Cryptoxanthin

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Cryptoxanthin[1]
Cryptoxanthin
300px
Names
IUPAC names
(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
472-70-8 YesY
ChEBI CHEBI:10362 YesY
ChemSpider 4444647 YesY
Jmol 3D model Interactive image
PubChem 5281235
  • 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 YesY
    Key: DMASLKHVQRHNES-FKKUPVFPSA-N YesY
  • 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
  • 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
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).
YesY verify (what is YesYN ?)
Infobox 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, apples, and bovine blood serum.[1]

Chemistry

In terms of structure, 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, 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, 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 cryptoxanthin (for second tertile and for highest tertile compared to lowest tertile, in all cases) was associated with poorer survival.[4]

Other uses

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

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  1. ↑ 1.0 1.1 1.2 Merck Index, 11th Edition, 2612.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ UK Food Standards Agency: Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Australia New Zealand Food Standards CodeLua error in package.lua at line 80: module 'strict' not found.
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