Structure Database (LMSD)

Common Name
9Z-Pentacosene
Systematic Name
9Z-Pentacosene
Synonyms
LM ID
LMFA11000114
Formula
C25H50
Exact Mass
Calculate m/z
350.391251
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Hydrocarbons [FA11]

Biological Context

9(Z)-Pentacosene is a cuticular hydrocarbon and insect sex hormone.1,2,3 It is found in the cuticle of female F. canicularis flies and is an attractant to males in a trap assay.1 9(Z)-Pentacosene is a contact sex hormone in scarab beetles and locust borers that is more abundant in females than males.2,3 It elicits arrestment, alignment, and mounting by males of both species in mating assays but only elicits copulation by the locust borer. 9(Z)-Pentacosene is also produced by the orchid O. exaltata and by C. cunicularius, a pollinator of O. exaltata.4

This information has been provided by Cayman Chemical

References

1. Mant, J., Brändli, C., Vereecken, N.J., et al. Cuticular hydrocarbons as sex pheromone of the bee Colletes cunicularius and the key to its mimicry by the sexually deceptive orchid, Ophrys exaltata. J. Chem. Ecol. 31(8), 1765-1787 (2005).
2. Ginzel, M.D., Millar, J.G., and Hanks, L.M. (Z)-9-Pentacosene - contact sex pheromone of the locust borer, Megacyllene robinbe. Chemoecology 13, 135-141 (2003).
3. Fombong, A.T., Teal, P.E., Arbogast, R.T., et al. Chemical communication in the honey bee scarab pest Oplostomus haroldi: Role of (Z)-9-pentacosene. J. Chem. Ecol. 38(12), 1463-1473 (2012).
4. Uebel, E.C., Schwarz, M., Sonnet, P.E., et al. Evaluation of the mating stimulant pheromones of Fannia canicularis, F. pusio, and F. femoralis as attractants. Fla. Entomol. 61(3), 139-143 (1978).

References

Comments
Pherobase Semiochemicals

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Cephus cinctus (#211228)
Insecta (#50557)
Cuticular hydrocarbons and novel alkenediol iacetates from wheat stem sawfly (Cephus cinctus): natural oxidation to pheromone components.,
J Chem Ecol, 2002
Pubmed ID: 11925075
Ophrys sphegodes subsp. sphegodes (#443042)
Magnoliopsida (#3398)
Cuticular hydrocarbons as sex pheromone of the bee Colletes cunicularius and the key to its mimicry by the sexually deceptive orchid, Ophrys exaltata.,
J Chem Ecol, 2005
Pubmed ID: 16222807

String Representations

InChiKey (Click to copy)
YJTCMKZGFBOKQS-ZPHPHTNESA-N
InChi (Click to copy)
InChI=1S/C25H50/c1-3-5-7-9-11-13-15-17-19-21-23-25-24-22-20-18-16-14-12-10-8-6-4-2/h17,19H,3-16,18,20-25H2,1-2H3/b19-17-
SMILES (Click to copy)
CCCCCCCC/C=C\CCCCCCCCCCCCCCC

Other Databases

PubChem CID
14159395
Cayman ID
9002807

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 0
Aromatic Rings 0
Rotatable Bonds 21
Van der Waals Molecular Volume 438.42
Topological Polar Surface Area 0.00
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 0
logP 9.77
Molar Refractivity 117.45

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Created at
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Updated at
21st Nov 2025