beta-Carotene

Base Information

• Chemical Name: beta-Carotene
• CAS No.: 7235-40-7
• Molecular Formula: C40H56
• Molecular Weight: 536.885
• Hs Code.: 2936.10
• Mol file: 7235-40-7.mol

Synonyms:Provitamin A;beta Carotene;CPD1F-129;Cyclohexene, 1,1-(3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis(2,6,6-trimethyl-, (all-E)-;trans-B-Carotene;KPMK;Betacarotenum [Latin];(1E,3Z,5E,7Z,9E,11E,13E,15E)-3,7,12,16-tetramethyl-1,18-bis(2,6,6-trimethyl-1-cyclohexenyl)octadeca-1,3,5,7,9,11,13,15,17-nonaene;(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-1,18-bis(2,6,6-trimethyl-1-cyclohexenyl)octadeca-1,3,5,7,9,11,13,15,17-nonaene;a,a-Carotene;Cyclohexene, 1,1-(3,7,12,16-tetramethyl-1,3,5, 7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis[2,6,6-trimethyl-, (all-E)-;all-trans-.beta.-Carotene;Solatene (caps);beta-Karotin;Cyclohexene, 1,1-(3,7,12,16-tetramethyl-1,3,5, {7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis[2,6,6-trimethyl-,} (all-E)-;Zlut prirodni 26 [Czech];Lucarotin;Provatene;(all-E)-1,1-(3,7,12,16-Tetramethyl-1,3,5, 7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis[2,6, 6-trimethylcyclohexene];Food orange 5;Betacaroteno [Spanish];all-trans-beta-Carotene;.beta.-Carotene, all-trans-;1,1-(3,7,12,16-Tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis(2,6,6-trimethylcyclohexene), (all E)-;Karotin [Czech];31797-85-0;(all-E)-1,1-(3,7,12,16-Tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis(2,6,6-trimethylcyclohexene);Solatene;Betacaroteno [INN-Spanish];b-Carotene;Diet,beta-carotene supplementation;beta,beta-Carotene;3,7,12,16-tetramethyl-1,18-bis(2,6,6-trimethyl-1-cyclohexenyl)octadeca-1,3,5,7,9,11,13,15,17-nonaene;Carotaben;beta-Carotene, all-trans-;β-Carotene;B-Carotene; Carotin; Provitanin A;Beta- Carotene Beta;natracol beta carotene wsp1;beta-Carotene natural;

Chemical Property of beta-Carotene

Chemical Property:

• Appearance/Colour: red to purple power
• Vapor Pressure: 2.71E-16mmHg at 25°C
• Melting Point: 176-184 °C (dec.)
• Refractive Index: 1.565
• Boiling Point: 654.7 °C at 760 mmHg
• Flash Point: 346 °C
• PSA: 0.00000
• Density: 0.941 g/cm³
• LogP: 12.60580
• Storage Temp.: −20°C
• Sensitive.: Air & Light Sensitive
• Solubility.: hexane: 100 μg/mL, soluble
• Water Solubility.: Soluble in hexane, dimethyl sulfoxide, benzene, chloroform, cyclohexane. Insoluble in water.

Purity/Quality:

99% ^*data from raw suppliers

Beta Carotene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 44-36/37/38-20/21/22
• Safety Statements: 7-15-18-36-26-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Precursor of Vitamin A (Retinol): Beta-carotene is enzymatically cleaved in the intestinal mucosa to form two molecules of vitamin A (retinol), making it an important provitamin A compound. Vitamin A is essential for various bodily functions, including vision, immune system function, and skin health.
• Antioxidant Properties: Beta-carotene acts as an antioxidant, helping to neutralize activated oxygen molecules that can damage cells. Its antioxidant properties contribute to protecting cells from oxidative stress and reducing the risk of chronic diseases associated with oxidative damage.
• Cancer Prevention: Dietary intake of beta-carotene-containing foods has been associated with cancer prevention. Beta-carotene's antioxidant properties may help reduce the risk of certain types of cancer by neutralizing free radicals and protecting cells from damage.
• Food Industry Applications: Beta-carotene is used in the food industry as a natural pigment and nutrient additive. It provides color to various food products and serves as a source of provitamin A, enhancing the nutritional value of processed foods.
• Nutritional Benefits: Beta-carotene is an important nutrient for human health, contributing to overall well-being and functioning. Despite low absorption from natural sources, beta-carotene intake from foods is generally considered beneficial and safe.
• Synthesis and Extraction Methods: Beta-carotene can be obtained through various methods, including extraction from natural resources (plants or algae), chemical synthesis, biosynthesis, and genetic engineering. Extraction methods include organic solvent extraction, ultrasonic wave extraction, supercritical fluid extraction (SFE), enzymatic extraction, and innovative synthesis techniques.
• Potential Role in Cognitive Health: Recent research suggests a potential association between beta-carotene intake and the maintenance of cognitive function. Beta-carotene, either alone or in combination with other dietary compounds, may play a role in maintaining mental health and cognitive performance, possibly acting synergistically with other micronutrients.

