isoformononetin → Pisatin

HRID 2118272Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:9]([C:11]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[CH:12][O:13][C:5]=2[CH:4]=1)=[O:10].[CH3:21][O:22]C1C=CC(C2C(=O)C3C=CC(O)=CC=3OC=2)=C(O)C=1.C[O:43]C1C=CC(C2C(=O)C3C=CC(O)=CC=3OC=2)=CC=1O.C1OC2C=C(C3C(=O)C4C=CC(O)=CC=4OC=3)C=CC=2O1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C@H:9]3[O:10][C:15]4[C:14](=[CH:19][C:18]5[O:22][CH2:21][O:20][C:17]=5[CH:16]=4)[C@@:11]3([OH:43])[CH2:12][O:13][C:5]=2[CH:4]=1

Participants

Reactant 4

HCID 3764isoformononetin

HCID 5280448Calycosin

HCID 5280551Xenognosin B

HCID 5281805Psi-baptigenin

Product 1

HCID 101689Pisatin

Procedure

Isoformononetin, 2′-hydroxyformononetin, 3′-hydroxyformononetin (calycosin) and pseudobaptigenin were purchased from Apin (Abingdon, UK). Maackiairi and pisatin were kindly provided by Dr. H. D. VanEtten, (University of Arizona, Tucson). Maackiain glucoside and maackiain glucose malonate standards were gifts from Dr. S. Tebayashi (Kochi University, Japan). Medicarpin was from a lab collection. Other isoflavonoids were from Indofine Chemical Company (Somerville, N.J.). CO was obtained from Aldrich and all other chemicals were from Sigma (St. Louis, Mo.).

Sources & evidence

ORD record: ord-ed9baa25a6204d659367d335296acaf6
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442851B2

Reaction notes

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