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 =

}}

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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}}

See also

References

{{reflist}}

{{procyanidin}}

Category:Procyanidin dimers

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