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Lutein

Alias: Xanthophyll; Lutein
Cat No.:V17963 Purity: ≥98%
Lutein (Xanthophyll) is a carotenoid with anti~inflammatory properties.
Lutein
Lutein Chemical Structure CAS No.: 127-40-2
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
250mg
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Product Description
Lutein (Xanthophyll) is a carotenoid with anti~inflammatory properties. Lutein has many beneficial effects, especially for eye health. Lutein exerts bioactivities like anti~inflammatory, antioxidant enzymes, and anti-apoptosis by affecting reactive oxygen species (ROS). Lutein is able to reach the brain and exhibit antidepressant-like and neuro-protective (neuro-protection) effects. Lutein is orally bioactive.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Lutein (100 or 200 μM) decreases A2E photooxidation and stops A2-PE photooxidation, which is a bis-retinoic acid molecule and the direct precursor of the lipofuscin fluorophore A2E [2].
ln Vivo
Through the anti-inflammatory and antioxidant activities of ICAM-1/Nrf-2, lutein (40–160 mg/kg; in diet for 5 weeks) protects severe traumatic brain injury in rats [3]. In addition to its antioxidant and neuroprotective properties, lutein (0.1–10 mg/kg; orally; once or daily for 7 and 21 days) inhibits the depressive-like behavior that corticosterone induces in mice [4].
Animal Protocol
Animal/Disease Models: SD (SD (Sprague-Dawley)) rat, severe traumatic brain injury (STBI) model [3]
Doses: 40, 80 and 160 mg/kg
Route of Administration: Diet for 5 weeks
Experimental Results: Inhibition of interleukin (IL)-1β, IL-6 and monocyte chemoattractant protein-1 expression, diminished serum ROS levels, and diminished superoxide dismutase and glutathione peroxidase activities. Effectively downregulates the expression of NF-κB p65, cyclooxygenase-2, and intercellular adhesion molecule (ICAM)-1 protein, and upregulates nuclear factor erythroid 2-like 2 (Nrf-2) and endothelin-1 protein levels.

Animal/Disease Models: Male Swiss mouse, chronic corticosterone depression model [4]
Doses: 0.1, 1 and 10 mg/kg
Route of Administration: Oral administration, once or daily for 7 and 21 days
Experimental Results: 10 mg/ Immobility time diminished at kg doses. Counteracts the behavioral changes demonstrated by corticosterone, exhibiting antidepressant-like effects. Exhibits antioxidant effects in mouse hippocampus, prefrontal cortex, and plasma, and exhibits the ability to
References

[1]. The Effect of Lutein on Eye and Extra-Eye Health.Nutrients. 2018 Sep 18;10(9). pii: E1321.

[2]. Photooxidation of A2-PE, a photoreceptor outer segment fluorophore, and protection by lutein and zeaxanthin. Exp Eye Res. 2006 May;82(5):828-39.

[3]. Lutein protects against severe traumatic brain injury through anti‑inflammation and antioxidative effects via ICAM‑1/Nrf‑2. Mol Med Rep. 2017 Oct;16(4):4235-4240.

[4]. Lutein prevents corticosterone-induced depressive-like behavior in mice with the involvement of antioxidant and neuroprotective activities. Pharmacol Biochem Behav. 2019 Apr;179:63-72.

