10153-97-6

Basic information

• Product Name: (15Z,9'Z)-Neoxanthin
• CAS NO: 10153-97-6
• Molecular Weight: 600.882
• Mol File: 10153-97-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (15Z,9'Z)-Neoxanthin(CAS DataBase Reference)
• NIST Chemistry Reference: (15Z,9'Z)-Neoxanthin(10153-97-6)
• EPA Substance Registry System: (15Z,9'Z)-Neoxanthin(10153-97-6)

Safety Data

• Hazardous Substances Data: 10153-97-6(Hazardous Substances Data)

Upstream product

• 142204-43-1 (9'Z)-15,15'-Didehydroneoxanthin 
• 10153-97-6 (15Z,9'Z)-Neoxanthin 
• 142204-43-1 15,15'-Didehydroneoxanthin 
• 10153-97-6 all-trans-neoxanthin 
• 7553-56-2 iodine 
• 71-43-2 benzene 

Downstream Products

• 10153-97-6 (15E,9'Z)-neoxanthin 
• 10153-97-6 neoxanthin 
• 23726-93-4 Damascenon 
• 63915-07-1 (1S,2S,4S)-1-[(1E,3E,5E,7E,9E,11E,13E,15E)-18-((2R,4S)-2,4-Dihydroxy-2,6,6-trimethyl-cyclohexylidene)-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,6,6-trimethyl-cyclohexane-1,2,4-triol 
• 28874-44-4 (1'S,2'R,4'S,2E,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienal 
• 62713-23-9 9'-cis-5',6'-epoxy-3'-hydroxy-5',6'-dihydro-12-apo-β-caroten-12-al 
• 62777-81-5 5,6-epoxy-3-hydroxy-5,6-dihydro-12'-apo-β-caroten-12'-al 
• 17237-68-2 5,6-epoxy-3-hydroxy-5,6-dihydro-10'-apo-β-caroten-10'-al 
• 62839-95-6 9'-cis-5',6'-epoxy-3'-hydroxy-5',6'-dihydro-10-apo-β-caroten-10-al 
• 8066-07-7 (1'S,2'R,4'S,2Z,4E)-(1',2'-epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-dienal 
• 133602-08-1 3,5-dihydroxy-6,7-didehydro-5,6-dihydro-10'-apo-β-caroten-10'-al 
• 133602-07-0 (all-E)-(3S,5R,6R)-3,5-dihydroxy-6,7-didehydro-5,6-dihydro-12'-apo-β-caroten-12'-al 
• 122203-82-1 <2R-<1R*(E),2α,4β>>-5-(2,4-Dihydroxy-2,6,6-trimethylcyclohexylidene)-3-methylpenta-2,4-dienal 
• 63915-07-1 6-epineoflor 

Relevant articles and documents

(6R,9'Z)-Neoxanthin: Synthesis, physical properties, spectra, and calculations of its conformation in solution

The synthesis of pure and crystalline (9'Z)-neoxanthin (6) is described. MnO2 Oxidation of (9Z)-C15-alcohol 7 at room temperature produces a mixture 8/9 of (9Z)- and (9E)-aldehydes. Predominant formation of the required (9Z)-aldehyde 8 is achieved by performing the oxidation at -10°. Condensation of 8 with the mono-Li salt of the symmetrical C10-diphosphonate 10 gave the (9Z)-C25-monophosphonate 11. The Wittig-Horner condensation of 10 with the allenic C15-aldehyde 1b, under selected conditions allows the preparation of pure and crystalline (9'Z)-15,15'-didehydroneoxanthin (12) and, after subsequent semireduction, of crystalline (15Z,9'Z)-neoxanthin (13). Thermal isomerisation of a AcOEt solution of 13 at 95° yields preferentially (9'Z)-neoxanthin (6). Our crystalline sample shows the highest ε-values in the UV/VIS spectra ever recorded. The CD spectra display a pronounced similarity with those of corresponding violaxanthin isomers. In contrast to the (all-E)-isomer 5, (9'Z)-neoxanthin undergoes very little isomerisation when heated to its melting point. For comparison purposes, a crystalline probe of 6 is also isolated from lawn mowings. Extensive 1H- and 13C-NMR investigations at 600 MHz of a (D6)benzene solution using 2D-experiments such as COSY, TOCSY, ROESY, HMBC, and HMQC techniques permit the unambiguous assignment of all signals. Force-field calculations of a model system of 6 indicate the presence of several interconverting conformers of the violaxanthin end group, 66% of which possess a pseudoequatorial and 34% a pseudoaxial OH-C(3'). The torsion angle (ω1) around the C(6')-C(7') bond, known to be of prime importance for the shape of the CD spectra, varies with values of 87° for 55% and 263° for 45% of the molecules. Therefore, the molecules clearly display a preference for the 'syn'-position of the C(7') = C(8') bond and the epoxy group. Unexpectedly, the double bonds of C(7') = C(8') and C(9') = C(10') are not coplanar. The deviation amounts to ± 20°, both in the 'syn'- and the 'anti'-conformation.