1973415-50-7

Basic information

• Product Name: (2RS)-Lotaustralin
• Synonyms: (2RS)-Lotaustralin
• CAS NO: 1973415-50-7
• Molecular Formula: C11H19NO6
• Molecular Weight: 261.27
• Mol File: 1973415-50-7.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2RS)-Lotaustralin(CAS DataBase Reference)
• NIST Chemistry Reference: (2RS)-Lotaustralin(1973415-50-7)
• EPA Substance Registry System: (2RS)-Lotaustralin(1973415-50-7)

Safety Data

• Hazardous Substances Data: 1973415-50-7(Hazardous Substances Data)

Usage

General Description

(2RS)-Lotaustralin is a naturally occurring cyanogenic glycoside found in the seeds and leaves of various plant species such as Lotus corniculatus and L. alpinus. It is a toxic compound that can release hydrogen cyanide when metabolized by certain enzymes in the body. (2RS)-Lotaustralin acts as a defense mechanism for the plant against herbivores by deterring consumption. It is known to have a bitter taste, which likely contributes to its deterrent effect. Ingestion of (2RS)-Lotaustralin can cause symptoms of cyanide poisoning in humans and animals, including nausea, headache, dizziness, and potentially life-threatening effects if consumed in large quantities. Due to its toxicity, precautions should be taken when handling or consuming plants containing this chemical.

Upstream product

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

Relevant articles and documents

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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.