Metabolites of polycyclic aromatic hydrocarbons. II. Isomeric k-region phenols and methyl ethers of benz []anthracene

Stereoselectivity and regioselectivity of uridine 5'-diphosphoglucuronosyltransferase toward vicinal dihydrodiols of polycyclic aromatic hydrocarbons

“…and 4/?,55 antipodes 6 and 7 of ds-4,5-dihydroxy-4,5-dihydrobenzo[ü]pyrene were obtained as previously described (Chang et al, 1979;Cobb et al, 1983a). 4-Hydroxybenzo[a]pyrene, 8, and 5-hydroxybenzo-[a] pyrene, 9, were prepared by acid-catalyzed dehydration of the m-dihydrodiol as described for 5-and 6-hydroxybenz- [zz] anthracene (Wiley et al, 1975).…”

Calculated properties of arene oxides of biological interest. 1. Molecular orbital examination of simple models

“…Experimentally, the epoxide ring-opening preference for benzanthracene 5,6-oxide is not so clear-cut, the reported yields of 5-and 6-hydroxybenzanthracene (from dehydration of the 5,6diol) being 43 and 33%, respectively. 19 The calculated energy differences are very nearly the same for the two possible pathways (+113.1 kcal/mol for the 5-hydroxy ion and +113.9 kcal/mol for the 6-hydroxy ion). The many approximations used in the semiempirical calculations preclude attaching great quantitative significance to these energy differences; however, within the context of parallel changes in structure among the various arene oxides, they appear to account very well for observed qualitative results and trends.…”

Hydrosolubilization of Large Aromatic Molecules: Facile Synthesis and Characterization of Water-Soluble Derivatives of Decacyclene

“…1 H NMR of (2) was recorded in D 2 O solution. MS spectra were acquired on a Bruker MALDI-TOF Reflex III spectrometer.…”

“…Water solubilization of aromatic hydrocarbons is a goal of aimed interest to achieve amphiphilic materials which can display several important properties in different ambits that range from metabolic biochemistry [1] to catalysis, [2][3][4] not to mention their potential chemical and physical roles as matters and precursors for surfactants, [5,6] foaming agents, [7,8] molecular carriers, [9][10][11] polyelectrolyte networks-based materials, [12] water soluble fluorescence markers, [13][14][15] pigments or inks. [16,17] Within this perspective, it is a challenge of importance the performing of efficient strategies of synthesis focused on largely available, nontoxic cheap organic frameworks that can be carried out in actual mild conditions.…”