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Phytoene
Phytoene.png
IUPAC name
Other names 15-cis-Phytoene; 7,7',8,8',11,11',12,12'-Octahydro-ψ,ψ-carotene
Identifiers
CAS number 13920-14-4
PubChem 9963391
SMILES
Properties
Molecular formula C40H64
Molar mass 544.94 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Phytoene is an intermediate in the biosynthesis of carotenoids.[1] It is produced from two molecules of geranylgeranyl pyrophosphate (GGPP) by the action of the enzyme phytoene synthase.[2] The two GGPP molecules are condensed together followed by removal of diphosphate and proton shift leading to the formation of phytoene.

Phytoene is a colorless symmetric molecule containing three conjugated double bonds. Phytoene has typical absorption spectra in the UVB range with maximum at 286 nm and with ε1% of 915.

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, are colorless and absorb light in the UV range only. It is important to note that dietary phytoene and phytofluene are accumulated in human skin. The accumulation of these colorless carotenoids can potentially protect the skin by several mechanisms: acting as UV absorbers, as antioxidants, as anti inflammatory.[4][5][6] The distribution of phytoene and phytofluene in human serum, prostate, and skin suggests that phytoene and phytofluene may be responsible for the carotenoid protective effects observed in beauty and skin applications.

Phytoene and phytofluene were initially discovered as a potent and stable substitutes to pigmented carotenoids to protect the skin via oral and mostly topical application. The colorless carotenoids may be beneficial for health protection and nutritional and beauty applications such as protection against UV and oxidative damage. Several articles summarized their protective activities against UV irradiation and free radicals derived from UV, damage to DNA and collagen, anti-inflammatory and the ability to reduce pigmentation. All of which lead to reduction in pre-mature aging and damaged skin resulting in brighter, younger looking and protected skin.[7][8]

References

  1. ^ Carotenoid Biosynthesis
  2. ^ Phytoene synthase
  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.  
  4. ^ L. von Oppen-Bezalel (2009). "Lightening, Boosting and Protecting with Colorless Carotenoids". Cosmetics & Toiletries magazine 124 (3): 66–75.  
  5. ^ L. von Oppen-Bezalel (2007). "UVA, A Main Concern in Sun Damage: Protection from the Inside and Outside with Phytoene, Phytofluene, the Colorless Carotenoids and more". SÖFW-Journal.  
  6. ^ L. von Oppen-Bezalel, A. Shaish "Application of the Colorless Carotenoids, Phytoene, and Phytofluene in Cosmetics, Wellness, Nutrition, and Therapeutics". In The alga Dunaliella: Biodiversity, Physiology, Genomics & Biotechnology Eds. Ami Ben-Amotz, Juergen Polle, and Subba Rao, released May 2009 by Science Publishers, Enfield, NH, USA (2009)
  7. ^ 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.  
  8. ^ 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.  
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