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Details

Stereochemistry ACHIRAL
Molecular Formula C16H32O2
Molecular Weight 256.4247
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 256.4247
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

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

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
SURFAXIN

Approved Use

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

Launch Date

1.33090561E12
PubMed

PubMed

TitleDatePubMed
Fatty acid and triglyceride composition of milk fat from lactating Holstein cows in response to supplemental canola oil.
2001 Apr
Effect of gamma-butyrobetaine on fatty liver in juvenile visceral steatosis mice.
2001 Apr
Identification of fatty acid molecules in a Fasciola hepatica immunoprophylactic fatty acid-binding protein.
2001 Apr
Effects of authentic and VLDL hydrolysis-derived fatty acids on vascular smooth muscle cell growth.
2001 Apr
Carotenoid esters in vegetables and fruits: a screening with emphasis on beta-cryptoxanthin esters.
2001 Apr
Uncoupling protein 2: a possible link between fatty acid excess and impaired glucose-induced insulin secretion?
2001 Apr
Pulmonary surfactant protein SP-B is significantly more immunoreactive in anionic than in zwitterionic bilayers.
2001 Apr 13
Regulation of surfactant-like particle secretion by Caco-2 cells.
2001 Apr 2
Tolerance induction by acylated peptides: suppression of EAE in the mouse with palmitoylated PLP peptides.
2001 Apr 2
Kinetics of the lipase-catalyzed synthesis of glucose esters in acetone.
2001 Apr 20
Plasma membrane localization of palmitoylated tubulin.
2001 Apr 27
Induction of apoptosis through B-cell receptor cross-linking occurs via de novo generated C16-ceramide and involves mitochondria.
2001 Apr 27
Participation of carnitine palmitoyltransferase in the synthesis of dipalmitoylphosphatidylcholine in rat alveolar type II cells.
2001 Feb
A stearic acid-rich diet improves thrombogenic and atherogenic risk factor profiles in healthy males.
2001 Feb
Fatty acid-induced apoptosis in neonatal cardiomyocytes: redox signaling.
2001 Feb
Lipotoxicity of the pancreatic beta-cell is associated with glucose-dependent esterification of fatty acids into neutral lipids.
2001 Feb
Myocardial fatty acid oxidation in patients with impaired glucose tolerance.
2001 Feb
Effect of fatty acids on phase behavior of hydrated dipalmitoylphosphatidylcholine bilayer: saturated versus unsaturated fatty acids.
2001 Feb
L-carnitine reduces malondialdehyde concentrations in isolated rat hearts in dependence on perfusion conditions.
2001 Jan
Insulin inhibits peroxisomal fatty acid oxidation in isolated rat hepatocytes.
2001 Jun
Systemic and regional free fatty acid metabolism in type 2 diabetes.
2001 Jun
Demonstration of direct effects of growth hormone on neonatal cardiomyocytes.
2001 Jun 22
Gbeta gamma isoforms selectively rescue plasma membrane localization and palmitoylation of mutant Galphas and Galphaq.
2001 Jun 29
Anaerobic biodegradation of alkanes by enriched consortia under four different reducing conditions.
2001 Mar
Optimization of methods and treatment conditions for studying effects of fatty acids on cell growth.
2001 Mar
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 Mar
Gas chromatographic analysis of total fatty acids in cider.
2001 Mar
Modelling of hexadecane degradation in continuous-flow cultures.
2001 Mar
Effects of antiinflammatory triterpenes isolated from Leptadenia hastata latex on keratinocyte proliferation.
2001 Mar
Atomic resolution structure analysis of beta' polymorph crystal of a triacylglycerol: 1,2-dipalmitoyl-3-myristoyl-sn-glycerol.
2001 Mar
JlpA, a novel surface-exposed lipoprotein specific to Campylobacter jejuni, mediates adherence to host epithelial cells.
2001 Mar
Palmitoylation of the luteinizing hormone/human chorionic gonadotropin receptor regulates receptor interaction with the arrestin-mediated internalization pathway.
2001 Mar
Direct regulatory effect of fatty acids on macrophage lipoprotein lipase: potential role of PPARs.
2001 Mar
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 Mar 15
Regulation of G proteins by covalent modification.
2001 Mar 26
Continuous fatty acid oxidation and reduced fat storage in mice lacking acetyl-CoA carboxylase 2.
2001 Mar 30
[Branched alkanes and other apolar compounds produced by the cyanobacterium Microcoleus vaginatus from the Negev desert].
2001 Mar-Apr
Chronic valproate treatment decreases the in vivo turnover of arachidonic acid in brain phospholipids: a possible common effect of mood stabilizers.
2001 May
Effects of lung surfactant proteins, SP-B and SP-C, and palmitic acid on monolayer stability.
2001 May
Effects of free fatty acids on beta-cell functions: a possible involvement of peroxisome proliferator-activated receptors alpha or pancreatic/duodenal homeobox.
2001 May
Imaging of monolayers composed of palmitic acid and lung surfactant protein B.
2001 May
The sites for fatty acylation, phosphorylation and intermolecular disulphide bond formation of influenza C virus CM2 protein.
2001 May
A high-sucrose diet increases gluconeogenic capacity in isolated periportal and perivenous rat hepatocytes.
2001 May
n-6 and n-3 polyunsaturated fatty acids differentially modulate oncogenic Ras activation in colonocytes.
2001 May
