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Details

Stereochemistry ACHIRAL
Molecular Formula C16H32O2
Molecular Weight 256.4241
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PALMITIC ACID

SMILES

CCCCCCCCCCCCCCCC(O)=O

InChI

InChIKey=IPCSVZSSVZVIGE-UHFFFAOYSA-N
InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)

HIDE SMILES / InChI
Molecular Formula C16H32O2
Molecular Weight 256.4241
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12496284 | https://www.ncbi.nlm.nih.gov/pubmed/14717706 | https://www.ncbi.nlm.nih.gov/pubmed/18511927 | https://www.ncbi.nlm.nih.gov/pubmed/23406428

Palmitic acid is a saturated fatty acid, the principal constituent of refined palm oil, present in the diet and synthesized endogenously. Palmitic acid is able to activate the orphan G protein-coupled receptor GPR40. Palmitic acid was also a weak ligand of peroxisome proliferator-activated receptor gamma. Palmitic acid is a ligand of lipid chaperones - the fatty acid-binding proteins (FABPs). Dietary palm oil and palmitic acid may play a role in the development of obesity, type 2 diabetes mellitus, cardiovascular diseases and cancer.

CNS Activity

CNS Penetrant
2588
Curator's Comment: Palmitic acid is produced endogenously in the brain and brain penetrant in the animals.

Originator

Approval Year

1990
111
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
 5.3 null [pEC50]
Binding Agent
1076
 156.0 µM [Kd]
Binding Agent
1076
Binding Agent
1076
Binding Agent
1076
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8583
SURFAXIN

Approved Use

SURFAXIN is indicated for the prevention of respiratory distress syndrome (RDS) in premature infants at high risk for RDS.

Launch Date

2012
PubMed

PubMed

TitleDatePubMed
Gbeta gamma isoforms selectively rescue plasma membrane localization and palmitoylation of mutant Galphas and Galphaq.
2001-06-29
Demonstration of direct effects of growth hormone on neonatal cardiomyocytes.
2001-06-22
Insulin inhibits peroxisomal fatty acid oxidation in isolated rat hepatocytes.
2001-06
Systemic and regional free fatty acid metabolism in type 2 diabetes.
2001-06
Physiological levels of mammalian uncoupling protein 2 do not uncouple yeast mitochondria.
2001-05-25
[Branched alkanes and other apolar compounds produced by the cyanobacterium Microcoleus vaginatus from the Negev desert].
2001-05-19
Differential palmitoylation of two mouse glutamate receptor interacting protein 1 forms with different N-terminal sequences.
2001-05-18
Biochemical characterization of the reverse activity of rat brain ceramidase. A CoA-independent and fumonisin B1-insensitive ceramide synthase.
2001-05-18
Identification and quantitation of unique fatty acid oxidation products in human atherosclerotic plaque using high-performance liquid chromatography.
2001-05-15
Palmitoylation of caveolin-1 in endothelial cells is post-translational but irreversible.
2001-05-11
Palmitate-induced apoptosis can occur through a ceramide-independent pathway.
2001-05-04
Thiazolidinediones increase plasma-adipose tissue FFA exchange capacity and enhance insulin-mediated control of systemic FFA availability.
2001-05
Chronic valproate treatment decreases the in vivo turnover of arachidonic acid in brain phospholipids: a possible common effect of mood stabilizers.
2001-05
Heparin-induced release of protein-bound solutes during hemodialysis is an in vitro artifact.
2001-05
Effects of lung surfactant proteins, SP-B and SP-C, and palmitic acid on monolayer stability.
2001-05
Effects of free fatty acids on beta-cell functions: a possible involvement of peroxisome proliferator-activated receptors alpha or pancreatic/duodenal homeobox.
2001-05
Imaging of monolayers composed of palmitic acid and lung surfactant protein B.
