Spermine
| Spermine | |
|---|---|
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| Identifiers | |
| CAS number | 71-44-3  |
| PubChem | 1103 |
| ChemSpider | 1072  |
| EC number | 200-754-2 |
| UN number | 3259 |
| DrugBank | DB00127 |
| KEGG | C00750 |
| MeSH | Spermine |
| ChEBI | CHEBI:15746 |
| ChEMBL | CHEMBL23194 |
| IUPHAR ligand | 710 |
| RTECS number | EJ7175000 |
| Beilstein Reference | 1750791 |
| Gmelin Reference | 454653 |
| 3DMet | B01325 |
| Jmol-3D images | Image 1 |
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| 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 |  |
| GHS signal word | DANGER |
| GHS hazard statements | H314 |
| GHS precautionary statements | P280, P305+351+338, P310 |
| EU classification |  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 |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| 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
- ↑ 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
Further reading
- 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