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Neoxanthin

Names

[ CAS No. ]:
14660-91-4

[ Name ]:
Neoxanthin

[Synonym ]:
(3S,3'S,5R,5'R,6'S)-6,7-Didehydro-5,5',6,6'-tetrahydro-5',6'-epoxy-β,β-carotene-3,3',5-triol
all-trans-neoxanthin
β,β-Carotene-3,3',5-triol, 6,7-didehydro-5',6'-epoxy-5,5',6,6'-tetrahydro-, (3S,3'S,5R,5'R,6'S)-
(3S,5R,6R,3'S,5'R,6'S)-6,7-didehydro-5',6'-epoxy-5,6,5',6'-tetrahydro-β,β-carotene-3,5,3'-triol
β,β-Carotene, 6,7-didehydro-5',6'-epoxy-5,5',6,6'-tetrahydro-3,3',5-trihydroxy-, (3S,3'S,5R,5'R,6R,6'S,9'-cis)-
cis-Neoxanthin
9'-cis-Neoxanthin
Neoxanthin

Biological Activity

[Description]:

Neoxanthin is a major xanthophyll carotenoid and a precursor of the plant hormone abscisic acid in dark green leafy vegetables. Neoxanthin is a potent antioxidant and light-harvesting pigment. Neoxanthin induces apoptosis and has anticancer actions[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

[In Vitro]

Neoxanthin (20 μM; 72 h) treatment significantly reduces cell viability to 10.9% for PC-3 cells, 15.0% for DU 145 cells, and nearly zero for LNCaP cells, respectively[1]. Neoxanthin strongly inhibits cell growth by suppressing DNA synthesis in C3H10T1/2 cells[1]. In photosynthetic organisms, Neoxanthin is the essential component of both the photosystem I (PSI) and photosystem II (PSII) reaction centers of oxygenic photosynthetic apparatus[2].

[In Vivo]

The gastrointestinal metabolism of Neoxanthin in mice is investigated. Two hours after the oral administration of Neoxanthin (40 nmol/mouse), Neoxanthin is found in the plasma and livers of mice. The concentrations of Neoxanthin is 13.6-9.0 nM in plasma, and 7.3 3.6 pmol/g in liver, respectively. (R/S)-Neochrome is also found in the small intestinal contents of Neoxanthin-administered mice[3].

[References]

[1]. E Kotake-Nara, et al. Carotenoids Affect Proliferation of Human Prostate Cancer Cells. J Nutr. 2001 Dec;131(12):3303-6.

[2]. Ramesh Kumar Saini, et al. An Efficient One-Step Scheme for the Purification of Major Xanthophyll Carotenoids From Lettuce, and Assessment of Their Comparative Anticancer Potential. Food Chem. 2018 Nov 15;266:56-65.

[3]. Akira Asai, et al. An Epoxide-Furanoid Rearrangement of Spinach Neoxanthin Occurs in the Gastrointestinal Tract of Mice and in Vitro: Formation and Cytostatic Activity of Neochrome Stereoisomers. J Nutr. 2004 Sep;134(9):2237-43.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
733.3±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C40H56O4

[ Molecular Weight ]:
600.870

[ Flash Point ]:
397.3±32.9 °C

[ Exact Mass ]:
600.417847

[ PSA ]:
73.22000

[ LogP ]:
8.77

[ Vapour Pressure ]:
0.0±5.4 mmHg at 25°C

[ Index of Refraction ]:
1.573

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Related Compounds