Zeaxanthin dipalmitate

Names

[ CAS No. ]:
144-67-2

[ Name ]:
Zeaxanthin dipalmitate

[Synonym ]:
Physalien
(-)-Di-O-palmitoyl-all-trans-zeaxanthin
(3R,3R')-b,b-Carotene-3,3'-diyl Dipalmitate
[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-Tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl]bis(1R)-3,5,5-trimethyl-3-cyclohexene-4,1-diyl dihexadecanoate
MFCD00198033
physalin
[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-Tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaen-1,18-diyl]bis(1R)-3,5,5-trimethyl-3-cyclohexen-4,1-diyldihexadecanoat
zeaxanthin dipalmitate
zeaxanthin-C16:0,C16:0
EINECS 205-635-9
Hexadecanoic acid, (3R,3'R)-β,β-carotene-3,3'-diyl ester
Dihexadécanoate de (3R,3'R)-β,β-carotene-3,3'-diyle
Dihexadécanoate de [(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tétraméthyl-1,3,5,7,9,11,13,15,17-octadécanonaène-1,18-diyl]bis(1R)-3,5,5-triméthyl-3-cyclohexène-4,1-diyle
(3R,3'R)-b,b-Carotene-3,3'-diol Dipalmitate
(3R,3'R)-3,3'-Bispalmitoyloxy-b,b-carotene
(-)-all-trans-Physalien
(3R,3'R)-β,β-Carotin-3,3'-diyldihexadecanoat
(3R,3'R)-β,β-Carotene-3,3'-diyl dihexadecanoate
(3R,3'R)-zeaxanthin bispalmitate

Biological Activity

[Description]:

Zeaxanthin dipalmitate (Physalien) is a wolfberry-derived carotenoid, has anti-inflammatory and anti-oxidative stress effects. Zeaxanthin dipalmitate directly interact with p2X7 receptor (Kd=81.2 nM) and adiponectin receptor 1 (AdipoR1; Kd=533 nM) in a positive dose-dependent manner. Zeaxanthin dipalmitate restores mitochondrial autophagy functions suppressed by ethanol intoxication. Zeaxanthin dipalmitate can be used in the research of alcoholic fatty liver disease (AFLD) and retinitis pigmentosa (RP)[1][2].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Adiponectin Receptor

Signaling Pathways >> Autophagy >> Autophagy

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Membrane Transporter/Ion Channel >> P2X Receptor

[Target]

p2X7/AdipoR1 receptor[1]

[In Vitro]

Zeaxanthin dipalmitate (1 µM; 2 h) totally or partially reverses the down-regulation of Atg5, beclin-1, and LC3A/B by ethanol (250 mM), and the up-regulation of p62 by ethanol in BRL-3A cells[1]. Zeaxanthin dipalmitate (1 µM; 2 h) partially recovers the ethanol-suppressed LC3B in BRL-3A cells[1]. Zeaxanthin dipalmitate (1 µM; 2 h) partially recovers the ethanol-suppressed cell viability and ethanol-induced aspase-3/7 activity of BRL-3A cells[1]. Zeaxanthin dipalmitate (1 µM; 2 h) recovers the ethanol-induced inhibition of mitophagy in BRL-3A cells[1].

[In Vivo]

Zeaxanthin dipalmitate (10 mg/kg; p.o.; daily for 2 weeks) reduces the serum ALT and AST levels increased by long-term ethanol challenge in at AFLD Model[1]. Zeaxanthin dipalmitate (10 mg/kg; p.o.; daily for 2 weeks) effectively attenuates the histological injury[1]. Zeaxanthin dipalmitate (10 mg/kg; p.o.; daily for 2 weeks) attenuates the AFLD-induced hepatic apoptosis (reveal by caspase-3/7 activity) and inflammation (TNF-α) in rat[1]. Zeaxanthin dipalmitate (approximately 4 μM; intravitreal injection for once) improves the visual behavior of rd10 mice and delays the degeneration of retinal photoreceptors[2]. Zeaxanthin dipalmitate (approximately 4 μM; intravitreal injection for once) improves the light responses of photoreceptors, bipolar cells and retinal ganglion cells[2]. Zeaxanthin dipalmitate (approximately 4 μM; intravitreal injection for once) reduces the expression of genes that are involved in inflammation, apoptosis and oxidative stress in rd10 mice[2].

[References]

[1]. Gao H, et al. Wolfberry-Derived Zeaxanthin Dipalmitate Attenuates Ethanol-Induced Hepatic Damage. Mol Nutr Food Res. 2019 Jun;63(11):e1801339.

[2]. Liu F, et al. Wolfberry-derived zeaxanthin dipalmitate delays retinal degeneration in a mouse model of retinitis pigmentosa through modulating STAT3, CCL2 and MAPK pathways. J Neurochem. 2021 Sep;158(5):1131-1150.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
956.4±65.0 °C at 760 mmHg

[ Melting Point ]:
98-100 °C

[ Molecular Formula ]:
C₇₂H₁₁₆O₄

[ Molecular Weight ]:
1045.689

[ Flash Point ]:
462.1±32.7 °C

[ Exact Mass ]:
1044.887329

[ PSA ]:
52.60000

[ LogP ]:
28.33

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.524

Related Compounds

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