Procyanidin B5

Procyanidin B5
Chemical structure of procyanidin B5
Chemical structure of procyanidin B5
Names
IUPAC name
[(2R,3R,4S)-Flavan-3,3′,4′,5,7-pentol]-(4→6)-[(2R,3R)-flavan-3,3′,4′,5,7-pentol]
Systematic IUPAC name
(2R,2′R,3R,3′R,4S)-2,2′-Bis(3,4-dihydroxyphenyl)-3,3′,4,4′-tetrahydro-2H,2′H-[4,6′-bi-1-benzopyran]-3,3′,5,5′,7,7′-hexol
Other names
Procyanidin B5
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • 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
  • 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
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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Procyanidin B5 is a B type proanthocyanidin.

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

Natural occurrences

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

Presence in food

It is found in cocoa beans and chocolate.

References

  1. ↑ Ricardo Da Silva, Jorge M.; Rigaud, Jacques; Cheynier, Véronique; Cheminat, Annie; Moutounet, Michel (January 1991). "Procyanidin dimers and trimers from grape seeds". Phytochemistry. 30 (4): 1259–1264. Bibcode:1991PChem..30.1259R. doi:10.1016/S0031-9422(00)95213-0.
  2. ↑ Van Tkhin', Fam; Makhsudova, B.; Otroshchenko, O. S. (1982). "Dimeric proanthocyanidins ofHibiscus cannabinus". Chemistry of Natural Compounds. 18 (3): 310–314. Bibcode:1982CNatC..18..310V. doi:10.1007/BF00580458.
  3. ↑ Esatbeyoglu, Tuba; Winterhalter, Peter (2010). "Preparation of Dimeric Procyanidins B1, B2, B5, and B7 from a Polymeric Procyanidin Fraction of Black Chokeberry (Aronia melanocarpa)". Journal of Agricultural and Food Chemistry. 58 (8): 5147–5153. doi:10.1021/jf904354n. PMID 20196608.
  4. ↑ Esatbeyoglu, Tuba; Wray, Victor; Winterhalter, Peter (2015). "Isolation of dimeric, trimeric, tetrameric and pentameric procyanidins from unroasted cocoa beans (Theobroma cacao L.) using countercurrent chromatography". Food Chemistry. 179: 278–289. doi:10.1016/j.foodchem.2015.01.130. hdl:10033/346408. PMID 25722166.
  5. ↑ Cooper, Karen A.; Campos-Giménez, Esther; Jiménez Alvarez, Diego; Nagy, Kornél; Donovan, Jennifer L.; Williamson, Gary (2007). "Rapid Reversed Phase Ultra-Performance Liquid Chromatography Analysis of the Major Cocoa Polyphenols and Inter-relationships of Their Concentrations in Chocolate". Journal of Agricultural and Food Chemistry. 55 (8): 2841–2847. doi:10.1021/jf063277c. PMID 17362030.