Ectoine

Chemical compound From Wikipedia, the free encyclopedia

Ectoine (3,4,5,6-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.[3] Furthermore it was shown to protect DNA against ionizing and ultraviolet radiation serving as a radical scavenger.[4] 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,[5][6] but has since been found in a wide range of Gram-negative and Gram-positive bacteria. Other species of bacteria in which ectoine was found include:

Quick facts Names, Identifiers ...
Ectoine[1]
Names
Preferred IUPAC name
(4S)-2-Methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid
Other names
  • Ectoine sodium salt monohydrate
  • THP(B)
  • RonaCare
  • Pyrostatin B
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • 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/s1 checkY
    Key: WQXNXVUDBPYKBA-YFKPBYRVSA-N checkY
  • 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/s1
    Key: WQXNXVUDBPYKBA-YFKPBYRVBN
  • CC1=NCCC(N1)C(=O)O
  • O=C(O)[C@H]1N\C(=N/CC1)C
Properties
C6H10N2O2
Molar mass 142.158 g·mol−1
Appearance White powder
Density 1.568 g/cm3
Soluble in water
Hazards
NFPA 704 (fire diamond)
[2]
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[8][7]

Use in cosmetics

Ectoine is used as an active ingredient in skin care and sun protection products.[13] It stabilizes proteins and other cellular structures and protects the skin from stresses like UV irradiation and dryness.[7][14][15]

Medical use

Due to its protein stabilizing properties, ectoine has been evaluated as a topical treatment for hay fever. Effectiveness of a nasal spray containing ectoine is comparable to cromoglycate and is reported to be well tolerated by the patients.[16] It is available over the counter in the European Union.

References

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