Phytofluene
Phytofluene is a colorless carotenoid found naturally in tomatoes and other vegetables. It is the second product of carotenoid biosynthesis.[2] It is formed from phytoene in a desaturation reaction leading to the formation of five conjugated double bonds. In the following step, addition of carbon-carbon conjugated double bonds leads to the formation of z-carotene and appearance of visible color.
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| IUPAC name
(6E,10E,12E,14E,16Z,18E,22E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta- 2,6,10,12,14,16,18,22,26,30-decaene | |
| Other names
15-cis-Phytofluene 15-cis-7,8,11,12,7',8'-Hexahydro-Ψ,Ψ-carotene | |
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CompTox Dashboard (EPA) |
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| Properties | |
| C40H62 | |
| Molar mass | 542.936 g·mol−1 |
| Appearance | Viscous orange oil |
| Boiling point | 140 to 185 °C (284 to 365 °F; 413 to 458 K) at 0.0001 mmHg |
| Insoluble | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Phytofluene has an absorption spectra in the UVA range, with maximal absorption at 348 nm and with ε1% of 1557.
Analysis of several fruits and vegetables showed that phytoene and phytofluene are found in majority of fruits and vegetables.[3] In contrast to all other carotenoids, phytoene and phytofluene, the first carotenoid precursors in the biosynthetic pathway of other carotenoids absorb light in the UV range.
Dietary phytoene and phytofluene are accumulated in human skin. The accumulation of these carotenoids may protect the skin by several mechanisms: acting as UV absorbers, as antioxidants, as anti-inflammatory agents.[4][5]
References
- Merck Index, 11th Edition, 7361.
- Tomato Metabolite Database, Cornell University
- Khachik, F., G.R. Beecher, M.B. Goli, and W.R. Lusby (1991). "Separation, identification, and quantification of carotenoids in fruits, vegetables and human plasma by high performance liquid chromatography". Pure Appl. Chem. 63 (1): 71–80. doi:10.1351/pac199163010071.CS1 maint: multiple names: authors list (link)
- Aust, W. Stahl, H. Sies, H. Tronnier, U. Heinrich (2005). "Supplementation with tomato-based products increases lycopene, phytofluene, and phytoene levels in human serum and protects against UV-light-induced erythema". Int J Vitam Nutr Res. 75 (1): 54–60. doi:10.1024/0300-9831.75.1.54. PMID 15830922.CS1 maint: multiple names: authors list (link)
- B. B. Fuller; D. R. Smith; A. J. Howerton; D. Kern (2006). "Anti-inflammatory effects of CoQ10 and colorless carotenoids". J. Cos. Derm. 5 (1): 30–38. doi:10.1111/j.1473-2165.2006.00220.x. PMID 17173569.