Myrmicacin

Myrmicacin
Names
	IUPAC name 3-hydroxydecanoic acid
	Other names 3-Hydroxydecanoic acid; β-Hydroxydecanoic acid; beta-Hydroxydecanoic acid
Identifiers
CAS Number	14292-26-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:132983 ;
ChEMBL	ChEMBL4448230;
ChemSpider	24790;
IUPHAR/BPS	5848;
MeSH	C017552
PubChem CID	26612;
UNII	IGH24U4AMF ;
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

Myrmicacin, also known as 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, but is also found in royal jelly. Myrmicacin is believed to act as a herbicide which prevents seeds collected by the ants from germinating within the nest. It is known to act as a GPR84 agonist.

References

1 2 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.
↑ 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.
↑ Peters A, Rabe P, Krumbholz P, Kalwa H, Kraft R, Schöneberg T, Stäubert C (February 2020). "Natural biased signaling of hydroxycarboxylic acid receptor 3 and G protein-coupled receptor 84". Cell Commun Signal. 18 (1) 31. doi:10.1186/s12964-020-0516-2. PMC 7045412. PMID 32102673. HCA3 is activated by both, 3HO and 3HDec [5]. 3HDec is also an agonist at GPR84 [7]. Although the role of MCFAs (C10 – C14), specifically decanoic acid (C10), as endogenous agonists at GPR84 is disputed [24], recent work supports their relevance as major endogenous ligands [8, 9].

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[SchildknechtKoob1971-1] 1 2 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.

[PetersRabeKrumbholz2020-3] Peters A, Rabe P, Krumbholz P, Kalwa H, Kraft R, Schöneberg T, Stäubert C (February 2020). "Natural biased signaling of hydroxycarboxylic acid receptor 3 and G protein-coupled receptor 84". Cell Commun Signal. 18 (1) 31. doi:10.1186/s12964-020-0516-2. PMC 7045412. PMID 32102673. HCA3 is activated by both, 3HO and 3HDec [5]. 3HDec is also an agonist at GPR84 [7]. Although the role of MCFAs (C10 – C14), specifically decanoic acid (C10), as endogenous agonists at GPR84 is disputed [24], recent work supports their relevance as major endogenous ligands [8, 9].

Myrmicacin

See also

References