14602-93-8

Basic information

• Product Name: (+)-6a-hydroxymaackiain
• CAS NO: 14602-93-8
• Molecular Weight: 300.268
• Mol File: 14602-93-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (+)-6a-hydroxymaackiain(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-6a-hydroxymaackiain(14602-93-8)
• EPA Substance Registry System: (+)-6a-hydroxymaackiain(14602-93-8)

Safety Data

• Hazardous Substances Data: 14602-93-8(Hazardous Substances Data)

Upstream product

• 469-01-2 Pisatin 
• 207232-32-4 7-Benzyloxy-3-(6-benzyloxy-benzo[1,3]dioxol-5-yl)-chromen-2-one 
• 207232-35-7 7-Benzyloxy-3-(6-benzyloxy-benzo[1,3]dioxol-5-yl)-2H-chromene 
• 485-72-3 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on 
• 485-80-3 S-adenosyl-L-methionine 
• 207232-36-8 (3R,4S)-7-Benzyloxy-3-(6-benzyloxy-benzo[1,3]dioxol-5-yl)-chroman-3,4-diol 

Downstream Products

• 469-01-2 Pisatin 

Relevant articles and documents

Inactivation of pea genes by RNAi supports the involvement of two similar O-methyltransferases in the biosynthesis of (+)-pisatin and of chiral intermediates with a configuration opposite that found in (+)-pisatin

(+)-Pisatin, the major phytoalexin of pea (Pisum sativum L.), is believed to be synthesized via two chiral intermediates, (-)-7,2′-dihydroxy-4′,5′-methylenedioxyisoflavanone [(-)-sophorol] and (-)-7,2′-dihydroxy-4′,5′-methylenedioxyisoflavanol [(-)-DMDI]; both have an opposite C-3 absolute configuration to that found at C-6a in (+)-pisatin. The expression of isoflavone reductase (IFR), which converts 7,2′-dihydroxy-4′,5′-methylenedioxyisoflavone (DMD) to (-)-sophorol, sophorol reductase (SOR), which converts (-)-sophorol to (-)-DMDI, and hydroxymaackiain-3-O-methyltransferase (HMM), believed to be the last step of (+)-pisatin biosynthesis, were inactivated by RNA-mediated genetic interference (RNAi) in pea hairy roots. Some hairy root lines containing RNAi constructs of IFR and SOR accumulated DMD or (-)-sophorol, respectively, and were deficient in (+)-pisatin biosynthesis supporting the involvement of chiral intermediates with a configuration opposite to that found in (+)-pisatin in the biosynthesis of (+)-pisatin. Pea proteins also converted (-)-DMDI to an achiral isoflavene suggesting that an isoflavene might be the intermediate through which the configuration is changed to that found in (+)-pisatin. Hairy roots containing RNAi constructs of HMM also were deficient in (+)-pisatin biosynthesis, but did not accumulate (+)-6a-hydroxymaackiain, the proposed precursor to (+)-pisatin. Instead, 2,7,4′-trihydroxyisoflavanone (TIF), daidzein, isoformononetin, and liquiritigenin accumulated. HMM has a high amino acid similarity to hydroxyisoflavanone-4′-O-methyltransferase (HI4′OMT), an enzyme that methylates TIF, an early intermediate in the isoflavonoid pathway. The accumulation of these four compounds is consistent with the blockage of the synthesis of (+)-pisatin at the HI4′OMT catalyzed step resulting in the accumulation of liquiritigenin and TIF and the diversion of the pathway to produce daidzein and isoformononetin, compounds not normally made by pea. Previous results have identified two highly similar "HMMs" in pea. The current results suggest that both of these O-methyltransferases are involved in (+)-pisatin biosynthesis and that one functions early in the pathway as HI4′OMT and the second acts at the terminal step of the pathway.

Asymmetric total synthesis of (+)-pisatin, a phytoalexin from garden peas (Pisum sativum L.)

A short asymmetric total synthesis of (+)-pisatin is described involving a Sharpless asymmetric dihydroxylation and an 'hydrogenative cyclisation' as key steps.