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β-Carotene

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β-Carotene Basic information
Product Name:β-Carotene
Synonyms:PROVITAMIN A1;TRANS-B-CAROTENE;TRANS-BETA-CAROTENE;(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);1,1’-(3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-cyclohexen;1,3,5,7,9,11,13,15,17-Octadecanonene,3,7,12,16-tetramethyl-1,18-cyclohex-1-ene,2,6,6-trimethyl-;6-trimethyl-18-diyl)bis((all-e)-6;all-E-beta-Carotene
CAS:7235-40-7
MF:C40H56
MW:536.89
EINECS:230-636-6
Product Categories:chemical reagent;Nutritional Ingredients;Inhibitors;SOLATENE;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Nutraceuticals;Vitamin Ingredients;Intermediates & Fine Chemicals;Pharmaceuticals;Retinoids;Vitamins and derivatives;Antioxidant;Biochemistry;Vitamins;Organics;7235-40-7
Mol File:7235-40-7.mol
β-Carotene Structure
β-Carotene Chemical Properties
Melting point 178-179 °C
Boiling point 644.94°C (rough estimate)
density 1.000
vapor pressure 0.004Pa at 25℃
refractive index 1.5630 (estimate)
Fp 103 °C
storage temp. -20°C
solubility hexane: 100 μg/mL, soluble
form powder
color red to purple
Water Solubility Soluble in hexane, dimethyl sulfoxide, benzene, chloroform, cyclohexane. Insoluble in water.
Sensitive Air & Light Sensitive
Merck 14,1853
BRN 1917416
Stability:Stable, but sensitive to air, heat and light. Store at -20C under nitrogen. Pyrophoric - may ignite spontaneously in air at room temperature.
InChIKeyOENHQHLEOONYIE-JLTXGRSLSA-N
LogP6.5 at 40℃ and pH6.5
CAS DataBase Reference7235-40-7(CAS DataBase Reference)
NIST Chemistry Reference«beta» Carotene(7235-40-7)
EPA Substance Registry System.beta.,.beta.-Carotene (7235-40-7)
Safety Information
Hazard Codes Xn
Risk Statements 44-36/37/38-20/21/22
Safety Statements 7-15-18-36-26-24/25
WGK Germany 1
RTECS FI0329500
1-8-10-16
TSCA Yes
HS Code 32030019
Hazardous Substances Data7235-40-7(Hazardous Substances Data)
MSDS Information
ProviderLanguage
beta,beta-Carotene English
SigmaAldrich English
β-Carotene Usage And Synthesis
Descriptionbeta-Carotene is widely distributed in both plant and animal kingdoms and is the most important pro-vitamin A. In plants, it is almost always found with chlorophyll.
Chemical PropertiesYellow to orange solid.beta-Carotene is insoluble in water, but is available in water-dispersible, oil-dispersible and oil-soluble forms. It has the activity of vitamin A.
OriginatorCarotaben,Hermal,W. Germany,1975
OccurrenceBeta-carotene is available naturally in fruits and vegetables. Synthetically, it may be manufactured from fungi or algae.
UsesBeta-carotene is a known antioxidant, and antioxidants are substances that may protect your cells from free radicals, which may play a role in heart disease, cancer and other diseases. beta-carotene is a coloring agent used in margarine, cheese and pudding to produce the desired color, and is also used as an additive to yellow-orange color. beta-carotene is also a precursor to carotenoids and vitamin A It is beneficial in protecting the skin from dryness and peeling. It also slows cognitive decline and is beneficial to human health.
DefinitionChEBI: A cyclic carotene obtained by dimerisation of all-trans-retinol. A strongly-coloured red-orange pigment abundant in plants and fruit and the most active and important provitamin A carotenoid.
Manufacturing Process3.6 g (0.023 mol) of 3,8-dimethyl-3,5,7-decatrien-1,9-diyne were dissolved in 50 ml of absolute ether, and to the solution was added 0.05 mol of ethereal phenyl-lithium solution. The mixture was refluxed for 30 minutes. Then a solution of 11 g (0.05 mol) of 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-methyl- 2-buten-1-al in 100 ml of ether was added dropwise, and the reaction mixture was boiled for 2 hours. The reaction mixture was then hydrolyzed with aqueous ammonium acetate solution, and the ethereal layer was separated, dried and concentrated. The residue, i.e., 1,18-di(2,6,6-trimethyl-1- cyclohexen-1-yl)-3,7,12,16-tetramethyl-4,15-dihydroxy-2,7,9,11,16- octadecapentaen-5,13-diyne, was a resinous product (having 1.9 active hydrogen atoms and absorption maxima in the ultraviolet spectrum at 326 and 341 nm) which was used for the next step without any further purification. The resin was dissolved in 200 ml of methylene chloride, 10 ml of glacial acetic acid were added to the solution, and the mixture was cooled to - 40°C in a carbon dioxide atmosphere, while stirring. Then, 9 ml of aqueous hydrobromic acid (60%) were added in one portion, the mixture was stirred at -35°C for 1.5 minutes, and subsequently 200 ml of ice water were run into the mixture. After further stirring the mixture for 2 hours at 0°C, the methylene chloride layer was separated, washed with water and sodium bicarbonate solution, dried with Na2SO4 andconcentrated in vacuo. The residue, i.e., 11,12-11',12'-bisdehydro-betta-carotene, was a tough resin or a foamy solid (having no active hydrogen atoms and possessing absorption maxima in the ultraviolet spectrum at 334 and 408 nm). This product can be purified by chromatography. The crude product can also be used for the next step without any preliminary purification.
