Jump to content
 







Main menu
   


Navigation  



Main page
Contents
Current events
Random article
About Wikipedia
Contact us
Donate
 




Contribute  



Help
Learn to edit
Community portal
Recent changes
Upload file
 








Search  

































Create account

Log in
 









Create account
 Log in
 




Pages for logged out editors learn more  



Contributions
Talk
 



















Contents

   



(Top)
 


1 Biological function  





2 Etymology  





3 References  














Homarine







Add links
 









Article
Talk
 

















Read
Edit
View history
 








Tools
   


Actions  



Read
Edit
View history
 




General  



What links here
Related changes
Upload file
Special pages
Permanent link
Page information
Cite this page
Get shortened URL
Download QR code
Wikidata item
 




Print/export  



Download as PDF
Printable version
 
















Appearance
   

 






From Wikipedia, the free encyclopedia
 


Homarine[1]
Names
Preferred IUPAC name

1-Methylpyridin-1-ium-2-carboxylate

Other names

N-methyl picolinic acid betaine, Betaine homarine

Identifiers

CAS Number

3D model (JSmol)

ChEBI
ChemSpider

PubChem CID

UNII

CompTox Dashboard (EPA)

  • InChI=1S/C7H7NO2/c1-8-5-3-2-4-6(8)7(9)10/h2-5H,1H3

    Key: BRTLKRNVNFIOPJ-UHFFFAOYSA-N

  • 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 phytoplanktontocrustaceans, although it is not found in vertebrates.[3][4]

Biological function

[edit]

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

[edit]

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

[edit]
  1. ^ "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.

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Homarine&oldid=1188059894"

    Categories: 
    Solutions
    Biosynthesis
    Physiology articles about cellular physiology
    Diffusion
    Methylation
    Hidden categories: 
    Articles without InChI source
    Articles without KEGG source
    Articles containing unverified chemical infoboxes
    Articles with short description
    Short description matches Wikidata
     



    This page was last edited on 3 December 2023, at 02:55 (UTC).

    Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.



    Privacy policy

    About Wikipedia

    Disclaimers

    Contact Wikipedia

    Code of Conduct

    Developers

    Statistics

    Cookie statement

    Mobile view



    Wikimedia Foundation
    Powered by MediaWiki