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Ectoine

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Revision as of 18:16, 8 August 2011 by CheMoBot (talk | contribs) (Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Ch)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
Ectoine
Names
IUPAC name (S)-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid
Other names THP(B)
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H10N2O2/c1-4-7-3-2-5(8-4)6(9)10/h5H,2-3H2,1H3,(H,7,8)(H,9,10)/t5-/m0/s1Key: WQXNXVUDBPYKBA-YFKPBYRVSA-N
  • InChI=1/C6H10N2O2/c1-4-7-3-2-5(8-4)6(9)10/h5H,2-3H2,1H3,(H,7,8)(H,9,10)/t5-/m0/s1Key: WQXNXVUDBPYKBA-YFKPBYRVBN
SMILES
  • CC1=NCCC(N1)C(=O)O
  • O=C(O)1N\C(=N/CC1)C
Properties
Chemical formula C6H10N2O2
Molar mass 142.16
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Ectoine (1,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) is a natural compound found in several species of bacteria. It is a compatible solute which serves as a protective substance by acting as an osmolyte and thus helps organisms survive extreme osmotic stress. Ectoine is found in high concentrations in halophilic microorganisms and confers resistance towards salt and temperature stress. Ectoine was first identified in the microorganism Ectothiorhodospira halochloris, but has since been found in a wide range of gram-negative and gram-positive bacteria. Some other species ectoine was found in:

Biosynthesis

Ectoine is synthesized in three successive enzymatic reactions starting from aspartic β-semialdehyde. The genes involved in the biosynthesis are called ectA, ectB and ectC and they encode the enzymes L-2,4-diaminobutyric acid acetyltransferase, L-2,4-diaminobutyric acid transaminase, and L-ectoine synthase respectively.

Use

Ectoine is used as an active ingredient in skin care and sun protection products. It stabilizes proteins and other cellular structures and protects the skin from stresses like UV irradiation and dryness.

References

  1. Ectoine at Sigma-Aldrich


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