LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

Zeaxanthin

Systematic Name

Synonyms

LM ID

LMPR01070261

Formula

C₄₀H₅₆O₂

Exact Mass

Calculate m/z

568.42803

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View MassBank spectra

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Zeaxanthin is a dietary carotenoid that has been found in orange and yellow fruits and has diverse biological activities.^1,2,3,4,5 In vivo, zeaxanthin (50 mg/kg) decreases immobility time in the forced swim test and reduces hippocampal levels of IL-6, IL-1β, and TNF-α in a rat model of diabetes induced by streptozotocin (STZ).¹ It also reduces albuminuria, serum levels of urea nitrogen and malondialdehyde (MDA), and kidney damage in a rat model of STZ-induced diabetic nephropathy.² It forms the macular pigment in human eyes, and high dietary intake of zeaxanthin is positively correlated with reduced risk of advanced neovascular age-related macular degeneration in humans.^3,4,5

This information has been provided by Cayman Chemical

References

1. SanGiovanni, J.P., Chew, E.Y., Clemons, T.E., et al. The relationship of dietary carotenoid and vitamin A, E, and C intake with age related macular degeneration in a case-control study. Arch. Ophthalmol. 125(9), 1225-1232 (2007).

2. Hammond, B.R., Jr. Possible role for dietary lutein and zeaxanthin in visual development. Nutr. Rev. 66(12), 695-702 (2008).

3. Jia, Y.-P., Sun, L., Yu, H.-S., et al. The pharmacological effects of lutein and zeaxanthin on visual disorders and cognition diseases. Molecules 22(4), 610 (2017).

4. Kou, L., Du, M., Zhang, C., et al. The hypoglycemic, hypolipidemic, and anti-diabetic nephritic activities of zeaxanthin in diet-streptozotocin-induced diabetic sprague dawley rats. Appl. Biochem. Biotechnol. 182(3), 944-955 (2017).

5. Zhou, X., Gan, T., Fang, G., et al. Zeaxanthin improved diabetes-induced anxiety and depression through inhibiting inflammation in hippocampus. Metab. Brain Dis. 33(3), 705-711 (2018).

String Representations

InChiKey (Click to copy)

JKQXZKUSFCKOGQ-QAYBQHTQSA-N

InChi (Click to copy)

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/h11-24,35-36,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36-/m1/s1

SMILES (Click to copy)

C1(/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C2=C(C)C[C@@H](O)CC2(C)C)=C(C)C[C@@H](O)CC1(C)C