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Cited in 1 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Zeaxanthin dipalmitate (Physalien) is a wolfberry-derived carotenoid, has anti-inflammatory and anti-oxidative stress effects. Zeaxanthin dipalmitate directly interact with p2X7 receptor ( K d =81.2 nM) and adiponectin receptor 1 ( AdipoR1 ; K d =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)
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. Zeaxanthin dipalmitate (1 µM; 2 h) partially recovers the ethanol-suppressed LC3B in BRL-3A cells. Zeaxanthin dipalmitate (1 µM; 2 h) partially recovers the ethanol-suppressed cell viability and ethanol-induced aspase-3/7 activity of BRL-3A cells. Zeaxanthin dipalmitate (1 µM; 2 h) recovers the ethanol-induced inhibition of mitophagy in BRL-3A cells. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
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 . Zeaxanthin dipalmitate (10 mg/kg; p.o.; daily for 2 weeks) effectively attenuates the histological injury . 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 . Zeaxanthin dipalmitate (approximately 4 μM; intravitreal injection for once) improves the visual behavior of rd10 mice and delays the degeneration of retinal photoreceptors. Zeaxanthin dipalmitate (approximately 4 μM; intravitreal injection for once) improves the light responses of photoreceptors, bipolar cells and retinal ganglion cells. 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. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Form:Solid
IC50& Target:p2X7/AdipoR1 receptor
| Canonical Smiles | CCCCCCCCCCCCCCCC(=O)OC1CC(=C(C(C1)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2=C(CC(CC2(C)C)OC(=O)CCCCCCCCCCCCCCC)C)C)C)C |
|---|---|
| IUPAC Name | [(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hexadecanoyloxy-2,6,6-trimethylcyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethylcyclohex-3-en-1-yl] hexadecanoate |
| InChIKey | XACHQDDXHDTRLX-XLVVAOPESA-N |
| INCHI | 1S/C72H116O4/c1-13-15-17-19-21-23-25-27-29-31-33-35-37-49-69(73)75-65-55-63(7)67(71(9,10)57-65)53-51-61(5)47-41-45-59(3)43-39-40-44-60(4)46-42-48-62(6)52-54-68-64(8)56-66(58-72(68,11)12)76-70(74)50-38-36-34-32-30-28-26-24-22-20-18-16-14-2/h39-48,51-54,65-66H,13-38,49-50,55-58H2,1-12H3/b40-39+,45-41+,46-42+,53-51+,54-52+,59-43+,60-44+,61-47+,62-48+/t65-,66-/m1/s1 |
| Isomeric SMILES | CCCCCCCCCCCCCCCC(=O)O[C@H]1CC(C(=C(C1)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C2=C(C[C@H](CC2(C)C)OC(=O)CCCCCCCCCCCCCCC)C)\C)\C)/C)/C)(C)C |
| Alternate CAS | 144-67-2 |
| PubChem CID | 5281250 |
| MeSH Entry Terms | zeaxanthin dipalmitate |
| Molecular Weight | 1045.69 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Prenol lipids |
| Subclass | Tetraterpenoids |
| Intermediate Tree Nodes | Carotenoids |
| Direct Parent | Xanthophylls |
| Alternative Parents | Fatty acid esters Dicarboxylic acids and derivatives Carboxylic acid esters Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aliphatic homomonocyclic compounds |
| Substituents | Xanthophyll - Fatty acid ester - Fatty acyl - Dicarboxylic acid or derivatives - Carboxylic acid ester - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. |
| External Descriptors | C40 isoprenoids (tetraterpenes) |
| Molecular Weight | 1045.700 g/mol |
|---|---|
| XLogP3 | 26.700 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 42 |
| Exact Mass | 1044.89 Da |
| Monoisotopic Mass | 1044.89 Da |
| Topological Polar Surface Area | 52.600 Ų |
| Heavy Atom Count | 76 |
| Formal Charge | 0 |
| Complexity | 1850.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 9 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 9 |
| Covalently-Bonded Unit Count | 1 |
| 1. Irma Belinda Yossa Nzeuwa, Baofu Guo, Ting Zhang, Liya Wang, Qian Ji, Hui Xia, Guiju Sun. (2019) Comparative Metabolic Profiling of Lycium Fruits (Lycium barbarum and Lycium chinense) from Different Areas in China and from Nepal. JOURNAL OF FOOD QUALITY, [PMID:] [10.1155/2019/4396027] |