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Revision as of 00:01, 30 December 2011 editCydebot (talk | contribs)6,812,251 editsm Robot - Removing category E numbers per CFD at Misplaced Pages:Categories for discussion/Log/2011 December 19.← Previous edit Latest revision as of 01:05, 30 March 2024 edit undoInnerstream (talk | contribs)Autopatrolled, Extended confirmed users4,014 editsNo edit summary 
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{{cs1 config|name-list-style=vanc}}
{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 457820344 | verifiedrevid = 476993564
| ImageFile = ascorbyl palmitate.png | ImageFile = Ascorbyl palmitate.svg
| ImageSize = 250px | ImageSize = 250px
| IUPACName = -2-hydroxy-ethyl] hexadecanoate | IUPACName = <small>L</small>-''threo''-Hex-2-enono-1,4-lactone 6-hexadecanoate
| SystematicName = (2''S'')-2--2-hydroxyethyl hexadecanoate
| OtherNames = Ascorbyl palmitate<br>L-Ascorbic acid 6-hexadecanoate<br>6-''O''-Palmitoylascorbic acid | OtherNames = Ascorbyl palmitate<br>L-Ascorbic acid 6-hexadecanoate<br>6-''O''-Palmitoylascorbic acid
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16736579 | ChemSpiderID = 16736579
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
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| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 137-66-6 | CASNo = 137-66-6
| Abbreviations = E304 | Abbreviations = E304
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 220190 | ChEMBL = 220190
| PubChem = 5282506 | PubChem = 5282506
| SMILES = OC=1(OC(=O)C=1O)(O)COC(=O)CCCCCCCCCCCCCCC | SMILES = OC=1(OC(=O)C=1O)(O)COC(=O)CCCCCCCCCCCCCCC
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=22|H=38|O=7
| Formula = C<sub>22</sub>H<sub>38</sub>O<sub>7</sub>
⚫ | Appearance = White to yellowish colored powder
| MolarMass = 414.533 g/mol
| Density =
⚫ | Appearance = White to yellowish colored powder
| Density = | MeltingPtC = 116 to 117
| MeltingPt_notes =
| MeltingPt = 116–117 °C
| BoilingPt = | BoilingPt =
| Solubility = Very slightly soluble in water; freely soluble in ethanol | Solubility = Very slightly soluble in water; freely soluble in ethanol
⚫ }}
⚫ | Section3 = {{Chembox Hazards
⚫ | MainHazards =
⚫ | FlashPt = 178.1 °C
| Autoignition =
}} }}
⚫ |Section3={{Chembox Hazards
⚫ | MainHazards =
⚫ | FlashPtC = 178.1
| AutoignitionPtC =
⚫ }}
}} }}


'''Ascorbyl palmitate''' is an ] formed from ] and ] creating a fat-soluble form of vitamin C. In addition to its use as a source of ], it is also used as an ] ] (] E304). It is approved for use as a food additive in the 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>, USA '''Ascorbyl palmitate''' is an ] formed from ] and ] creating a fat-soluble form of vitamin C. In addition to its use as a source of ], it is also used as an ] ] (] E304). It is approved for use as a food additive in the 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> the U.S.,<ref>US Food and Drug Administration: {{cite web|url=https://www.fda.gov/Food/FoodIngredientsPackaging/FoodAdditives/FoodAdditiveListings/ucm091048.htm |title=Listing of Food Additives Status Part I |website=] |accessdate=2011-10-27 |url-status=dead |archiveurl=https://web.archive.org/web/20120117060614/https://www.fda.gov/Food/FoodIngredientsPackaging/FoodAdditives/FoodAdditiveListings/ucm091048.htm |archivedate=2012-01-17 }}</ref> Canada,<ref>Health Canada: {{cite web|url=http://webprod.hc-sc.gc.ca/nhpid-bdipsn/ingredReq.do?id=972&lang=eng |title=Chemical Substance - Ascorbyl palmitate |date=26 July 2004 |accessdate=2016-08-13}}</ref> 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>
<ref>US Food and Drug Administration: {{cite web |url=http://www.fda.gov/Food/FoodIngredientsPackaging/FoodAdditives/FoodAdditiveListings/ucm091048.htm |title=Listing of Food Additives Status Part I |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 |accessdate=2011-10-27}}</ref>


