Ectoine

Ectoine^[1]

Names
IUPAC name (S)-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid
Other names THP(B)
Identifiers
CAS Number	96702-03-3 Y
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:27592 Y
ChemSpider	112069 Y
KEGG	C06231 Y
PubChem	126041
UNII	7GXZ3858RY Y
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/s1 Y Key: WQXNXVUDBPYKBA-YFKPBYRVSA-N Y 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
SMILES CC1=NCCC(N1)C(=O)O O=C(O)[C@H]1N\C(=N/CC1)C
Properties
Chemical formula	C6H10N2O2
Molar mass	142.16 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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,^[2][3] but has since been found in a wide range of Gram-negative and Gram-positive bacteria. Other species of ectoine were found in

• Brevibacterium linens^[3]
• Halomonas elongata^[2][4]
• Marinococcus halophilus^[5]
• Pseudomonas stutzeri^[4]

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.^[5][4]

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.^[4]

References