Myrmicacin

Myrmicacin (3-hydroxydecanoic acid) is a chemical compound of the β-hydroxycarboxylic acid class. It is named after the South American leaf-cutter ants (Myrmicinae) in which it was first discovered,[1] but is also found in royal jelly.[2] Myrmicacin is believed to act as a herbicide which prevents seeds collected by the ants from germinating within the nest.[1]

Myrmicacin

Names
Other names 3-Hydroxydecanoic acid; β-Hydroxydecanoic acid; beta-Hydroxydecanoic acid
Identifiers
3D model (JSmol)	Interactive image
ChEBI	CHEBI:84254
ChemSpider	132983
IUPHAR/BPS	5848
MeSH	C017552
PubChem CID	26612
CompTox Dashboard (EPA)	DTXSID40864486
InChI InChI=1S/C10H20O3/c1-2-3-4-5-6-7-9(11)8-10(12)13/h9,11H,2-8H2,1H3,(H,12,13) Key: FYSSBMZUBSBFJL-UHFFFAOYSA-N InChI=1/C10H20O3/c1-2-3-4-5-6-7-9(11)8-10(12)13/h9,11H,2-8H2,1H3,(H,12,13) Key: FYSSBMZUBSBFJL-UHFFFAOYAJ
SMILES CCCCCCCC(CC(=O)O)O
Properties
Chemical formula	C10H20O3
Molar mass	188.267 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

• 3,10-Dihydroxydecanoic acid
• 3,11-Dihydroxydodecanoic acid

References

1. Schildknecht, Hermann; Koob, Knut (1971). "Myrmicacin, The First Insect Herbicide". Angewandte Chemie International Edition in English. 10 (2): 124–125. doi:10.1002/anie.197101241. ISSN 0570-0833. PMID 4995467.
2. Kodai, T; Nakatani, T; Noda, N (2011). "The absolute configurations of hydroxy fatty acids from the royal jelly of honeybees (Apis mellifera)". Lipids. 46 (3): 263–70. doi:10.1007/s11745-010-3497-x. PMID 21082360. S2CID 4039489.