75665-89-3Relevant articles and documents
Preparation method and application of apocynin and derivatives of apocynin
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, (2020/01/12)
The invention belongs to the technical field of chemical biology, and particularly relates to a preparation method of apocynin and derivatives of the apocynin and an application of the apocynin and the derivatives of the apocynin in skin care products. The apocynin and the derivatives of the apocynin provided by the invention can promote collagen synthesis, help skin damage repair, and can be usedin the skin care products.
Hydrogenolysis of β-O-4 lignin model dimers by a ruthenium-xantphos catalyst
Wu, Adam,Patrick, Brian O.,Chung, Enoch,James, Brian R.
, p. 11093 - 11106 (2012/10/30)
Hydrogenolysis reactions of so-called lignin model dimers using a Ru-xantphos catalyst are presented (xantphos = 4,5-bis(diphenylphosphino)-9,9- dimethylxanthene). For example, of some nine models studied, the alcohol, 2-(2-methoxyphenoxy)-1-phenylethanol (1), with 5 mol% Ru(H)2(CO) (PPh3)(xantphos) (18) in toluene-d8 at 135 °C for 20 h under N2, gives in ~95% yield the C-O cleavage hydrogenolysis products, acetophenone (14) and guaiacol (17), and a small amount (1H NMR spectroscopy. The in situ Ru(H)2(CO)(PPh 3)3/xantphos system gives similar findings, confirming a recent report (J. M. Nichols et al., J. Am. Chem. Soc., 2010, 132, 12554). The active catalyst is formulated 'for convenience' as 'Ru(CO)(xantphos)'. The hydrogenolysis mechanism proceeds by initial dehydrogenation to give the ketone 4, which then undergoes hydrogenolysis of the C-O bond to give 14 and 17. Hydrogenolysis of 4 to 14 and 17 also occurs using the Ru catalyst under 1 atm H2; in contrast, use of 3-hydroxy-2-(2-methoxyphenoxy)-1-phenyl-1- propanone (7), for example, where the CH2 of 4 has been changed to CHCH2OH, gives a low yield (≤15%) of hydrogenolysis products. Similarly, the diol substrate, 2-(2-methoxyphenoxy)-1-phenyl-1,3-propanediol (9), gives low yields of hydrogenolysis products. These low yields are due to formation of the catalytically inactive complexes Ru(CO)(xantphos)[C(O)C(OC 6H4OMe)C(Ph)O] (20) and/or Ru(CO)(xantphos)[C(O)CHC(Ph)O] (21), where the organic fragments result from dehydrogenation of CH 2OH moieties in 7 and 9. Trace amounts of Ru(CO)(xantphos)(OC 6H4O), a catecholate complex, are isolated from the reaction of 18 with 1. Improved syntheses of 18 and lignin models are also presented.
Singlet oxygen in the photodegradation of lignin models
Crestini, Claudia,D'Auria, Maurizio
, p. 7877 - 7888 (2007/10/03)
The photochemical oxidation of lignin models in the presence of singlet oxygen was studied. The treatment of the non-phenolic β-O-4 aryl ether derivatives 6, 7, and 8 in the presence of both oxygen and Rose Bengal gave products deriving from a formal β-C-O cleavage formation. By this way. the derivatives 12, 13, and 15 were obtained. The photochemical oxidation of the phenolic β-O-4 aryl ether 9 gave the same type of product confirming that, in this case, the presence of the carbonyl group is not indispensable to have the cleavage reaction. The use of the model compound 10 showed that, when the phenoxy part of the molecule shows a lower reactivity towards singlet oxygen, the oxidation of the phenol moiety to hydroquinone call occur. The photochemical behaviour of these model compounds can be rationalised from a reaction of singlet oxygen with the phenoxy part of the molecule.