Procyanidin B1

Procyanidin B1
	Chemical structure of procyanidin B2
Names
	IUPAC name (2R,2ʼR,3R,3ʼS,4R)-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 B1; cis,trans′′-4,8′′-Bi-(3,3′,4′,5,7-Pentahydroxyflavane)
Identifiers
CAS Number	20315-25-7
ChEBI	CHEBI:75633
Jmol 3D model	Interactive image
PubChem	11250133
	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
Vapor pressure	{{{value}}}
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Procyanidin B1^[1] is a procyanidin dimer.

It is a molecule with a 4→8 bond (epicatechin-(4β→8)-catechin).^[2] Proanthocyanidin-B1 can be found in Cinnamomum verum (Ceylon cinnamon, in the rind, bark or cortex), in Uncaria guianensis (cat's claw, in the root), and in Vitis vinifera (common grape vine, in the leaf)^[3] or in peach.^[4]

Procyanidin B1 can be converted into procyanidin A1 by radical oxidation using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals under neutral conditions.^[5]

References

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↑ Procyanidin B1 on Sigma-Aldrich website
↑ Procyanidin B1 is detected in human serum after intake of proanthocyanidin-rich grape seed extract. Sano Atsushi; Yamakoshi Jun; Tokutake Shoichi; Tobe Koichiro; Kubota Yoshiro; Kikuchi Mamoru, 2003
↑ Proanthocyanidin-B1 on liberherbarum.com
↑ Postharvest sensory and phenolic characterization of ‘Elegant Lady’ and ‘Carson’ peaches. Rodrigo Infante, Loreto Contador, Pía Rubio, Danilo Aros and Álvaro Peña-Neira, Chilean Journal Of Agricultural Research, 71(3), July-September 2011, pages 445-451 (article)
↑ Conversion of procyanidin B-type (catechin dimer) to A-type: evidence for abstraction of C-2 hydrogen in catechin during radical oxidation. Kazunari Kondo, Masaaki Kurihara, Kiyoshi Fukuhara, Takashi Tanaka, Takashi Suzuki, Naoki Miyata and Masatake Toyoda, Tetrahedron Letters, 22 January 2000, Volume 41, Issue 4, Pages 485–488, doi:10.1016/S0040-4039(99)02097-3

v t e Types of procyanidins
A-type proanthocyanidins	Dimers : Procyanidin A1 A2 Trimers:Cinnamtannin B1 Tetramers: Arecatannin A2
B type proanthocyanidins	Dimers : Procyanidin B1 B2 B3 B4 B5 B6 B8 Trimers: Arecatannin B1 (epicatechin-(4β→8)-epicatechin-(4β→6)-catechin) Procyanidin C1 (epicatechin-(4β→8)-epicatechin-(4β→8)-epicatechin) Procyanidin C2 (catechin-(4α→8)-catechin-(4α→8)-catechin)
Types	Arecatannins Arecatannin A1 Arecatannin A3 Arecatannin B2 Arecatannin C1

Names
Chemical structure of procyanidin B2
IUPAC name (2R,2ʼR,3R,3ʼS,4R)-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 B1 cis,trans′′-4,8′′-Bi-(3,3′,4′,5,7-Pentahydroxyflavane)
Identifiers
CAS Number	20315-25-7^Y
ChEBI	CHEBI:75633
Jmol 3D model	Interactive image
PubChem	11250133
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
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references