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Chemistry and Industry of Forest Products ›› 2014, Vol. 34 ›› Issue (2): 77-84.doi: 10.3969/j.issn.0253-2417.2014.02.014

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Synthesis and UV Property of Rosin-derived Azo Compounds

YAO Gui-yang1, LIN Ning1 2, DAI Wei-long1, WEI Jing-chen3, PAN Ying-ming1, WANG Heng-shan1   

  1. 1. Key Laboratory of Chemistry and Molecular Engineering of Medicinal Resources; School of Chemistry & Chemical Engineering, Guangxi Normal University, Guilin 541004, China;
    2. School of Parmaceutical Sciences, Guangxi University of Chinese Medicine, Nanning 530001, China;
    3. Department of Pharmacology, Guilin Medical College, Guilin 541004, China
  • Received:2013-02-25 Online:2014-04-25 Published:2014-04-26

Abstract: Starting from methyl dehydroabietate, eight rosin-derived azo compounds were synthesized by nitration, reduction, diazonization and coupling reaction. The structures of eight azo compounds (1R,4aS)-methyl 6-((E)-(4-(dimethylamino)phenyl)diazenyl)-7-isopropyl-1,4a-di-methyl-8-nitro-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate (2a), (1R,4aS)-methyl-6-((E)-(5-cyano-2-hydroxy-1,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)diazenyl)-7-isopropyl-1,4a-dimethyl-8-nitro-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate (2b), (1R,4aS)-meth-yl-((E)-(5-cyano-1-ethyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridin-3-yl)diazenyl)-7-isopropyl-1,4a-dimethyl-8-nitro-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate (2c), (1R,4aS)-methyl-7-((E)-(4-(dimethylamino)phenyl)diazenyl)-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate (3a), (1R,4aS)-methyl-7-((E)-(2-hydroxynaphthalen-1-yl)diazenyl)-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate (3b), (1R,4aS)-methyl-7-((E)-(4-(dimethylamino)phenyl)diazenyl)-1,4a-dimethyl-9-oxo-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate (5a), (1R,4aS)-methyl-7-((E)-(2-hydroxynaphthalen-1-yl)diazenyl)-1,4a-dimethyl-9-oxo-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate (5b) and (1R,4aS)-methyl 6-bromo-7-((E)-(2-hydroxynaphthalen-1-yl)diazenyl)-1,4a-dimethyl-9-oxo-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate (5c) were characterized by MNR, IR and elemental analysis. The yields were 57%, 33%, 30%, 36%, 39%, 39%, 40% and 38%, respectively. Comparing with methyl dehydroabietate, their UV maximum absorption wavelength were 420, 454, 457, 541, 493, 549, 482 and 550 nm in chloroform, which were increased 200, 234, 237, 321, 273, 329, 262 and 330 nm, respectively.

Key words: rosin, azo compounds, UV absorption

CLC Number: