Chemistry:β-Cryptoxanthin

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β-Cryptoxanthin[1]
Cryptoxanthin
Cryptoxanthin ball and stick.png
Names
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)
ChEBI
ChemSpider
UNII
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).
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Infobox references
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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]

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;[citation needed] however, it is approved for use in Australia and New Zealand.[6]

References

  1. 1.0 1.1 1.2 Merck Index, 11th Edition, 2612.
  2. 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. 
  3. 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. 
  4. 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. PMID 20482871. 
  5. UK Food Standards Agency: "Current EU approved additives and their E Numbers". http://www.food.gov.uk/safereating/chemsafe/additivesbranch/enumberlist_____________________. Retrieved 2011-10-27. 
  6. Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". http://www.comlaw.gov.au/Details/F2011C00827. Retrieved 2011-10-27.