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Zeaxanthin dipalmitate (Physalien)

Cat No.:V35102 Purity: ≥98%
Zeaxanthin dipalmitate (Physalien) is a wolfberry-derived carotenoid with anti-inflammatory and antioxidant stress effects.
Zeaxanthin dipalmitate (Physalien)
Zeaxanthin dipalmitate (Physalien) Chemical Structure CAS No.: 144-67-2
Product category: Autophagy
This product is for research use only, not for human use. We do not sell to patients.
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1mg
5mg
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Product Description
Zeaxanthin dipalmitate (Physalien) is a wolfberry-derived carotenoid with anti-inflammatory and antioxidant stress effects. Zeaxanthin dipalmitate interacts directly with p2X7 receptor (Kd=81.2 nM) and adiponectin receptor 1 (AdipoR1; Kd=533 nM) in a positive dose-dependent manner. Zeaxanthin dipalmitate restores mitophagy (autophagy) function inhibited by ethanol intoxication. Zeaxanthin dipalmitate may be utilized in the study of alcoholic fatty liver disease (AFLD) and retinitis pigmentosa (RP).
Zeaxanthin dipalmitate (Physalien) (CAS#: 144-67-2) is a diester of zeaxanthin with palmitic acid. It is a carotenoid pigment found in various plants and fruits, and is known for its antioxidant properties. As a xanthophyll carotenoid, it is related to lutein and zeaxanthin, which are important for eye health. Zeaxanthin dipalmitate is used in research on oxidative stress, eye health, and as a natural pigment.
Biological Activity I Assay Protocols (From Reference)
Targets
p2X7/AdipoR1 receptor[1]
Reactive oxygen species (ROS) and oxidative stress pathways. Zeaxanthin dipalmitate, like other carotenoids, functions as an antioxidant by scavenging free radicals and quenching singlet oxygen. It may also modulate signaling pathways involved in inflammation and cell survival.
ln Vitro
Zeaxanthin dipalmitate (1 µM; 2 h) completely or partially reverses the ethanol (250 mM)-induced up-regulation of p62 and the down-regulation of Atg5, beclin-1, and LC3A/B in BRL-3A cells[1]. In BRL-3A cells, zeaxanthin dipalmitate (1 µM; 2 h) partially restores the ethanol-suppressed LC3B[1]. BRL-3A cells' ethanol-suppressed cell viability and ethanol-induced aspase -3/7 activity are partially restored by zeaxanthin dipalmitate (1 µM; 2 h)[1]. In BRL-3A cells, the ethanol-induced suppression of mitophagy is recovered by zeaxanthin dipalmitate (1 µM; 2 h)[1].
Zeaxanthin dipalmitate exhibits antioxidant activity in vitro by scavenging free radicals and reducing oxidative damage. It can protect cells from oxidative stress-induced damage. Its specific activities and EC₅0 values have not been detailed in available literature.
ln Vivo
In an AFLD model, zeaxanthin dipalmitate (10 mg/kg; po; daily for 2 weeks) lowers the serum ALT and AST levels elevated by a prolonged ethanol challenge[1]. Effectively reducing the histological damage is zeaxanthin dipalmitate (10 mg/kg; po; daily for 2 weeks)[1]. Rats treated with zeaxanthin dipalmitate (10 mg/kg; po; daily for 2 weeks) exhibit reduced liver inflammation (TNF-α) and apoptosis (asserted by caspase-3/7 activity) in response to AFLD[1]. Retinal photoreceptor degradation is postponed and the visual behavior of rd10 mice is improved with an intravitreal injection of zeaxanthin dipalmitate (about 4 μM)[2]. The light responses of photoreceptors, bipolar cells, and retinal ganglion cells are enhanced by zeaxanthin dipalmitate (about 4 μM; intravitreal injection for once)[2]. For once, intravitreal injection of zeaxanthin dipalmitate (about 4 μM) lowers the expression of genes linked to oxidative stress, apoptosis, and inflammation in rd10 mice[2].
No detailed in vivo activity data has been reported for Zeaxanthin dipalmitate in animal models. As a dietary carotenoid, it is studied for its potential benefits in eye health and oxidative stress-related conditions.
Enzyme Assay
Antioxidant assays: Zeaxanthin dipalmitate is tested in cell-free antioxidant assays such as DPPH radical scavenging, ABTS radical scavenging, or oxygen radical absorbance capacity (ORAC) assays. Its ability to quench singlet oxygen can also be measured.
Cell Assay
Cells are treated with Zeaxanthin dipalmitate, and oxidative stress markers (ROS levels, lipid peroxidation, protein oxidation) are measured. Protection against oxidative stress-induced cell death is assessed using cell viability assays. Anti-inflammatory activity can be assessed by measuring cytokine production.
Animal Protocol
Animal models of oxidative stress, age-related macular degeneration, or inflammation could be used to evaluate Zeaxanthin dipalmitate in vivo. Efficacy would be assessed by measuring oxidative stress markers, tissue damage, and functional outcomes.
ADME/Pharmacokinetics
Zeaxanthin dipalmitate has a molecular formula of C₇2H11₆O4 and a molecular weight of approximately 1045.7. It is a lipophilic compound with poor water solubility. It is a diester of zeaxanthin with palmitic acid.
Toxicity/Toxicokinetics
No toxicity data has been published for Zeaxanthin dipalmitate. As a dietary carotenoid and research compound, it is generally considered safe.
References

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

[2]. 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.

Additional Infomation
Physalien is a lutein. Physalien has been reported in wolfberry and Alkekengi officinarum var. var. . Data for franchetii are available.
Zeaxanthin dipalmitate (Physalien) is a diester of zeaxanthin with palmitic acid. It is a carotenoid pigment with antioxidant properties. The compound is for research use only and has not entered clinical trials.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C72H116O4
Molecular Weight
1045.69
Exact Mass
1044.887
CAS #
144-67-2
PubChem CID
5281250
Appearance
Brown to reddish brown solid powder
Density
1.0±0.1 g/cm3
Boiling Point
956.4±65.0 °C at 760 mmHg
Melting Point
98-100 °C
Flash Point
462.1±32.7 °C
Vapour Pressure
0.0±0.3 mmHg at 25°C
Index of Refraction
1.524
LogP
28.33
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
42
Heavy Atom Count
76
Complexity
1850
Defined Atom Stereocenter Count
2
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
InChi Key
XACHQDDXHDTRLX-XLVVAOPESA-N
InChi Code
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
Chemical 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
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 0.9563 mL 4.7815 mL 9.5631 mL
5 mM 0.1913 mL 0.9563 mL 1.9126 mL
10 mM 0.0956 mL 0.4782 mL 0.9563 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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