144-68-3

Basic information

• Product Name: Zeaxanthin
• Synonyms: Zeaxanthin-20%,60%;all-trans-b-Carotene-3,3diol;Anchovyxanthin;Zeaxanthol;.beta.,.beta.-Carotene-3,3-diol, (3R,3R)-;(3R,3'R) b,b-carotene-3,3'-diol;ZEAXANTHIN(P);ZEAXANTHIN(SH)
• CAS NO: 144-68-3
• Molecular Formula: C40H56O2
• Molecular Weight: 568.87
• EINECS: 205-636-4
• Product Categories: Carotenoids;Intermediates & Fine Chemicals;Pharmaceuticals;Plant extract;Plant extracts
• Mol File: 144-68-3.mol
• Article Data: 50

Chemical Properties

• Melting Point: 203-2050C
• Boiling Point: 572.66°C (rough estimate)
• Flash Point: 273.4 °C
• Appearance: yellow crystalline solid
• Density: 0.9944 (rough estimate)
• Vapor Pressure: 2.19E-23mmHg at 25°C
• Refractive Index: 1.5250 (estimate)
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.60±0.70(Predicted)
• Stability: Light Sensitive, Temperature Sensitive
• CAS DataBase Reference: Zeaxanthin(CAS DataBase Reference)
• NIST Chemistry Reference: Zeaxanthin(144-68-3)
• EPA Substance Registry System: Zeaxanthin(144-68-3)

Safety Data

• F: 3-8-10
• Hazardous Substances Data: 144-68-3(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Crystalline Solid

Uses

Different sources of media describe the Uses of 144-68-3 differently. You can refer to the following data:
1. It is one of the two carotenoids contained within the retina
2. It is one of the two carotenoids contained within the retina.

InChI:InChI=1/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

Synthetic route

all-trans lutein (7481-64-3) → zeaxanthin (144-68-3)

Conditions	Yield
With ethanol; sodium ethanolate; benzene at 100 - 110℃;

3,3'-di-keto-β-carotene (14656-56-5, 26543-85-1) + aluminum isopropoxide (555-31-7) + isopropyl alcohol (67-63-0) + benzene (71-43-2) → zeaxanthin (144-68-3)

(2E,4E,6E,8E,10E,12E,14E)-15-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-4,9,13-trimethylpentadeca-2,4,6,8,10,12,14-heptaenal (15486-31-4) + <3-(4-hydroxy-2,2,6-trimethylcyclohexenyl)-1-methyl-2-propen-1-yl>triphenylphosphonium bromide → zeaxanthin (144-68-3)

Conditions	Yield
With potassium hydroxide In isopropyl alcohol at 20℃; for 3h;	8.5 mg

zeaxanthin radical cation → zeaxanthin (144-68-3)

Conditions	Yield
With TX-100 In water Rate constant; Irradiation;

4',5'-didehydro-4,5'-retro-β,β-carotene-3,3'-dione (116-30-3) → zeaxanthin (144-68-3) + lutein (127-40-2) + (3R,3'S,6'R)-lutein (89673-72-3)

Conditions	Yield
With tellurium; sodium tetrahydroborate In carbon disulfide; ethanol at 40℃; for 0.333333h; Title compound not separated from byproducts;	A 24 % Chromat. B 44 % Chromat. C 31 % Chromat.
With tellurium; sodium tetrahydroborate In carbon disulfide; ethanol at 40℃; for 0.333333h;	A 24 % Chromat. B 44 % Chromat. C 31 % Chromat.

lycopene (502-65-8) + zeaxanthin radical cation → zeaxanthin (144-68-3) + lycopene radical cation

Conditions	Yield
In benzene Rate constant; pulse radiolysis;

all-trans-β-carotenedione-(3,3') → zeaxanthin (144-68-3)

Conditions	Yield
With aluminum isopropoxide; isopropyl alcohol; benzene

(E)-4,9-dimethyl-2,4,6,8,10-dodecapentaene-1,12-dial (53163-53-4) + 4-triphenylphosphoranylidene-pent-2t(?)-enoic acid methyl ester → zeaxanthin (144-68-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 11 mg / aq. KOH / propan-2-ol / 24 h / 20 °C 2: 8.5 mg / aq. KOH / propan-2-ol / 3 h / 20 °C View Scheme

4-(1,4-dihydroxy-2,2,6-trimethylcyclohexyl)-3-butyn-2-ol (32469-38-8) → zeaxanthin (144-68-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 3.5 g / lithium aluminium hydride / tetrahydrofuran / 3 h / Heating 2: 2.21 g / CHCl3 / 18 h / 20 °C 3: 11 mg / aq. KOH / propan-2-ol / 24 h / 20 °C 4: 8.5 mg / aq. KOH / propan-2-ol / 3 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 3.5 g / lithium aluminium hydride / tetrahydrofuran / 3 h / Heating 2: 2.21 g / CHCl3 / 18 h / 20 °C 3: 8.5 mg / aq. KOH / propan-2-ol / 3 h / 20 °C View Scheme

4-(4-hydroxy-2,2,6-trimethylcyclohexylidene)-3-buten-2-ol (53342-69-1) → zeaxanthin (144-68-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 2.21 g / CHCl3 / 18 h / 20 °C 2: 11 mg / aq. KOH / propan-2-ol / 24 h / 20 °C 3: 8.5 mg / aq. KOH / propan-2-ol / 3 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 2.21 g / CHCl3 / 18 h / 20 °C 2: 8.5 mg / aq. KOH / propan-2-ol / 3 h / 20 °C View Scheme

