Geranylfarnesol

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Geranylfarnesol
Geranylfarnesol.svg
Names
IUPAC name
(2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaen-1-ol
Other names
  • (E)-geranyl farnesol
  • (E)-neryl farnesol
Identifiers
3D model (JSmol)
ChEBI
PubChem CID
  • InChI=1S/C25H42O/c1-21(2)11-7-12-22(3)13-8-14-23(4)15-9-16-24(5)17-10-18-25(6)19-20-26/h11,13,15,17,19,26H,7-10,12,14,16,18,20H2,1-6H3/b22-13+,23-15+,24-17+,25-19+ X mark.svgN
    Key: YHTCXUSSQJMLQD-GIXZANJISA-N
  • CC(=CCC/C(=C/CC/C(=C/CC/C(=C/CC/C(=C/CO)/C)/C)/C)/C)C
Properties
C25H42O
Molar mass 358.610 g·mol−1
Appearancecolorless 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 their standard state (at 25 °C [77 °F], 100 kPa).

Geranylfarnesol is a naturally occurring irregular, long-chain, acyclic isoprenoid alcohol. This is a C25 compound, positioned between the ubiquitous C15 farnesol and the C30 triterpenoid squalene in the isoprenoid biosynthesis pathway. Its chemical formula is C25H42O. [1] Geranylfarnesol has garnered scientific interest primarily due to its role as a key biosynthetic intermediate and its potent biological activity as an inducer of apoptosis (programmed cell death). [2]

Contents

Structure

The compound is a member of sesterterpenoid group. [3] The chemical structure consists of a linear chain of five isoprene units (C5H8) in a head-to-tail arrangement, terminated by a hydroxyl (—OH) group. It is the C25 homolog of the more common C15 isoprenoid farnesol and the direct precursor to the C30 isoprenoid squalene. The "geranyl" prefix indicates its structural relationship to geraniol (C10) and farnesol (C15).

Natural occurence

The compound was isolated from the wax of the insect Ceroplastes albolineatus via hydrolysis. [4] [5] Geranylfarnesol was also isolated from sponge Fasciospongia fovea [6] and identified in the frontal glands of the termites Reticulitermes santonensis . [7]

Physical properties

Geranylfarnesol forms a colorless, viscous oil. Insoluble in water. [8]

Uses

Geranylfarnesol is known as an inducer of apoptosis 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]

See also

References

  1. ↑ "Geranylfarnesol | Chemical Substance Information | J-GLOBAL". jglobal.jst.go.jp. Retrieved 5 February 2026.
  2. ↑ Ríos, Tirso; C, S. Pérez (1 January 1969). "Geranylfarnesol, a new acyclic C25 isoprenoid alcohol isolated from insect wax". Journal of the Chemical Society D: Chemical Communications (5): 214–215. doi:10.1039/C29690000214. ISSN   0577-6171 . Retrieved 5 February 2026.
  3. ↑ Peters, K. E.; Walters, C. C.; Moldowan, J. M. (2005). The Biomarker Guide. Cambridge University Press. p. 55. ISBN   978-0-521-78158-9 . Retrieved 5 February 2026.
  4. ↑ Morgan, E. David (22 March 2019). Biosynthesis in Insects: Advanced Edition. Royal Society of Chemistry. p. 7-40. ISBN   978-1-78801-822-7 . Retrieved 5 February 2026.
  5. ↑ Reinhold, L.; Harborne, J. B.; Swain, T. (13 October 2016). Progress in Phytochemistry: Volume 4. Elsevier. p. 211. ISBN   978-1-4831-4442-9 . Retrieved 5 February 2026.
  6. ↑ Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Springer Science & Business Media. 6 December 2012. p. 186. ISBN   978-3-7091-8505-6 . Retrieved 5 February 2026.
  7. ↑ Morgan, Eric David (13 July 2004). Biosynthesis in Insects. Royal Society of Chemistry. p. 107. ISBN   978-0-85404-691-1 . Retrieved 5 February 2026.
  8. ↑ "geranyl farnesol, 79577-58-5". thegoodscentscompany.com. Retrieved 5 February 2026.
  9. ↑ Herrmann, Wolfgang; Obeid, Rima (2011). Vitamins in the Prevention of Human Diseases. Walter de Gruyter. p. 546. ISBN   978-3-11-021448-2 . Retrieved 5 February 2026.
  10. ↑ Joo, Joung Hyuck; Jetten, Anton M. (28 January 2010). "Molecular mechanisms involved in farnesol-induced apoptosis". Cancer Letters . 287 (2): 123–135. doi:10.1016/j.canlet.2009.05.015. ISSN   0304-3835 . Retrieved 5 February 2026.
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