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
• Article Data: 9

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

General Description

(3R,3'R,6'R,9-cis)-Carotene-3,3'-diol is a type of carotenoid, a group of pigments found in plants that are responsible for their vibrant colors. It is a type of β-carotene, which is a precursor to vitamin A. This specific carotenoid is known for its antioxidant properties, which can help protect cells from damage caused by free radicals. Additionally, it is a provitamin A carotenoid, meaning that it can be converted into vitamin A in the body, which is essential for maintaining healthy vision, skin, and immune function. Its chemical structure consists of a long chain of alternating double and single bonds, which gives it its characteristic orange color. (3R,3'R,6'R,9-cis)-Carotene-3,3'-diol is commonly found in fruits and vegetables, such as carrots, sweet potatoes, and spinach, and is an important part of a healthy diet.

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.

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.