42352-86-3Relevant academic research and scientific papers
A value-added use of volatile turpentine: antifungal activity and QSAR study of β-pinene derivatives against three agricultural fungi
Li, Jian,Tian, Xiangrong,Gao, Yanqing,Shang, Shibin,Feng, Juntao,Zhang, Xing
, p. 66947 - 66955 (2015/08/24)
In consideration of turpentine and its analogues possessing some agricultural biological activity, persistent efforts to take advantage of renewable, abundant natural resources have been made. Three series of derivatives from β-pinene were synthesized and their fungicidal activities against Rhizoctonia solani, Fusarium graminearum, and Botrytis cinerea were investigated. Most of the synthesized compounds exhibited moderate to significant fungicidal activity. Among them, the acylthiourea derivatives from β-pinene showed more promising results than the other compounds. It was worth noting that compounds 7b and 7d displayed excellent fungicidal activity against Rhizoctonia solani, with IC50 values of 2.439 and 1.857 μg mL-1, which was close to or even better than the control triadimenol (1.945 μg mL-1, a commercial fungicide). The structure-activity relationship (SAR) analysis indicated that the compounds with more net positive charge possessed better fungicidal activity. The quantitative structure-activity relationship (QSAR) model (R2 = 0.9879, F = 348.41, S2 = 0.0047) was obtained through the best multi-linear regression. The built model revealed a strong correlation of fungicidal activity against Rhizoctonia solani with the molecular features of the title compounds. Additionally, the SAR and QSAR studies showed that the introduction of an electron-withdrawing group, which can increase the positive charge, was favorable towards the fungicidal activity. These encouraging results may provide an alternative, promising use of β-pinene through the design and exploration of eco-friendly fungicides with low toxicity and high efficiency.
Synthesis and antibacterial activity of amide derivatives from dihydrocumic acid
Gao, Yan-Qinga,Shang, Shi-Bin,Wang, Dan,Cui, Yan-Jie
, p. 613 - 619 (2013/08/23)
Dihydrocumic acid was prepared from β-pinene through oxidation and dehydration. Then a series of amide derivatives from dihydrocumic acid were synthesized. Reaction conditions of dihydrocumic acid were discussed and structures of amide derivatives were characterized by IR, 1H NMR, MS, and X-ray diffraction. The antibacterial activities of these newly synthesized amide derivatives against six bacteria were also investigated by an inhibition zone method. It was shown that compounds 5a, 5b, 5d, and 5f display better anti-bacterial activities with inhibition zones 11.83, 12.33, 10.83 and 12.67 mm against Escherichia coli compared with Bromogeramine (9.67 mm), one commercially available antibacterial agent, and compounds 5a and 5d display better anti-bacterial activities against Staphyloccocus aureu compared with Ampicillin Na.
Biotransformation of α-Terpinene in Common Cutworm Larvae (Spodoptera litura Fabricius)
Miyazawa, Mitsuo,Wada, Takashi,Kameoka, Hiromu
, p. 2889 - 2893 (2007/10/03)
α-Terpinene was mixed in an artificial diet at a concentration of 10 mg/g of diet, and the diet was fed to the last instar larvae of common cutworm, Spodoptera litura Fabricius. Metabolites were recovered from frass and analyzed spectroscopically. The α-terpinene was transformed mainly to 4-isopropyl-1,3-cyclohexadienoic acid and cumic acid. The allylic methyl group of α-terpinene was preferentially oxidized. The results indicate that the intestinal bacteria probably participated in the metabolism of α-terpinene. The aerobically active intestinal bacteria transformed α-terpinene to 4-isopropyl-1,3-cyclohexadienemethanol, and the anaerobically active intestinal bacteria transformed α-terpinene to p-cymene.
