Neoxanthin

Neoxanthin
Names

IUPAC name (1R,3S)-6-((R,3E,5E,7E,9E,11E,13E,15Z,17E)-18-((1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-ylidene)-1,5,5-trimethylcyclohexane-1,3-diol
Other names Foliaxanthin; Neoxanthine
Identifiers
CAS Number	14660-91-4^Y
3D model (Jmol)	Interactive image
ChemSpider	4444659
PubChem	5282217
InChI InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-22-35-36(5,6)25-33(41)27-38(35,9)43)15-11-12-16-30(2)18-14-20-32(4)23-24-40-37(7,8)26-34(42)28-39(40,10)44-40/h11-21,23-24,33-34,41-43H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,24-23+,29-15+,30-16+,31-19+,32-20-/t22-,33-,34-,38+,39+,40-/m0/s1
SMILES CC(/C=C/[C@@]12[C@@](O2)(C)C[C@@H](O)CC1(C)C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C([H])=[C@@]=C3C(C)(C)C[C@H](O)C[C@]3(O)C
Properties
Chemical formula	C₄₀H₅₆O₄
Molar mass	600.88 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

all-trans Neoxanthin

Neoxanthin is a carotenoid and xanthophyll. In plants, it is an intermediate in the biosynthesis of the plant hormone abscisic acid. It is often present in two forms: all-trans and 9-cis isomers. It is produced from violaxanthin, but a suspected neoxanthin synthase ^[1] is still to be confirmed. Two different genes were confirmed to be implied in violaxanthin conversion to neoxanthin in Arabidopsis and tomato.,^[2]^[3] It has a specific role in protection against photooxidative stress.^[4] It is a major xanthophyll found in green leafy vegetables such as spinach.

References

↑ Bouvier, Florence; D'harlingue, Alain; Backhaus, Ralph A.; Kumagai, Monto H.; Camara, Bilal (2000). "Identification of neoxanthin synthase as a carotenoid cyclase paralog". European Journal of Biochemistry. 267 (21): 6346–6352. doi:10.1046/j.1432-1327.2000.01722.x. PMID 11029576.
↑ North, Helen M.; de Almeida, Aurélie; Boutin, Jean-Pierre; Frey, Anne; To, Alexandra; Botran, Lucy; Sotta, Bruno; Marion-Poll, Annie (2007). "The Arabidopsis ABA-deficient mutant aba4 demonstrates that the major route for stress-induced ABA accumulation is via neoxanthin isomers". Plant Journal. 50 (5): 810–824. doi:10.1111/j.1365-313X.2007.03094.x. PMID 17470058.
↑ Neuman, Hadar; Galpaz, Navot; Cunningham Jr, Francis X.; Zamir, Dani; Hirschberg, Joseph (2014). "The tomato mutation nxd1 reveals a gene necessary for neoxanthin biosynthesis and demonstrates that violaxanthin is a sufficient precursor for abscisic acid biosynthesis". Plant Journal. 78 (1): 80–93. doi:10.1111/tpj.12451. PMID 24506237.
↑ Dall'osto, Luca; Cazzaniga, Stefano; North, Helen; Marion-Poll, Annie; Bassi, Roberto (2007). "The Arabidopsis aba4-1 mutant reveals a specific function for neoxanthin in protection against photooxidative stress". Plant Cell. 19 (3): 1048–1064. doi:10.1105/tpc.106.049114. PMC 1867355. PMID 17351115.

Carotenoids

Carotenes (C₄₀)	α-Carotene β-Carotene γ-Carotene δ-Carotene ε-Carotene ζ-Carotene Lycopene Neurosporene Phytoene Phytofluene Torulene Lycopersene

Xanthophylls (C₄₀)	Antheraxanthin Astaxanthin Canthaxanthin Citranaxanthin Cryptoxanthin Diadinoxanthin Diatoxanthin Dinoxanthin Echinenone Flavoxanthin Fucoxanthin Lutein Neoxanthin Rhodoxanthin Rubixanthin Violaxanthin Zeaxanthin

Apocarotenoids (C_<40)	Abscisic acid Apocarotenal Bixin Crocetin Food orange 7 Ionones Peridinin

Vitamin A retinoids (C₂₀)	Retinal Retinoic acid Retinol

Retinoid drugs	Acitretin Alitretinoin Bexarotene Etretinate Fenretinide Isotretinoin Tazarotene Temarotene Tretinoin Zuretinol acetate

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