11.4 g of 11,12-11',12'-bisdehydro-β-carotene were dissolved in 100 ml of petroleum ether (boiling range 80° to100°C), and the solution was hydrogenated under normal conditions after the addition of 0.5 ml of quinoline and 5 g of a lead-poisoned palladium catalyst. After the calculated amount of hydrogen had been absorbed, the catalyst was removed by filtration and the filtrate was extracted with dilute sulfuric acid to remove the quinoline. By concentrating the solution in the usual manner there was obtained 11,12- 11',12'-di-cis-carotene. The product was purified by recrystallization from benzene-alcohol. The purified product melts at 154°C; absorption maxima in the ultraviolet spectrum at 276, 334, 338, 401 and 405 nm. The isomerization was effected by heating the product for 10 hours at 90 to 100°C in high-boiling petroleum ether in a carbon dioxide atmosphere. The resulting and carotene melted at 180°C; ultraviolet absorption maxima at 452 and 480 nm.
Preparation of the intermediates for the above chemical synthesis are also described in US. Patent 2,917,539. The other patents cited below describe a fermentation route. US Patent 2,848,508 describes preparation from carrots.
Brand nameBetaVit (BASF); Lucaratin (BASF); Solatene (Hoffmann-LaRoche).
Therapeutic FunctionVitamin A precursor, Sunscreen agent
General Descriptionbeta-Carotene is an antioxidant and is one of the most important carotenoids and a source of vitamin A. It is abundantly present in fruits and vegetables which is also used as a food supplement and a colorant.
Biochem/physiol ActionsThe most important of the provitamins A, β-carotene can be classified as an antioxidant due to its inhibition of radical initiated peroxidation in vitro. However, in vivo it appears to act either as an antioxidant or a prooxidant depending on cellular environment. It reduces the incidence of many cancers, but enhances lung cancer incidence in smokers.
Side effectsSide effects from β-Carotene include: Skin discoloration (yellowing that eventually goes away); Loose stools; Bruising; Joint pain.
Safety ProfileWhen heated to decomposition it emits acrid smoke and irritating fumes.
SourceThe richest sources of β-Carotene are yellow, orange, and green leafy fruits and vegetables (such as carrots, spinach, lettuce, tomatoes, sweet potatoes, broccoli, cantaloupe, and winter squash). In general, the more intense the color of the fruit or vegetable, the more beta-carotene it has.
Purification MethodsIt forms purple prisms when crystallised from *C6H6/MeOH and red rhombs from pet ether. Its solubility in hexane is 0.1% at 0o. It is oxygen sensitive and should be stored under N2 at -20o in the dark. It gives a deep blue colour with λmax at 590nm when mixed with SbCl3 in CHCl3. UV: (*C6H6) 429infl, max at 454 and 484nm. The principal peak at 454nm has 1cm 1% 2000. [Synthesis: Surmatis & Ofner J Org Chem 26 1171 1961; Milas et al. J Am Chem Soc 72 4844 1950.] β-Carotene is also purified by column chromatography (Al2O3 activity I-II). It is dissolved in pet ether/*C6H6 (10:1), applied to the column and eluted with pet ether/EtOH; the desired fraction is evaporated and the residue is recrystallised from *C6H6/MeOH (violet-red plates). [UV: Inhoffen et al. Justus Liebigs Ann Chem 570 54, 68 1950; Review: Fleming Selected Organic Synthesis (J Wiley, Lond) pp. 70-74 1973.] Alternatively it can be purified by chromatography on a magnesia column, thin layer of Kieselguhr or magnesia. Crystallise it from CS2/MeOH, Et2O/pet ether, acetone/pet ether or toluene/MeOH. Store it in the dark, under an inert atmosphere, at -20o. Recrystallise it also from 1:1 EtOH/CHCl3. [Bobrowski & Das J Phys Chem 89 5079 1985, Johnston & Scaiano J Am Chem Soc 1 0 8 2349 1986, Strain J Biol Chem 105 523 1934, Meth Biochem Anal 4 1 1957, Beilstein 5 II 638, 5 III 2453, 5 IV 2617.]
Tag:β-Carotene(7235-40-7) Related Product Information
trans,trans-2,4-Undecadienal (3R,3R')-beta,beta-carotene-3,3'-diyl dipalmitate Fucoxanthin ω,ω-Carotene, 2,6,10,14,19,23,27,31-Octamethyl-dotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene all-trans-a-Carotene,Carotene,R(+)-alpha-Carotene,α-Carotene solution,-Carotene(natural),(6'R)-b,e-Carotene,TRANSALPHA-CAROTENE,ALPHA/BETA-CAROTENE MIX beta-Carotene-4,4'-diol dipalmitate,beta-Carotene-4,4'-diol dipalmitate Caricaxanthin, Hydroxy-β-carotene ,-Carotene-4,4'-dione,BETA,BETA-CAROTENE-4,4'-DIONE,all-trans,beta-carotene-4,4’-dion (3R,3’R)-Dihydroxy--carotene,all-trans--Carotene-3,3’-diol,b,b-Carotene-3,3'-diol, (3R,3'R),BETA,BETA-CAROTENE-3,3'-DIOL,(3R,3'R)-beta,beta-Carotene-3,3'-diol 3,3'-dihydro-beta,beta-carotene-4,4'-dione ,3,3'-DIHYDROXY-B,B-CAROTENE-4,4'-DIONE Methylglyoxal 1,1-dimethyl acetal α-Carotene-3,3μ-diol, β, ε-carotene-3,3μ-diol, β, ε-carotene, Lutein,6'-Hydro-4',5'-dehydro-b-carotene-3,3'-diol,β,ε-Carotene-3,3'-diol,(3R,3'R,6'R)- Astaxanthin NeoB-beta-Carotene 5,6-epoxy-beta,beta-carotene ZETA-CAROTENE decapreno-beta-carotene β-Carotene