Procyanidin B3

Procyanidin B3 is a B type proanthocyanidin. Procyanidin B3 is a catechin dimer (catechin-(4α→8)-catechin).

Procyanidin B3

Names
IUPAC name (2R,2ʼR,3S,3ʼS,4S)-2,2ʼ-bis(3,4-dihydroxyphenyl)-3,3ʼ,4,4ʼ-tetrahydro-2H,2ʼH-4,8ʼ-bichromene-3,3ʼ,5,5ʼ,7,7ʼ-hexol
Other names Procyanidin B3
Identifiers
3D model (JSmol)	Interactive image
ChEBI	CHEBI:75630
ChemSpider	129476
ECHA InfoCard	100.150.578
PubChem CID	146798
CompTox Dashboard (EPA)	DTXSID60178193
InChI InChI=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 Key: XFZJEEAOWLFHDH-AVFWISQGSA-N
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
Properties
Chemical formula	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).
verify (what is  ?)
Infobox references

Natural occurrences

It can be found in red wine,[1] in barley,[2][3] in beer,[4] in peach[5] or in Jatropha macrantha, the Huanarpo Macho.[6]

Health effects

It has been identified as a hair-growth stimulant.[2]

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).[7]

See also

• Phenolic content in wine

References

1. C. Dallas, J.M. Ricardo-Da-Silva and Olga Laureano (1995). "Degradation of oligomeric procyanidins and anthocyanins in a Tinta Roriz red wine during maturation" (PDF). Vitis. 34 (1): 51–56. Archived from the original (PDF) on 2013-12-03. Retrieved 2013-06-24.
2. Kamimura, A; Takahashi, T (2002). "Procyanidin B-3, isolated from barley and identified as a hair-growth stimulant, has the potential to counteract inhibitory regulation by TGF-beta1". Experimental Dermatology. 11 (6): 532–41. doi:10.1034/j.1600-0625.2002.110606.x. PMID 12473061. S2CID 39454993.
3. Quinde-Axtell, Zory; Baik, Byung-Kee (2006). "Phenolic Compounds of Barley Grain and Their Implication in Food Product Discoloration". Journal of Agricultural and Food Chemistry. 54 (26): 9978–84. doi:10.1021/jf060974w. PMID 17177530.
4. Delcour, Jan (1985). Structure elucidation of proanthocyanidins: Direct synthesis and isolation from Pilsener beer.
5. Infante, Rodrigo; Contador, Loreto; Rubio, Pía; Aros, Danilo; Peña-Neira, Álvaro (2011). "Postharvest Sensory and Phenolic Characterization of 'Elegant Lady' and 'Carson' Peaches" (PDF). Chilean Journal of Agricultural Research. 71 (3): 445–451. doi:10.4067/S0718-58392011000300016.
6. Benavides, Angelyne; Montoro, Paola; Bassarello, Carla; Piacente, Sonia; Pizza, Cosimo (2006). "Catechin derivatives in Jatropha macrantha stems: Characterisation and LC/ESI/MS/MS quali–quantitative analysis". Journal of Pharmaceutical and Biomedical Analysis. 40 (3): 639–47. doi:10.1016/j.jpba.2005.10.004. PMID 16300918.
7. Delcour, Jan. A.; Ferreira, Daneel; Roux, David G. (1983). "Synthesis of condensed tannins. Part 9. The condensation sequence of leucocyanidin with (+)-catechin and with the resultant procyanidins". Journal of the Chemical Society, Perkin Transactions 1: 1711. doi:10.1039/P19830001711.