Procyanidin B3

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Procyanidin B3
Chemical structure of procyanidin B3
Identifiers
PubChem 146798
ChEBI CHEBI:75630
Jmol-3D images Image 1
Properties
Molecular formula C30H26O12
Molar mass 578.52 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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

Natural occurrences[edit]

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[edit]

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

Chemical synthesis[edit]

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[edit]

References[edit]

  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". Vitis 34 (1): 51–56. 
  2. ^ a b 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. 
  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". Chilean journal of agricultural research 71 (3): 445. 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.