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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 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 taken orally is, in all probability, far less effective than the claims made by advertisers and marketers. This is due to the fact that ascorbyl palmitate is known to be broken down (through the digestive process) into ] and ] (a ] ]) before being absorbed into the bloodstream. <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".


==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: