β-Cryptoxanthin^[1]

Names
IUPAC name (3R)-β,β-Caroten-3-ol
Systematic IUPAC name (1R)-3,5,5-Trimethyl-4-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 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:10362 Y
ChemSpider	4444647 Y
E number	E161c (colours)
PubChem CID	5281235
UNII	6ZIB13GI33 Y
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 Y Key: DMASLKHVQRHNES-FKKUPVFPSA-N Y 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 O2C/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 , 100 kPa). Y verify (what is YN ?) 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, 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