Misplaced Pages

Procyanidin B1

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.

This is the current revision of this page, as edited by LegionMammal978 (talk | contribs) at 21:31, 6 May 2023 (move systematic name). The present address (URL) is a permanent link to this version.

Revision as of 21:31, 6 May 2023 by LegionMammal978 (talk | contribs) (move systematic name)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
Procyanidin B1
Chemical structure of procyanidin B2
Names
IUPAC name -(4→8)-
Systematic IUPAC name (2R,2′R,3R,3′S,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 B1
cis,trans′′-4,8′′-Bi-(3,3′,4′,5,7-Pentahydroxyflavane)
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
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/s1Key: XFZJEEAOWLFHDH-UKWJTHFESA-N
SMILES
  • O1Cc2c(O)cc(O)c(3(O)(Oc4cc(O)cc(O)c34)c3ccc(O)c(O)c3)c2O1c1ccc(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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Procyanidin B1 is a procyanidin dimer.

It is a molecule with a 4→8 bond (epicatechin-(4β→8)-catechin). 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) or in peach.

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

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
Types of procyanidins
A-type proanthocyanidins
B type proanthocyanidins
Types


Stub icon

This article about an aromatic compound is a stub. You can help Misplaced Pages by expanding it.

Categories: