Procyanidin B5

Procyanidin B5 is an epicatechin-(4β → 6)-epicatechin dimer.

Procyanidin B5

Names
IUPAC name (2R,2ʼR,3R,3ʼR,4S)-2,2'-bis(3,4-dihydroxyphenyl)-3,3ʼ,4,4ʼ-tetrahydro-2H,2ʼH-4,6ʼ-bichromene-3,3ʼ,5,5ʼ,7,7ʼ-hexol
Other names Procyanidin B5
Identifiers
CAS Number	12798-57-1^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:75621
ChEMBL	ChEMBL506487
ChemSpider	110533
KEGG	C17640
PubChem CID	124017
UNII	W51N19H6K6^Y
CompTox Dashboard (EPA)	DTXSID00155761
InChI InChI=1S/C30H26O12/c31-13-7-19(36)24-23(8-13)42-30(12-2-4-16(33)18(35)6-12)28(40)26(24)25-20(37)10-22-14(27(25)39)9-21(38)29(41-22)11-1-3-15(32)17(34)5-11/h1-8,10,21,26,28-40H,9H2/t21-,26-,28-,29-,30-/m1/s1 Key: GMISZFQPFDAPGI-CVJZBMGUSA-N InChI=1/C30H26O12/c31-13-7-19(36)24-23(8-13)42-30(12-2-4-16(33)18(35)6-12)28(40)26(24)25-20(37)10-22-14(27(25)39)9-21(38)29(41-22)11-1-3-15(32)17(34)5-11/h1-8,10,21,26,28-40H,9H2/t21-,26-,28-,29-,30-/m1/s1 Key: GMISZFQPFDAPGI-CVJZBMGUBO
SMILES O[C@@H]1Cc2c(O[C@@H]1c1ccc(O)c(O)c1)cc(O)c([C@@H]1[C@@H](O)[C@H](Oc3cc(O)cc(O)c13)c1ccc(O)c(O)c1)c2O
Properties
Chemical formula	C30H26O12
Molar mass	578.52 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Procyanidin B5 is a B type proanthocyanidin.

Natural occurrences

It can be found in grape seeds,[1] in Hibiscus cannabinus (kenaf) root and bark,[2] and in black chokeberries (Aronia melanocarpa).[3]

Presence in food

It is found in cocoa beans[4] and chocolate.[5]

References

1. Procyanidin dimers and trimers from grape seeds. Jorge M. Ricardo da Silva, Jacques Rigaud, Véronique Cheynier, Annie Cheminat and Michel Moutounet, Phytochemistry, Volume 30, Issue 4, 1991, Pages 1259-1264
2. Dimeric proanthocyanidins of Hibiscus cannabinus. Fam Van Tkhin', B. Makhsudova and O. S. Otroshchenko, Chemistry of Natural Compounds, Volume 18, Number 3, pages 310-314, doi:10.1007/BF00580458
3. Preparation of Dimeric Procyanidins B1, B2, B5, and B7 from a Polymeric Procyanidin Fraction of Black Chokeberry (Aronia melanocarpa). Tuba Esatbeyoglu and Peter Winterhalter, J. Agric. Food Chem., 2010, 58 (8), pages 5147–5153, doi:10.1021/jf904354n
4. Isolation of dimeric, trimeric, tetrameric and pentameric procyanidins from unroasted cocoa beans (Theobroma cacao L.) using countercurrent chromatography. Esatbeyoglu T, Wray Vand Winterhalter P, Food Chem., 2015 Jul 15, number 179, pages 278-89, doi:10.1016/j.foodchem.2015.01.130
5. Rapid Reversed Phase Ultra-Performance Liquid Chromatography Analysis of the Major Cocoa Polyphenols and Inter-relationships of Their Concentrations in Chocolate. Karen A. Cooper, Esther Campos-Gimenez, Diego Jimenez-Alvarez, Kornel Nagy, Jennifer L. Donovan and Gary Williamson, J. Agric. Food Chem., 2007, 55, pages 2841−2847, doi:10.1021/jf063277c