β-Carotene
| Names | |
|---|---|
| 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
Betacarotene (INN), β-Carotene, Food Orange 5, Provitamin A | |
| Identifiers | |
3D model (JSmol) |
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| 3DMet | |
| 1917416 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| 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 |
| Melting point | 183 °C (361 °F; 456 K) decomposes |
| 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) = 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) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
β-Carotene (beta-carotene) is an organic, strongly colored red-orange pigment abundant in fungi, 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.
Dietary β-carotene is a provitamin A compound, converting in the body to retinol (vitamin A). In foods, it has rich content in carrots, pumpkin, spinach, and sweet potato. It is used as a dietary supplement and may be prescribed to treat erythropoietic protoporphyria, an inherited condition of sunlight sensitivity.
β-carotene is the most common carotenoid in plants. When used as a food coloring, it has the E number E160a.: 119 The structure was deduced in 1930.
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. 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 lipophilic.