Prodelphinidin B3
Chemical structure of prodelphinidin B3
Names
IUPAC name
2-(3,4-dihydroxyphenyl)-8-[3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
Other names
gallocatechin-(4α→8)-catechin
GC-(4,8)-C
Dimer GC-C
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C30H26O13/c31-12-6-17(35)23-22(7-12)42-29(11-4-19(37)26(40)20(38)5-11)27(41)25(23)24-18(36)9-15(33)13-8-21(39)28(43-30(13)24)10-1-2-14(32)16(34)3-10/h1-7,9,21,25,27-29,31-41H,8H2
    Key: ZYDDITZPGFXQSD-UHFFFAOYSA-N
  • C1C(C(OC2=C1C(=CC(=C2C3C(C(OC4=CC(=CC(=C34)O)O)C5=CC(=C(C(=C5)O)O)O)O)O)O)C6=CC(=C(C(=C6))O)O)O
Properties
C30H26O13
Molar mass 594.525 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Prodelphinidin B3 is a prodelphinidin dimer found in food products such as barley[1][2] and beer, in fruits and pod vegetables. It can also be found in pomegranate peels.[3]

It can also be synthesized.[4]

References

  1. ^ Klausen, K; Mortensen, AG; Laursen, B; Haselmann, KF; Jespersen, BM; Fomsgaard, IS (2010). "Phenolic compounds in different barley varieties: Identification by tandem mass spectrometry (QStar) and NMR; quantification by liquid chromatography triple quadrupole-linear ion trap mass spectrometry (Q-Trap)". Natural Product Communications. 5 (3): 407–14. doi:10.1177/1934578X1000500314. PMID 20420318. S2CID 45699900.
  2. ^ Quinde-Axtell, Zory; Baik, Byung-Kee (2006). "Phenolic Compounds of Barley Grain and Their Implication in Food Product Discoloration". Journal of Agricultural and Food Chemistry. 54 (26): 9978–84. doi:10.1021/jf060974w. PMID 17177530.
  3. ^ Plumb, G. W.; De Pascual-Teresa, S.; Santos-Buelga, C.; Rivas-Gonzalo, J. C.; Williamson, G. (2002). "Antioxidant properties of gallocatechin and prodelphinidins from pomegranate peel". Redox Report. 7 (1): 41–6. doi:10.1179/135100002125000172. PMID 11981454.
  4. ^ Delcour, Jan A.; Vercruysse, Sabine A. R. (1986). "Direct Synthesis of the Barley Proanthocyanidins Prodelphinidin B3, Prodelphinidin C2 and Two Trimeric Proanthocyanidins with a Mixed Prodelphinidin-Procyanidin Stereochemistry". Journal of the Institute of Brewing. 92 (3): 244. doi:10.1002/j.2050-0416.1986.tb04409.x.

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