29414-89-9

Basic information

• Product Name: (3R,3'R,6'R,9-cis)-Carotene-3,3'-diol
• Synonyms: (3R,3'R,6'R,9-cis)-Carotene-3,3'-diol
• CAS NO: 29414-89-9
• Molecular Formula: C₄₀H₅₆O₂
• Molecular Weight: 568.87144
• Mol File: 29414-89-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3R,3'R,6'R,9-cis)-Carotene-3,3'-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,3'R,6'R,9-cis)-Carotene-3,3'-diol(29414-89-9)
• EPA Substance Registry System: (3R,3'R,6'R,9-cis)-Carotene-3,3'-diol(29414-89-9)

Safety Data

• Hazardous Substances Data: 29414-89-9(Hazardous Substances Data)

Usage

Uses

Used in Nutritional Supplements:
(3R,3'R,6'R,9-cis)-Carotene-3,3'-diol is used as a nutritional supplement for its provitamin A properties, helping to support healthy vision, skin, and immune function.
Used in Food Industry:
(3R,3'R,6'R,9-cis)-Carotene-3,3'-diol is used as a natural colorant in the food industry, providing an orange hue to various products.
Used in Pharmaceutical Industry:
(3R,3'R,6'R,9-cis)-Carotene-3,3'-diol is used as an antioxidant in the pharmaceutical industry, helping to protect cells from damage caused by free radicals.
Used in Cosmetic Industry:
(3R,3'R,6'R,9-cis)-Carotene-3,3'-diol is used in cosmetic products for its antioxidant properties, promoting skin health and protection.

Upstream product

• 127-40-2 lutein 
• 23984-55-6 (3R,6'R)-3-hydroxy-β,ε-caroten-3'-one 

Downstream Products

• 23984-55-6 (3R,6'R)-3-hydroxy-β,ε-caroten-3'-one 

Relevant articles and documents

Combination of carotenoids and epi-lutein

The invention describes the preparation and use of carotenoid and epi-lutein compositions to treat various ocular diseases.

Effect of ultrasonic waves on the stability of all-trans lutein and its degradation kinetics

Abstract Ultrasound treatment has been widely applied in the extraction of biologically active compounds including carotenoids. However, there are few reports on their effects on the stability of these compounds. In the present study, the stability of all-trans lutein, one of the carotenoids, was investigated under the action of ultrasound. Results showed that ultrasound induced the isomerization of all-trans lutein to its isomers, namely to 13-cis lutein, 13′-cis lutein, 9-cis lutein and 9′-cis lutein as analyzed by HPLC coupled with DAD and LC-MS; and the percentage of the isomerization increased with increasing both ultrasonic frequency and power. The stability of all-trans lutein in dichloromethane was worst among multiple kinds of solvents. Interestingly, the retention rate of all-trans lutein improved as the temperature increased, which runs counter to the Arrhenius law. Under ultrasound irradiation, the degradation mechanism might be different with various temperatures, the degradation of all-trans lutein followed first-order kinetics at 20 °C, while second-order kinetics was followed at 30-50 °C. As the ultrasonic reaction time prolonged, lutein epoxidation nearly occurred. Those results presented here emphasized that UAE techniques should be carefully used in the extraction of all-trans lutein.

Total synthesis of (3R,3′R,6′R)-lutein and its stereoisomers

(Chemical Equation Presented) (3R,3′R,6′R)-Lutein (1) is a major dietary carotenoid that is abundant in most fruits and vegetables commonly consumed in the U.S. and that accumulates in the human plasma, major organs, and ocular tissues. Numerous epidemiol

Process for Synthesis of (3R,3'R,6'R)-Lutein and its Stereoisomers

(3R,3′R,6′R)-Lutein and (3R,3′R)-zeaxanthin are two dietary carotenoids that are present in most fruits and vegetables commonly consumed in the US. These carotenoids accumulate in the human plasma, major organs, and ocular tissues. In the past decade, numerous epidemiological and experimental studies have shown that lutein and zeaxanthin play an important role in the prevention of age-related macular degeneration (AMD) that is the leading cause of blindness in the U.S. and Western World. The invention provides a process for the synthesis of (3R,3′R,6′R)-lutein and its stereoisomers from commercially available (rac)-α-ionone by a C15+C10+C15 coupling strategy. In addition, the present invention also provides access to the precursors of optically active carotenoids with 3-hydroxy-ε-end group that are otherwise difficult to synthesize. The process developed for the synthesis of lutein and its stereoisomers is straightforward and has potential for commercialization.

