Procyanidin A1 information

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 ;
3D model (JSmol)	Interactive image;
ChemSpider	552773;
PubChem CID	637122;
UNII	LX492GRN5W ;
CompTox Dashboard (EPA)	DTXSID401028817 ;
	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;
	SMILES 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). verify (what is ?) Infobox references

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]

^ 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.
^ 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.
^ 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.
^ 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

[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.

[Lie-Chwen-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

Procyanidin A1 information

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