procyanidin B3
{{chembox
| verifiedrevid = 449573603
| Name = Procyanidin B3
| Reference =
| ImageFile = Procyanidin B3.svg
| ImageName = Chemical structure of procyanidin B3
| ImageSize = 200px
| IUPACName = [(2R,3S,4S)-Flavan-3,3′,4′,5,7-pentol]-(4→8)-[(2R,3S)-flavan-3,3′,4′,5,7-pentol]
| SystematicName = (2R,2′R,3S,3′S,4S)-2,2′-Bis(3,4-dihydroxyphenyl)-3,3′,4,4′-tetrahydro-2H,2′H-[4,8′-bi-1-benzopyran]-3,3′,5,5′,7,7′-hexol
| OtherNames = Procyanidin B3
|Section1={{Chembox Identifiers
| CASNo_Ref = {{Cascite|changed|CAS}}
| CASNo = 23567-23-9
| ChEBI = 75630
| ChEMBL = 501490
| ChemSpiderID = 129476
| EINECS = 621-754-2
| PubChem = 146798
| UNII = 2TC1A0KEAQ
| SMILES = O[C@H]1Cc2c(O)cc(O)c([C@H]3[C@H](O)[C@H](Oc4cc(O)cc(O)c34)c3ccc(O)c(O)c3)c2O[C@@H]1c1ccc(O)c(O)c1
| StdInChI = 1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28+,29+/m0/s1
| StdInChIKey = XFZJEEAOWLFHDH-AVFWISQGSA-N
}}
|Section2={{Chembox Properties
| Formula = C30H26O12
| MolarMass = 578.52 g/mol
| Appearance=
| Density=
| MeltingPtC =
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
Procyanidin B3 is a B type proanthocyanidin. Procyanidin B3 is a catechin dimer (catechin-(4α→8)-catechin).
Natural occurrences
It can be found in red wine,{{Cite journal|title= Degradation of oligomeric procyanidins and anthocyanins in a Tinta Roriz red wine during maturation|author= C. Dallas, J.M. Ricardo-Da-Silva and Olga Laureano|journal= Vitis|year= 1995|volume= 34|issue= 1|pages= 51–56|url= http://www.vitis-vea.de/admin/volltext/e034753.pdf|access-date= 2013-06-24|archive-url= https://web.archive.org/web/20131203051305/http://www.vitis-vea.de/admin/volltext/e034753.pdf|archive-date= 2013-12-03|url-status= dead}} in barley,{{Cite journal|pmid=12473061|year=2002|last1=Kamimura|first1=A|last2=Takahashi|first2=T|title=Procyanidin B-3, isolated from barley and identified as a hair-growth stimulant, has the potential to counteract inhibitory regulation by TGF-beta1|volume=11|issue=6|pages=532–41|journal=Experimental Dermatology|doi=10.1034/j.1600-0625.2002.110606.x|s2cid=39454993}}{{Cite journal|doi=10.1021/jf060974w|title=Phenolic Compounds of Barley Grain and Their Implication in Food Product Discoloration|year=2006|last1=Quinde-Axtell|first1=Zory|last2=Baik|first2=Byung-Kee|journal=Journal of Agricultural and Food Chemistry|volume=54|issue=26|pages=9978–84|pmid=17177530}} in beer,{{Cite book|title=Structure elucidation of proanthocyanidins: Direct synthesis and isolation from Pilsener beer|url=https://books.google.com/books?id=Zc8wGwAACAAJ|first= Jan |last=Delcour|year=1985}} in peach{{Cite journal|doi=10.4067/S0718-58392011000300016|url=http://www.scielo.cl/pdf/chiljar/v71n3/at16.pdf|title=Postharvest Sensory and Phenolic Characterization of 'Elegant Lady' and 'Carson' Peaches |year=2011|last1=Infante|first1=Rodrigo|last2=Contador|first2=Loreto|last3=Rubio|first3=Pía|last4=Aros|first4=Danilo|last5=Peña-Neira|first5=Álvaro|journal=Chilean Journal of Agricultural Research|volume=71|issue=3|pages=445–451 |doi-access=free}} or in Jatropha macrantha, the Huanarpo Macho.{{Cite journal|doi=10.1016/j.jpba.2005.10.004|title=Catechin derivatives in Jatropha macrantha stems: Characterisation and LC/ESI/MS/MS quali–quantitative analysis|year=2006|last1=Benavides|first1=Angelyne|last2=Montoro|first2=Paola|last3=Bassarello|first3=Carla|last4=Piacente|first4=Sonia|last5=Pizza|first5=Cosimo|journal=Journal of Pharmaceutical and Biomedical Analysis|volume=40|issue=3|pages=639–47|pmid=16300918}}
Health effects
It has been identified as a hair-growth stimulant.
Chemical synthesis
Molar equivalents of synthetic (2R,3S,4R or S)-leucocyanidin and (+)-catechin condense with exceptional rapidity at pH 5 under ambient conditions to give the all-trans-[4,8]- and [4,6]-bi-[(+)-catechins] (procyanidins B3, B6) the all-trans-[4,8:4,8]- and [4,8:4,6]-tri-[(+)-catechins] (procyanidin C2 and isomer).{{Cite journal|doi=10.1039/P19830001711|title=Synthesis of condensed tannins. Part 9. The condensation sequence of leucocyanidin with (+)-catechin and with the resultant procyanidins|year=1983|last1=Delcour|first1=Jan. A.|last2=Ferreira|first2=Daneel|last3=Roux|first3=David G.|journal=Journal of the Chemical Society, Perkin Transactions 1|pages=1711}}