Zeaxanthin

Base Information

• Chemical Name: Zeaxanthin
• CAS No.: 144-68-3
• Deprecated CAS: 32638-35-0,34182-33-7
• Molecular Formula: C40H56O2
• Molecular Weight: 568.883
• Hs Code.: 29062990
• European Community (EC) Number: 205-636-4
• UNII: CV0IB81ORO
• ChEMBL ID: CHEMBL2359248
• DSSTox Substance ID: DTXSID5046807
• Metabolomics Workbench ID: 28986
• NCI Thesaurus Code: C68310
• Nikkaji Number: J5.830K,J522.346F,J522.347D,J522.348B
• NSC Number: 713073
• Wikidata: Q169337
• Wikipedia: Zeaxanthin
• Mol file: 144-68-3.mol

Synonyms:3R,3'R Zeaxanthin;3R,3'R-Zeaxanthin;Beta Carotene 3,3' Diol;beta-carotene-3,3'-diol;zeaxanthin;Zeaxanthins

Chemical Property of Zeaxanthin

Chemical Property:

• Appearance/Colour: yellow crystalline solid
• Vapor Pressure: 2.19E-23mmHg at 25°C
• Melting Point: 203-205 °C
• Refractive Index: 1.585
• Boiling Point: 711.4 °C at 760 mmHg
• PKA: 14.60±0.70(Predicted)
• Flash Point: 273.4 °C
• PSA: 40.46000
• Density: 1.008 g/cm³
• LogP: 10.54740
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 10.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 10
• Exact Mass: 568.42803102
• Heavy Atom Count: 42
• Complexity: 1190

Purity/Quality:

5%, ^*data from raw suppliers

Zeaxanthin(TechnicalGrade) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(CC(C1)O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2=C(CC(CC2(C)C)O)C)C)C
• Isomeric 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/C2=C(C[C@H](CC2(C)C)O)C)\C)\C)/C)/C
• Recent ClinicalTrials: Determine Safety & Recommended Phase 2 Dosing of Zeaxanthin Alone or in Combination w/Pembrolizumab in Patients With Metastatic Cancer
• Uses: It is one of the two carotenoids contained within the retina It is one of the two carotenoids contained within the retina.

Technology Process of Zeaxanthin

There total 117 articles about Zeaxanthin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(all-E,3R,3'R)-β,β-carotene-3,3'-diol 3,3'-diacetate (115406-45-6,16638-61-2) → zeaxanthin (144-68-3,3309-19-1,24502-92-9,29472-68-2,31272-50-1,31272-53-4,57820-80-1,60046-54-0,60497-64-5,60497-65-6,72002-36-9,72580-10-0,100347-92-0,100347-97-5,136656-95-6,136733-98-7,136733-99-8,136734-01-5,136734-02-6)

Guidance literature:

With methanol; potassium hydroxide; In tetrahydrofuran; at 20 ℃; for 1h; optical yield given as %de; Inert atmosphere;

DOI:10.1055/s-0031-1289662

Reference yield: 81.0%

(4R,2ZE,4Z)-[5-(4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]triphenylphosphonium chloride + C12H20O4 (696647-73-1) → zeaxanthin (144-68-3,3309-19-1,24502-92-9,29472-68-2,31272-50-1,31272-53-4,57820-80-1,60046-54-0,60497-64-5,60497-65-6,72002-36-9,72580-10-0,100347-92-0,100347-97-5,136656-95-6,136733-98-7,136733-99-8,136734-01-5,136734-02-6)

Guidance literature:

With ethyloxirane; In ethanol; at 0 ℃; for 21h; Heating / reflux;

Reference yield: 55.0%

(1E,3E,5E,7E,9E)-1,10-di(benzyldimethylsilyl)-3,8-dimethyldeca-1,3,5,7,9-pentaene + (R)-4-((1E,3E)-4-iodo-3-methylbuta-1,3-dien-1-yl)-3,5,5-trimethylcyclohex-3-en-1-ol (444122-16-1) → zeaxanthin (144-68-3,3309-19-1,24502-92-9,29472-68-2,31272-50-1,31272-53-4,57820-80-1,60046-54-0,60497-64-5,60497-65-6,72002-36-9,72580-10-0,100347-92-0,100347-97-5,136656-95-6,136733-98-7,136733-99-8,136734-01-5,136734-02-6)

Guidance literature:

(1E,3E,5E,7E,9E)-1,10-di(benzyldimethylsilyl)-3,8-dimethyldeca-1,3,5,7,9-pentaene; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.666667h; Inert atmosphere;

(R)-4-((1E,3E)-4-iodo-3-methylbuta-1,3-dien-1-yl)-3,5,5-trimethylcyclohex-3-en-1-ol; With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; at 0 - 25 ℃; for 1.25h; Inert atmosphere;

DOI:10.1002/chem.201903080

upstream raw materials:

ethanol

all-trans lutein

sodium ethanolate

benzene

Downstream raw materials:

O-acetyl-β-citraurin

C₆₀H₇₀F₆O₆

C₆₀H₇₀F₆O₆

lutein

Refernces

• 1、 Rivas, Aurea,Pérez-Revenga, Víctor,Alvarez, Rosana,de Lera, Angel R.. "Bidirectional Hiyama–Denmark Cross-Coupling Reactions of Bissilyldeca-1,3,5,7,9-pentaenes for the Synthesis of Symmetrical and Non-Symmetrical Carotenoids". supporting information. p. 14399 - 14407. Retrieved 2019/11/03.
• 2、 Shyam, Rajalekshmy,Gorusupudi, Aruna,Nelson, Kelly,Horvath, Martin P.,Bernstein, Paul S.. "RPE65 has an additional function as the lutein to meso-zeaxanthin isomerase in the vertebrate eye". . p. 10882 - 10887. Retrieved 2017/10/13.