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Revision as of 19:57, 6 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi← Previous edit Latest revision as of 16:06, 11 September 2024 edit undoCitation bot (talk | contribs)Bots5,424,088 edits Added date. | Use this bot. Report bugs. | Suggested by Abductive | Category:E-number additives | #UCB_Category 143/313 
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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 443394430 | verifiedrevid = 443396159
|ImageFile=apocarotenal.png
| ImageFile = Apocarotenal Structural Formula V1.svg
|ImageSize=250px | ImageSize = 320px
⚫ |IUPACName= (''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
| ImageAlt = Skeletal formula of apocarotenal
|IUPACName_hidden=yes
| ImageFile1 = Apocarotenal 3D spacefill.png
|OtherNames=''trans''-beta-apo-8'-carotenal<br>C.I. Food Orange 6<br>E number 160E
| ImageSize1 = 300
⚫ |Section1= {{Chembox Identifiers
| ImageAlt1 = Space-filling model of the apocarotenal molecule
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | IUPACName = 8′-Apo-β-caroten-8′-al
⚫ | SystematicName = (2''E'',4''E'',6''E'',8''E'',10''E'',12''E'',14''E'',16''E'')-2,6,11,15-Tetramethyl-17-(2,6,6-trimethylcyclohex-1-en-1-yl)heptadeca-2,4,6,8,10,12,14,16-octaenal
| OtherNames={{Unbulleted list
| ''trans''-beta-apo-8'-carotenal
| C.I. Food Orange 6
| E number 160E
}}
⚫ |Section1={{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4585625 | ChemSpiderID = 4585625
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| InChI = 1S/C30H40O/c1-24(13-8-9-14-25(2)16-11-18-27(4)23-31)15-10-17-26(3)20-21-29-28(5)19-12-22-30(29,6)7/h8-11,13-18,20-21,23H,12,19,22H2,1-7H3/b9-8+,15-10+,16-11+,21-20+,24-13+,25-14+,26-17+,27-18+ | InChI = 1S/C30H40O/c1-24(13-8-9-14-25(2)16-11-18-27(4)23-31)15-10-17-26(3)20-21-29-28(5)19-12-22-30(29,6)7/h8-11,13-18,20-21,23H,12,19,22H2,1-7H3/b9-8+,15-10+,16-11+,21-20+,24-13+,25-14+,26-17+,27-18+
| InChIKey1 = DFMMVLFMMAQXHZ-DOKBYWHISA-N | InChIKey1 = DFMMVLFMMAQXHZ-DOKBYWHISA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=1107-26-2 | CASNo=1107-26-2
| PubChem=5478003 | PubChem=5478003
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = V22N3E2U32 | UNII = V22N3E2U32
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
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| SMILES=CC=1CCCC(C)(C)C=1/C=CC(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)C=O | SMILES=CC=1CCCC(C)(C)C=1/C=CC(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)C=O
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C = 30| H = 40 | O = 1 | C=30 | H=40 | O=1
| Appearance= | Appearance=
| Density= | Density=
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}


'''Apocarotenal''', or ''trans''-β-apo-8'-carotenal, is a ] found in ] and ] fruits. Like other carotenoids, apocarotenal plays a role as a precursor of ], even though it has 50% less pro-vitamin A activity than ]. The empirical chemical formula for apocarotenal is C<sub>30</sub>H<sub>40</sub>O. '''Apocarotenal''', or ''trans''-β-apo-8'-carotenal, is a ] found in ] and ] fruits. Like other carotenoids, apocarotenal plays a role as a precursor of ], even though it has 50% less pro-vitamin A activity than ]. The empirical chemical formula for apocarotenal is C<sub>30</sub>H<sub>40</sub>O.


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 (], sauces, ]), beverages, dairy products and sweets. Its ] is 160E. 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 (], sauces, ]), beverages, dairy products and sweets. Its ] is E160e and it is approved for usage as a ] in the US,<ref>US FDA:{{cite web |url=https://www.fda.gov/ForIndustry/ColorAdditives/ColorAdditiveInventories/ucm106626.htm |title=Colour Additive Status List |website=] |accessdate=2011-10-27}}</ref> EU<ref>UK Food Standards Agency: {{cite web |url=http://www.food.gov.uk/safereating/chemsafe/additivesbranch/enumberlist |title=Current EU approved additives and their E Numbers |accessdate=2011-10-27}}</ref> and Australia and New Zealand.<ref>Australia New Zealand Food Standards Code{{cite web |url=http://www.comlaw.gov.au/Details/F2011C00827 |title=Standard 1.2.4 - Labelling of ingredients |date=8 September 2011 |accessdate=2011-10-27}}</ref>


==Possible carcingenicity== ==Possible carcinogenicity==
] studies have shown that people with high β-carotene intake and high plasma levels of β-carotene have a significantly reduced risk of lung ]. However, studies of supplementation with large doses of β-carotene in smokers have shown an increase in ] risk, possibly because excessive β-carotene results in breakdown products that reduce plasma ] and worsen the lung ] 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 to be mutagenic and genotoxic in cell cultures which do not respond to β-carotene itself.<ref>{{cite journal |author=Alija AJ, Bresgen N, Sommerburg O, Siems W, Eckl PM |title=Cytotoxic and genotoxic effects of β-carotene breakdown products on primary rat hepatocytes |journal=Carcinogenesis |volume=25 |issue=5 |pages=827–31 |year=2004 |pmid=14688018 |doi=10.1093/carcin/bgh056 |url=http://carcin.oxfordjournals.org/cgi/content/full/25/5/827}}</ref> ] studies have shown that people with high β-carotene intake and high plasma levels of β-carotene have a significantly reduced risk of lung ]{{Citation needed|date=June 2022}}. However, studies of supplementation with large doses of β-carotene in smokers have shown an increase in ] risk, possibly because excessive β-carotene results in breakdown products that reduce plasma ] and worsen the lung ] induced by smoke {{Citation needed|date=June 2022}}. The chief β-carotene breakdown product suspected of this behavior is ''trans''-''beta''-apo-8'-carotenal (common apocarotenal) {{Citation needed|date=June 2022}}, which has been found in one study to be mutagenic and genotoxic in cell cultures which do not respond to β-carotene itself.<ref>{{cite journal |vauthors=Alija AJ, Bresgen N, Sommerburg O, Siems W, Eckl PM |title=Cytotoxic and genotoxic effects of β-carotene breakdown products on primary rat hepatocytes |journal=Carcinogenesis |volume=25 |issue=5 |pages=827–31 |year=2004 |pmid=14688018 |doi=10.1093/carcin/bgh056 |doi-access=free }}</ref>


==References== ==References==
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==External links== ==External links==
* *
*{{cite journal | url = http://www.jlr.org/cgi/reprint/5/3/281.pdf | author = Olson A.J. | year = 1964 | title = The biosynthesis and metabolism of carotenoids and retinol (vitamin A) | journal = J.of Lipid Research | volume = 5 | pages = 281–298 | issue=3}} *{{cite journal |url= http://www.jlr.org/cgi/reprint/5/3/281.pdf |last= Olson |first= A.J. |year= 1964 |title= The biosynthesis and metabolism of carotenoids and retinol (vitamin A) |journal= Journal of Lipid Research |volume= 5 |pages= 281–298 |issue= 3|doi= 10.1016/S0022-2275(20)40196-8 |pmid= 5334361 }}


{{Carotenoids}} {{Carotenoids}}
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