Np mrd loader

Record Information
Version2.0
Created at2024-09-11 10:12:54 UTC
Updated at2024-09-11 10:12:54 UTC
NP-MRD IDNP0337296
Secondary Accession NumbersNone
Natural Product Identification
Common NameAscorbyl palmitate
DescriptionAscorbyl palmitate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Ascorbyl palmitate was first documented in 2024 (PMID: 38794309). Based on a literature review a significant number of articles have been published on Ascorbyl palmitate (PMID: 39309138) (PMID: 39268798) (PMID: 39252190) (PMID: 39241420) (PMID: 39191334) (PMID: 39140411).
Structure
Thumb
Synonyms
ValueSource
Ascorbyl palmitic acidGenerator
Chemical FormulaC22H38O7
Average Mass414.5390 Da
Monoisotopic Mass414.26175 Da
IUPAC Name2-(3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl hexadecanoate
Traditional Nameascorbyl palmitate
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)OCC(O)C1OC(=O)C(O)=C1O
InChI Identifier
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
InChI KeyQAQJMLQRFWZOBN-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • 2-furanone
  • Dicarboxylic acid or derivatives
  • Dihydrofuran
  • Enoate ester
  • Vinylogous acid
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Enediol
  • Lactone
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.01ChemAxon
pKa (Strongest Acidic)4.25ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity110.62 m³·mol⁻¹ChemAxon
Polarizability48.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAscorbyl palmitate
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kulkarni CP, Yang J, Koleske ML, Lara G, Alam K, Raw A, Rege B, Zhao L, Lu D, Zhang L, Yu LX, Lionberger RA, Giacomini KM, Kroetz DL, Yee SW: Effect of Antioxidants in Medicinal Products on Intestinal Drug Transporters. Pharmaceutics. 2024 May 10;16(5):647. doi: 10.3390/pharmaceutics16050647. [PubMed:38794309 ]
  2. Shamiya Y, Chakraborty A, Zahid AA, Bainbridge N, Guan J, Feng B, Pjontek D, Chakrabarti S, Paul A: Ascorbyl palmitate nanofiber-reinforced hydrogels for drug delivery in soft issues. Commun Mater. 2024;5(1):197. doi: 10.1038/s43246-024-00641-x. Epub 2024 Sep 20. [PubMed:39309138 ]
  3. Corovic M, Veljkovic M, Milivojevic A, Ivankovic AP, Blagojevic S, Pjanovic R, Bezbradica D: In vitro assessment of skin permeation properties of enzymatically derived oil-based fatty acid esters of vitamin C. Arch Pharm (Weinheim). 2024 Nov;357(11):e2400538. doi: 10.1002/ardp.202400538. Epub 2024 Sep 13. [PubMed:39268798 ]
  4. Banik SP, Kumar P, Basak P, Goel A, Ohia SE, Bagchi M, Chakraborty S, Kundu A, Bagchi D: A critical insight into the physicochemical stability of macular carotenoids with respect to their industrial production, safety profile, targeted tissue delivery, and bioavailability. Toxicol Mech Methods. 2025 Mar;35(3):215-229. doi: 10.1080/15376516.2024.2401924. Epub 2024 Sep 13. [PubMed:39252190 ]
  5. Li Q, Qian J, Huang A, Shi B, Gu G: Biocatalytic synthesis of L-ascorbyl palmitate using oleic acid imprinted Aspergillus niger lipase immobilized on resin. Food Chem. 2025 Jan 15;463(Pt 1):141075. doi: 10.1016/j.foodchem.2024.141075. Epub 2024 Aug 31. [PubMed:39241420 ]
  6. Pittiu A, Pannuzzo M, Casula L, Pireddu R, Valenti D, Cardia MC, Lai F, Rosa A, Sinico C, Schlich M: Production of liposomes by microfluidics: The impact of post-manufacturing dilution on drug encapsulation and lipid loss. Int J Pharm. 2024 Oct 25;664:124641. doi: 10.1016/j.ijpharm.2024.124641. Epub 2024 Aug 25. [PubMed:39191334 ]
  7. Cheng W, Xu J, Wang X, Li X, Chen Y, Liu G, Zhou X, Ding Y, Liu S: Multiple Mechanisms of Haematococcus pluvialis-Derived Carotenoids to Inhibit Glycidyl Ester Formation in Rice Oil and a Chemical Model at High Temperatures. J Agric Food Chem. 2024 Aug 28;72(34):19177-19186. doi: 10.1021/acs.jafc.4c04019. Epub 2024 Aug 14. [PubMed:39140411 ]
  8. Keceli TM, Mertoglu TS: Antioxidant and antimicrobial activities of Myrtus communis essential oils in cold-stored lactic butter. J Sci Food Agric. 2024 Dec;104(15):9660-9672. doi: 10.1002/jsfa.13791. Epub 2024 Aug 2. [PubMed:39092905 ]
  9. Favarin FR, Forrati EM, Bassoto VA, da Silva Gundel S, Velho MC, Ledur CM, Verdi CM, Lemos JG, Sagrillo MR, Fagan SB, Gundel A, Copetti MV, Santos RCV, de Oliveira Fogaca A, Ourique AF: Ascorbic acid and ascorbyl palmitate-loaded liposomes: Development, characterization, stability evaluation, in vitro security profile, antimicrobial and antioxidant activities. Food Chem. 2024 Dec 1;460(Pt 2):140569. doi: 10.1016/j.foodchem.2024.140569. Epub 2024 Jul 23. [PubMed:39083967 ]
  10. Stolic Jovanovic A, Tadic VM, Martinovic M, Zugic A, Nesic I, Blagojevic S, Jasnic N, Tosti T: Liposomal Encapsulation of Ascorbyl Palmitate: Influence on Skin Performance. Pharmaceutics. 2024 Jul 20;16(7):962. doi: 10.3390/pharmaceutics16070962. [PubMed:39065659 ]
  11. Zhang L, Li G, Lin B, He H, Zhou R, Jiang W: Corrigendum to "Ascorbyl palmitate ameliorates inflammatory diseases by inhibition of NLRP3 inflammasome" [Int. Immunopharmacol. 131 (2024) 111915]. Int Immunopharmacol. 2024 Sep 10;138:112726. doi: 10.1016/j.intimp.2024.112726. Epub 2024 Jul 22. [PubMed:39043482 ]
  12. Lai Y, Zhang T, Yin X, Zhu C, Du Y, Li Z, Gao J: An antibiotic-free platform for eliminating persistent Helicobacter pylori infection without disrupting gut microbiota. Acta Pharm Sin B. 2024 Jul;14(7):3184-3204. doi: 10.1016/j.apsb.2024.03.014. Epub 2024 Mar 10. [PubMed:39027245 ]
  13. Maslovski F, Angelina E, Alonso M, Leiva L, Fusco L: Ascorbyl palmitate (ASC16) as a potential inhibitor of toxicity induced by Crotalus durissus terrificus venom. Comp Biochem Physiol C Toxicol Pharmacol. 2024 Oct;284:109973. doi: 10.1016/j.cbpc.2024.109973. Epub 2024 Jul 26. [PubMed:39002622 ]
  14. Zvonar Pobirk A, Roskar R, Bester-Rogac M, Gasperlin M, Gosenca Matjaz M: The Impact of Phospholipid-Based Liquid Crystals' Microstructure on Stability and Release Profile of Ascorbyl Palmitate and Skin Performance. Molecules. 2024 Jul 3;29(13):3173. doi: 10.3390/molecules29133173. [PubMed:38999123 ]
  15. Gabbanini S, Neba JN, Matera R, Valgimigli L: Photochemical and Oxidative Degradation of Chamazulene Contained in Artemisia, Matricaria and Achillea Essential Oils and Setup of Protection Strategies. Molecules. 2024 Jun 1;29(11):2604. doi: 10.3390/molecules29112604. [PubMed:38893479 ]
  16. Ampem G, Le Gresley A, Grootveld M, Patrick Naughton D: Effectiveness of different antioxidants in suppressing the evolution of thermally induced peroxidation products in hemp seed oil. Food Res Int. 2024 Jul;188:114415. doi: 10.1016/j.foodres.2024.114415. Epub 2024 May 3. [PubMed:38823855 ]
  17. Marin C, Ruiz Moreno FN, Sanchez Vallecillo MF, Pascual MM, Dho ND, Allemandi DA, Palma SD, Pistoresi-Palencia MC, Crespo MI, Gomez CG, Moron G, Maletto BA: Improved biodistribution and enhanced immune response of subunit vaccine using a nanostructure formed by self-assembly of ascorbyl palmitate. Nanomedicine. 2024 Jun;58:102749. doi: 10.1016/j.nano.2024.102749. Epub 2024 May 6. [PubMed:38719107 ]
  18. Li WB, Xu LL, Wang SL, Wang YY, Pan YC, Shi LQ, Guo DS: Co-Assembled Nanoparticles toward Multi-Target Combinational Therapy of Alzheimer's Disease by Making Full Use of Molecular Recognition and Self-Assembly. Adv Mater. 2024 Jul;36(28):e2401918. doi: 10.1002/adma.202401918. Epub 2024 May 6. [PubMed:38662940 ]
  19. Zhang L, Li G, Lin B, He H, Zhou R, Jiang W: Ascorbyl palmitate ameliorates inflammatory diseases by inhibition of NLRP3 inflammasome. Int Immunopharmacol. 2024 Apr 20;131:111915. doi: 10.1016/j.intimp.2024.111915. Epub 2024 Mar 23. [PubMed:38522141 ]