Prunasin
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| General | ||||||||||||||||
| Surname | Prunasin | |||||||||||||||
| other names |
D -mandelonitrile-β- D -glucoside |
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| Molecular formula | C 14 H 17 NO 6 | |||||||||||||||
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| Molar mass | 295.29 g mol −1 | |||||||||||||||
| Physical state |
firmly |
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| Melting point |
157 ° C |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||
Prunasin is a chemical compound from the group of cyanogenic glycosides . The stereoisomer L -configured on the nitrile is called sambunigrin , the racemate with this compound is called prulaurasin .
Occurrence
Prunasin occurs naturally in the kernels of various types of prunus , for example the cherry laurel (Prunus laurocerasus). It has also been detected in almonds, the unripe fruits of Passiflora species and the leaves of Perilla (Perilla frutescens var. Acuta).
In addition to the seeds, it can also occur in all other parts of the rose family. When isolated therefrom, racemization easily takes place, so that the prulaurasin is obtained in its place. It has also been found in many other plants such as Myrtaceae, Polypodiaceae, Saxifragaceae and Scrophulariaceae.
properties
Prunasin is a solid. It has a rotation of −29.6 ° in water. Prunasin beta-glucosidase is an enzyme that converts prunasin and water to D- glucose and mandelonitrile . Amygdalin-beta-glucosidase is an enzyme that converts ( R ) -amygdalin and water to prunasin and D- glucose.
See also
Individual evidence
- ↑ a b c d e data sheet Prunasin, ≥90% (LC / MS-ELSD) from Sigma-Aldrich , accessed on June 25, 2017 ( PDF ).
- ↑ Entry on prunasin in the Human Metabolome Database (HMDB) , accessed on June 25, 2017.
- ^ R. Sanchez-Perez, FS Belmonte, J. Borch, F. Dicenta, BL Moller, K. Jorgensen: Prunasin Hydrolases during Fruit Development in Sweet and Bitter Almonds. In: PLANT PHYSIOLOGY. 158, 2012, p. 1916, doi : 10.1104 / pp.111.192021 .
- ↑ R. Hegnauer: Chemotaxonomie der Pflanzen An overview of the distribution and the systematic importance of plant substances . Springer-Verlag, 2013, ISBN 978-3-0348-9379-4 , pp. 87 ( limited preview in Google Book search).
- ↑ Richard F. Keeler, Anthony T. Tu: Handbook of Natural Toxins . CRC Press, 1983, ISBN 978-0-8247-1893-0 , pp. 127 ( limited preview in Google Book search).
- ↑ Entry on cyanogenic glycosides. In: Römpp Online . Georg Thieme Verlag, accessed on June 25, 2017.
- ^ Emil Lehnartz: Introduction to Chemical Physiology . Springer-Verlag, 2013, ISBN 978-3-662-36817-6 , pp. 267 ( limited preview in Google Book search).