:Procyanidin B5
{{chembox
| Watchedfields = changed
| verifiedrevid = 387950174
| Name = Procyanidin B5
| Reference =
| ImageFile = Procyanidin B5.svg
| ImageName = Chemical structure of procyanidin B5
| ImageSize = 200px
| IUPACName = [(2R,3R,4S)-Flavan-3,3′,4′,5,7-pentol]-(4→6)-[(2R,3R)-flavan-3,3′,4′,5,7-pentol]
| SystematicName = (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
| OtherNames = Procyanidin B5
|Section1={{Chembox Identifiers
| CASNo = 12798-57-1
| CASNoOther =
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = W51N19H6K6
| PubChem = 124017
| ChEBI = 75621
| ChEMBL = 506487
| KEGG = C17640
| ChemSpiderID = 110533
| 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
| 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
| InChIKey = GMISZFQPFDAPGI-CVJZBMGUBO
| StdInChI = 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
| StdInChIKey = GMISZFQPFDAPGI-CVJZBMGUSA-N
}}
|Section2={{Chembox Properties
| Formula = C30H26O12
| MolarMass = 578.52 g/mol
| Appearance=
| Density=
| MeltingPtC=
| BoilingPt=
| Solubility=
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|Section3={{Chembox Hazards
| MainHazards=
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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,{{cite journal | url=http://www.sciencedirect.com/science/article/pii/S0031942200952130 | doi=10.1016/S0031-9422(00)95213-0 | title=Procyanidin dimers and trimers from grape seeds | journal=Phytochemistry | date=January 1991 | volume=30 | issue=4 | pages=1259–1264 | last2=Rigaud | first2=Jacques | last3=Cheynier | first3=Véronique | last4=Cheminat | first4=Annie | last5=Moutounet | first5=Michel | bibcode=1991PChem..30.1259R | last1=Ricardo Da Silva | first1=Jorge M. | url-access=subscription }} in Hibiscus cannabinus (kenaf) root and bark,{{Cite journal |doi=10.1007/BF00580458 |title=Dimeric proanthocyanidins ofHibiscus cannabinus |date=1982 |last1=Van Tkhin' |first1=Fam |last2=Makhsudova |first2=B. |last3=Otroshchenko |first3=O. S. |journal=Chemistry of Natural Compounds |volume=18 |issue=3 |pages=310–314 |bibcode=1982CNatC..18..310V }} and in black chokeberries (Aronia melanocarpa).{{Cite journal |doi=10.1021/jf904354n |title=Preparation of Dimeric Procyanidins B1, B2, B5, and B7 from a Polymeric Procyanidin Fraction of Black Chokeberry (Aronia melanocarpa) |date=2010 |last1=Esatbeyoglu |first1=Tuba |last2=Winterhalter |first2=Peter |journal=Journal of Agricultural and Food Chemistry |volume=58 |issue=8 |pages=5147–5153 |pmid=20196608 }}
; Presence in food
It is found in cocoa beans{{Cite journal |doi=10.1016/j.foodchem.2015.01.130 |title=Isolation of dimeric, trimeric, tetrameric and pentameric procyanidins from unroasted cocoa beans (Theobroma cacao L.) using countercurrent chromatography |date=2015 |last1=Esatbeyoglu |first1=Tuba |last2=Wray |first2=Victor |last3=Winterhalter |first3=Peter |journal=Food Chemistry |volume=179 |pages=278–289 |pmid=25722166 |hdl=10033/346408 |hdl-access=free }} and chocolate.{{Cite journal |doi=10.1021/jf063277c |title=Rapid Reversed Phase Ultra-Performance Liquid Chromatography Analysis of the Major Cocoa Polyphenols and Inter-relationships of Their Concentrations in Chocolate |date=2007 |last1=Cooper |first1=Karen A. |last2=Campos-Giménez |first2=Esther |last3=Jiménez Alvarez |first3=Diego |last4=Nagy |first4=Kornél |last5=Donovan |first5=Jennifer L. |last6=Williamson |first6=Gary |journal=Journal of Agricultural and Food Chemistry |volume=55 |issue=8 |pages=2841–2847 |pmid=17362030 }}