Procyanidin A1

Procyanidin A1
Chemical structure of procyanidin A1
Names
IUPAC name
(2R,3S,8S,14R,15R)-2,8-bis(3,4-dihydroxyphenyl)-2,3,4,14-tetrahydro-8,14-methanobenzo[7,8][1,3]dioxocino[4,5-h]chromene-3,5,11,13,15-pentaol
Identifiers
CAS Number
  • 103883-03-0 checkY
3D model (JSmol)
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ChemSpider
  • 552773
PubChem CID
  • 637122
UNII
  • LX492GRN5W checkY
CompTox Dashboard (EPA)
  • DTXSID401028817 Edit this at Wikidata
InChI
  • InChI=1S/C30H24O13/c31-12-6-17(35)23-21(7-12)42-30(11-4-18(36)26(39)19(37)5-11)29(40)25(23)24-22(43-30)9-15(33)13-8-20(38)27(41-28(13)24)10-1-2-14(32)16(34)3-10/h1-7,9,20,25,27,29,31-40H,8H2/t20-,25-,27-,29-,30+/m1/s1
    Key: WODBGULXKVZGQF-QCPBNORNSA-N
  • O[C@@H]1[C@@H](C2=C(O[C@H](C3=CC(O)=C(O)C=C3)[C@@H](O)C4)C4=C(O)C=C2O5)C6=C(C=C(O)C=C6O)O[C@]15C7=CC(O)=C(O)C=C7
Properties
Chemical formula
 C30H24O12
Molar mass 576.510 g·mol−1
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 A1 is an A type proanthocyanidin dimer.

It is an epicatechin-(2β→7,4β→8)-catechin dimer found in Rhododendron spiciferum,[1] in peanut skins[2] and in Ecdysanthera utilis.[3]

Procyanidin B1 can be converted into procyanidin A1 by radical oxidation using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals under neutral conditions.[4]

References

  1. ^ Liu, YZ; Cao, YG; Ye, JQ; Wang, WG; Song, KJ; Wang, XL; Wang, CH; Li, RT; Deng, XM (2009). "Immunomodulatory effects of proanthocyanidin A-1 derived in vitro from Rhododendron spiciferum". Fitoterapia. 81 (2): 108–14. doi:10.1016/j.fitote.2009.08.005. PMID 19686816.
  2. ^ Hongxiang Lou; Yamazaku Y.; Sasaku T.; Uchida M.; Tanaka H.; Oka S. (1999). "A-type proanthocyanidins from peanut skins". Phytochemistry. 51 (2): 297–308. doi:10.1016/S0031-9422(98)00736-5.
  3. ^ Lin, Lie-Chwen; Kuo, Yuh-Chi; Chou, Cheng-Jen (2002). "Immunomodulatory Proanthocyanidins from Ecdysantherautilis". Journal of Natural Products. 65 (4): 505–8. doi:10.1021/np010414l. PMID 11975489.
  4. ^ 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
Types
  • Arecatannins
    • Arecatannin A1
    • Arecatannin A3
    • Arecatannin B2
    • Arecatannin C1


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