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 ;
3D model (JSmol)	Interactive image;
ChemSpider	4444659;
PubChem CID	5282217;
UNII	KK8M5T48AI ;
	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	600.884 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

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.

all-trans Neoxanthin

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.

[1] 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.

[2] 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.

[3] 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.

[4] 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.

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