Additional Infomation
Lutein is a carotenol. It has a role as a food colouring and a plant metabolite. It derives from a hydride of a (6'R)-beta,epsilon-carotene.
Lutein is an xanthophyll and one of 600 known naturally occurring carotenoids. Lutein is synthesized only by plants and like other xanthophylls is found in high quantities in green leafy vegetables such as spinach, kale and yellow carrots. In green plants, xanthophylls act to modulate light energy and serve as non-photochemical quenching agents to deal with triplet chlorophyll (an excited form of chlorophyll), which is overproduced at very high light levels, during photosynthesis.
Lutein has been reported in Erythrophleum fordii, Nephrolepis cordifolia, and other organisms with data available.
Lutein is lutein (LOO-teen) is a oxygenated carotenoid found in vegetables and fruits. lutein is found in the macula of the eye, where it is believed to act as a yellow filter. Lutein acts as an antioxidant, protecting cells against the damaging effects of free radicals.
A xanthophyll found in the major LIGHT-HARVESTING PROTEIN COMPLEXES of plants. Dietary lutein accumulates in the MACULA LUTEA.
See also: Calendula Officinalis Flower (part of); Corn (part of); Chicken; lutein (component of) ... View More ...
Drug Indication
Xanthophylls are taken for nutritional supplementation, and also for treating dietary shortage or imbalance.
Mechanism of Action
Xanthophylls have antioxidant activity and react with active oxygen species, producing biologically active degradation products. They also can inhibit peroxidation of membrane phospholipids and reduce lipofuscin formation, both of which contribute to their antioxidant properties. Lutein is naturally present in the macula of the human retina. It filters out potentially phototoxic blue light and near-ultraviolet radiation from the macula. The protective effect is due in part, to the reactive oxygen species quenching ability of these carotenoids. Lutein is more stable to decomposition by pro-oxidants than are other carotenoids such as beta-carotene and lycopene. Lutein is abundant in the region surrounding the fovea, and lutein is the predominant pigment at the outermost periphery of the macula. Zeaxanthin, which is fully conjugated (lutein is not), may offer somewhat better protection than lutein against phototoxic damage caused by blue and near-ultraviolet light radiation. Lutein is one of only two carotenoids that have been identified in the human lens, may be protective against age-related increases in lens density and cataract formation. Again, the possible protection afforded by lutein may be accounted for, in part, by its reactive oxygen species scavenging abilities. Carotenoids also provide protection from cancer. One of the mechanisms of this is by increasing the expression of the protein connexin-43, thereby stimulating gap junctional communication and preventing unrestrained cell proliferation.
Pharmacodynamics
Lutein was found to be present in a concentrated area of the macula, a small area of the retina responsible for central vision. The hypothesis for the natural concentration is that lutein helps protect from oxidative stress and high-energy light. Several studies show that an increase in macula pigmentation decreases the risk for eye diseases such as Age-related Macular Degeneration (AMD).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C40H56O2
Molecular Weight
568.886
Exact Mass
568.428
CAS #
127-40-2
PubChem CID
5281243
Appearance
Orange to red solid powder
Density
1.0±0.1 g/cm3
Boiling Point
702.3±60.0 °C at 760 mmHg
Melting Point
183℃
Flash Point
269.1±27.5 °C
Vapour Pressure
0.0±5.0 mmHg at 25°C
Index of Refraction
1.583
LogP
11.78
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
10
Heavy Atom Count
42
Complexity
1270
Defined Atom Stereocenter Count
3
SMILES
CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@H]2C(=C[C@@H](CC2(C)C)O)C)/C)/C
InChi Key
KBPHJBAIARWVSC-RGZFRNHPSA-N
InChi Code
InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36+,37-/m0/s1
Chemical Name
(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethylcyclohex-3-en-1-ol
Synonyms
Xanthophyll; Lutein
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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
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)
DMSO : ~50 mg/mL (~87.89 mM)
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 1.7578 mL 8.7890 mL 17.5781 mL
5 mM 0.3516 mL 1.7578 mL 3.5156 mL
10 mM 0.1758 mL 0.8789 mL 1.7578 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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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.

Clinical Trial Information
The clinical study for the effect of oral supplementary drugs containing lutein on macular pigment density
CTID: UMIN000011512
Phase:    Status: Complete: follow-up complete
Date: 2013-08-29
A multi-center, randomized, parallel-group study to assess the changes in macular pigment density and visual performance in the patients with age-related macular degeneration, who received a lutein supplement
CTID: UMIN000007628
PhaseNot applicable    Status: Complete: follow-up complete
Date: 2012-04-20
A prospective, randomized, double blind study comparing lutein to placebo for reducing occurrence and severity of retinopathy of prematurity, and evaluating antioxidative power and central visual function.
CTID: UMIN000007041
Phase:    Status: Complete: follow-up complete
Date: 2012-01-20
Effectiveness for macular pigment with lutein supplementation in central serous chorioretinopathy
CTID: UMIN000005849
Phase:    Status: Complete: follow-up complete
Date: 2011-06-26
Randomized, three-group, parallel comparative study on changes in macular pigment optical density and visual function due to administration of supplements containing lutein and omega3 fatty acids to patients with age-related macular degeneration (patients treated with ranibizumab)
CTID: UMIN000004804
PhaseNot applicable    Status: Complete: follow-up complete
Date: 2010-12-28
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The effects of 2 types of lutein supplements on macular pigment and visual functions
CTID: UMIN000004593
PhaseNot applicable    Status: Complete: follow-up complete
Date: 2010-11-22


macular pigment optical density in Japanese age-related macular degeneration and the effect of lutein intake
CTID: UMIN000001320
PhaseNot applicable    Status: Complete: follow-up complete
Date: 2009-01-01

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