Betacarotene
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| 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 | |
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3D model (Jmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.027.851 |
| EC Number | 230-636-6 |
| E number | E160a(i) (colours) |
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PubChem CID
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| UNII | |
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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 |
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Refractive index (nD)
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1.565 |
| Pharmacology | |
| A11CA02 (WHO) D02BB01 (WHO) | |
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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) |
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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   ?) |
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| 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.
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Wikipedia