2001-05
The sites for fatty acylation, phosphorylation and intermolecular disulphide bond formation of influenza C virus CM2 protein.
2001-05
A high-sucrose diet increases gluconeogenic capacity in isolated periportal and perivenous rat hepatocytes.
2001-05
n-6 and n-3 polyunsaturated fatty acids differentially modulate oncogenic Ras activation in colonocytes.
2001-05
Plasma membrane localization of palmitoylated tubulin.
2001-04-27
Induction of apoptosis through B-cell receptor cross-linking occurs via de novo generated C16-ceramide and involves mitochondria.
2001-04-27
Kinetics of the lipase-catalyzed synthesis of glucose esters in acetone.
2001-04-20
Thioacylation is required for targeting G-protein subunit G(o1alpha) to detergent-insoluble caveolin-containing membrane domains.
2001-04-15
Pulmonary surfactant protein SP-B is significantly more immunoreactive in anionic than in zwitterionic bilayers.
2001-04-13
Regulation of surfactant-like particle secretion by Caco-2 cells.
2001-04-02
Tolerance induction by acylated peptides: suppression of EAE in the mouse with palmitoylated PLP peptides.
2001-04-02
Fatty acid and triglyceride composition of milk fat from lactating Holstein cows in response to supplemental canola oil.
2001-04
Effect of gamma-butyrobetaine on fatty liver in juvenile visceral steatosis mice.
2001-04
Identification of fatty acid molecules in a Fasciola hepatica immunoprophylactic fatty acid-binding protein.
2001-04
Effects of authentic and VLDL hydrolysis-derived fatty acids on vascular smooth muscle cell growth.
2001-04
Carotenoid esters in vegetables and fruits: a screening with emphasis on beta-cryptoxanthin esters.
2001-04
Uncoupling protein 2: a possible link between fatty acid excess and impaired glucose-induced insulin secretion?
2001-04
Continuous fatty acid oxidation and reduced fat storage in mice lacking acetyl-CoA carboxylase 2.
2001-03-30
Regulation of G proteins by covalent modification.
2001-03-26
Expression of rat liver long-chain acyl-CoA synthetase and characterization of its role in the metabolism of R-ibuprofen and other fatty acid-like xenobiotics.
2001-03-15
Anaerobic biodegradation of alkanes by enriched consortia under four different reducing conditions.
2001-03
Optimization of methods and treatment conditions for studying effects of fatty acids on cell growth.
2001-03
Effects of diets enriched in n-6 or n-3 fatty acids on cholesterol metabolism in older rats chronically fed a cholesterol-enriched diet.
2001-03
Brain and hippocampus fatty acid composition in phospholipid classes of aged-relative cognitive deficit rats.
2001-03
Gas chromatographic analysis of total fatty acids in cider.
2001-03
Modelling of hexadecane degradation in continuous-flow cultures.
2001-03
Effects of antiinflammatory triterpenes isolated from Leptadenia hastata latex on keratinocyte proliferation.
2001-03
Participation of carnitine palmitoyltransferase in the synthesis of dipalmitoylphosphatidylcholine in rat alveolar type II cells.
2001-02
A stearic acid-rich diet improves thrombogenic and atherogenic risk factor profiles in healthy males.
2001-02
Fatty acid-induced apoptosis in neonatal cardiomyocytes: redox signaling.
2001-02
Lipotoxicity of the pancreatic beta-cell is associated with glucose-dependent esterification of fatty acids into neutral lipids.
2001-02
Myocardial fatty acid oxidation in patients with impaired glucose tolerance.
2001-02
Effect of fatty acids on phase behavior of hydrated dipalmitoylphosphatidylcholine bilayer: saturated versus unsaturated fatty acids.
2001-02
L-carnitine reduces malondialdehyde concentrations in isolated rat hearts in dependence on perfusion conditions.
2001-01
Patents

