Lutein
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MedKoo CAT#: 584624

CAS#: 127-40-2

Description: Lutein is a xanthophyll found in the major light-harvesting protein complexes of plants. Dietary lutein accumulates in the macula lutea. Note: this product was a natural extract mixture with lutein ~ 80%.

Chemical Structure

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Lutein
CAS# 127-40-2
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 584624
Name: Lutein
CAS#: 127-40-2
Chemical Formula: C40H56O2
Exact Mass: 568.43
Molecular Weight: 568.886
Elemental Analysis: C, 84.45; H, 9.92; O, 5.62

Price and Availability

Size Price Availability Quantity
1g USD 250 Ready to ship
2g USD 450 Ready to ship
5g USD 750 Ready to ship
10g USD 1350 Ready to ship
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Synonym: Lutein; Xanthophyll;

IUPAC/Chemical Name: beta,epsilon-Carotene-3,3'-diol

InChi Key: KBPHJBAIARWVSC-DKLMTRRASA-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+

SMILES Code: CC(/C=C/C(C(C)=CC(O)C1)C1(C)C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(C)\C=C\C(C(C)(CC2O)C)=C(C2)C

Appearance: Solid powder

Purity: >80% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Product Data:
Product Data
Certificate of Analysis:
View CoA: current batch, Lot#A23M07B20
Safety Data Sheet (SDS):
View Safety Data Sheet (SDS)
Instruction:
View handling instruction
Biological target: Lutein exerts its biological activities, including anti-inflammation, anti-oxidase and anti-apoptosis, through effects on reactive oxygen species (ROS).
In vitro activity: The data revealed that lutein effectively reduces the protein levels of major inflammatory markers such as NF-κB, IL-1β, MCP-1, and TNF-α in differentiated adipocytes. Interestingly, lutein hampered inflammation in the RAW264 cells that were cultured in adipocyte-conditioned media by lowering the protein expression of IL-1β, MCP-1, and TNF-α. Reference: J Food Biochem. 2022 Sep;46(9):e14211. https://pubmed.ncbi.nlm.nih.gov/35488719/
In vivo activity: Thus, this study sought to evaluate antidepressant-like, antioxidant and neuroprotective effects of LUT (lutein) (0.1, 1 and 10 mg/kg) and fluoxetine (10 mg/kg) given orally (p.o.), acute, 7 or 21 days, once a day, in combination or not with corticosterone (20 mg/kg) in mice. LUT and fluoxetine in acute or subchronic treatment decreased immobility time at the dose 10 mg/kg. In addition, both LUT and fluoxetine presented antioxidant effect in the hippocampus, prefrontal cortex and plasma of mice, and exhibited a capability to protect hippocampal and prefrontal cortex slices against glutamatergic toxicity. Reference: Pharmacol Biochem Behav. 2019 Apr;179:63-72. https://pubmed.ncbi.nlm.nih.gov/30786251/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Chloroform 5.0 8.79
DMF 10.0 17.58
DMF:PBS (pH 7.2) (1:1) 0.5 0.88
DMSO 15.0 26.37

Preparing Stock Solutions

The following data is based on the product molecular weight 568.89 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Gopal SS, Kasiappan R, Vallikannan B, Ponesakki G. Effective inhibition of adipogenesis-mediated inflammation by a macular carotenoid, lutein in vitro. J Food Biochem. 2022 Sep;46(9):e14211. doi: 10.1111/jfbc.14211. Epub 2022 Apr 30. PMID: 35488719. 2. Chen Y, Wang L, Huang S, Ke J, Wang Q, Zhou Z, Chang W. Lutein attenuates angiotensin II- induced cardiac remodeling by inhibiting AP-1/IL-11 signaling. Redox Biol. 2021 Aug;44:102020. doi: 10.1016/j.redox.2021.102020. Epub 2021 May 25. PMID: 34077894; PMCID: PMC8181194. 3. Zeni ALB, Camargo A, Dalmagro AP. 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. doi: 10.1016/j.pbb.2019.02.004. Epub 2019 Feb 17. PMID: 30786251. 4. Tan D, Yu X, Chen M, Chen J, Xu J. 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. doi: 10.3892/mmr.2017.7040. Epub 2017 Jul 20. PMID: 28731190.
In vitro protocol: 1. Gopal SS, Kasiappan R, Vallikannan B, Ponesakki G. Effective inhibition of adipogenesis-mediated inflammation by a macular carotenoid, lutein in vitro. J Food Biochem. 2022 Sep;46(9):e14211. doi: 10.1111/jfbc.14211. Epub 2022 Apr 30. PMID: 35488719. 2. Chen Y, Wang L, Huang S, Ke J, Wang Q, Zhou Z, Chang W. Lutein attenuates angiotensin II- induced cardiac remodeling by inhibiting AP-1/IL-11 signaling. Redox Biol. 2021 Aug;44:102020. doi: 10.1016/j.redox.2021.102020. Epub 2021 May 25. PMID: 34077894; PMCID: PMC8181194.
In vivo protocol: 1. Zeni ALB, Camargo A, Dalmagro AP. 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. doi: 10.1016/j.pbb.2019.02.004. Epub 2019 Feb 17. PMID: 30786251. 2. Tan D, Yu X, Chen M, Chen J, Xu J. 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. doi: 10.3892/mmr.2017.7040. Epub 2017 Jul 20. PMID: 28731190.

