neoxanthin

{{Chembox

| ImageFile = Neoxanthin2.svg

| ImageSize = 250px

| IUPACName = (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

| OtherNames = Foliaxanthin; Neoxanthine

|Section1={{Chembox Identifiers

| CASNo = 14660-91-4

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = KK8M5T48AI

| PubChem = 5282217

| ChemSpiderID = 4444659

| 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

| 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

}}

|Section2={{Chembox Properties

| C=40 | H=56 | O=4

| Appearance =

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|Section3={{Chembox Hazards

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File:Neoxanthin.svg

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{{cite journal | doi = 10.1046/j.1432-1327.2000.01722.x | title = Identification of neoxanthin synthase as a carotenoid cyclase paralog | year = 2000 | last1 = Bouvier | first1 = Florence | last2 = D'harlingue | first2 = Alain | last3 = Backhaus | first3 = Ralph A. | last4 = Kumagai | first4 = Monto H. | last5 = Camara | first5 = Bilal | journal = European Journal of Biochemistry | volume = 267 | issue = 21 | pages = 6346–6352 | pmid = 11029576| doi-access = free }} is still to be confirmed. Two different genes were confirmed to be implied in violaxanthin conversion to neoxanthin in Arabidopsis and tomato.{{cite journal | doi = 10.1111/j.1365-313X.2007.03094.x | title = The Arabidopsis ABA-deficient mutant aba4 demonstrates that the major route for stress-induced ABA accumulation is via neoxanthin isomers | year = 2007 | last1 = North | first1 = Helen M. | last2 = de Almeida | first2 = Aurélie | last3 = Boutin | first3 = Jean-Pierre | last4 = Frey | first4 = Anne | last5 = To | first5 = Alexandra | last6 = Botran | first6 = Lucy | last7 = Sotta | first7 = Bruno | last8 = Marion-Poll | first8 = Annie | journal = Plant Journal | volume = 50 | issue = 5 | pages = 810–824 | pmid = 17470058| doi-access = free }}{{cite journal | doi = 10.1111/tpj.12451 | title = The tomato mutation nxd1 reveals a gene necessary for neoxanthin biosynthesis and demonstrates that violaxanthin is a sufficient precursor for abscisic acid biosynthesis | year = 2014 | last1 = Neuman | first1 = Hadar | last2 = Galpaz | first2 = Navot | last3 = Cunningham Jr | first3 = Francis X. | last4 = Zamir | first4 = Dani | last5 = Hirschberg | first5 = Joseph | journal = Plant Journal | volume = 78 | issue = 1 | pages = 80–93 | pmid = 24506237| doi-access = }} It has a specific role in protection against photooxidative stress.{{cite journal | doi = 10.1105/tpc.106.049114 | title = The Arabidopsis aba4-1 mutant reveals a specific function for neoxanthin in protection against photooxidative stress | year = 2007 | last1 = Dall'osto | first1 = Luca | last2 = Cazzaniga | first2 = Stefano | last3 = North | first3 = Helen | last4 = Marion-Poll | first4 = Annie | last5 = Bassi | first5 = Roberto | journal = Plant Cell| volume = 19 | issue = 3 | pages = 1048–1064 | pmid = 17351115 | pmc=1867355}} It is a major xanthophyll found in green leafy vegetables such as spinach.

References