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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]

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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.

v • d • e Carotenoids
Carotenes:	Lycopene · Carotene · Beta-carotene · Alpha-carotene · Phytofluene · Neurosporene · Phytoene
Retinoids:	Acitretin · Alitretinoin · Bexarotene · Etretinate · Fenretinide · Isotretinoin · Retinaldehyde · Tazarotene · Vitamin A (Retinol, Tretinoin)
Xanthophylls:	Astaxanthin · Canthaxanthin · Fucoxanthin · Lutein · Zeaxanthin · Cryptoxanthin · Rubixanthin