Procyanidin B3
| |
| Names | |
|---|---|
| IUPAC name
[(2R,3S,4S)-Flavan-3,3′,4′,5,7-pentol]-(4→8)-[(2R,3S)-flavan-3,3′,4′,5,7-pentol]
| |
| Systematic IUPAC name
(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 | |
| Other names
Procyanidin B3
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.150.578 |
| EC Number |
|
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C30H26O12 | |
| Molar mass | 578.52 g/mol |
| Hazards | |
| GHS labelling: | |
| |
| Warning | |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
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 a 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]- ^ 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.
- ^ 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. S2CID 39454993.
- ^ 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.
- ^ Delcour, Jan (1985). Structure elucidation of proanthocyanidins: Direct synthesis and isolation from Pilsener beer.
- ^ 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.
- ^ 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.
- ^ 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.
 | This article about an aromatic compound is a stub. You can help Wikipedia by expanding it. |