β-Carotene
Red-orange pigment of the terpenoids class / From Wikipedia, the free encyclopedia
β-Carotene (beta-carotene) is an organic, strongly colored red-orange pigment abundant in fungi,[7] 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.
Names | |
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IUPAC name
β,β-Carotene | |
Systematic IUPAC name
1,1′-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-Tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl]bis(2,6,6-trimethylcyclohex-1-ene) | |
Other names | |
Identifiers | |
3D model (JSmol) |
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3DMet | |
1917416 | |
ChEBI | |
ChEMBL | |
ChemSpider |
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ECHA InfoCard | 100.027.851 |
EC Number |
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E number | E160a (colours) |
KEGG | |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C40H56 | |
Molar mass | 536.888 g·mol−1 |
Appearance | Dark orange crystals |
Density | 1.00 g/cm3[4] |
Melting point | 183 °C (361 °F; 456 K)[4] decomposes[5] |
Boiling point | 654.7 °C (1,210.5 °F; 927.9 K) at 760 mmHg (101324 Pa) |
Insoluble | |
Solubility | Soluble in CS2, benzene, CHCl3, ethanol Insoluble in glycerin |
Solubility in dichloromethane | 4.51 g/kg (20 °C)[6] = 5.98 g/L (given BCM density of 1.3266 g/cm3 at 20°C) |
Solubility in hexane | 0.1 g/L |
log P | 14.764 |
Vapor pressure | 2.71·10−16 mmHg |
Refractive index (nD) |
1.565 |
Pharmacology | |
A11CA02 (WHO) D02BB01 (WHO) | |
Hazards | |
GHS labelling: | |
Warning | |
H315, H319, H412 | |
P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, P501 | |
NFPA 704 (fire diamond) | |
Flash point | 103 °C (217 °F; 376 K)[5] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dietary β-carotene is a provitamin A compound, converting in the body to retinol (vitamin A).[8] In foods, it has rich content in carrots, pumpkin, spinach, and sweet potato.[8] It is used as a dietary supplement and may be prescribed to treat erythropoietic protoporphyria, an inherited condition of sunlight sensitivity.[9]
β-carotene is the most common carotenoid in plants.[8] When used as a food coloring, it has the E number E160a.[10]: 119 The structure was deduced in 1930.[11]
Isolation of β-carotene from fruits abundant in carotenoids is commonly done using column chromatography. It is industrially extracted from richer sources such as the algae Dunaliella salina.[12] 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.[13] Being highly conjugated, it is deeply colored, and as a hydrocarbon lacking functional groups, it is lipophilic.