<3-(4-hydroxy-2,2,6-trimethylcyclohexenyl)-1-methyl-2-propen-1-yl>triphenylphosphonium bromide → zeaxanthin (144-68-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 11 mg / aq. KOH / propan-2-ol / 24 h / 20 °C 2: 8.5 mg / aq. KOH / propan-2-ol / 3 h / 20 °C View Scheme

Upstream product

• 103955-77-7 (all-E,3S,3'R,5R,6R)-3,6-epoxy-5,6-dihydro-β,β-carotene-3',5-diol 
• 637-05-8 (3R,3'R)-zeaxanthin dipalmitate 
• 7553-56-2 iodine 
• 127-40-2 lutein 
• 7481-64-3 all-trans lutein 
• 14656-56-5 3,3'-di-keto-β-carotene 
• 555-31-7 aluminum isopropoxide 
• 67-63-0 isopropyl alcohol 
• 71-43-2 benzene 
• 502-65-8 lycopene 
• 55452-60-3 15,15'-didehydro-β,β-carotene-3,3'-diol 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 60046-54-0 central-cis-zeaxanthin 

Downstream Products

• 143693-54-3 3,7,12,16-Tetramethyl-1t,18t-bis-((Ξ)-4-propionyloxy-2,2,6-trimethyl-cyclohexen-(6)-yl)-octadecanonaen-(1,3t,5t,7t,9t,11t,13t,15t,17) 
• 637-05-8 (3R,3'R)-zeaxanthin dipalmitate 
• 25494-52-4 O-acetyl-β-citraurin 
• 84432-70-2 C₆₀H₇₀F₆O₆ 
• 84432-70-2 C₆₀H₇₀F₆O₆ 
• 144-68-3 lutein 
• 116877-23-7 2',3'-didehydro-β,β-caroten-3-ol 
• 72002-36-9 (3S,3'S)-zeaxanthin 
• 42273-19-8 2,3,2',3'-tetradehydro-β,β-carotene 
• 153499-20-8 (3R,3'S)-3'-azido-β,β-caroten-3-ol 
• 126412-42-8 (3S,3'S)-3,3'-diazido-β,β-carotene 
• 1107-26-2 trans-β-apo-8'-carotenal 
• 7542-45-2 3,3'-dihydroxy-β,β-carotene-4,4'-dione 

Related news

Singlet oxygen triggers chloroplast rupture and cell death in the Zeaxanthin (cas 144-68-3) epoxidase defective mutant aba1 of Arabidopsis thaliana under high light stress09/29/2019

The two Arabidopsis thaliana mutants, aba1 and max4, were previously identified as sharing a number of co-regulated genes with both the flu mutant and Arabidopsis cell suspension cultures exposed to high light (HL). On this basis, we investigated whether aba1 and max4 were generating high amount...detailed

Randomized, double-blind, placebo-controlled study of Zeaxanthin (cas 144-68-3) and visual function in patients with atrophic age-related macular degeneration09/28/2019

The purpose of this study is to evaluate whether dietary supplementation with the carotenoid zeaxanthin (Zx) raises macula pigment optical density (MPOD) and has unique visual benefits for patients with early atrophic macular degeneration having visual symptoms but lower-risk National Institute ...detailed

Relevant articles and documents

Chemoenzymatic Synthesis of all-trans-Isomers of Lutein and Zeaxanthin

Abstract: A method for the synthesis of all-trans-isomers of lutein and zeaxanthin has been proposed, which includes the stage of esterification of lutein and zeaxanthin with benzoic acid in the presence of enantioselective lipase Novozyme 435. Further hydrolysis of lutein and zeaxanthin dibenzoates has led to the formation of the initial xanthophylls in the all-trans configuration.

A simple and efficient method for the partial synthesis of pure (3R,3’s)-astaxanthin from (3R,3’r,6’r)-lutein and lutein esters via (3R,3’s)-zeaxanthin and theoretical study of their formation mechanisms

Carotenoids are natural compounds that have important roles in promoting and maintaining human health. Synthetic astaxanthin is a highly requested product by the aquaculture industry, but natural astaxanthin is not. Various strategies have been developed

Synthesis of (3 R,3 R)-zeaxanthin and its meso -stereoisomer from (3 R,3 R,6 R)-lutein via (3 R)-3,4-anhydrolutein

A process has been developed for the partial synthesis of (3R,3R)-zeaxanthin and (3R,3S; meso)-zeaxanthin from commercially available (3R,3R,6R)-lutein. This involves the regioselective hydroboration of a dehydration product of lutein, namely (3R)-3,4-didehydro-,-caroten-3-ol [(3R)-3,4-anhydrolutein], to yield a mixture of (3R,3R)-zeaxanthin and (3R,3S; meso)-zeaxanthin followed by separation of these carotenoids by enzyme-mediated acylation. (3R,3R,6R)-Lutein, (3R,3R)-zeaxanthin and its meso-isomer accumulate in human ocular tissues and have been implicated in the prevention of age-related macular degeneration (AMD). Georg Thieme Verlag Stuttgart New York.