procyanidin c1 procyanidin c1 procyanidin c1 (pcc1) is a b type proanthocyanidin. it is an epicatechin trimer found in grape (vitis vinifera), unripe apples, and cinnamon. procyanidin c1 names iupac name -(4→8)--(4→8)- systematic iupac name (12r,13r,14r,22r,23r,24s,32r,33r)-12,22,32-tris(3,4-dihydroxyphenyl)-12h,22h,32h--13,15,17,23,25,27,33,35,37-nonol other names procyanidin c1procyanidol c1epicatechin-(4.beta.-->8)epicatechin-(4.beta.-->8)epicatechinepicatechin-(4β→8)-epicatechin--(4β→8)-epicatechin identifiers cas number 37064-30-5 y 3d model (jsmol) interactive image chebi chebi:75643 chembl chembl290632 chemspider 148540 kegg c17624 pubchem cid 169853 unii 33516lcw4f y comptox dashboard (epa) dtxsid10190562 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/s1key: mojzmwjrukiqgl-xilrtyjmsa-ninchi=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/s1key: mojzmwjrukiqgl-xilrtyjmbw smiles c1cc(c(cc12(cc3c(cc(c(c3o2)4c5c(cc(c(c5o(4o)c6ccc(c(c6)o)o)7c8c(cc(cc8o(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 , 100 kpa). y verify (what is yn ?) infobox references natural occurrence and function procyanidin c1 can be isolated from grape seed extract. 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. research procyanidin c1 has been found to extend life in mice and to make them fitter. it was also found to greatly increase the effectiveness of chemotherapy in mice in which human prostate tumor cells were implanted.