130817-80-0Relevant academic research and scientific papers
Synthesis and phytotoxicity evaluation of substituted para-benzoquinones
Lima, Larissa S.,De A. Barbosa, Luiz Claudio,De Alvarenga, Elson S.,Demuner, Antonio J.,Da Silva, Antonio A.
, p. 625 - 630 (2007/10/03)
Sorgoleone (1) is one of the major constituents of sorghum root exudates. Sorgoleone is an allelochemical that reduces the growth of broad-leaf plants. The 3,5-dimethoxybenzylic alcohol (3) was used as starting material for the synthesis of 2-methoxy-6-(non-1-yl)benzo-1,4-quinone(9) in 69% yield. Acetylation of (9) with acetic anhydride gave the triacetate (10) in 82% yield. The triacetate (10) was then converted in two steps in 2-hydroxy-5-methoxy-3-(non-1-yl)benzo-1,4-quinone (11) and 2-acetoxy-5-methoxy-3-(non-1-yl)benzo-1,4-quinone (12) in 8% and 37% yield, respectively. Quinone (11) was obtained also by reaction of (12) with DBU in 63% yield. Alkylation of (3) and oxidation with chromic anhydride formed the new quinones (16) (17) and (18) in 23%, 16% and 12% overall yield, respectively. The effect of these quinones and sorgoleone (1) at concentrations of 5.5 μg g-1 on the development of radicle and aerial parts of Cucumis sativus, Brachiaria decumbens, Hyptis lophanta, and Euphorbia heterophylla was tested.
Synthesis of Side-Chain-Modified Analogues of the Allergen Primin
Koenig, Wilfried A.,Faasch, Holger,Heitsch, Holger,Colberg, Cornelia,Hausen, Bjoern M.
, p. 387 - 393 (2007/10/02)
Benzoquinones such as primin (2-methoxy-6-pentyl-1,4-benzoquinone) from Primula obconica HANCE (Primulaceae) are known to be strong sensitizers and thus the source of severe allergic contact dermatitis (cell-mediated type of allergy).In order to determine
