| Identification | More | [Name]
beta-Carotene | [CAS]
7235-40-7 | [Synonyms]
B-CAROTENE
BETA,BETA-CAROTANE
BETA,BETA-CAROTENE
BETA-CAROTENE
BETA CAROTENE NATURAL
CAROTENE, B-
CAROTENE TYPE I
CAROTENE TYPE II
PROVITAMIN A
PROVITAMIN A1
SOLATENE
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
all-trans-beta-caroten
All-trans-beta-Carotene | [EINECS(EC#)]
230-636-6 | [Molecular Formula]
C40H56 | [MDL Number]
MFCD00001556 | [Molecular Weight]
536.87 | [MOL File]
7235-40-7.mol |
| Chemical Properties | Back Directory | [Appearance]
solid | [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
| [Stability:]
Stable, but sensitive to air, heat and light. Store at-20C under nitrogen. Pyrophoric-may ignite spontaneously in air at room temperature. | [Water Solubility ]
Soluble in hexane, dimethyl sulfoxide, benzene, chloroform, cyclohexane. Insoluble in water. | [Sensitive ]
Air & Light Sensitive | [Usage]
Most important of the provitamins A. Widely distributed in the plant and animal kingdom. In plants it occurs almost always together with chlorophyll. Vitamin A precursor. Ultraviolet screen | [Detection Methods]
HPLC | [Merck ]
1853 | [BRN ]
1917416 | [InChIKey]
OENHQHLEOONYIE-JLTXGRSLSA-N | [LogP]
6.5 at 40℃ and pH6.5 | [Uses]
Beta-Carotene(7235-40-7) is a colorant that is a carotenoid producing a yellow
to orange hue. it has good tinctorial strength, fair light stability,
poor oxidation stability, and good ph stability. it is insoluble in
water but is available in water-dispersible, oil-dispersible, and oil-
soluble forms. it has vitamin a activity. it has a natural resistance to
ascorbic acid reduction in beverages and thus is used in orange-
colored liquid products. it is used in margarine, oils, cheese, and
puddings at levels required to produce the desired color. related
colorants are canthaxanthin and beta-apo-8-carotenal.
| [CAS DataBase Reference]
7235-40-7(CAS DataBase Reference) | [NIST Chemistry Reference]
«beta» Carotene(7235-40-7) | [Storage Precautions]
Light sensitive;Air sensitive;Store under nitrogen | [EPA Substance Registry System]
7235-40-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R44:Risk of explosion if heated under confinement.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S7:Keep container tightly closed .
S15:Keep away from heat .
S18:Handle and open container with care .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
1
| [RTECS ]
FI0329500
| [F ]
1-8-10-16 | [TSCA ]
Yes | [HS Code ]
29362100 | [Safety Profile]
When heated to
decomposition it emits acrid smoke and
irritating fumes. | [Hazardous Substances Data]
7235-40-7(Hazardous Substances Data) |
| Hazard Information | Back Directory | [Description]
b-Carotene(7235-40-7) is applied as a food coloring additive, as provitamin A in food and
feed, in multivitamin products, as an antioxidant, and as a colorant for cosmetics.
In the literature, a number of microorganisms are described that are capable of
accumulating b-carotene up to relatively high levels, for example, the fungi
B. trispora, Phycomyces blakesleanus, the yeast Rhodotorula glutinis, and the
above-mentioned alga D. salina. Production processes were developed with
mutants of B. trispora in the former Soviet Union (cf. Sect. 2.3) and for D. salina.
Among the b-carotene–producing algae, D. salina is currently the best-known
and most efficient producer: D. salina cells are able to synthesize b-carotene in
levels a thousand times higher than those of carrots. Dunaliella is also able to
synthesize a-carotene, violaxanthin, neoxanthin, zeaxanthin, and lutein. The unicellular
green alga D. salina is grown in open ponds without (hardly any) process
control. It was shown that the highest production levels were
obtained with high light intensities, nitrogen limitation, and stress-inducing temperatures. This has resulted in b-carotene levels up to 12 % of the dry mass.
The production facilities are located in places where optimum conditions are
found, namely in Australia, Israel, and in the United States; these places benefit
from a lot of sunshine, little cloudiness, the availability of saline water, and high
average temperatures.
| [Chemical Properties]
solid | [Physical properties]
β-Carotene is a tetraterpene with 11 conjugated double bonds that give the molecule an orange color. It is a carotenoid compound that is present in large quantities in the human diet and subsequently is found in all human tissues, including blood. High temperature encourages the isomerization of the double bonds, which lightens the color. Absorption (blue) and fluorescence emission (red) spectra at four excitation wavelengths from β-carotene in hexane solvent at 23 °C are shown below.
| [Originator]
Carotaben,Hermal,W. Germany,1975 | [Occurrence]
Beta-carotene is available naturally in fruits and vegetables. Synthetically, it may be manufactured from fungi or algae. | [Definition]
ChEBI: 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 Process]
3.6 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 name]
BetaVit (BASF); Lucaratin (BASF);
Solatene (Hoffmann-LaRoche). | [Therapeutic Function]
Vitamin A precursor, Sunscreen agent | [General Description]
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
β-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 Actions]
The 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 effects]
Side effects from β-Carotene include:
Skin discoloration (yellowing that eventually goes away); Loose stools; Bruising; Joint pain. | [Source]
The 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. | [Properties and Applications]
： yellow to orange. | [Purification Methods]
It 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.] |
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