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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H38O7
Molecular Weight 414.5329
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ASCORBYL PALMITATE

SMILES

[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)COC(=O)CCCCCCCCCCCCCCC

InChI

InChIKey=QAQJMLQRFWZOBN-LAUBAEHRSA-N
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/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.drlam.com/blog/ascorbyl-palmitate/862/ http://www.fda.gov/Food/IngredientsPackagingLabeling/GRAS/SCOGS/ucm260868.htm

Ascorbyl palmitate is a fat soluble vitamin C ester. An ester is simply a compound formed by the combination of an organic acid and an alcohol – in this case it is ascorbic acid and palmitic acid (a fat – which is composed of fatty acids and glycerol - an alcohol). Therefore, ascorbyl palmitate is formed by the esterification of ascorbic acid with palmitic acid to form vitamin C ester. Ascorbyl palmitate is an amphipathic molecule, meaning one end is water-soluble and the other end is fat-soluble. This dual solubility allows it to be incorporated into cell membranes. When incorporated into the cell membranes of human red blood cells, ascorbyl palmitate has been found to protect them from oxidative damage and to protect alpha-tocopherol (a fat-soluble antioxidant) from oxidation by free radicals. Basically, the fat-soluble aspect of ascorbyl palmitate extends vitamin C free radical protection into the fat parts of the body. However, the protective effects of ascorbyl palmitate on cell membranes have only been demonstrated in the test tube (in vitro). Taking ascorbyl palmitate orally may not result in any significant incorporation into cell membranes because most of it appears to be hydrolyzed (broken apart into palmitate and ascorbic acid) in the human digestive tract before it is absorbed. The ascorbic acid released by the hydrolysis of ascorbyl palmitate appears to be as bioavailable as ascorbic acid alone. The presence of ascorbyl palmitate in oral supplements contributes to the ascorbic acid content of the supplement and probably helps protect fat-soluble antioxidants in the supplement. This is also true for food products. Ascorbyl palmitate is used to increase the shelf life of vegetable oils and potato chips. The role of vitamin C in promoting collagen synthesis and its antioxidant properties have generated interest in its use on the skin. Ascorbyl palmitate is frequently used in topical preparations because it is more stable than some aqueous (water-soluble) forms of vitamin C. It is also suggested that this form of vitamin C is better able to penetrate the skin and the thin membrane of cells (due to its dual solubility), which can then go on to help produce collagen and elastin.

CNS Activity

Curator's Comment: Known to be CNS penetrant in rat. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Validation of an in vitro screening test for predicting the tumor promoting potential of chemicals based on gene expression.
2010 Apr
Patents

Sample Use Guides

As a dietary supplement, take two (2) capsules daily, preferably with a meal.
Route of Administration: Oral
In Vitro Use Guide
Reversible and mechanism-based inhibitions of nifedipine oxidation were studied in human liver microsomes. Ascorbyl palmitate was more potent, K(i) = 12.3 +/- 0.5 uM
Name Type Language
ASCORBYL PALMITATE
EP   FCC   HSDB   II   INCI   MART.   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
ASCORBYL MONOPALMITATE
Common Name English
L-ASCORBIC ACID, 6-HEXADECANOATE
Common Name English
INS-304
Common Name English
INS NO.304
Common Name English
NSC-402451
Code English
CETYL ASCORBATE
Common Name English
L-ASCORBIC ACID 6-PALMITATE
Common Name English
ASCORBYL PALMITATE [MART.]
Common Name English
ASCORBYL PALMITATE [VANDF]
Common Name English
6-O-PALMITOYLASCORBIC ACID
Common Name English
Ascorbyl palmitate [WHO-DD]
Common Name English
E-304
Common Name English
ASCORBYL PALMITATE [EP MONOGRAPH]
Common Name English
ASCORBYL PALMITATE [HSDB]
Common Name English
ASCORBYL PALMITATE [INCI]
Common Name English
ASCORBYL PALMITATE [II]
Common Name English
ASCORBYL PALMITATE [FCC]
Common Name English
ASCORBYL PALMITATE [USP-RS]
Common Name English
Classification Tree Code System Code
CODEX ALIMENTARIUS (GSFA) INS-304
Created by admin on Fri Dec 15 15:21:39 GMT 2023 , Edited by admin on Fri Dec 15 15:21:39 GMT 2023
NCI_THESAURUS C275
Created by admin on Fri Dec 15 15:21:39 GMT 2023 , Edited by admin on Fri Dec 15 15:21:39 GMT 2023
DSLD 2831 (Number of products:221)
Created by admin on Fri Dec 15 15:21:39 GMT 2023 , Edited by admin on Fri Dec 15 15:21:39 GMT 2023
JECFA EVALUATION INS-304
Created by admin on Fri Dec 15 15:21:39 GMT 2023 , Edited by admin on Fri Dec 15 15:21:39 GMT 2023
Code System Code Type Description
SMS_ID
100000076680
Created by admin on Fri Dec 15 15:21:39 GMT 2023 , Edited by admin on Fri Dec 15 15:21:39 GMT 2023
PRIMARY
CAS
1330-84-3
Created by admin on Fri Dec 15 15:21:39 GMT 2023 , Edited by admin on Fri Dec 15 15:21:39 GMT 2023
ALTERNATIVE
FDA UNII
QN83US2B0N
Created by admin on Fri Dec 15 15:21:39 GMT 2023 , Edited by admin on Fri Dec 15 15:21:39 GMT 2023
PRIMARY
PUBCHEM
54680660
Created by admin on Fri Dec 15 15:21:39 GMT 2023 , Edited by admin on Fri Dec 15 15:21:39 GMT 2023
PRIMARY
RXCUI
1088438
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PRIMARY RxNorm
HSDB
418
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PRIMARY
CAS
137-66-6
Created by admin on Fri Dec 15 15:21:39 GMT 2023 , Edited by admin on Fri Dec 15 15:21:39 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-305-4
Created by admin on Fri Dec 15 15:21:39 GMT 2023 , Edited by admin on Fri Dec 15 15:21:39 GMT 2023
PRIMARY
ChEMBL
CHEMBL220190
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PRIMARY
EVMPD
SUB11717MIG
Created by admin on Fri Dec 15 15:21:39 GMT 2023 , Edited by admin on Fri Dec 15 15:21:39 GMT 2023
PRIMARY
DAILYMED
QN83US2B0N
Created by admin on Fri Dec 15 15:21:39 GMT 2023 , Edited by admin on Fri Dec 15 15:21:39 GMT 2023
PRIMARY
NCI_THESAURUS
C81556
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PRIMARY
MESH
C031226
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PRIMARY
RS_ITEM_NUM
1043105
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PRIMARY
NSC
402451
Created by admin on Fri Dec 15 15:21:39 GMT 2023 , Edited by admin on Fri Dec 15 15:21:39 GMT 2023
PRIMARY
WIKIPEDIA
ASCORBYL PALMITATE
Created by admin on Fri Dec 15 15:21:39 GMT 2023 , Edited by admin on Fri Dec 15 15:21:39 GMT 2023
PRIMARY
ECHA (EC/EINECS)
215-550-9
Created by admin on Fri Dec 15 15:21:39 GMT 2023 , Edited by admin on Fri Dec 15 15:21:39 GMT 2023
ALTERNATIVE
EPA CompTox
DTXSID3041611
Created by admin on Fri Dec 15 15:21:39 GMT 2023 , Edited by admin on Fri Dec 15 15:21:39 GMT 2023
PRIMARY