Patents

2682549
4
2791596
4
JP2000178208A
15
JPH06345802A
21

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
The conditioned media from palmitic acid (0.2 mM) treated rat cortical astroglia, but not the cerebellar astroglia, significantly elevated levels of phosphorylated tau and BACE1 in cortical neurons as compared to controls
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:35:19 GMT 2025
Edited
by admin
on Mon Mar 31 17:35:19 GMT 2025
Record UNII
2V16EO95H1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CETYL ACID
VANDF  
Preferred Name English
PALMITIC ACID
INCI  
Official Name English
SURFAXIN COMPONENT PALMITIC ACID
Brand Name English
HYDROFOL ACID 1690
Code English
PALMITIC ACID [USAN]
Common Name English
KORTACID 1698
Code English
PALMITATE
Common Name English
N-HEXADECANOIC ACID
Common Name English
PALMITIC ACID [FHFI]
Common Name English
PALMITIC ACID [FCC]
Common Name English
PALMITIC ACID [USP-RS]
Common Name English
1-PENTADECANECARBOXYLIC ACID
Systematic Name English
PALMITIC ACID (CONSTITUENT OF BORAGE SEED OIL) [DSC]
Common Name English
PALMITIC ACID (CONSTITUENT OF SPIRULINA) [DSC]
Common Name English
HEXADECANOIC ACID
Systematic Name English
CETYL ACID [VANDF]
Common Name English
PALMITIC ACID [EP MONOGRAPH]
Common Name English
CETYLIC ACID
Common Name English
PALMITIC ACID (CONSTITUENT OF EVENING PRIMROSE OIL) [DSC]
Common Name English
IMEX C 1498
Code English
PALMITIC ACID [DSC]
Common Name English
LOXIOL EP 278
Code English
FEMA NO. 2832
Code English
NSC-5030
Code English
PALMITIC ACID [MI]
Common Name English
PALMITIC ACID [HSDB]
Common Name English
PRIFAC-2960
Common Name English
PALMITIC ACID (CONSTITUENT OF FLAX SEED OIL) [DSC]
Common Name English
PRISTERENE-4934
Common Name English
PALMITIC ACID [MART.]
Common Name English
PALMITIC ACID [II]
Common Name English
PALMITIC ACID [VANDF]
Common Name English
Palmitic acid [WHO-DD]
Common Name English
EDENOR C 16-98-100
Code English
PALMITIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC]
Common Name English
LUCINACTANT COMPONENT PALMITIC ACID
Common Name English
Classification Tree Code System Code
LOINC 47641-6
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
NCI_THESAURUS C68421
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
LOINC 55873-4
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
LOINC 2719-3
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
EU-Orphan Drug EU/3/04/217
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
LOINC 74625-5
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
DSLD 1603 (Number of products:186)
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
LOINC 75115-6
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
NCI_THESAURUS C68388
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
LOINC 35161-9
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
JECFA EVALUATION PALMITIC ACID
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
CFR 21 CFR 172.860
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
CFR 21 CFR 357.210
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
LOINC 74624-8
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
Code System Code Type Description
NSC
5030
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
USAN
LL-31
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
CHEBI
15756
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
RS_ITEM_NUM
1492007
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
WIKIPEDIA
PALMITIC ACID
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
CAS
57-10-3
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
SMS_ID
100000091751
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
MERCK INDEX
m8367
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY Merck Index
HSDB
5001
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
ChEMBL
CHEMBL82293
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
NCI_THESAURUS
C61873
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
JECFA MONOGRAPH
1091
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
RXCUI
1426390
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY RxNorm
EVMPD
SUB14744MIG
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
PUBCHEM
985
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
DAILYMED
2V16EO95H1
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-312-9
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
CHEBI
7896
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
FDA UNII
2V16EO95H1
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
DRUG BANK
DB03796
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
EPA CompTox
DTXSID2021602
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
RXCUI
1370621
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
ALTERNATIVE
MESH
D019308
Created by admin on Mon Mar 31 17:35:19 GMT 2025 , Edited by admin on Mon Mar 31 17:35:19 GMT 2025
PRIMARY
Related Record Type Details
PALM OIL
LIPID -> FATTY ACID
PEANUT OIL
LIPID -> FATTY ACID
CORN OIL
LIPID -> FATTY ACID
Value is fatty acid composition (%) for international corn oil w/std. deviation of 1.4% LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
Structure of POTASSIUM PALMITATE
SALT/SOLVATE -> PARENT
EVENING PRIMROSE OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SAFFLOWER OIL
LIPID -> FATTY ACID
Structure of TRIETHANOLAMINE PALMITATE
SALT/SOLVATE -> PARENT
RICE BRAN OIL
LIPID -> FATTY ACID
Structure of MANNITAN MONOPALMITATE
SALT/SOLVATE -> PARENT
Structure of PHENYLEPHRINE PALMITATE
SALT/SOLVATE -> PARENT
Structure of PICOPERINE PALMITATE
SALT/SOLVATE -> PARENT
Structure of ALUMINUM PALMITATE
SALT/SOLVATE -> PARENT
Structure of MAGNESIUM PALMITATE
SALT/SOLVATE -> PARENT
Structure of SODIUM PALMITATE
SALT/SOLVATE -> PARENT
Structure of ZINC PALMITATE
SALT/SOLVATE -> PARENT
ARCTIUM LAPPA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
OLIVE OIL
LIPID -> FATTY ACID
ELYMUS REPENS ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
Compound measured as 23.50% of the composition of the steam distillate of Elymus repens rhizome as per R Boesel in Planta Medica iss:4 pg:399-400, 1989.
SAW PALMETTO
PARENT -> CONSTITUENT ALWAYS PRESENT
SESAME OIL
LIPID -> FATTY ACID
Structure of NEAMINE PALMITATE
SALT/SOLVATE -> PARENT
COTTONSEED OIL
LIPID -> FATTY ACID
G Jurriens and ACJ Kroesen, J Am Oil Chem Soc, 42(9)(1965)(average value). Range values as of FAO/WHO Codex Alimentarius Committee on commercial fats and oils.(unspecified percent)
IRIS VERSICOLOR ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
CORN OIL
LIPID -> FATTY ACID
Value is fatty acid composition (%) for US corn oil w/std. deviation of 0.55% LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
SOYBEAN OIL
LIPID -> FATTY ACID
Values are % of weight of fatty acid composition. O?Connor, RT, Herb, SF; J Am Oil Chem Soc 47, 186A, 195A, 197A(1970)(range) Brignoli, CA et al: J Am Diet Assoc 68, 224(1976)(average)
Structure of NEOMYCIN C PALMITATE
SALT/SOLVATE -> PARENT
AVOCADO OIL
LIPID -> FATTY ACID
Structure of FRAMYCETIN PALMITATE
SALT/SOLVATE -> PARENT
FISH OIL
LIPID -> FATTY ACID
MAY BE PRESENT
USP
CANOLA OIL
LIPID -> FATTY ACID
MENYANTHES TRIFOLIATA LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
COD LIVER OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
SPIRULINA
PARENT -> CONSTITUENT ALWAYS PRESENT
Coconut oil
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean.
Structure of LITHIUM PALMITATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of PALMITIC ACID
ACTIVE MOIETY
NIH
NCATS
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