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β-Carotene

CAS No.
7235-40-7
Chemical Name:
β-Carotene
Synonyms
β-carotene;Carotene;B-CAROTENE;Daucene;Karotin;PROVITAMIN A;β-Carotene Beadlet;C40H56;SOLATENE;Betacarotin
CBNumber:
CB4148267
Molecular Formula:
C40H56
Molecular Weight:
536.89
MDL Number:
MFCD00001556
MOL File:
7235-40-7.mol
MSDS File:
SDS
Last updated:2024-04-17 13:26:39

β-Carotene 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)
Flash point 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.
InChIKey OENHQHLEOONYIE-JLTXGRSLSA-N
LogP 6.5 at 40℃ and pH6.5
FDA 21 CFR 184.1245; 582.5245; 73.1095; 73.2095; 73.95
Substances Added to Food (formerly EAFUS) BETA-CAROTENE
SCOGS (Select Committee on GRAS Substances) Carotene (beta-carotene)
CAS DataBase Reference 7235-40-7(CAS DataBase Reference)
NCI Dictionary of Cancer Terms beta carotene
FDA UNII 01YAE03M7J
NCI Drug Dictionary beta carotene
ATC code A11CA02,D02BB01
NIST Chemistry Reference «beta» Carotene(7235-40-7)
EPA Substance Registry System .beta.,.beta.-Carotene (7235-40-7)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H319-H315-H252
Precautionary statements  P264-P280-P302+P352-P321-P332+P313-P362-P235+P410-P280-P407-P413-P420-P264-P280-P305+P351+P338-P337+P313P
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
NFPA 704
0
0 0

β-Carotene price More Price(56)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 217538 β-Carotene - CAS 7235-40-7 - Calbiochem VitaminAprecursor. 7235-40-7 1g $81.5 2024-03-01 Buy
Sigma-Aldrich 1065480 Beta Carotene United States Pharmacopeia (USP) Reference Standard 7235-40-7 7x100mg $436 2024-03-01 Buy
TCI Chemical C0560 Beta Carotene >97.0%(E) 7235-40-7 1g $32 2024-03-01 Buy
TCI Chemical C0560 Beta Carotene >97.0%(E) 7235-40-7 5g $94 2024-03-01 Buy
Alfa Aesar H60106 Beta Carotene 7235-40-7 1g $30.7 2024-03-01 Buy
Product number Packaging Price Buy
217538 1g $81.5 Buy
1065480 7x100mg $436 Buy
C0560 1g $32 Buy
C0560 5g $94 Buy
H60106 1g $30.7 Buy

β-Carotene Chemical Properties,Uses,Production

Description

beta-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 Properties

Yellow 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.

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.
β-Carotene

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.

Uses

Beta-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.

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

beta-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.

Safety Profile

When heated to decomposition it emits acrid smoke and irritating fumes.

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.
β-Carotene

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.]

161023-01-4
7235-40-7
Synthesis of β-Carotene from β,β-Carotene, (cis,cis)-
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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 all-trans-beta-caroten All-trans-beta-Carotene beta-Carotene, all-trans- BetaVit C.I. 75130 c.i.75130 Carotaben CAROTENE, beta Cyclohexene, 1,1'-(3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,1 8-diyl)bis*2,6,6-trimethyl-, (all-E)- BETA-CAROTENE BETA CAROTENE NATURAL CAROTENE TYPE II CAROTENE TYPE I CAROTENE, B- BETA-CAROTENE, ~1600 U/MG TRANS-B-CAROTENE, TYPE I, SYNTHETIC B-CAROTENE TYPE II SYNTHETIC Beta-Carotene,Crystalline beta,beta-all-trans-Carotene beta-Carotene,naturalvegetableOilSolution beta-Carotene,naturaldry,waterdispersable beta-Carotene,natural,crystal BETA-CAROTENE,10%,POWDER (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 CAROTENE, B-(SH) BETA-CAROTENESUPPLEMENTS RETRODEHYDRO-BETA-CAROTENE DUNALIELLACAROTENE CAROTENES(VEGETABLE) BETA-CAROTENEEXTRACTSFROMALGAE CAROTENES(ALGAE) CARROTPIGMENT ALGALBETA-CAROTENE BETA-CAROTENEFROMBLAKESLEATRISPORA 15-CIS-BETA-CAROTENE FOODORANGE5 ALL-TRANS-BETA-CARROTENE 9-CIS-BETA-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)- C.I.Food Orange 5 β-Carotine trans-$-Carotene,96% beta-Carotene,95% Carotin Provitanin A β-Carotene,β,β-Carotene, Provitamin A β-Carotene ,97% B-Carotene 1% CWS B-Carotene 1% CWS/M B-Carotene 10% B