Procyanidin B1

Procyanidin B1
Chemical structure of procyanidin B2
Names
IUPAC name
[(2R,3R,4R)-Flavan-3,3′,4′,5,7-pentol]-(4→8)-[(2R,3S)-flavan-3,3′,4′,5,7-pentol]
Systematic IUPAC name
(2R,2′R,3R,3′S,4R)-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 B1
cis,trans′′-4,8′′-Bi-(3,3′,4′,5,7-Pentahydroxyflavane)
Identifiers
CAS Number
  • 20315-25-7 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:75633
ChEMBL
  • ChEMBL504937
ChemSpider
  • 9425166
PubChem CID
  • 11250133
UNII
  • 0566J48E7X
InChI
  • InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26+,27+,28+,29+/m0/s1
    Key: XFZJEEAOWLFHDH-UKWJTHFESA-N
  • 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
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
Chemical compound

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]

See also

References

  1. ^ Procyanidin B1 on Sigma-Aldrich website
  2. ^ 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
  3. ^ Proanthocyanidin-B1 on liberherbarum.com
  4. ^ 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)
  5. ^ 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
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Types of procyanidins
A-type proanthocyanidins
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


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