|Molar mass||202.34 g·mol−1|
|Density||937 mg mL−1|
|Melting point||28 °C (82 °F; 301 K)|
|Boiling point||150.1 °C; 302.1 °F; 423.2 K at 700 Pa|
|GHS signal word||DANGER|
|P280, P305+351+338, P310|
|S-phrases||S26, S36/37/39, S45|
|Flash point||110 °C (230 °F; 383 K)|
|Spermidine, Putrescine, Cadaverine, Diethylenetriamine|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
Spermine is a polyamine involved in cellular metabolism found in all eukaryotic cells. The precursor for synthesis of spermine is the amino acid ornithine. 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. The name spermin was first used by the German chemists Ladenburg and Abel in 1888, and the correct structure of spermine was not finally established until 1926, simultaneously in England (by Dudley, Rosenheim, and Starling) and Germany (by Wrede et al.).
- 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.
- Ladenburg A., Abel J. (1888) Über das Aethylenimin (Spermin?). Ber. Dtsch. chem. Ges. 21: 758-766
- Dudley H. W., Rosenheim O., Starling W. W. (1926) The chemical constitution of spermine. III.Structure and synthesis. Biochemical Journal 20(5): 1082-1094
- Wrede F. (1925) Über die aus menschlichem Sperma isolierte Base Spermin. Dtsch. Med. Wochenschr. 51: 24
- Klein, David (2013) Organic Chemistry, 2nd Edition.