Palmitoylation of caveolin-1 in endothelial cells is post-translational but irreversible.
2001 May 11
Identification and quantitation of unique fatty acid oxidation products in human atherosclerotic plaque using high-performance liquid chromatography.
2001 May 15
Differential palmitoylation of two mouse glutamate receptor interacting protein 1 forms with different N-terminal sequences.
2001 May 18
Biochemical characterization of the reverse activity of rat brain ceramidase. A CoA-independent and fumonisin B1-insensitive ceramide synthase.
2001 May 18
Physiological levels of mammalian uncoupling protein 2 do not uncouple yeast mitochondria.
2001 May 25
Palmitate-induced apoptosis can occur through a ceramide-independent pathway.
2001 May 4
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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 Fri Jun 25 21:17:03 UTC 2021
Edited
by admin
on Fri Jun 25 21:17:03 UTC 2021
Record UNII
2V16EO95H1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PALMITIC ACID
Common Name English
SURFAXIN COMPONENT PALMITIC ACID
Brand Name English
HYDROFOL ACID 1690
Code English
PALMITIC ACID [USAN]
Common Name English
KORTACID 1698
Code 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 [INCI]
Common Name 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
CETYL ACID
VANDF  
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
EDENOR C 16-98-100
Code English
PALMITIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC]
Common Name English
PALMITIC ACID [WHO-DD]
Common Name English
LUCINACTANT COMPONENT PALMITIC ACID
Common Name English
Classification Tree Code System Code
LOINC 47641-6
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
NCI_THESAURUS C68421
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
LOINC 55873-4
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
LOINC 2719-3
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
EU-Orphan Drug EU/3/04/217
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
LOINC 74625-5
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
DSLD 1603 (Number of products:186)
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
LOINC 75115-6
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
NCI_THESAURUS C68388
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
LOINC 35161-9
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
JECFA EVALUATION PALMITIC ACID
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
CFR 21 CFR 172.860
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
CFR 21 CFR 357.210
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
LOINC 74624-8
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
Code System Code Type Description
WIKIPEDIA
PALMITIC ACID
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
PRIMARY
CAS
57-10-3
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
PRIMARY
MERCK INDEX
M8367
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
PRIMARY Merck Index
HSDB
5001
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
PRIMARY
ChEMBL
CHEMBL82293
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
PRIMARY
NCI_THESAURUS
C61873
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
PRIMARY
RXCUI
1426390
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
PRIMARY RxNorm
USP_CATALOG
1492007
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
PRIMARY USP-RS
EVMPD
SUB14744MIG
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
PRIMARY
PUBCHEM
985
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-312-9
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
PRIMARY
FDA UNII
2V16EO95H1
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
PRIMARY
DRUG BANK
DB03796
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
PRIMARY
EPA CompTox
57-10-3
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
PRIMARY
RXCUI
1370621
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
PRIMARY
MESH
D019308
Created by admin on Fri Jun 25 21:17:03 UTC 2021 , Edited by admin on Fri Jun 25 21:17:03 UTC 2021
PRIMARY
Related Record Type Details
LIPID -> FATTY ACID
Value is % of total fatty acids. Goden VJ, Spensley PC; Oils and Oilseeds, TPI, London, 1971, p.151
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)
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Values are % of total.
LIPID -> FATTY ACID
Value is % of composition. Oleic safflower variety UC-1 cited by Knowles, P, Calif. Agr. 19(12), 15(1965), produced 4.5% by composition.
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Values given are in undefined precent. Average is typical for U.S. Sunflower oil.
LIPID -> FATTY ACID
IOOC limits
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
LIPID -> FATTY ACID
VARIES ACCORDING TO METHOD OF EXTRACTION.
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.
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
LIPID -> FATTY ACID
Values are % of total.
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)
PARENT -> CONSTITUENT ALWAYS PRESENT
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)
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)
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
LIPID -> FATTY ACID
MAY BE PRESENT
USP
LIPID -> FATTY ACID
U.S produced rice oil. Values are % of composition.
LIPID -> FATTY ACID
PARENT -> CONSTITUENT ALWAYS PRESENT
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean.
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY