72002-36-9

Basic information

• Product Name: (3S,3'S)-zeaxanthin
• Synonyms: (3S,3'S)-zeaxanthin
• CAS NO: 72002-36-9
• Molecular Weight: 568.883
• Mol File: 72002-36-9.mol
• Article Data: 46

Chemical Properties

• CAS DataBase Reference: (3S,3'S)-zeaxanthin(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,3'S)-zeaxanthin(72002-36-9)
• EPA Substance Registry System: (3S,3'S)-zeaxanthin(72002-36-9)

Safety Data

• Hazardous Substances Data: 72002-36-9(Hazardous Substances Data)

Usage

Description

(3S,3'S)-Zeaxanthin, a carotenoid pigment, is found in plants, algae, and microorganisms. It is a stereoisomer of zeaxanthin, known for its antioxidant properties and is characterized by its yellow pigmentation. (3S,3'S)-zeaxanthin is prevalent in various fruits and vegetables, such as peppers, corn, and egg yolks, and plays a crucial role in human health and nutrition.

Uses

Used in Eye Health Applications:
(3S,3'S)-Zeaxanthin is used as a natural blue light filter in the human body, specifically in the macula of the eye, to protect the retina from damage. Its presence in the eye helps maintain optimal vision and overall ocular health.
Used in Nutritional Supplements:
(3S,3'S)-Zeaxanthin is used as an essential nutrient in the formulation of dietary supplements, contributing to the maintenance of good health and well-being.
Used in Pharmaceutical Applications:
(3S,3'S)-Zeaxanthin is used as a potential therapeutic agent for reducing the risk of age-related macular degeneration and other eye-related conditions, due to its antioxidant properties and its role in protecting the retina.
Used in Food Industry:
(3S,3'S)-Zeaxanthin is used as a natural colorant in the food industry, adding a vibrant yellow hue to various products while also providing health benefits due to its antioxidant properties.
Used in Agricultural Applications:
(3S,3'S)-Zeaxanthin is used in the agricultural sector to enhance the nutritional value of crops, particularly those known for their health benefits, such as peppers and corn.

Upstream product

• 106-88-7 ethyloxirane 
• 5056-17-7 (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial 
• 62742-02-3 (all-E)-(3R)-3-hydroxy-12'-apo-β-caroten-12'-al 
• 54422-80-9 (3R)-3-hydroxy-3',4'-didehydro-β,β-carotene 
• 127-40-2 lutein 
• 1187923-67-6 (3R,3'S)-zeaxanthin-3-acetate 
• 444122-15-0 (S)-4-[(E)-but-1-en-3-ynyl]-3,5,5-trimethylcyclohex-3-en-1-ol 
• 444122-14-9 (S,E)-tert-butyldimethylsilyl 4-(but-1-en-3-yn-1-yl)-3,5,5-trimethylcyclohex-3-en-1-yl ether 
• 83021-07-2 (S,E)-4-[4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one 
• 444122-13-8 tert-butyldimethylsilyl (R)-4-iodo-3,5,5-trimethylcyclohex-3-en-1-yl ether 
• 6153-06-6 3-methylpent-2-en-4-yn-1-ol 
• 444122-16-1 (R)-4-((1E,3E)-4-iodo-3-methylbuta-1,3-dien-1-yl)-3,5,5-trimethylcyclohex-3-en-1-ol 
• 106895-13-0 (E)-3-methyl-5-(trimethylsilyl)-pent-2-en-4-ynal 

Downstream Products

• 84432-70-2 C₆₀H₇₀F₆O₆ 
• 84432-70-2 C₆₀H₇₀F₆O₆ 
• 144-68-3 lutein 
• 116877-23-7 2',3'-didehydro-β,β-caroten-3-ol 
• 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 
• 60497-65-6 (3R,3'R)-13-cis-β,β-carotene-3,3'-diol 
• 87891-75-6 (3R,3'R)-zeaxanthin palmitate 
• 637-05-8 (3R,3'R)-zeaxanthin dipalmitate 
• 1187923-67-6 (3R,3'S)-zeaxanthin-3-acetate 
• 1353023-75-2 zeaxanthin t-butyldimethylsilylether 

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.

Bidirectional Hiyama–Denmark Cross-Coupling Reactions of Bissilyldeca-1,3,5,7,9-pentaenes for the Synthesis of Symmetrical and Non-Symmetrical Carotenoids

The construction of the carotenoid skeleton by Pd-catalyzed Csp2?Csp2 cross-coupling reactions of symmetrical and non-symmetrical 1,10-bissilyldeca-1,3,5,7,9-pentaenes and the corresponding complementary alkenyl iodides has been developed. Reaction conditions for these bidirectional and orthogonal Hiyama–Denmark cross-coupling reactions of bisfunctionalized pentaenes are mild and the carotenoid products preserve the stereochemical information of the corresponding oligoene partners. The carotenoids synthesized in this manner include β,β-carotene and (3R,3′R)-zeaxanthin (symmetrical) as well as 9-cis-β,β-carotene, 7,8-dihydro-β,β-carotene and β-cryptoxanthin (non-symmetrical).

Process or synthesis of (3S)- and (3R)-3-hydroxy-beta-ionone, and their transformation to zeaxanthin and beta-cryptoxanthin

Disclosed is a process for the synthesis of (3R)-3-hydroxy-β-ionone and its (3S)-enantiomer in high optical purity from commercially available (rac)-α-ionone. The key intermediate for the synthesis of these hydroxyionones is 3-keto-α-ionone ketal that was prepared from (rac)-α-ionone after protection of this ketone as a 1,3-dioxolane. Reduction of 3-keto-α-ionone ketal followed by deprotection, lead to 3-hydroxy-α-ionone that was transformed into (rac)-3-hydrox-β-ionone by base-catalyzed double bond isomerization in 46% overall yield from (rac)-α-ionone. The racemic mixture of these hydroxyionones was then resolved by enzyme-mediated acylation in 96% ee. (3R)-3-Hydroxy-β-ionone and its (3S)-enantiomer were respectively transformed to (3R)-3-hydroxy-(β-ionylideneethyl)triphenylphosphonium chloride [(3R)-C15-Wittig salt] and its (3S)-enantiomer [(3S)-C15-Wittig salt] according to known procedures. Double Wittig condensation of these Wittig salts with commercial available 2,5- dimethtylocta-2,4,6-triene-1,8-dial provided all 3 stereoisomers of zeaxanthin. Similarly, (3R)-C15-Wittig and its (3S)-enantiomer were each coupled with β-apo-12′-carotenal.