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1: Leonelli L, Brooks MD, Niyogi KK. Engineering the lutein epoxide cycle into Arabidopsis thaliana. Proc Natl Acad Sci U S A. 2017 Aug 15;114(33):E7002-E7008. doi: 10.1073/pnas.1704373114. Epub 2017 Jul 31. PubMed PMID: 28760990; PubMed Central PMCID: PMC5565435.

2: Mellado-Ortega E, Hornero-Méndez D. Isolation and identification of lutein esters, including their regioisomers, in tritordeum (×Tritordeum Ascherson et Graebner) grains: Evidence for a preferential xanthophyll acyltransferase activity. Food Chem. 2012 Dec 1;135(3):1344-52. doi: 10.1016/j.foodchem.2012.05.046. Epub 2012 May 17. PubMed PMID: 22953864.

3: Jeon S, Ranard KM, Neuringer M, Johnson EE, Renner L, Kuchan MJ, Pereira SL, Johnson EJ, Erdman JW Jr. Lutein Is Differentially Deposited across Brain Regions following Formula or Breast Feeding of Infant Rhesus Macaques. J Nutr. 2018 Jan 1;148(1):31-39. doi: 10.1093/jn/nxx023. PubMed PMID: 29378053.

4: Howard AN, Thurnham DI. Lutein and atherosclerosis: Belfast versus Toulouse revisited. Med Hypotheses. 2017 Jan;98:63-68. doi: 10.1016/j.mehy.2016.10.030. Epub 2016 Nov 23. PubMed PMID: 28012609.

5: Johnson MP, Zia A, Ruban AV. Elevated ΔpH restores rapidly reversible photoprotective energy dissipation in Arabidopsis chloroplasts deficient in lutein and xanthophyll cycle activity. Planta. 2012 Jan;235(1):193-204. doi: 10.1007/s00425-011-1502-0. Epub 2011 Aug 25. PubMed PMID: 21866345.

6: Leuenberger M, Morris JM, Chan AM, Leonelli L, Niyogi KK, Fleming GR. Dissecting and modeling zeaxanthin- and lutein-dependent nonphotochemical quenching in Arabidopsis thaliana. Proc Natl Acad Sci U S A. 2017 Aug 15;114(33):E7009-E7017. doi: 10.1073/pnas.1704502114. Epub 2017 Jun 26. PubMed PMID: 28652334; PubMed Central PMCID: PMC5565437.

7: Zheng YF, Min JS, Kim D, Park JB, Choi SW, Lee ES, Na K, Bae SK. In Vitro Inhibition of Human UDP-Glucuronosyl-Transferase (UGT) Isoforms by Astaxanthin, β-Cryptoxanthin, Canthaxanthin, Lutein, and Zeaxanthin: Prediction of in Vivo Dietary Supplement-Drug Interactions. Molecules. 2016 Aug 12;21(8). pii: E1052. doi: 10.3390/molecules21081052. PubMed PMID: 27529203.

8: Gleize B, Tourniaire F, Depezay L, Bott R, Nowicki M, Albino L, Lairon D, Kesse-Guyot E, Galan P, Hercberg S, Borel P. Effect of type of TAG fatty acids on lutein and zeaxanthin bioavailability. Br J Nutr. 2013 Jul 14;110(1):1-10. doi: 10.1017/S0007114512004813. Epub 2012 Dec 11. PubMed PMID: 23228631; PubMed Central PMCID: PMC3734536.

9: Panova IG, Yakovleva MA, Tatikolov AS, Kononikhin AS, Feldman TB, Poltavtseva RA, Nikolaev EN, Sukhikh GT, Ostrovsky MA. Lutein and its oxidized forms in eye structures throughout prenatal human development. Exp Eye Res. 2017 Jul;160:31-37. doi: 10.1016/j.exer.2017.04.008. Epub 2017 Apr 25. PubMed PMID: 28454979.

