin trimer and epicatechin-(4β-8)-catechin-(4α-8)-epicatechin trimer derivatives) can be achieved with TMSOTf-catalyzed condensation reaction, in excellent yields. The structure of benzylated procyanidin C2 was confirmed by comparing the 1H NMR spectra of protected procyanidin C2 that was synthesized by two different condensation approaches. Finally, deprotection of (+)-catechin and (-)-epicatechin trimers derivatives gives four natural procyanidin trimers in good yields.^[2]

See also

• Phenolic content in wine

References

1. Proanthocyanidin composition of red Vitis vinifera varieties from the Douro valley during ripening : Influence of cultivation altitude. Mateus Nuno, Marques Sara, Goncalves Ana C., Machado José M. and De Freitas Victor, American journal of enology and viticulture, 2001, vol. 52, no2, pp. 115-121, INIST:1129642
2. Efficient Stereoselective Synthesis of Proanthocyanidin Trimers with TMSOTf-Catalyzed Intermolecular Condensation. Akiko Saito, Akira Tanaka, Makoto Ubukata and Noriyuki Nakajima, Synlett, 2004, volume 6, pages 1069-1073, doi:10.1055/s-2004-822905