Technology Process of beta-Carotene

There total 156 articles about beta-Carotene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.5%

β-carotene (161023-01-4) → beta-carotene (7235-40-7)

Guidance literature:

With rhodium chloride solid catalyst; at 45 ℃; for 15h; Temperature;

Reference yield: 95.0%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + (1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol (59057-30-6) + triphenylphosphine (603-35-0) → beta-carotene (7235-40-7)

Guidance literature:

(1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol; triphenylphosphine; With hydrogenchloride; In methanol; water; at 45 ℃; for 1h;

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial; With 1,2-bis (3-methylimidazolium-1-yl) ethane dihydroxide; sodium carbonate; In methanol; water; at 20 ℃; for 3h; Reagent/catalyst; Temperature; Inert atmosphere;

Reference yield: 90.6%

Retinol acetate (127-47-9,64536-04-5) → beta-carotene (7235-40-7)

Guidance literature:

Retinol acetate; With sulfuric acid; triphenylphosphine; In methanol; at 0 - 5 ℃; for 10.5h;

With palladium diacetate; fipronilβ-cyclodextrin; In ethanol; dichloromethane; water; for 8h; under 16501.7 Torr; Reagent/catalyst; Solvent; Pressure; Temperature; Autoclave;

upstream raw materials:

hexane

15-cis-β-carotene

sodium ethanolate

9-cis-β-carotene

Downstream raw materials:

isocryptoxanthin

4-methoxy-β,β-carotene

3,4,3',4'-tetradehydro-β,β-carotene

canthaxanthin

Refernces

Cross metathesis of β-carotene with electron-deficient dienes. A direct route to retinoids

10.1016/j.tetlet.2009.06.032

The study focuses on the cross metathesis (CM) reactions of β-carotene with electron-deficient dienes, specifically using the Hoveyda second generation catalyst, to synthesize retinoids, which are compounds related to vitamin A and play a crucial role in various biological processes such as vision, reproduction, cell differentiation, and growth. The primary chemicals used in the study include β-carotene, ethyl (2E,4E/Z)-3-methylhexa-2,4-dienoate, and the Hoveyda II catalyst. The purpose of these chemicals is to undergo CM reactions, which are a type of olefin metathesis reaction that forms new carbon-carbon bonds under mild conditions, to produce retinoids like ethyl all-trans-retinoate. The study explores the regioselectivity and diastereoselectivity of these reactions, aiming to develop an effective and fast method for the preparation of retinoids for biological and structural studies.

Molecular-shape selectivity by molecular gel-forming compounds: Bioactive and shape-constrained isomers through the integration and orientation of weak interaction sites

10.1039/c1cc13397g

The study investigates a molecular gel system assembled on carrier particles for the separation of bioactive and shape-constrained isomers of tocopherols, β-carotene, and polycyclic aromatic hydrocarbons (PAHs). The key chemical involved is poly(octadecyl acrylate)-grafted silica (Sil-ODAn), which forms nanogels with temperature-responsive phase transitions, enhancing selectivity for PAHs through multiple carbonyl–π interactions at lower temperatures. Another crucial component is the L-glutamide-derived low-molecular organogelator, which forms a gel containing nanometre-scale organized assemblies in organic solvents and can be immobilized onto silica to create a functional group-integrated organic phase (Sil-FIP). This Sil-FIP phase demonstrates significantly higher molecular shape selectivity compared to conventional phases like monomeric and polymeric C18, and C30 columns, enabling the separation of challenging isomers such as β- and γ-tocopherol and β-carotene isomers.

Synthesis of C15,C14′-ring locked all-trans-β-carotene

10.1016/S0040-4039(02)00663-9

The study presents the synthesis of a C15,C14-ring locked all-trans-β-carotene analog, which is a significant compound due to its role in the production of retinoids, essential for vision and cell differentiation. The synthesis involved the use of various chemicals, including cyclohexenone-3-carboxaldehyde, diethyl(1-cyanoethyl)phosphonate, and β-ionone, which served as starting materials and reagents in the reaction sequences. Key reactions such as Wittig and HWE olefinations were employed to construct the carbon framework, with the final product being synthesized through bis-olefination with a C15 ylide bearing the ionone moiety. This unnatural β-carotene analog preserves molecular connectivity upon oxidative cleavage, which is crucial for isotopic labeling studies to determine the source of oxygen in retinal production. The synthesized compound will be used for enzymatic oxidation studies, furthering understanding of β-carotene-15,15'-dioxygenase (BCDOX), an enzyme vital for retinoid production.

Isolation and Identification of the Polyenes Formed During the Thermal Degradation of β,β-Carotene

10.1021/jo00157a026

The research investigates the thermal degradation of β,β-carotene to understand the mechanisms by which carotenoids are converted to aromatic products, with the hypothesis that carotenoid natural products may be a source of the aromatic fraction of petroleum. Four polyene intermediates were isolated and identified during this process: 1,12-bis(2,6,6-trimethylcyclohex-1-enyl)-3,6,10-trimethyldodeca-1,3,5,7,9,11-hexaene, 1,12-bis(2,6,6-trimethylcyclohex-1-enyl)-3,7-dimethyl-dodeca-1,3,5,7,9,11-hexaene, 1,6-bis(2,6,6-trimethylcyclohex-1-enyl)-3-methylhexa-1,3,5-triene, and 1,6-bis(2,6,6-trimethylcyclohex-1-enyl)hexa-1,3,5-triene. Independent syntheses confirmed the structures of these polyene intermediates, with 'H NMR establishing the type and number of methyl substituents and mass spectra of the saturated analogues confirming the positions of the in-chain methyl substituents. The study suggests that β,β-carotene thermally degrades by a series of symmetry-allowed electrocyclic processes followed by a thermal elimination, but also indicates that disproportionation reactions occur, as evidenced by the presence of 1,1,3-trimethylcyclohexane and long-chain aromatics. Key chemicals involved in the research include β,β-carotene, the polyene intermediates, diethyl (cyanomethyl)phosphonate, sodium hydride, diisobutylaluminum hydride, methanolic HCl, triphenylphosphine, and retinyltriphenylphosphonium chloride, among others used in the synthesis and identification processes.