Ascorbyl palmitate taken orally is less effective, due to the substance's breaking down again into ] (not necessarily ]) and ] (a ] ]) before being digested. <ref>{{cite journal | author = DeRitter E. | title = Physiologic availability of dehydro-L-ascorbic acid and palmitoyl-L-ascorbic acid | journal = Science | year = 1951 | volume = 113 | pages = 628–631 | doi = 10.1126/science.113.2944.628 | pmid = 14845692 | last2 = Cohen | first2 = N | last3 = Rubin | first3 = SH | issue = 2944}}</ref> Ascorbyl palmitate is also marketed as "vitamin C ester". It is synthesized by acylation of vitamin C using different acyl donors.<ref name="pmid19030854 ">{{cite journal | vauthors = Karmee SK | title = Biocatalytic synthesis of ascorbyl esters and their biotechnological applications | journal = Applied Microbiology and Biotechnology | volume = 81 | issue = 6 Suppl | pages = 1013–1022 | date = January 2009 | pmid = 19030854 | doi = 10.1007/s00253-008-1781-y| s2cid = 35465409 }}</ref>
Ascorbyl palmitate is also marketed as "vitamin C ester".


==See also== ==See also==
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⚫ ==References==
⚫ == External links ==
{{Reflist}}

⚫ ==External links==
*
* *
* {{HPD|2088}} * {{CPID|id=801}}

⚫ ==References==
<references/>


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Latest revision as of 01:05, 30 March 2024

Ascorbyl palmitate
Names
IUPAC name L-threo-Hex-2-enono-1,4-lactone 6-hexadecanoate
Systematic IUPAC name (2S)-2--2-hydroxyethyl hexadecanoate
Other names Ascorbyl palmitate
L-Ascorbic acid 6-hexadecanoate
6-O-Palmitoylascorbic acid
Identifiers
CAS Number
3D model (JSmol)
Abbreviations E304
ChEMBL
ChemSpider
ECHA InfoCard 100.004.824 Edit this at Wikidata
E number E304 (antioxidants, ...)
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C22H38O7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(24)28-16-17(23)21-19(25)20(26)22(27)29-21/h17,21,23,25-26H,2-16H2,1H3/t17-,21+/m0/s1Key: QAQJMLQRFWZOBN-LAUBAEHRSA-N
  • InChI=1/C22H38O7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(24)28-16-17(23)21-19(25)20(26)22(27)29-21/h17,21,23,25-26H,2-16H2,1H3/t17-,21+/m0/s1Key: QAQJMLQRFWZOBN-LAUBAEHRBD
SMILES
  • OC=1(OC(=O)C=1O)(O)COC(=O)CCCCCCCCCCCCCCC
Properties
Chemical formula C22H38O7
Molar mass 414.539 g·mol
Appearance White to yellowish colored powder
Melting point 116 to 117 °C (241 to 243 °F; 389 to 390 K)
Solubility in water Very slightly soluble in water; freely soluble in ethanol
Hazards
Flash point 178.1 °C (352.6 °F; 451.2 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Ascorbyl palmitate is an ester formed from ascorbic acid and palmitic acid creating a fat-soluble form of vitamin C. In addition to its use as a source of vitamin C, it is also used as an antioxidant food additive (E number E304). It is approved for use as a food additive in the EU, the U.S., Canada, Australia, and New Zealand.

Ascorbyl palmitate is also marketed as "vitamin C ester". It is synthesized by acylation of vitamin C using different acyl donors.

See also

References

  1. UK Food Standards Agency: "Current EU approved additives and their E Numbers". Retrieved 2011-10-27.
  2. US Food and Drug Administration: "Listing of Food Additives Status Part I". Food and Drug Administration. Archived from the original on 2012-01-17. Retrieved 2011-10-27.
  3. Health Canada: "Chemical Substance - Ascorbyl palmitate". 26 July 2004. Retrieved 2016-08-13.
  4. Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". 8 September 2011. Retrieved 2011-10-27.
  5. Karmee SK (January 2009). "Biocatalytic synthesis of ascorbyl esters and their biotechnological applications". Applied Microbiology and Biotechnology. 81 (6 Suppl): 1013–1022. doi:10.1007/s00253-008-1781-y. PMID 19030854. S2CID 35465409.

External links

Categories: