Sperm

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Structural formula
Structure of Spermin
General
Surname Sperm
other names
  • N , N '-bis (3-aminopropyl) -1,4-butanediamine
  • 1,12-diamino-4,9-diazadodecane
  • Diaminopropylputreszin
  • Gerontin
  • Musculamine
  • Neuridin
Molecular formula C 10 H 26 N 4
Brief description

hygroscopic crystals

External identifiers / databases
CAS number
  • 71-44-3
  • 403982-64-9 (dihydrate)
EC number 200-754-2
ECHA InfoCard 100,000,686
PubChem 1103
ChemSpider 1072
DrugBank DB00127
Wikidata Q424597
properties
Molar mass 202.34 g mol −1
Physical state

firmly

Melting point

55-60 ° C

boiling point

141–142 ° C (at 66.5 Pa)

solubility

Easily soluble in water and ethanol

safety instructions
GHS labeling of hazardous substances
05 - Corrosive

danger

H and P phrases H: 314
P: 280-305 + 351 + 338-310
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Spermine is a naturally occurring polyamine , which in human sperm occurs and other body fluids and has a characteristic smell and taste. It is involved as a polycation in the cellular metabolism of all eukaryotes in various tissue types (e.g. blockade of the potassium channels during the initiation phase of the action potential ). Technical use is possible due to its property of forming water-soluble complexes with nitrogen monoxide (NO) , which makes the gas easier to handle. It also serves as a starting material for the synthesis of medicinally interesting derivatives.

Extraction

One synthetic route to spermine leads from succinonitrile by reduction to 1,4-diaminobutane , subsequent cyanoethylation with acrylonitrile to the dicyano precursor and subsequent further reduction.

biochemistry

Functionally, spermine has a stabilizing effect on the DNA , especially the sperm. Spermine is formed from methionine via the intermediate stage spermidine . Both spermidine and spermine could also be detected in ribosomes , tRNA and viruses , in this case probably to stabilize the RNA or DNA .

Research history

In 1677 Antoni van Leeuwenhoek first mentioned the occurrence of crystals in sperm and other human body fluids. These were interpreted by Schreiner in 1878 as spermine phosphate. The chemical structure of spermine was elucidated between 1923 and 1927 by Harold Dudley , Otto Rosenheim and F. Wrede; The synthesis also succeeded at this time.

use

In cosmetics, spermine is added to anti-aging products to reduce wrinkles .

See also

literature

  • Alexander Poehl: The physiological-chemical basics of the sperm theory together with clinical material for the therapeutic use of Sperminum Poehl. Hirschwald, Berlin 1896 ( digitized version )

Individual evidence

  1. ↑ a b c d Entry on Spermin. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.
  2. ↑ a b Spermine data sheet at Sigma-Aldrich , accessed on October 17, 2016 ( PDF ).
  3. ↑ Harry P. Schultz: The Preparation of Spermine Tetrahydrochloride1 (1,12-Diamino-4,9-diazadodecane Tetrahydrochloride). In: J. Am. Chem. Soc. 70 (8), 1948, pp. 2666-2667.
  4. ↑ L. Jovine, S. Djordjevic, D. Rhodes: The crystal structure of yeast phenylalanine tRNA at 2.0 angstrom resolution: Cleavage by Mg2 + in 15-year old crystals. In: Journal of Molecular Biology . 301, 2000, pp. 401-414.
  5. ↑ A. van Leeuwenhoek: Observationes D. Anthonii Leeuwenhoek, de natis e semine genitali animalculis. Letter dated November 1677. In: Philos. Trans. Roy. Soc. London. 12, 1678, pp. 1040-1043.
  6. ↑ HW Dudley, O. Rosenheim, WW Starling: The chemical constitution of spermine. III. Structure and synthesis. In: Biochem. J. 20, 1926, pp. 1082-1094. PMID 16743746
  7. ^ F. Wrede: About the base spermine isolated from human sperm. In: Dtsch. Med. Wochenschr. 51, 1925, p. 24.
  8. ↑ Patent WO2005013932 : Use of Spermine and / or Spermidine against skin ageting in dietary, pharmaceutical or cosmetic compositions. Published on July 30, 2004 , Inventors: Fabio Rinaldi, Elisabetta Sorbellini, Sergio Baroni, Anna Benedusi. ‌