29065-03-0

Basic information

• Product Name: β,β-Carotene-4,4'-diol
• Synonyms: Isozeaxanthin;β,β-Carotene-4,4'-diol
• CAS NO: 29065-03-0
• Molecular Formula: C₄₀H₅₆O₂
• Molecular Weight: 568.87144
• Mol File: 29065-03-0.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Stability: Light Sensitive, Temperature Sensitive
• CAS DataBase Reference: β,β-Carotene-4,4'-diol(CAS DataBase Reference)
• NIST Chemistry Reference: β,β-Carotene-4,4'-diol(29065-03-0)
• EPA Substance Registry System: β,β-Carotene-4,4'-diol(29065-03-0)

Safety Data

• Hazardous Substances Data: 29065-03-0(Hazardous Substances Data)

Usage

Description

β,β-Carotene-4,4'-diol, also known as Isozeaxanthin, is an antioxidant β-carotene derivative found in soybean oil. It possesses potent antioxidant properties and has been identified for its anti-cancer properties.

Uses

Used in Anticancer Applications:
β,β-Carotene-4,4'-diol is used as an anticancer agent for its ability to exhibit antioxidant properties and combat cancer cells. Its presence in soybean oil makes it a natural and potentially beneficial component in the fight against cancer.
Used in Food Industry:
β,β-Carotene-4,4'-diol is used as a natural antioxidant in the food industry to extend the shelf life of products and protect them from oxidative damage, thus maintaining their quality and nutritional value.
Used in Pharmaceutical Industry:
β,β-Carotene-4,4'-diol is used as a potential therapeutic agent in the pharmaceutical industry due to its anti-cancer properties. It may be incorporated into drug formulations or supplements to support cancer treatment and prevention.

Upstream product

• 7235-40-7 beta-carotene 
• 817203-15-9 rac-(E)-3-(2-iodovinyl)-2,4,4-trimethylcyclohex-2-en-1-ol 
• 1353023-69-4 rac-(E)-tert-butyl-[3-(2-iodovinyl)-2,4,4-trimethylcyclohex-2-enyloxy]dimethylsilane 
• 1353023-70-7 rac-all-trans-4-(tert-butyldimethylsilyloxy)retinol 
• 1353023-71-8 rac-all-trans-4-(tert-butyldimethylsilyloxy)retinal 
• 1353023-74-1 rac-tert-butyl-{3-[(1E,3E,5E,7E)-3,7-dimethyldeca-1,3,5,7,9-pentaenyl]-2,4,4-trimethylcyclohex-2-enyloxy}dimethylsilane 
• 14398-34-6 4-(3-hydroxy-2,6,6-trimethylcyclohex-1-enyl)but-3-en-2-one 
• 127-41-3 alpha-ionone 
• 190059-33-7 (E)-4-(1,3,3-Trimethyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-but-3-en-2-one 
• 5056-17-7 (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial 
• 4441-44-5 3',4'-didehydro-β,β-caroten-4-ol 
• 991-90-2 3',4'-didehydro-β,β-caroten-4-one 
• 25394-27-8 isocryptoxanthin 
• 514-78-3 canthaxanthin 

Downstream Products

• 13761-10-9 retro-bisdehydrocarotene 
• 846539-06-8 4'-acetylthio-β,β-carotene 
• 514-78-3 canthaxanthin 
• 106356-06-3 4'-hydroxy-β,β-caroten-4-one 
• 128260-91-3 4,4'-diacetylthio-β,β-carotene 
• 1225465-70-2 C₇₄H₈₀O₉S 
• 1225465-68-8 C₁₀₈H₁₀₈O₁₈S₂ 
• 58540-69-5 4,4'-diacetoxy-β,β-carotene 

Relevant articles and documents

Practical synthesis of canthaxanthin

In this study, a novel route for the total synthesis of canthaxanthin is described. The synthesis is firstly based on an epoxidation of α-ionone with metachloroperbenzoic acid to afford the epoxide, followed by conversion of the epoxide to 3-hydroxyl-β-ionone in the presence of sodium methoxide. Next, 3-hydroxyl-C14-aldehyde was obtained by a Darzens condensation with 4-hydroxyl-β-ionone and methyl chloroacetate, which can be converted to 3-hydroxyl-C15-phophonate via a Wittig–Horner condensation with tetraethyl methylenebisphosphonate. Then, a Wittig–Horner condensation with 3-hydroxyl-C15-phosphonate and C10-trienedial resulted in 4,4′-dihydroxyl-β-carotene, followed by an oxidation afforded the target product canthaxanthin. The overall yield of this route is 37% from α-ionone. The synthetic steps are easily operated and are practical for the large-scale production.

Nucleophilic reactions of charge delocalised carotenoid mono- and dications

In the present study insight was gained on the larger complexity of cationic mixtures of diaryl (φ,φcarotene, isorenieratene) and aliphatic (Φ,Φ-carotene, lycopene) carotenes, prepared by reaction with BF 3-etherate, compared with β,β-carotene. Chemical reactions of the mono- and dications prepared in situ from the allylic carotenols β,β-caroten-4-ol (isocryptoxanthin) and β,β-carotene-4,4'- diol (isozeaxanthin), and from isorenieratene and lycopene were investigated using selected O, N and S nucleophiles; water, methanol, azide and thioacetate. In total 22, including 18 new, neutral carotenoid products were isolated and identified by VIS, MS and NMR (in part) spectroscopy. Their structures were compatible with the structures of the cationic intermediates. The formal addition of hydride to the various dications, required to rationalise minor reaction products, is discussed in terms of more likely hydrogen radical or proton transfer in cationic reactions. Extensive E/Z isomerisation was observed for all quenching products. The potential use of carotenoid cations for the synthesis of 4,(4')-substituted β,β-carotenes and 7-oxabicycloheptane derivatives is discussed.

Electronic Relaxation in Long Polyenes

A series of carotenols with from 7 to 11 conjugated double bonds have been synthesized and purified using HPLC techniques.Absorption, fluorescence, and fluorescence excitation spectra have been obtained in 77 K glasses.The shorter members of this series e