Procyanidin B3
Names | |
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IUPAC name
[(2R,3S,4S)-Flavan-3,3′,4′,5,7-pentol]-(4→8)-[(2R,3S)-flavan-3,3′,4′,5,7-pentol]
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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
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.150.578 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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).
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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,[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
References
- ^ 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.
- ^ S2CID 39454993.
- PMID 17177530.
- ^ Delcour, Jan (1985). Structure elucidation of proanthocyanidins: Direct synthesis and isolation from Pilsener beer.
- .
- PMID 16300918.
- .