Phytofluene

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Phytofluene[1]
Skeletal formula
Ball-and-stick model
Identifiers
CAS number 27664-65-9 YesY
PubChem 6857557
ChEBI CHEBI:35165 N
Jmol-3D images Image 1
Properties
Molecular formula C40H62
Molar mass 542.92 g mol−1
Appearance Viscous orange oil
Boiling point 140-185 °C at 0.0001 mmHg
Solubility in water Insoluble
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Phytofluene is a carotenoid pigment with an orange color 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.

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.[citation needed] 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[edit]

  1. ^ Merck Index, 11th Edition, 7361.
  2. ^ Tomato Metabolite Database, Cornell University
  3. ^ Khachik, F., G.R. Beecher, M.B. Goli, and W.R. Lusby (1991). "Separation, identifi cation, and quantification of carotenoids in fruits, vegetables and human plasma by high performance liquid chromatography". Pure & App. Chemistry 63 (1): 71–80. doi:10.1351/pac199163010071. 
  4. ^ 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. 
  5. ^ 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.