CAS 144-68-3 Zeaxanthin - Analytical Products / Alfa Chemistry

CAT	APS144683A
CAS	144-68-3
Structure
MDL Number	MFCD08435940
Synonyms	Anchovyxanthin, all-trans-, (3R,3'R)-Zeaxanthin, all-trans-3R,3'R-Zeaxanthin, all-E-Zeaxanthin,β,β-Carotene-3,3'-diol, (3R,3'R)-, Xanthophyll 3, ZeaGold, Optisharp, Zeaxanthin, all-trans-, Zeaxanthol, Zeaxanthin (7CI), E 161H, (3R,3'R)-β,β-Carotene-3,3'-diol, Luteinofta, β-Carotene-3,3'-diol, (3R,3'R)-all-trans- (6CI,8CI), Anchovyxanthin, all-trans-Anchovyxanthin, all-trans-Zeaxanthin
IUPAC Name	(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-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-ol
Molecular Weight	568.87
Molecular Formula	C40H56O2
EC Number	205-636-4
Canonical SMILES	C\C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C)\C=C\C=C(/C)\C=C\C2=C(C)C[C@@H](O)CC2(C)C
InChI	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
InChI Key	JKQXZKUSFCKOGQ-QAYBQHTQSA-N

Description	analytical standard
Accurate Mass	568.428
Assay	≥95.0% (HPLC)
Form	neat; gas chromatography (GC): suitable
Format	Neat
Grade	analytical standard
Shipping	Room Temperature
Size	1MG
Storage Conditions	-18°C
Subcategory	Nutritional composition compounds

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Case Study

Zeaxanthin Used for the Preparation of Nanostructured Lipid Carriers to Enhance Bioavailability in Nutraceutical Applications

Osanlou, Roya, et al. Colloids and Surfaces A: Physicochemical and Engineering Aspects 641 (2022): 128588.

Zeaxanthin, a lipophilic carotenoid with potent antioxidant activity, plays a crucial role in ocular health, particularly in protecting the macula from oxidative damage. However, its poor water solubility and low chemical stability have limited its incorporation into aqueous food and beverage systems. To overcome these challenges, zeaxanthin was encapsulated into solid lipid nanoparticles (SLNs) and nanostructured lipid carriers (NLCs) using a high-shear homogenization-ultrasonication approach.
In this formulation, zeaxanthin was loaded into a lipid matrix composed of glycerol-based solid lipids and medium-chain triglycerides (MCTs), with 20% of the solid lipid replaced by MCT to engineer NLCs. The resulting NLCs exhibited superior physicochemical properties, with particle sizes below 130 nm, narrow size distribution (PDI 0.23-0.30), and stable zeta potentials (-22.23 mV to -16.88 mV). Encapsulation efficiency and drug loading were significantly higher in NLCs compared to SLNs, ensuring effective protection and delivery of zeaxanthin.
SEM imaging confirmed spherical morphology, and FTIR/DSC analysis verified successful encapsulation without chemical alteration of zeaxanthin. Notably, nanocarriers stabilized with glycerol distearate exhibited no phase separation over 60 days at 4 °C and 25 °C. This work demonstrates that NLC-based delivery systems substantially improve the solubility, stability, and functionality of zeaxanthin, making them ideal for use in functional foods and nutraceutical beverages.

Zeaxanthin Is Used for the Intervention of NAFLD via Ferroptosis Inhibition and Antioxidative Pathways

Liu, H., Yan, J., Guan, F., Jin, Z., Xie, J., Wang, C., ... & Liu, J. (2023). Biochimica et Biophysica Acta (BBA)-Molecular and Cell Biology of Lipids, 1868(4), 159287.

Zeaxanthin, a dietary xanthophyll carotenoid present in human serum, has demonstrated multifaceted biological activities including antioxidative, anti-inflammatory, and lipid-lowering effects. This study elucidates its novel application in the intervention of non-alcoholic fatty liver disease (NAFLD), a global metabolic disorder linked to obesity, insulin resistance, and hepatic ferroptosis.
Using a free fatty acid (FFA)-induced HepG2 cell model to mimic NAFLD conditions, zeaxanthin (ZEA) significantly alleviated lipid accumulation, reduced oxidative stress, and improved mitochondrial integrity. Mechanistically, ZEA functioned as a potent ferroptosis inhibitor. It markedly reduced intracellular reactive oxygen species (ROS) and iron overload-two hallmarks of ferroptotic cell death-and restored redox balance within hepatocytes.
Further molecular analysis revealed that ZEA downregulated p53 expression and favorably modulated key ferroptosis-associated targets, including GPX4, SLC7A11, SAT1, and ALOX15. These changes collectively suppressed lipid peroxidation and protected hepatocytes from ferroptotic damage. Additionally, ZEA improved dyslipidemia by mitigating inflammatory markers and normalizing lipid metabolism in the hepatocyte model.
These findings highlight zeaxanthin's therapeutic potential in NAFLD prevention through a dual mechanism of ferroptosis inhibition and oxidative stress modulation. As a natural bioactive compound with excellent safety and bioavailability profiles, ZEA holds significant promise for future clinical applications targeting liver metabolic disorders.

Zeaxanthin Is Used for the Amelioration of Acetic Acid-Induced Ulcerative Colitis via Antioxidative and Anti-Inflammatory Mechanisms

El-Akabawy, Gehan, and Neveen M. El-Sherif. Biomedicine & Pharmacotherapy 111 (2019): 841-851.

Zeaxanthin, a xanthophyll carotenoid renowned for its antioxidative properties, has shown promising therapeutic potential in inflammatory bowel diseases. This study investigated the efficacy of zeaxanthin in mitigating ulcerative colitis (UC) induced by acetic acid (AA) in a rat model. Oral administration of zeaxanthin (50 mg/kg/day) over 14 days prior to AA induction significantly attenuated colonic injury compared to untreated UC controls.
Zeaxanthin pretreatment notably reduced disease activity index (DAI), wet colon weight, ulceration area, and macroscopic and histopathological scores. On the biochemical level, zeaxanthin downregulated key markers of oxidative stress, including myeloperoxidase (MPO) and malondialdehyde (MDA), while enhancing endogenous antioxidant defense systems by upregulating superoxide dismutase (SOD), catalase (CAT), and glutathione (GSH) levels.
Additionally, zeaxanthin exerted a strong anti-inflammatory response by suppressing the expression of pro-inflammatory cytokines such as TNF-α, IFN-γ, IL-6, and IL-1β, along with downregulating NF-κB activity. Protein expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) was also significantly inhibited.
These findings suggest that zeaxanthin effectively attenuates acute experimental colitis through its dual antioxidative and anti-inflammatory actions. Although the AA-induced UC model differs mechanistically from human UC, these results underscore zeaxanthin's potential as a natural therapeutic agent for managing ulcerative colitis and warrant further investigation in chronic models and clinical settings.