10: Komuro M, Shimizu N, Onuma R, Otoki Y, Ito J, Kato S, Higuchi O, Sudo K, Suzuki S, Miyazawa T, Eitsuka T, Nakagawa K. Analysis of Lutein in Mugwort (Artemisia princeps Pamp.) Paste and Evaluation of Manufacturing Processes. J Oleo Sci. 2017 Nov 1;66(11):1257-1262. doi: 10.5650/jos.ess17117. Epub 2017 Oct 11. PubMed PMID: 29021494.

11: Mora-Gutierrez A, Attaie R, Núñez de González MT, Jung Y, Woldesenbet S, Marquez SA. Complexes of lutein with bovine and caprine caseins and their impact on lutein chemical stability in emulsion systems: Effect of arabinogalactan. J Dairy Sci. 2018 Jan;101(1):18-27. doi: 10.3168/jds.2017-13105. Epub 2017 Nov 2. PubMed PMID: 29103708.

12: Vishwanathan R, Neuringer M, Snodderly DM, Schalch W, Johnson EJ. Macular lutein and zeaxanthin are related to brain lutein and zeaxanthin in primates. Nutr Neurosci. 2013 Jan;16(1):21-9. doi: 10.1179/1476830512Y.0000000024. Epub 2012 Jul 9. PubMed PMID: 22780947; PubMed Central PMCID: PMC3824968.

13: Jahns P, Holzwarth AR. The role of the xanthophyll cycle and of lutein in photoprotection of photosystem II. Biochim Biophys Acta. 2012 Jan;1817(1):182-93. doi: 10.1016/j.bbabio.2011.04.012. Epub 2011 May 1. Review. PubMed PMID: 21565154.

14: Picone S, Ritieni A, Fabiano A, Graziani G, Paolillo P, Livolti G, Galvano F, Gazzolo D. Lutein levels in arterial cord blood correlate with neuroprotein activin A in healthy preterm and term newborns: A trophic role for lutein? Clin Biochem. 2018 Feb;52:80-84. doi: 10.1016/j.clinbiochem.2017.11.017. Epub 2017 Nov 28. PubMed PMID: 29195833.

15: Ranard KM, Jeon S, Mohn ES, Griffiths JC, Johnson EJ, Erdman JW Jr. Dietary guidance for lutein: consideration for intake recommendations is scientifically supported. Eur J Nutr. 2017 Dec;56(Suppl 3):37-42. doi: 10.1007/s00394-017-1580-2. Review. PubMed PMID: 29149368; PubMed Central PMCID: PMC5715043.

16: Evans M, Beck M, Elliott J, Etheve S, Roberts R, Schalch W. Effects of formulation on the bioavailability of lutein and zeaxanthin: a randomized, double-blind, cross-over, comparative, single-dose study in healthy subjects. Eur J Nutr. 2013 Jun;52(4):1381-91. doi: 10.1007/s00394-012-0447-9. Epub 2012 Sep 30. PubMed PMID: 23052623; PubMed Central PMCID: PMC3663991.

17: Mein JR, Dolnikowski GG, Ernst H, Russell RM, Wang XD. Enzymatic formation of apo-carotenoids from the xanthophyll carotenoids lutein, zeaxanthin and β-cryptoxanthin by ferret carotene-9',10'-monooxygenase. Arch Biochem Biophys. 2011 Feb 1;506(1):109-21. doi: 10.1016/j.abb.2010.11.005. Epub 2010 Nov 21. PubMed PMID: 21081106; PubMed Central PMCID: PMC3026080.

18: Johnson EJ. Role of lutein and zeaxanthin in visual and cognitive function throughout the lifespan. Nutr Rev. 2014 Sep;72(9):605-12. doi: 10.1111/nure.12133. Epub 2014 Aug 8. Review. PubMed PMID: 25109868.

19: Lin H, Mares JA, LaMonte MJ, Brady WE, Sahli MW, Klein R, Klein BEK, Nie J, Millen AE. Association between Dietary Xanthophyll (Lutein and Zeaxanthin) Intake and Early Age-Related Macular Degeneration: The Atherosclerosis Risk in Communities Study. Ophthalmic Epidemiol. 2017 Oct;24(5):311-322. doi: 10.1080/09286586.2017.1290259. Epub 2017 Mar 23. PubMed PMID: 28332910; PubMed Central PMCID: PMC6025894.

20: Silva JTDP, Silva ACD, Geiss JMT, de Araújo PHH, Becker D, Bracht L, Leimann FV, Bona E, Guerra GP, Gonçalves OH. Analytical validation of an ultraviolet-visible procedure for determining lutein concentration and application to lutein-loaded nanoparticles. Food Chem. 2017 Sep 1;230:336-342. doi: 10.1016/j.foodchem.2017.03.059. Epub 2017 Mar 14. PubMed PMID: 28407919.