Names | |
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IUPAC name
beta,beta-Carotene
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Systematic IUPAC name
1,3,3-Trimethyl-2-[3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene
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Other names
Betacarotene, β-Carotene, Food Orange 5, Provitamin A, 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]
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Identifiers | |
7235-40-7 | |
3D model (Jmol) | Interactive image |
ChEBI | CHEBI:17579 |
ChEMBL | ChEMBL1293 |
ChemSpider | 4444129 |
ECHA InfoCard | 100.027.851 |
EC Number | 230-636-6 |
E number | E160a(i) (colours) |
PubChem | 5280489 |
UNII | 01YAE03M7J |
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Properties | |
C40H56 | |
Molar mass | 536.89 g·mol−1 |
Appearance | Dark orange crystals |
Density | 0.941 g/cm3 |
Melting point | 176–184 °C (349–363 °F; 449–457 K) decomposes |
Boiling point | 654.7 °C (1,210.5 °F; 927.9 K) at 760 mmHg |
Insoluble | |
Solubility | Soluble in CS2, benzene, CHCl3, ethanol Insoluble in glycerin |
Solubility in dichloromethane | 4.51 g/kg (20 °C) |
Solubility in hexane | 0.1 g/L |
log P | 14.764 |
Vapor pressure | 2.71·10−16 mmHg |
Refractive index (nD)
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1.565 |
Pharmacology | |
A11CA02 (WHO) D02BB01 (WHO) | |
Hazards | |
EU classification (DSD)
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Xn |
R-phrases | R20/21/22, R36/37/38, R44 |
S-phrases | S7, S15, S18, S26, S36 |
NFPA 704 | |
Flash point | 103 °C (217 °F; 376 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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what is ?) | (|
Infobox references | |
β-Carotene is an organic, strongly colored red-orange pigment abundant in plants and fruits. It is a member of the carotenes, which are terpenoids (isoprenoids), synthesized biochemically from eight isoprene units and thus having 40 carbons. Among the carotenes, β-carotene is distinguished by having beta-rings at both ends of the molecule. β-Carotene is biosynthesized from geranylgeranyl pyrophosphate.
β-Carotene is the most common form of carotene in plants. When used as a food coloring, it has the E number E160a. The structure was deduced by Karrer et al. in 1930. In nature, β-carotene is a precursor (inactive form) to vitamin A via the action of beta-carotene 15,15'-monooxygenase.
Isolation of β-carotene from fruits abundant in carotenoids is commonly done using column chromatography. It can also be extracted from the beta-carotene rich algae, Dunaliella salina. The separation of β-carotene from the mixture of other carotenoids is based on the polarity of a compound. β-Carotene is a non-polar compound, so it is separated with a non-polar solvent such as hexane. Being highly conjugated, it is deeply colored, and as a hydrocarbon lacking functional groups, it is very lipophilic.
Plant carotenoids are the primary dietary source of provitamin A worldwide, with β-carotene as the most well-known provitamin A carotenoid. Others include α-carotene and β-cryptoxanthin. Carotenoid absorption is restricted to the duodenum of the small intestine and dependent on class B scavenger receptor (SR-B1) membrane protein, which are also responsible for the absorption of vitamin E (α-tocopherol). One molecule of β-carotene can be cleaved by the intestinal enzyme β,β-carotene 15,15'-monooxygenase into two molecules of vitamin A.