Β-Cryptoxanthin

β-Cryptoxanthin^[1]
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
CAS Number	472-70-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:10362 ;
ChemSpider	4444647 ;
E number	E161c (colours)
PubChem CID	5281235;
UNII	6ZIB13GI33 ;
CompTox Dashboard (EPA)	DTXSID30912309 ;
	InChI InChI=1S/C40H56O/c1-30(18-13-20-32(3)23-25-37-34(5)22-15-27-39(37,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-38-35(6)28-36(41)29-40(38,9)10/h11-14,16-21,23-26,36,41H,15,22,27-29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+/t36-/m1/s1 Key: DMASLKHVQRHNES-FKKUPVFPSA-N ; InChI=1/C40H56O/c1-30(18-13-20-32(3)23-25-37-34(5)22-15-27-39(37,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-38-35(6)28-36(41)29-40(38,9)10/h11-14,16-21,23-26,36,41H,15,22,27-29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+/t36-/m1/s1 Key: DMASLKHVQRHNES-FKKUPVFPBQ;
	SMILES O[C@@H]2C/C(=C(/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(\C)CCCC1(C)C)C)C)C)C)C(C)(C)C2)C;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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, winter squashes such as butternut, papaya, egg yolk, butter, apples, and bovine blood serum.^[1]

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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]
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. PMID 16841329.
[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. PMC 2880992. PMID 20482871.
[5]
UK Food Standards Agency: "Current EU approved additives and their E Numbers". Retrieved 2011-10-27.^{[permanent dead link]}
[6]
Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". Retrieved 2011-10-27.

[Merck-1] [1]
Merck Index, 11th Edition, 2612.

[2] [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] [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. PMID 16841329.

[4] [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. PMC 2880992. PMID 20482871.

[5] [5]
UK Food Standards Agency: "Current EU approved additives and their E Numbers". Retrieved 2011-10-27.^{[permanent dead link]}

[6] [6]
Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". Retrieved 2011-10-27.

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