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{{chembox |
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{{chembox |
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| Name = Proanthocyanidin B5 |
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| verifiedrevid = 387950174 |
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| Reference = |
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| ImageFile = Procyanidin B5.svg |
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| Name = Procyanidin B5 |
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| Reference = |
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| ImageName = Chemical structure of proanthocyanidin B5 |
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| ImageFile = Procyanidin B5.svg |
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| ImageSize = 200px |
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| ImageName = Chemical structure of procyanidin B5 |
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| IUPACName = |
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| ImageSize = 200px |
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| OtherNames = Procyanidin B5 |
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| IUPACName = -(4→6)- |
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| Section1= {{Chembox Identifiers |
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| SystematicName = (2''R'',2′''R'',3''R'',3′''R'',4''S'')-2,2′-Bis(3,4-dihydroxyphenyl)-3,3′,4,4′-tetrahydro-2''H'',2′''H''--3,3′,5,5′,7,7′-hexol |
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| CASNo = |
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| OtherNames = Procyanidin B5 |
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| CASOther = |
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|Section1={{Chembox Identifiers |
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| PubChem = 124017 |
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| SMILES = |
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| CASNo = 12798-57-1 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = W51N19H6K6 |
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| PubChem = 124017 |
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| ChEBI = 75621 |
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| ChEMBL = 506487 |
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| KEGG = C17640 |
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| ChemSpiderID = 110533 |
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| SMILES = O1Cc2c(O1c1ccc(O)c(O)c1)cc(O)c(1(O)(Oc3cc(O)cc(O)c13)c1ccc(O)c(O)c1)c2O |
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| 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 |
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| InChIKey = GMISZFQPFDAPGI-CVJZBMGUBO |
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| 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 |
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| StdInChIKey = GMISZFQPFDAPGI-CVJZBMGUSA-N |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>30</sub>H<sub>26</sub>O<sub>12</sub> |
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| Formula = C<sub>30</sub>H<sub>26</sub>O<sub>12</sub> |
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| MolarMass = 578.52 g/mol |
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| MolarMass = 578.52 g/mol |
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| Appearance= |
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| ExactMass = 578.142426 |
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|Section3= {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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'''Proanthocyanidin B5''' is a ]. |
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'''Procyanidin B5''' is a ]. |
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Procyanidin B5 is an ]-(4β → 6)-epicatechin dimer. |
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Proanthocyanidin B5 is an ]-(4β → 6)-epicatechin dimer. It can be found in grape seeds<ref name="da Silva"></ref> and in '']'' (kenaf) root and bark<ref></ref>. |
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== Natural occurrences == |
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==References== |
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It can be found in grape seeds,<ref name="da Silva">{{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. }}</ref> in '']'' (kenaf) root and bark,<ref>{{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 }}</ref> and in black chokeberries ('']'').<ref>{{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 }}</ref> |
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; Presence in food |
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It is found in cocoa beans<ref>{{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 }}</ref> and chocolate.<ref>{{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 }}</ref> |
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== References == |
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{{reflist}} |
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{{reflist}} |
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{{procyanidin}} |
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{{proanthocyanidin}} |
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] |
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] |
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] |
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{{polyphenol-stub}} |
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{{Aromatic-stub}} |