Procyanidin B8

Procyanidin B8
Names
	IUPAC name -(4→6)-
	Systematic IUPAC name (2R,2′R,3S,3′R,4R)-2,2′-Bis(3,4-dihydroxyphenyl)-3,3′,4,4′-tetrahydro-2H,2′H--3,3′,5,5′,7,7′-hexol
	Other names Procyanidin B8
Identifiers
CAS Number	12798-60-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:75618;
ChEMBL	ChEMBL451115;
ChemSpider	416636;
PubChem CID	474541;
UNII	KW4926C35L ;
CompTox Dashboard (EPA)	DTXSID701028816 ;
	InChI InChI=1S/C30H26O12/c31-13-7-19(36)24-23(8-13)42-30(12-2-4-16(33)18(35)6-12)28(40)26(24)25-20(37)10-22-14(27(25)39)9-21(38)29(41-22)11-1-3-15(32)17(34)5-11/h1-8,10,21,26,28-40H,9H2/t21-,26+,28+,29-,30-/m1/s1 Key: GMISZFQPFDAPGI-JJYFIROESA-N; InChI=1/C30H26O12/c31-13-7-19(36)24-23(8-13)42-30(12-2-4-16(33)18(35)6-12)28(40)26(24)25-20(37)10-22-14(27(25)39)9-21(38)29(41-22)11-1-3-15(32)17(34)5-11/h1-8,10,21,26,28-40H,9H2/t21-,26+,28+,29-,30-/m1/s1 Key: GMISZFQPFDAPGI-JJYFIROEBQ;
	SMILES O1Cc2c(O1c1ccc(O)c(O)c1)cc(O)c(1(O)(Oc3cc(O)cc(O)c13)c1ccc(O)c(O)c1)c2O;
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 , 100 kPa). verify (what is ?) Infobox references

Procyanidin B8 is a B type proanthocyanidin.

Procyanidin B8 is a catechin-(4α→6)-epicatechin dimer. It can be found in grape seeds^[1] and in beer.^[2]

References

^ Procyanidin dimers and trimers from grape seeds. Jorge M. Ricardo da Silva, Jacques Rigaud, Véronique Cheynier, Annie Cheminat and Michel Moutounet,Phytochemistry, 1991, Volume 30, Issue 4, Pages 1259–1264, doi:10.1016/S0031-9422(00)95213-0
^ Structure elucidation of proanthocyanidins: Direct synthesis and isolation from Pilsener beer. Jan Delcour, Thesis, 1985

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[da_Silva-1] Procyanidin dimers and trimers from grape seeds. Jorge M. Ricardo da Silva, Jacques Rigaud, Véronique Cheynier, Annie Cheminat and Michel Moutounet,Phytochemistry, 1991, Volume 30, Issue 4, Pages 1259–1264, doi:10.1016/S0031-9422(00)95213-0

[Delcour-2] Structure elucidation of proanthocyanidins: Direct synthesis and isolation from Pilsener beer. Jan Delcour, Thesis, 1985

[1]

[2]

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 D (ent-Epicatechin(4α→8)catechin) 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) Tetramers : Cinnamtannin A2
Types	Arecatannins Arecatannin A1 Arecatannin A3 Arecatannin B2 Arecatannin C1