Apocarotenal

Apocarotenal
Names
IUPAC name
(2E,4E,6E,8E,10E,12E,14E,16E)-2,6,11,15-tetramethyl-17-(2,6,6-trimethyl-1-cyclohexenyl)heptadeca-2,4,6,8,10,12,14,16-octaenal
Other names
trans-beta-apo-8'-carotenal
C.I. Food Orange 6
E number 160E
Identifiers
1107-26-2 Yes
ChEBI CHEBI:53154 Yes
ChemSpider 4585625 Yes
Jmol-3D images Image
Image
PubChem 5478003
UNII V22N3E2U32 Yes
Properties
Molecular formula
 C30H40O
Molar mass 416.64 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Apocarotenal, or trans-β-apo-8'-carotenal, is a carotenoid found in spinach and citrus fruits. Like other carotenoids, apocarotenal plays a role as a precursor of vitamin A, even though it has 50% less pro-vitamin A activity than β-carotene. The empirical chemical formula for apocarotenal is C30H40O.

Apocarotenal has an orange to orange-red colour and is used in foods, pharmaceuticals and cosmetic products. Depending on the product forms, apocarotenal is used in fat based food (margarine, sauces, salad dressing), beverages, dairy products and sweets. Its E number is E160e and it is approved for usage as a food additive in the USA,[1] EU [2] and Australia and New Zealand[3] (where it is listed as 160e).

Possible carcinogenicity

Epidemiological studies have shown that people with high β-carotene intake and high plasma levels of β-carotene have a significantly reduced risk of lung cancer. However, studies of supplementation with large doses of β-carotene in smokers have shown an increase in cancer risk, possibly because excessive β-carotene results in breakdown products that reduce plasma vitamin A and worsen the lung cell proliferation induced by smoke. The chief β-carotene breakdown product suspected of this behavior is trans-beta-apo-8'-carotenal (common apocarotenal), which has been found in one study to be mutagenic and genotoxic in cell cultures which do not respond to β-carotene itself.[4]

References

  1. ↑ US FDA:"Colour Additive Status List". Retrieved 2011-10-27.
  2. ↑ UK Food Standards Agency: "Current EU approved additives and their E Numbers". Retrieved 2011-10-27.
  3. ↑ Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". Retrieved 2011-10-27.
  4. ↑ Alija AJ, Bresgen N, Sommerburg O, Siems W, Eckl PM (2004). "Cytotoxic and genotoxic effects of β-carotene breakdown products on primary rat hepatocytes". Carcinogenesis 25 (5): 827–31. doi:10.1093/carcin/bgh056. PMID 14688018.

External links