isoformononetin → (-)-Maackiain

HRID 1092935Notes

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.[CH3:42][O:43][C:44]1[CH:49]=[CH:48][C:47]([C:50]2[C:55](=[O:56])[C:54]3[CH:57]=[CH:58][C:59]([OH:61])=[CH:60][C:53]=3[O:52][CH:51]=2)=[CH:46][C:45]=1[OH:62].C1OC2C=C(C3C(=O)C4C=CC(O)=CC=4OC=3)C=CC=2[O:64]1>>[CH:58]1[C:59]([OH:61])=[CH:60][C:53]2[O:52][CH2:51][C@H:50]3[C:47]4[CH:46]=[C:45]5[O:62][CH2:42][O:43][C:44]5=[CH:49][C:48]=4[O:56][C@H:55]3[C:54]=2[CH:57]=1.[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:64])[CH2:12][O:13][C:5]=2[CH:4]=1

Participants

Reactant 4

HCID 3764isoformononetin

HCID 5280448Calycosin

HCID 5280551Xenognosin B

HCID 5281805Psi-baptigenin

Product 2

HCID 91510(-)-Maackiain

HCID 101689Pisatin

Procedure

Isoformononetin, 2′-hydroxyformononetin, 3′-hydroxyformononetin (calycosin) and pseudobaptigenin were purchased from Apin (Abingdon, UK). Maackiain 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-bf1f3f84deec4ac89b5ac4c2cb65cf7d
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129592B2

Reaction notes

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