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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
2554
Curator's Comment: Palmitic acid is produced endogenously in the brain and brain penetrant in the animals.

Originator

Approval Year

1990
108
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 5.3 null [pEC50]
Binding Agent
1064
 156.0 µM [Kd]
Binding Agent
1064
Binding Agent
1064
Binding Agent
1064
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8429
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
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
Lysosomal-type PLA2 and turnover of alveolar DPPC.
2001 Apr
Pulmonary surfactant protein SP-B is significantly more immunoreactive in anionic than in zwitterionic bilayers.
2001 Apr 13
Arachidonic acid causes cell death through the mitochondrial permeability transition. Implications for tumor necrosis factor-alpha aopototic signaling.
2001 Apr 13
Thioacylation is required for targeting G-protein subunit G(o1alpha) to detergent-insoluble caveolin-containing membrane domains.
2001 Apr 15
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
Induction of apoptosis through B-cell receptor cross-linking occurs via de novo generated C16-ceramide and involves mitochondria.
2001 Apr 27
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
DAG accumulation from saturated fatty acids desensitizes insulin stimulation of glucose uptake in muscle cells.
2001 Feb
The growth inhibitory effect of conjugated linoleic acid on a human hepatoma cell line, HepG2, is induced by a change in fatty acid metabolism, but not the facilitation of lipid peroxidation in the cells.
2001 Feb 26
OspA, a lipoprotein antigen of the obligate intracellular bacterial pathogen Piscirickettsia salmonis.
2001 Jan
Free fatty acid-induced inhibition of glucose and insulin-like growth factor I-induced deoxyribonucleic acid synthesis in the pancreatic beta-cell line INS-1.
2001 Jan
Characterization of a novel triphosphonooctaosylceramide from the eggs of the sea hare, Aplysia kurodai.
2001 Jan
Functional analysis of mutant human carnitine acylcarnitine translocases in yeast.
2001 Jan 26
Determination of retinoids in galenicals by column liquid chromatography with fluorescence and diode-array detection.
2001 Jan 5
Insulin inhibits peroxisomal fatty acid oxidation in isolated rat hepatocytes.
2001 Jun
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
JlpA, a novel surface-exposed lipoprotein specific to Campylobacter jejuni, mediates adherence to host epithelial cells.
2001 Mar
Purification and characterization of the fatty acid synthase from Bugula neritina.
2001 Mar
Development and characterization of an animal model of carnitine deficiency.
2001 Mar
Palmitoylation of the luteinizing hormone/human chorionic gonadotropin receptor regulates receptor interaction with the arrestin-mediated internalization pathway.
2001 Mar
Role of fatty acids in the recovery of cardiac function during resuscitation from hemorrhagic shock.
2001 Mar
Macrophages transfer [14C]-labelled fatty acids to pancreatic islets in culture.
2001 Mar
Monounsaturated fatty acid diets improve glycemic tolerance through increased secretion of glucagon-like peptide-1.
2001 Mar
Increased uncoupling proteins and decreased efficiency in palmitate-perfused hyperthyroid rat heart.
2001 Mar
Regulation of G proteins by covalent modification.
2001 Mar 26
Bowman-Birk protease inhibitor and its palmitic acid conjugate prevent 7,12-dimethylbenz[a]anthracene-induced transformation in cultured mouse mammary glands.
2001 Mar 26
Continuous fatty acid oxidation and reduced fat storage in mice lacking acetyl-CoA carboxylase 2.
2001 Mar 30
Molecular dynamics simulations of stratum corneum lipid models: fatty acids and cholesterol.
2001 Mar 9
[Branched alkanes and other apolar compounds produced by the cyanobacterium Microcoleus vaginatus from the Negev desert].
2001 Mar-Apr
Thiazolidinediones increase plasma-adipose tissue FFA exchange capacity and enhance insulin-mediated control of systemic FFA availability.
2001 May
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
Imaging of monolayers composed of palmitic acid and lung surfactant protein B.
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
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

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 Fri Dec 15 15:01:00 GMT 2023
Edited
by admin
on Fri Dec 15 15:01:00 GMT 2023
Record UNII
2V16EO95H1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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 [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
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 Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
NCI_THESAURUS C68421
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
LOINC 55873-4
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
LOINC 2719-3
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
EU-Orphan Drug EU/3/04/217
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
LOINC 74625-5
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
DSLD 1603 (Number of products:186)
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
LOINC 75115-6
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
NCI_THESAURUS C68388
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
LOINC 35161-9
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
JECFA EVALUATION PALMITIC ACID
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
CFR 21 CFR 172.860
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
CFR 21 CFR 357.210
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
LOINC 74624-8
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
Code System Code Type Description
NSC
5030
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
USAN
LL-31
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
CHEBI
15756
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
RS_ITEM_NUM
1492007
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
WIKIPEDIA
PALMITIC ACID
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
CAS
57-10-3
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
SMS_ID
100000091751
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
MERCK INDEX
m8367
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY Merck Index
HSDB
5001
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
ChEMBL
CHEMBL82293
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
NCI_THESAURUS
C61873
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
JECFA MONOGRAPH
1091
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
RXCUI
1426390
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY RxNorm
EVMPD
SUB14744MIG
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
PUBCHEM
985
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
DAILYMED
2V16EO95H1
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-312-9
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
CHEBI
7896
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
FDA UNII
2V16EO95H1
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
DRUG BANK
DB03796
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID2021602
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
RXCUI
1370621
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
ALTERNATIVE
MESH
D019308
Created by admin on Fri Dec 15 15:01:00 GMT 2023 , Edited by admin on Fri Dec 15 15:01:00 GMT 2023
PRIMARY
Related Record Type Details
SAW PALMETTO
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
PEANUT OIL
LIPID -> FATTY ACID
Values are % of total.
SPIRULINA
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
COD LIVER OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
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
Structure of TRIETHANOLAMINE PALMITATE
SALT/SOLVATE -> PARENT
SESAME OIL
LIPID -> FATTY ACID
Value is % of total fatty acids. Maiti, S, et al; Handbook of Annual Oilseed Crops, OIBH, New Delhi, India(1988), pp.1987-90
Structure of MANNITAN MONOPALMITATE
SALT/SOLVATE -> PARENT
Structure of PHENYLEPHRINE PALMITATE
SALT/SOLVATE -> PARENT
Structure of PICOPERINE PALMITATE
SALT/SOLVATE -> PARENT
SUNFLOWER OIL
LIPID -> FATTY ACID
Values given are in undefined precent. Average is typical for U.S. Sunflower oil.
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
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.
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)
EVENING PRIMROSE OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
Structure of NEOMYCIN C PALMITATE
SALT/SOLVATE -> PARENT
RICE BRAN OIL
LIPID -> FATTY ACID
U.S produced rice oil. Values are % of composition.
OLIVE OIL
LIPID -> FATTY ACID
TURKISH SOURCE
AVOCADO OIL
LIPID -> FATTY ACID
VARIES ACCORDING TO METHOD OF EXTRACTION.
Structure of FRAMYCETIN PALMITATE
SALT/SOLVATE -> PARENT
SAFFLOWER OIL
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.
FISH OIL
LIPID -> FATTY ACID
MAY BE PRESENT
USP
PALM OIL
LIPID -> FATTY ACID
Values are % of total.
CANOLA OIL
LIPID -> FATTY ACID
MENYANTHES TRIFOLIATA LEAF
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
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