Spermine

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Spermine
Skeletal formula of spermine
Ball and stick model of spermine
Spacefill model of spermine
Identifiers
CAS number 71-44-3 YesY
PubChem 1103
ChemSpider 1072 N
EC number 200-754-2
UN number 3259
DrugBank DB00127
KEGG C00750 N
MeSH Spermine
ChEBI CHEBI:15746 N
ChEMBL CHEMBL23194 N
IUPHAR ligand 710
RTECS number EJ7175000
Beilstein Reference 1750791
Gmelin Reference 454653
3DMet B01325
Jmol-3D images Image 1
Properties
Molecular formula C10H26N4
Molar mass 202.34 g mol−1
Appearance Colourless crystals
Odor Ichtyal, ammoniacal
Density 937 mg mL−1
Melting point 28 to 30 °C (82 to 86 °F; 301 to 303 K)
Boiling point 150.1 °C; 302.1 °F; 423.2 K at 700 Pa
log P −0.543
Hazards
GHS pictograms The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
GHS hazard statements H314
GHS precautionary statements P280, P305+351+338, P310
EU classification Corrosive C
R-phrases R34
S-phrases S26, S36/37/39, S45
Flash point 110 °C (230 °F; 383 K)
Related compounds
Related compounds Spermidine, Putrescine, Cadaverine, Diethylenetriamine
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Spermine is a polyamine involved in cellular metabolism found in all eukaryotic cells. Formed from spermidine, it is found in a wide variety of organisms and tissues and is an essential growth factor in some bacteria. It is found as a polycation at physiological pH. Spermine is associated with nucleic acids and is thought to stabilize helical structure, in particular, in viruses.

Crystals of spermine phosphate were first described in 1678, in human semen, by Anton van Leeuwenhoek.[1] The name spermin was first used by the German chemists Ladenburg and Abel in 1888,[2] and the correct structure of spermine was not finally established until 1926, simultaneously in England (by Dudley, Rosenheim, and Starling)[3] and Germany (by Wrede et al.).[4]

References[edit]

  1. ^ Leeuwenhoek, A. van (1678) Observationes D. Anthonii Leeuwenhoek, de natis e semine genitali animalculis. Letter dated November 1677. Philos. Trans. Roy. Soc. London, 12,1040-1043.
  2. ^ Ladenburg A., Abel J. (1888) Über das Aethylenimin (Spermin?). Ber. Dtsch. chem. Ges. 21: 758-766
  3. ^ Dudley H. W., Rosenheim O., Starling W. W. (1926) The chemical constitution of spermine. III.Structure and synthesis. Biochemical Journal 20(5): 1082-1094
  4. ^ Wrede F. (1925) Über die aus menschlichem Sperma isolierte Base Spermin. Dtsch. Med. Wochenschr. 51: 24

Further reading[edit]

  • Slocum, R. D., Flores, H. E., "Biochemistry and Physiology of Polyamines in Plants", CRC Press, 1991, USA, ISBN 0-8493-6865-0
  • Uriel Bachrach, "The Physiology of Polyamines", CRC Press, 1989, USA, ISBN 0-8493-6808-1