14660-91-4

Basic information

• Product Name: NEOXANTHIN
• Synonyms: NEOXANTHIN;(1R,3S)-6-[(3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenylidene]-1,5,5-trimethyl-cyclohexane-1,3-diol;NEOXANTHIN(SH);(3S,3'S,5R,5'R,6R,6'S,9'Z)-6,7-Didehydro-5',6'-epoxy-5,5',6,6'-tetrahydro-β,β-caroten-3,3',5-triol;(3S,3'S,5R,5'R,6R,6'S,9'Z)-6,7-Didehydro-5',6'-epoxy-5,5',6,6'-tetrahydro-β,β-carotene-3,3',5-triol;(3S,3'S,5R,5'R,6S,6'R,9Z)-5,6-Epoxy-6',7'-didehydro-5,6,5',6'-tetrahydro-β,β-carotene-3,3',5'-triol;cis-Neoxanthin;9'-cis-Neoxanthin
• CAS NO: 14660-91-4
• Molecular Formula: C₄₀H₅₆O₄
• Molecular Weight: 602.89
• Mol File: 14660-91-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 733.3 °C at 760 mmHg
• Flash Point: 397.3 °C
• Appearance: /
• Density: 1.06 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.573
• Storage Temp.: -20°C
• PKA: 14.65±0.60(Predicted)
• CAS DataBase Reference: NEOXANTHIN(CAS DataBase Reference)
• NIST Chemistry Reference: NEOXANTHIN(14660-91-4)
• EPA Substance Registry System: NEOXANTHIN(14660-91-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 14660-91-4(Hazardous Substances Data)

Usage

Description

Neoxanthin is an allenic xanthophyll, a type of carotenoid pigment, and serves as a precursor to the plant hormone abscisic acid. It is formed as the final product of carotenoid synthesis in green plants and is characterized by having all trans geometry in its double bonds.

Uses

Used in Analytical Chemistry:
NEOXANTHIN is used as a reference standard for the determination of the analyte in fruits. This application utilizes high-performance liquid chromatography (HPLC) coupled with a diode array detector (DAD) and mass spectrometry (MS) to accurately measure and identify the presence of NEOXANTHIN in various samples.
Used in Plant Biology and Agriculture:
NEOXANTHIN, being a precursor to the plant hormone abscisic acid, plays a crucial role in plant growth and development. It is used in research and development within the fields of plant biology and agriculture to study the effects of carotenoid synthesis on plant health, stress responses, and overall plant productivity.
Used in Food Industry:
NEOXANTHIN, due to its presence in fruits and its role in plant hormone synthesis, can be used in the food industry for enhancing the nutritional value, color, and flavor of various products. Additionally, it can be employed in the development of natural colorants and additives for the food industry, contributing to healthier and more appealing food options.

Biochem/physiol Actions

Neoxanthin is a carotenoid and intermediate in the synthesis of abscisic acid from violaxanthin. Neoxanthin is found in apple and a constituent of paprika, lucerne, orange, and other species and has been shown to exhibit apoptotic and anti-proliferative functions.

InChI:InChI=1/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

Upstream product

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

Downstream Products

• 144-68-3 zeaxanthin 
• 63915-07-1 6-epineoflor 
• 63915-07-1 neoflor 
• 122203-82-1 <2R-<1R*(E),2α,4β>>-5-(2,4-Dihydroxy-2,6,6-trimethylcyclohexylidene)-3-methylpenta-2,4-dienal 
• 133602-07-0 (all-E)-(3S,5R,6R)-3,5-dihydroxy-6,7-didehydro-5,6-dihydro-12'-apo-β-caroten-12'-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 
• 62713-23-9 9'-cis-5',6'-epoxy-3'-hydroxy-5',6'-dihydro-12-apo-β-caroten-12-al 
• 133602-08-1 3,5-dihydroxy-6,7-didehydro-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 
• 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 
• 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 
• 10153-97-6 (15E,9'Z)-neoxanthin 
• 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 

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.