Homarine

Homarine^[1]
Names
	Preferred IUPAC name 1-Methylpyridin-1-ium-2-carboxylate
	Other names N-methyl picolinic acid betaine, Betaine homarine
Identifiers
CAS Number	445-30-7;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:69061;
ChemSpider	3494;
PubChem CID	3620;
UNII	KQ3VHX1490;
CompTox Dashboard (EPA)	DTXSID10196201 ;
	InChI InChI=1S/C7H7NO2/c1-8-5-3-2-4-6(8)7(9)10/h2-5H,1H3 Key: BRTLKRNVNFIOPJ-UHFFFAOYSA-N;
	SMILES C[N+]1=CC=CC=C1C(=O)[O-];
Properties
Chemical formula	C7H7NO2
Molar mass	137.138 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

Homarine (N-methyl picolinic acid betaine) is an organic compound with the chemical formula C₇H₇NO₂.^[2] It is commonly found in aquatic organisms from phytoplankton to crustaceans, although it is not found in vertebrates.^[3]^[4]

Biological function

Homarine functions as an osmolyte by affecting the ionic strength of the cytosol and thereby maintaining osmotic pressure within the cell.^[5]

Homarine may also act as a methyl group donor in the biosynthesis of various other N-methylated chemicals, such as glycine betaine and choline. The process of methyl donation converts homarine into picolinic acid and is reversible.^[6]

Etymology

The name of this chemical comes from the initial discovery of the molecule in 1933 in lobster tissue:^[4] the word homarine as an adjective means "of, or relating to, lobsters" (i.e. genus Homarus).

References

^ "Homarine". pubchem.ncbi.nlm.nih.gov. Retrieved 1 October 2020.
^ Hoppe-Seyler, F. A. (January 1933). "Über das Homarin, eine bisher unbekannte tierische Base". Hoppe-Seyler's Zeitschrift für physiologische Chemie. 222 (3–4): 105–115. doi:10.1515/bchm2.1933.222.3-4.105.
^ Dickson, D. M. J.; Kirst, G. O. (August 1987). "Osmotic Adjustment in Marine Eukaryotic Algae: The Role of Inorganic Ions, Quaternary Ammonium, Tertiary Sulphonium and Carbohydrate Solutes. I. Diatoms and a Rhodophyte". New Phytologist. 106 (4): 645–655. doi:10.1111/j.1469-8137.1987.tb00165.x.
^ ^a ^b Gasteiger, E. L.; Haake, P. C.; Gergen, J. A. (15 December 2006). "An Investigation of the Distribution and Function of Homarine (N-Methyl Picolinic Acid)". Annals of the New York Academy of Sciences. 90 (3): 622–636. doi:10.1111/j.1749-6632.1960.tb26410.x. PMID 13703887.
^ Gebser, Björn; Pohnert, Georg (17 June 2013). "Synchronized Regulation of Different Zwitterionic Metabolites in the Osmoadaption of Phytoplankton". Marine Drugs. 11 (6): 2168–2182. doi:10.3390/md11062168. PMC 3721227. PMID 23774888.
^ Netherton, James; Gurin, Samuel (1982). "Biosynthesis and Physiological Role of Homarine in Marine Shrimp". Journal of Biological Chemistry. 257 (20): 11971–11975. PMID 7118923. Retrieved 1 October 2020.

[1] "Homarine". pubchem.ncbi.nlm.nih.gov. Retrieved 1 October 2020.

[2] Hoppe-Seyler, F. A. (January 1933). "Über das Homarin, eine bisher unbekannte tierische Base". Hoppe-Seyler's Zeitschrift für physiologische Chemie. 222 (3–4): 105–115. doi:10.1515/bchm2.1933.222.3-4.105.

[3] Dickson, D. M. J.; Kirst, G. O. (August 1987). "Osmotic Adjustment in Marine Eukaryotic Algae: The Role of Inorganic Ions, Quaternary Ammonium, Tertiary Sulphonium and Carbohydrate Solutes. I. Diatoms and a Rhodophyte". New Phytologist. 106 (4): 645–655. doi:10.1111/j.1469-8137.1987.tb00165.x.

[Gasteiger1960-4] Gasteiger, E. L.; Haake, P. C.; Gergen, J. A. (15 December 2006). "An Investigation of the Distribution and Function of Homarine (N-Methyl Picolinic Acid)". Annals of the New York Academy of Sciences. 90 (3): 622–636. doi:10.1111/j.1749-6632.1960.tb26410.x. PMID 13703887.

[5] Gebser, Björn; Pohnert, Georg (17 June 2013). "Synchronized Regulation of Different Zwitterionic Metabolites in the Osmoadaption of Phytoplankton". Marine Drugs. 11 (6): 2168–2182. doi:10.3390/md11062168. PMC 3721227. PMID 23774888.

[Netherton1982-6] Netherton, James; Gurin, Samuel (1982). "Biosynthesis and Physiological Role of Homarine in Marine Shrimp". Journal of Biological Chemistry. 257 (20): 11971–11975. PMID 7118923. Retrieved 1 October 2020.

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