 | |
| Names | |
|---|---|
| IUPAC name (2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaen-1-ol | |
Other names
| |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider | |
| |
| |
| Properties | |
| C25H42O | |
| Molar mass | 358.610 g·mol−1 |
| Appearance | colorless oil |
| Density | 0.9±0.1 g/cm3 |
| Melting point | °C |
| Boiling point | 464 to 466 °C |
| insoluble | |
| Hazards | |
| Flash point | 278 °F |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Geranylfarnesol is a naturally occurring irregular, long-chain, acyclicisoprenoid alcohol. This is aC25 compound, positioned between the ubiquitousC15farnesol and theC30 triterpenoidsqualene in the isoprenoid biosynthesis pathway. Its chemical formula isC25H42O.[1] Geranylfarnesol has garnered scientific interest primarily due to its role as a key biosynthetic intermediate and its potent biological activity as an inducer ofapoptosis (programmed cell death).[2]
The compound is a member ofsesterterpenoid group.[3] The chemical structure consists of a linear chain of fiveisoprene units (C5H8) in a head-to-tail arrangement, terminated by a hydroxyl (—OH) group. It is theC25 homolog of the more commonC15 isoprenoidfarnesol and the direct precursor to theC30 isoprenoidsqualene. The "geranyl" prefix indicates its structural relationship togeraniol (C10) andfarnesol (C15).
The compound was isolated from the wax of the insectCeroplastes albolineatus via hydrolysis.[4][5] Geranylfarnesol was also isolated from spongeFasciospongia fovea[6] and identified in the frontal glands of the termitesReticulitermes santonensis.[7]
Geranylfarnesol forms a colorless, viscous oil. Insoluble in water.[8]
Geranylfarnesol is known as an inducer ofapoptosis in mammalian cells, often exhibiting greater potency than its shorter-chain relative, farnesol.[9] It appears to trigger the mitochondrial (intrinsic) pathway of apoptosis.[10]
