Phytoene (/ˈfaɪtoʊiːn/) is a 40-carbon intermediate in the biosynthesis of carotenoids.[1] The synthesis of phytoene is the first committed step in the synthesis of carotenoids in plants. Phytoene 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.
Dietary phytoene and phytofluene are found in a number of human tissues including the liver, lung, breast, prostate, colon, and skin.[3] Accumulation of these carotenoids in the skin may protect the skin by several mechanisms: acting as UV absorbers, as antioxidants, and as anti-inflammatory agents.[4][5]
Phytoene is a symmetric molecule containing three conjugated double bonds. Phytoene has a UV-Vis absorption spectrum typical for a triply conjugated system with its main absorption maximum in the UVB range at 286 nm and with ε1% of 915.[clarification needed][citation needed]
Sourcesedit
Analysis of several fruits and vegetables showed that phytoene and phytofluene are found in majority of fruits and vegetables.[6] 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.
Historyedit
The structure of phytoene was established and proven by total synthesis, by the Basil Weedon group in 1966.[7]
Referencesedit
^. Archived from the original on 2016-11-05. Retrieved 2009-02-25.
^Khachik, Frederick; Carvalho, Lorena; Bernstein, Paul S.; Muir, Garth J.; Zhao, Da-You; Katz, Nikita B. (November 2002). "Chemistry, Distribution, and Metabolism of Tomato Carotenoids and Their Impact on Human Health". Experimental Biology and Medicine. 227 (10): 845–851. doi:10.1177/153537020222701002. ISSN 1535-3702. PMID 12424324. S2CID 22671223.
^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.{{cite journal}}: 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". Journal of Cosmetic Dermatology. 5 (1): 30–38. doi:10.1111/j.1473-2165.2006.00220.x. PMID 17173569. S2CID 9407768.
^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 Appl. Chem. 63 (1): 71–80. doi:10.1351/pac199163010071. S2CID 36564853.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^J. B. Davis; L. M. Jackman; P. T. Siddons; B. C. L. Weedon (1966). "Carotenoids and related compounds. XV. The structure and synthesis of phytoene, phytofluene, zeta-carotene, and neurosporene". J. Chem. Soc. C: 2154–2165. doi:10.1039/J39660002154.
7.Book chapter: Liki von Oppen-Bezalel, Aviv 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)
January 01, 1970
phytoene, carbon, intermediate, biosynthesis, carotenoids, synthesis, phytoene, first, committed, step, synthesis, carotenoids, plants, produced, from, molecules, geranylgeranyl, pyrophosphate, ggpp, action, enzyme, phytoene, synthase, ggpp, molecules, condens. Phytoene ˈ f aɪ t oʊ iː n is a 40 carbon intermediate in the biosynthesis of carotenoids 1 The synthesis of phytoene is the first committed step in the synthesis of carotenoids in plants Phytoene 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 Names IUPAC name 15 cis 7 8 11 12 7 8 11 12 Octahydro ps ps carotene Systematic IUPAC name 6E 10E 14E 16Z 18E 22E 26E 2 6 10 14 19 23 27 31 Octamethyldotriaconta 2 6 10 14 16 18 22 26 30 nonaene Other names 15 cis Phytoene Identifiers CAS Number 13920 14 4 Y 3D model JSmol Interactive image ChEBI CHEBI 27787 N ChemSpider 8138988 N KEGG C05421 N PubChem CID 9963391 UNII 876K2ZK1OF N CompTox Dashboard EPA DTXSID10433340 InChI InChI 1S C40H64 c1 33 2 19 13 23 37 7 27 17 31 39 9 29 15 25 35 5 21 11 12 22 36 6 26 16 30 40 10 32 18 28 38 8 24 14 20 34 3 4 h11 12 19 22 27 30H 13 18 23 26 31 32H2 1 10H3 b12 11 35 21 36 22 37 27 38 28 39 29 40 30 NKey YVLPJIGOMTXXLP BHLJUDRVSA N N SMILES CC CCC C C CC C C CC C C C C C C C CC C C C CC C C C CCC C C C C C C C Properties Chemical formula C 40H 64 Molar mass 544 952 g mol 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Dietary phytoene and phytofluene are found in a number of human tissues including the liver lung breast prostate colon and skin 3 Accumulation of these carotenoids in the skin may protect the skin by several mechanisms acting as UV absorbers as antioxidants and as anti inflammatory agents 4 5 Contents 1 Structure 2 Sources 3 History 4 ReferencesStructure editPhytoene is a symmetric molecule containing three conjugated double bonds Phytoene has a UV Vis absorption spectrum typical for a triply conjugated system with its main absorption maximum in the UVB range at 286 nm and with e1 of 915 clarification needed citation needed Sources editAnalysis of several fruits and vegetables showed that phytoene and phytofluene are found in majority of fruits and vegetables 6 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 History editThe structure of phytoene was established and proven by total synthesis by the Basil Weedon group in 1966 7 References edit Carotenoid Biosynthesis Archived from the original on 2016 11 05 Retrieved 2009 02 25 Phytoene synthase Khachik Frederick Carvalho Lorena Bernstein Paul S Muir Garth J Zhao Da You Katz Nikita B November 2002 Chemistry Distribution and Metabolism of Tomato Carotenoids and Their Impact on Human Health Experimental Biology and Medicine 227 10 845 851 doi 10 1177 153537020222701002 ISSN 1535 3702 PMID 12424324 S2CID 22671223 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 a href Template Cite journal html title Template Cite journal cite journal a 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 Journal of Cosmetic Dermatology 5 1 30 38 doi 10 1111 j 1473 2165 2006 00220 x PMID 17173569 S2CID 9407768 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 Appl Chem 63 1 71 80 doi 10 1351 pac199163010071 S2CID 36564853 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link J B Davis L M Jackman P T Siddons B C L Weedon 1966 Carotenoids and related compounds XV The structure and synthesis of phytoene phytofluene zeta carotene and neurosporene J Chem Soc C 2154 2165 doi 10 1039 J39660002154 7 Book chapter Liki von Oppen Bezalel Aviv Shaish Application of the Colorless Carotenoids Phytoene and Phytofluene in Cosmetics Wellness Nutrition and Therapeutics In The alga Dunaliella Biodiversity Physiology Genomics amp Biotechnology Eds Ami Ben Amotz Juergen Polle and Subba Rao released May 2009 by Science Publishers Enfield NH USA 2009 Retrieved from https en wikipedia org w index php title Phytoene amp oldid 1191713134, wikipedia, wiki, book, books, library,
