1973415-50-7

Usage

Uses

Due to the provided materials, there are no specific applications listed for (2RS)-Lotaustralin. However, it is important to note that its primary function is as a natural defense mechanism in plants against herbivores. The toxicity of (2RS)-Lotaustralin makes it unsuitable for direct use in most industries, and its presence in plants should be considered a caution for human and animal consumption.

Upstream product

• 72229-42-6 neolinustatin 
• 25570-03-0 (+)-(S)-2-methylbutane nitrile 

Relevant academic research and scientific papers

Linustatin and Neolinustatin: Cyanogenic Glycosides of Linseed Meal That Protect Animals against Selenium Toxicity

Two new cyanogenic glycosides - linustatin (1a) and neolinustatin (1b) - have been isolated from linseed meal.These glycosides are responsible for linseed's unique property of protecting animals against the toxic effects of ingested selenium.This investigation demonstrates the facility with which glycosidic structures can be elucidated by 13C NMR spectroscopy.

Biosynthesis of cyanohydrin glucosides from unnatural nitriles in intact tissue of Passiflora morifolia and Turnera angustifolia

Passiflora morifolia, which under natural conditions contains cyanohydrin glucosides linamarin, lotaustralin and epilotaustralin, converted cyclopentanecarbonitrile, 2-cyclopentenecarbonitrile and 3- methylbutanenitrile into the corresponding cyanohydrin glucosides. Turnera angustifolia, which normally produces glucosides of cyclopentenone cyanohydrin, converted cyclopentanecarbonitrile, 2-methylpropanenitrile and 2-methylbutanenitrile, but not 3-methylbutanenitrile, into the corresponding cyanohydrin glucosides. Mixtures of epimers were produced when these glucosides contained chiral cyanohydrin carbon atoms. Feeding with cyclopentanecarbonitrile resulted in formation of 1-(β-D- glucopyranosyloxy)cyclopentanecarbonitrile, a saturated analogue of deidaclin and tetraphyllin A. Neither plant utilized cyclopropanecarbonitrile as substrate. The experiments demonstrate broad substrate specificity of nitrile hydroxylases present in these plants. A novel glycoside, 2-[6-O-(β-D- xylopyranosyl)-β-D-glucopyranosyloxy]propane (isopropyl primeveroside), was isolated from P. morifolia. The compound represents a rare example of natural isopropyl glycoside; its characterization included assignment of all 1H and (13C) NMR signals of the primeverosyl group using two-dimensional NMR methods. Biosynthesis of the isopropyl moiety of the primeveroside is unclear, but the formation of alcohols corresponding to natural cyanohydrins may be a previously unrecognized extension of the cyanohydrin biosynthesis pathway in higher plants.