60046-54-0

Basic information

• Product Name: (3R,3'R,15-cis)-b,b-Carotene-3,3'-diol
• Synonyms: (3R,3'R,15-cis)-b,b-Carotene-3,3'-diol
• CAS NO: 60046-54-0
• Molecular Formula: C₄₀H₅₆O₂
• Molecular Weight: 568.89
• Mol File: 60046-54-0.mol
• Article Data: 45

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3R,3'R,15-cis)-b,b-Carotene-3,3'-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,3'R,15-cis)-b,b-Carotene-3,3'-diol(60046-54-0)
• EPA Substance Registry System: (3R,3'R,15-cis)-b,b-Carotene-3,3'-diol(60046-54-0)

Safety Data

• Hazardous Substances Data: 60046-54-0(Hazardous Substances Data)

Usage

Description

(3R,3'R,15-cis)-β,β-Carotene-3,3'-diol, also known as astaxanthin, is a red-orange pigment found in plants and algae. It is a member of the carotenoid family and is a powerful antioxidant with strong anti-inflammatory properties.

Uses

Used in Skin Health Applications:
Astaxanthin is used as a skin health supplement for its potential benefits in supporting skin health and protecting against UV damage. Its antioxidant and anti-inflammatory properties help to reduce inflammation and oxidative stress, promoting a healthy and youthful appearance.
Used in Exercise Performance Applications:
Astaxanthin is used as a dietary supplement to improve exercise performance. Its antioxidant properties help to reduce muscle damage and inflammation, enhancing recovery and endurance.
Used in Chronic Disease Prevention Applications:
Astaxanthin is being investigated for its potential role in reducing the risk of certain chronic diseases, such as cardiovascular disease and age-related macular degeneration. Its antioxidant and anti-inflammatory properties may help to protect against oxidative stress and inflammation, reducing the risk of these conditions.
Used in Food Industry:
Astaxanthin is commonly used as a natural food dye, particularly in seafood products, to enhance their color and appearance. Its vibrant red-orange hue adds visual appeal and is a healthier alternative to synthetic dyes.
Used in Dietary Supplements:
Astaxanthin is used as a dietary supplement for its potential health benefits, including its antioxidant and anti-inflammatory properties. It can be taken as a standalone supplement or combined with other nutrients to support overall health and well-being.

Upstream product

• 64-17-5 ethanol 
• 7481-64-3 all-trans lutein 
• 141-52-6 sodium ethanolate 
• 71-43-2 benzene 
• 60497-64-5 (9Z)-zeaxanthin 
• 60497-65-6 (3R,3'R)-13-cis-β,β-carotene-3,3'-diol 
• 637-05-8 (3R,3'R)-zeaxanthin dipalmitate 
• 7553-56-2 iodine 
• 106-88-7 ethyloxirane 
• 5056-17-7 (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial 
• 130696-70-7 <(2Z,4E)-5-<(R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl>-3-methylpenta-2,4-dienyl>triphenylphosphonium chloride 
• 127-41-3 alpha-ionone 
• 14398-37-9 (E)-4-<2',6',6'-trimethylcyclohex-2'-enyl>but-3-en-2-one ethylene ketal 
• 1200125-02-5 (rac)-(E)-4-(4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-2,2-ethylenedioxy-3-butene 

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) 
• 115406-45-6 (all-E,3R,3'R)-β,β-carotene-3,3'-diol 3,3'-diacetate 
• 637-05-8 (3R,3'R)-zeaxanthin dipalmitate 
• 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 

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.