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

• 55452-60-3 15,15'-didehydro-β,β-carotene-3,3'-diol 
• 68831-78-7 (3S,5R,6S,3'R)-neoantheraxanthin B'' 
• 60046-54-0 central-cis-zeaxanthin 
• 637-05-8 (3R,3'R)-zeaxanthin dipalmitate 
• 7553-56-2 iodine 
• 116947-92-3 lutein 
• 127-40-2 lutein 
• 144-68-3 zeaxanthin 
• 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 
• 1187923-67-6 (3R,3'S)-zeaxanthin-3-acetate 
• 54422-80-9 (3R)-3-hydroxy-3',4'-didehydro-β,β-carotene 
• 50281-38-4 (3R)-3-hydroxy-β-ionone 

Downstream Products

• 115406-45-6 (all-E,3R,3'R)-β,β-carotene-3,3'-diol 3,3'-diacetate 
• 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 
• 851854-29-0 (3R,3'R,6'R)-lutein 3'-propyl ether 
• 7542-45-2 3,3'-dihydroxy-β,β-carotene-4,4'-dione 
• 1187923-67-6 (3R,3'S)-zeaxanthin-3-acetate 

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).

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.