Flexirubin
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| Preferred IUPAC name
2-Dodecyl-3-hydroxy-5-methylphenyl (2E,4E,6E,8E,10E,12E,14E,16E)-17-(4-hydroxy-3-methylphenyl)heptadeca-2,4,6,8,10,12,14,16-octaenoate | |
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3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
PubChem CID
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| UNII |
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CompTox Dashboard (EPA)
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| Properties | |
| C43H54O4 | |
| Molar mass | 634.901 g·mol−1 |
| Appearance | Violet-red needles |
| Melting point | 174–176 °C (345–349 °F; 447–449 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Flexirubin is the main pigment in the bacteria genera Flexibacter , Flavobacterium , Chryseobacterium , and Cytophaga .[1] It was isolated for the first time from Flexibacter elegans . Flexirubin is found in these genera, as well as those that produce carotenoids. The pigment mixture of flexirubin and carotenoids imparts colonies with an intense yellow-orange color.[2] Structurally, this bacteria pigment is based on a polycarboxylic-chromophore that is linked with a phenol by an ester, resulting in an alkyl side-chain.[3] [2] The first total synthesis of flexirubin was reported in 1977.[4]
To test for the presence of flexirubin, a cultural strain with a 20% potassium hydroxide solution is created. A color change from gold to red-brown indicates the presence of flexirubin.[1] Alternatively, the pigment can also be extracted with acetone and chromatographic methods can be used to ascertain its presence.[1]
References
[edit ]- ^ a b c Reichenbach, H., W. Kohl, et al. (1980). FLEXIRUBIN-TYPE PIGMENTS IN FLAVOBACTERIUM. Archives of Microbiology 126(3): 291–293.
- ^ a b Hans Achenbach, W. Kohl, et al. (1976). INVESTIGATIONS ON METABOLITES OF MICROORGANISMS .11. FLEXIRUBIN, A NOVEL PIGMENT FROM FLEXIBACTER-ELEGANS. Chemische Berichte-Recueil 109(7): 2490–2502.
- ^ Achenbach, H., W. Kohl, et al. (1974). STRUCTURE OF FLEXIRUBIN. Tetrahedron Letters(30): 2555–2556.
- ^ Achenbach, H. and J. Witzke (1977). TOTAL SYNTHESIS OF FLEXIRUBIN DIMETHYL ETHER. Angewandte Chemie-International Edition in English 16(3): 191–192.