β-Cryptoxanthin
β-Cryptoxanthin is a natural carotenoid pigment. It has been isolated from a variety of sources including the fruit of plants in the genus Physalis, orange rind, papaya, egg yolk, butter, apples, and bovine blood serum.[1]
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| Names | |
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| IUPAC name
(3R)-β,β-Caroten-3-ol | |
| Systematic IUPAC name
(1R)-3,5,5-Trimethyl-4-[(3E,5E,7E,9E,11E,13E,15E)-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-3-en-1-ol | |
| Other names
Cryptoxanthol Caricaxanthin (R)-all-trans-β-Caroten-3-ol Hydroxy-β-carotene kryptoxanthin | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| E number | E161c (colours) |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C40H56O | |
| Molar mass | 552.85 g/mol |
| Melting point | 169 °C (336 °F; 442 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
Chemistry
In terms of structure, β-cryptoxanthin is closely related to β-carotene, with only the addition of a hydroxyl group. It is a member of the class of carotenoids known as xanthophylls.
In a pure form, β-cryptoxanthin is a red crystalline solid with a metallic luster. It is freely soluble in chloroform, benzene, pyridine, and carbon disulfide.[1]
Biology and medicine
In the human body, β-cryptoxanthin is converted to vitamin A (retinol) and is, therefore, considered a provitamin A. As with other carotenoids, β-cryptoxanthin is an antioxidant and may help prevent free radical damage to cells and DNA, as well as stimulate the repair of oxidative damage to DNA.[2]
Recent findings of an inverse association between β-cryptoxanthin and lung cancer risk in several observational epidemiological studies suggest that β-cryptoxanthin could potentially act as a chemopreventive agent against lung cancer.[3] On the other hand, in the Grade IV histology group of adult patients diagnosed with malignant glioma, moderate to high intake of β-cryptoxanthin (for second tertile and for highest tertile compared to lowest tertile, in all cases) was associated with poorer survival.[4]
Other uses
β-Cryptoxanthin is also used as a substance to colour food products (INS number 161c). It is not approved for use in the EU[5] or USA; however, it is approved for use in Australia and New Zealand.[6]
References
- Merck Index, 11th Edition, 2612.
- Lorenzo, Y.; Azqueta, A.; Luna, L.; Bonilla, F.; Dominguez, G.; Collins, A. R. (2008). "The carotenoid β-cryptoxanthin stimulates the repair of DNA oxidation damage in addition to acting as an antioxidant in human cells". Carcinogenesis. 30 (2): 308–314. doi:10.1093/carcin/bgn270. PMID 19056931.
- Lian, Fuzhi; Hu, Kang-Quan; Russell, Robert M.; Wang, Xiang-Dong (2006). "β-Cryptoxanthin suppresses the growth of immortalized human bronchial epithelial cells and non-small-cell lung cancer cells and up-regulates retinoic acid receptor b expression". International Journal of Cancer. 119 (9): 2084–2089. doi:10.1002/ijc.22111.
- Delorenze, Gerald N; McCoy, Lucie; Tsai, Ai-Lin; Quesenberry, Charles P; Rice, Terri; Il'yasova, Dora; Wrensch, Margaret (2010). "Daily intake of antioxidants in relation to survival among adult patients diagnosed with malignant glioma". BMC Cancer. 10: 215. doi:10.1186/1471-2407-10-215. PMC 2880992. PMID 20482871.
- UK Food Standards Agency: "Current EU approved additives and their E Numbers". Retrieved 2011-10-27.
- Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". Retrieved 2011-10-27.