Cryptoxanthin
| Cryptoxanthin[1] |
|
| IUPAC name |
(R)-3,5,5-Trimethyl-4-[3,7,12,16-
tetramethyl-18-(2,6,6-trimethylcyclohex-
1-enyl)-octadeca-1,3,5,7,9,11,13,15,17-
nonaenyl]-cyclohex-3-enol |
| Other names |
(3R)-β,β-Caroten-3-ol
Cryptoxanthol
Caricaxanthin
(R)-all-trans-β-Caroten-3-ol
Hydroxy-β-carotene |
| Identifiers |
| CAS number |
472-70-8 |
| SMILES |
CC1(C)C[C@@H](O)CC(C)=C1/C=C/C
(C)=C/C=C/C(C)=C/C=C/C=C(C)/C
=C/C=C(C)/C=C/C2=C(C)CCCC(C)2C |
| Properties |
| Molecular formula |
C40H56O |
| Molar mass |
552.85 g/mol |
| Density |
? g/cm3 |
| Melting point |
169 °C
|
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references |
Cryptoxanthin is a natural carotenoid pigment. It has been isolated from a variety of sources including the petals and flowers of plants in the genus Physalis, orange rind, papaya, egg yolk, butter, and bovine blood serum.[1]
Chemistry
Structurally, cryptoxanthin is closely related to beta-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, 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, cryptoxanthin is converted to vitamin A (retinol) and is therefore considered a provitamin A. As with other carotenoids, cryptoxanthin is an antioxidant and may help prevent free radical damage to cells and DNA.
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.[2]
References
- ^ a b c Merck Index, 11th Edition, 2612.
- ^ 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. Lian, Fuzhi; Hu, Kang-Quan; Russell, Robert M.; Wang, Xiang-Dong. International Journal of Cancer (2006), 119(9), 2084-2089.
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