3881-05-8

Upstream product

• 106-51-4 p-benzoquinone 

Downstream Products

• 106-51-4 p-benzoquinone 
• 1032336-13-2 [1-⁽¹³⁾C]benzene-1,2,4-triol 
• 1032336-11-0 [1-(13C)]-1,2,4-triacetoxybenzene 
• 1032336-07-4 [4-(13C)]-1,2,4-triacetoxybenzene 

Relevant academic research and scientific papers

Studies on the structure and biosynthesis of tridentoquinone and related meroterpenoids from the mushroom Suillus tridentinus (Boletales)

Tridentoquinone (1), the main pigment of Suillus tridentinus, is accompanied by the known meroterpenoid bolegrevilol (3) and a dimer, tridentorubin (5). The absolute configuration of 1 was unambiguously established by a single-crystal X-ray analysis of the corresponding (-)-camphanoate. The structure of 5 was elucidated by 2D NMR techniques including a 2D INADEQUATE experiment. Feeding experiments with [1-13C]-labeled 4-hydroxybenzoic acid (6*) and 3,4-dihydroxybenzoic acid (7*) proved the incorporation of these precursors into all three metabolites. Tridentoquinone (1) was monolabeled at C-1 suggesting the formation of the ansa ring by oxidative cyclisation of 2-geranylgeranyl-6-hydroxybenzoquinone (10). This was supported by the isolation of the expected intermediate, deoxytridentoquinone (11), from the mushroom extract. Tridentorubin (5) may be formed by addition of precursor 10 to tridentoquinone (1). This hypothesis is backed up by the in vitro formation of an analogous product 13 from 1 and 1,4-benzoquinone. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Altered Condensed-Phase Electron Affinities of Carbonyl- 13C-, 14C-, and 17O-Substituted Ketones

Electron spin resonance experiments have shown that the solution electron affinities of both benzoquinone (BQ) and benzophenone (BZO) in liquid ammonia are diminished when a 13C replaces the 12C in the carbonyl position.For the reaction *R+R.-=*R.-+R, where *R represents the 13C-substituted material (either BZO-13C or BQ-13C), the equilibrium constants (Keq) are 0.80 and 0.50 at -75 deg C for the BQ and BZO systems, respectively.The reduction of radioactive samples of benzophenone (mixtures of BZO and BZO-14C, 14C substitution at the carbonyl carbon) with deficient amounts of sodium metal in liquid ammonia followed by removal of the ammonia leaves a solid mixture of benzophenone and benzophenone ketyl.Sublimation of the neutral benzophenone from the anion radical salt produces benzophenone that is enhanced in radioactivity relative to the starting BZO/BZO-14C mixture.This enhancement in radioactivity is consistent with the equilibrium constant again being less than unity when *R represents the 14C-substituted benzophenone.In contrast to these results, substitution of the oxygen atom with 17O results in an increase in the relative solution electron affinity.This is explained in terms of the increase in "bonding" involving the oxygen upon reduction, due to ion association.