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松脂中树脂酸的酸异构分离与枞酸分子结构(英文) 被引量:4

Acid Isomer Separation of Resin Acids in Rosin and Abietic Acid Molecular Structure
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摘要 松脂中枞酸型树脂酸在酸的作用下经过异构反应、结晶分离得到99.15%高纯度(-)-(4R,10R,9S,5R)-7,13-二烯-18-枞酸,得率74.2%。通过MS,1HNMR,13CNMR,IR光谱分析和单晶X-光衍射研究确证其化合物分子结构,其单晶X-光衍射测试数据与湿地松松香和马尾松松香直接经过重结晶分离得到枞酸样品的结果一致,都为单斜晶系,P21空间群,分子绝对构型和天然枞酸构型一样。在枞酸晶体结构中2个枞酸分子的羧基生成氢键连接是得到高纯度结晶的主要原因。 The (-)-(4R,10R,9S,5R)-7,13-abietadien-18-oic acid with 99. 15% high purity was prepared in 74. 2% yield by a isomerization,crystallization separation method with the acid as catalyst. Its structure was determined by MS, 1 HNMR,13CNMR,IR spectral methods and single-crystal X-ray diffraction analysis. The data of abietic acid by single- crystal X-ray diffraction analysis was in accordance with that having obtained from Pinus elliottii rosin and Pinus massoniana rosin directly. Crystals are monoclinic,space group P21 and their absolute configuation from rearrangement are the same as natural abietic acid. In the crystal structure of abietic acid,the carboxyls of two abietic acid molecules generated hydrogen bonds,which is the main reason for high purity crystal.
出处 《林业科学》 EI CAS CSCD 北大核心 2010年第8期140-144,共5页 Scientia Silvae Sinicae
基金 Supported by national significant industry and technology special projects ( high-tech development and reform commission [2008]No. 2441) the president of Chinese Academy of Forestry foundation (CAFYBB2008009) the 948 program of the State Forestry Administration (2009 - 4 - 55)
关键词 枞酸 异构化反应 单晶X-光衍射 结构 松脂 abietic acid isomerization single-crystal X-ray diffraction structure pine gum
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参考文献16

  • 1Chuang H S, Lin C H. 2004. Use of abietic acid or derivative thereof for modulation permeability of plasma membrane. US,7015248.
  • 2Fernandez M A, Tornos M P, Garcia M D. 2001. Anti-inflammatory activity of abietic acid, a diterpene isolated from Pimenta racemosa var. grissea. Journal of Pharmacy and Pharmacology, 53 (6) : 867 - 872.
  • 3韩春蕊,宋湛谦,商士斌.提纯枞酸的新方法[J].林产化学与工业,2007,27(4):42-46. 被引量:17
  • 4Harris G C,Sanderson T F. 1948. Resin acids I. An improved method of method of isolation of resin acids: the isolation of a new abietic-type acid,neoabietic acid. Journal American Chemical Society, 70:334 -339.
  • 5Hrobonova K, lehotay J, Skacani I. 2005. HPLC determiuation and MS identification of dehydroabietie acid and abietic acid in propolis. Journal of Liquid Chromatography & Related Technologies, 28:1725 - 1735.
  • 6Jin Z M,Pan Y J,Liu J G. 2000. Separation of rosin acids by molecular recognition: crystal structure of the complex of neoabietic acid with 2-amino-6. Methyl-pyridine. Journal of Chemical Crystal lography,30 (3) : 195 - 198.
  • 7Legrouyellec A. 1985. Use of abietic acid as a film-forming product to be used on wounds and bums. FR 8400611A.
  • 8LiuHongjun(刘红军),ZhouYonghong(周永红).2008. A preparation method of abietic acid. CN,101219949A.
  • 9Okada K, Takekuma S. 1994. Crystal structure and conformational analysis of 7, 13-abietadien-18 oic acid. Bull Chem Soc Jpn, 67(3) : 807 -815.
  • 10Shulman M. 1976. Methods of treating burns using colophony containing preparations. US 3943248.

二级参考文献14

  • 1Matsubara Y,J Japan Oil Chem,1990年,499页
  • 2程芝.天然树脂生产工艺学[M].北京:中国林业出版社,1995:70.
  • 3LIN C H,CHUANG H S.Use of abietic acid and derivatives thereof for inhibiting cancer:US,7015248[P].2006-01-01.
  • 4IMAMURA P M,DOS S C.Synthesis of an oidiolactone analogue from abietic acid[J].Synth Commun,2005,35 (15):2057-2065.
  • 5KHLEBNIKOVA T B,KARPYSHEV N N,TOLSTIKOVA O V,et al.Synthesis of new chiral phosphorous-and nitrogen-containing ligands from resin acids[J].Chirality,2004,16:S40-S50.
  • 6GIGANTE B,SANTOS C,SILVA A M,et al.Catechols from abietic acid-synthesis and evaluation as bioactive compounds[J].Bioorganic and Medicinal Chemistry,2003,11(8):1631-1638.
  • 7ALVAREZ E J,CHAHBOUN R,GUARDIA J J,et al.New route to 15-hydroxydehydroabietic acid derivatives:application to the first synthesis of some bioactive abietane and nor-abietane type terpenoids[J].Tetrahedron Letters,2006,47(15):2577-2580.
  • 8ALVAREZ E J,CHAHBOUN R,BENTALEB F,et al.First enantiospecific synthesis of antileishmanial 12-deoxyroyleanone from abietic acid[J].Synlett,2004,15:2701-2704.
  • 9PRESSER A,POTSCHGER I,HASLINGER E,et al.Synthetic transformations of abietic acid ⅴ:structure modification and ozonization[J].Monatshefte fur Chemie,2002,133:231-239.
  • 10KOICHI M,TAKESHI I,HIROKAZU N,et al.Regio-and stereo-selective hydroxylation of abietic acid derivatives by Mucor circinelloides and Mortierella isabellina[J].Biotechnology Letters,2005,27(17):1305-1310.

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