Confirmation of the absolute (3R,3′S,6′R)-configuration of (all-E)-3′-epilutein

Circular dichroism (CD) spectroscopy was used to distinguish between the isomeric (all-E)-configured 3′-epilutein (2) and 6′-epilutein (8) to establish the absolute configuration of epilutein samples of different (natural and semisynthetic) origin, including samples of 2 obtained from thermally processed sorrel. Thus, the CD data of lutein (1) and epilutein samples (2) were compared. Our results unambiguously confirmed the (3R,3′S,6′R)- configuration of all epilutein samples. Compound 2 was thoroughly characterized, and its 13C-NMR data are published herewith for the first time.

Separation and identification of carotenoids and their oxidation products in the extracts of human plasma

Eighteen carotenoids as well as vitamin A and two forms of vitamin E (γ- and α-tocopherol) have been separated from extracts of human plasma by high-performance liquid chromatography (HPLC) on reversed-phase and silica-based nitrile-bonded columns. In the order of chromatographic elution on a C18 reversed-phase column, the carotenoids were identified as (3R,3′R,6′R)-β,ε-carotene-3,3′-dlol [(3R,3′R,6′R)-lutein], (3R,3′R)-β,β-carotene-3,3′-dlol [(3R,3′R)-zeaxanthin], 5,6-dihydroxy-5,6-dihydro-ψ,ψ-carotene,3-hydroxy-2′,3′- didehy-dro-β,ε-carotene,β,ε-caroten-3-ol,3-hydroxy-β- carotene,ψ,ψ-carotene, 7,8-dihydro-ψ,ψ-carotene, β,ψ-carotene, 7,8,7′,8′-tetrahydro-′,′-carotene, β,ε-carotene, β,β-carotene, 7,8,11,12,7′,8′-hexahydro-ψ,ψ-carotene, and 7,8,11,12,7′,8′,-11′,12′-octahydro-ψ,ψ-carotene. The polar carotenoids, which eluted in the vicinity of lutein and were unresolved on the C18 column, have been separated on a nitrile-bonded column employing isocratic HPLC conditions. In the order of elution, the carotenoids were ε,ε-carotene-3,3′-dione, 3′-hydroxy-ε,ε-caroten-3-one, 5,6-dihydroxy-5,6-dihydro-ψ,ψ-carotene, 3-hydroxy-β,ε-caroten-3′-one, (all-E,3r,3′R,6′R)-lutein, (all-E,3R,3′R)-zeaxanthin, and (all-E,3R,3′S,6′R)-β,ε-carotene-3,3′-diol (3′-epilutein) followed by several geometrical isomers of lutein and zeaxanthin.

Partial Syntheses of Diastereomeric Carotenols

The application of the Mitsunobu reaction was successfully tested on (3R,3'R)-zeaxanthin, giving the (3S,3'S)-enantiomer and meso form.Applied to natural (3R,3'R,6'R)-lutein, this inversion reaction allowed the preparation of the three other 6'R diastereomers. (3S,3'S,6'R)-lutein with 3',6'-cis-configuration of the ε-ring has not been synthesized before.The observed Cotton effects of the eight lutein diastereomers are rationalized by application of the additivity hypothesis.New trivial names are suggested for the eight lutein isomers on the basis of structural relationships.

DETERMINATION OF THE GEOMETRIC CONFIGURATION OF THE POLYENE CHAIN OF MONO-CIS C40 CAROTENOIDS II A 13C NMR STUDY OF MONO-CIS LUTEINS AND MONO-CIS CAPSANTHINS

Systematic chromatography has resulted in the isolation of four geometric isomers as products of iodine-catalysed isomerisation of lutein. 13C NMR spectral analysis has established their stereochemistry as mono-cis luteins with a cis-configured double bond at C-9, C-9', C-13 and C-13', respectively.Carbon-13 NMR has also provided unambiguous stereochemical assignment for the previously isolated four mono-cis capsanthins.