Spermine

• N, N'- bis (3- aminopropyl ) -1,4- butanediamine
• 1,12- diamino-4 ,9- diazadodekan
• Diaminopropylputreszin
• Gerontin
• Musculamin
• Neuridin

• 71-44-3
• 403982-64-9 (dihydrate )

Hygroscopic crystals

Fixed

55-60 ° C

141-142 ° C ( 66.5 Pa)

Slightly soluble in water and ethanol

Risk

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Spermine is a naturally occurring polyamine, which is present in human semen and other body fluids and has a characteristic odor and taste. It is as polycation in the cellular metabolism of all eukaryotes involved in various tissue types (eg: blockade of potassium channels during the initiation phase of the action potential ). A technical use is possible due to his capacity, with nitric oxide ( NO) to form water- soluble complexes, whereby the gas is easier to handle. It also serves as a starting material for the synthesis of medicinally significant derivatives.

Extraction

A synthetic route to the spermine leads of succinonitrile by reduction to 1,4-diaminobutane, followed by cyanoethylation with acrylonitrile and subsequent to Dicyanovorläufer still times reduction.

Biochemistry

Functionally acts spermine stabilizing effect on the DNA, in particular the sperm. Made is spermine from methionine via the intermediate spermidine. Both spermidine and spermine could also be detected in ribosomes, tRNA and in viruses, in this case probably to stabilize the RNA or DNA.

History of Research

Antoni van Leeuwenhoek in 1677 mentioned for the first time the presence of crystals in the sperm, and other body fluids of man. These were interpreted in 1878 by Schreiner as Sperminphosphat. The chemical structure of spermine was elucidated 1923-1927 by Dudley, Rosenheim and Wrede; During this time, the synthesis.

Use

In cosmetics, spermine is added in anti -aging products for wrinkle reduction.