Cryptoxanthin

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Cryptoxanthin[1]
Cryptoxanthin
Chemical 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
Chemical formula C40H56O
Molecular mass 552.85 g/mol
CAS number [472-70-8]
Density  ? g/cm3
Melting point 169 °C
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
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

  1. 1.0 1.1 1.2 Merck Index, 11th Edition, 2612.
  2. 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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