Record Information
Version1.0
Creation date2010-04-08 22:09:46 UTC
Update date2020-09-17 15:42:18 UTC
Primary IDFDB011679
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHexadecanoic acid
DescriptionPalmitic acid, also known as palmitate or C16, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Palmitic acid is a very hydrophobic molecule, practically insoluble in water and relatively neutral. Palmitic acid, or hexadecanoic acid, is one of the most common saturated fatty acids found in animals, plants, and microorganisms. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). In humans and other mammals, excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. As a consequence, palmitic acid is a major lipid component of animals. In humans, one analysis found it to make up 21–30% (molar) of human depot fat (PMID: 13756126), and it is a major, but highly variable, lipid component of human breast milk (PMID: 352132). Palmitic acid has been detected, but not quantified in, several different foods, such as sea-buckthornberries, avocado, star fruits, babassu palms, and acerola. Palmitic acid is used to produce soaps, cosmetics, and industrial mould release agents. These applications use sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil triglycerides, rendered from palm trees (species Elaeis guineensis), are treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups, yielding glycerol and sodium palmitate. Aluminium salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm. The word "napalm" is derived from the word’s naphthenic acid and palmitic acid. Palmitic acid is also used in the determination of water hardness and is a surfactant of Levovist, an intravenous ultrasonic contrast agent.
CAS Number57-10-3
Structure
Thumb
Synonyms
SynonymSource
1-Hexyldecanoic acidChEBI
1-Pentadecanecarboxylic acidChEBI
16:00ChEBI
C16ChEBI
C16 Fatty acidChEBI
C16:0ChEBI
Cetylic acidChEBI
CH3-[CH2]14-COOHChEBI
FA 16:0ChEBI
HexadecanoateChEBI
Hexadecoic acidChEBI
Hexadecylic acidChEBI
Hexaectylic acidChEBI
N-Hexadecanoic acidChEBI
N-Hexadecoic acidChEBI
PalmitateChEBI
Palmitinic acidChEBI
PalmitinsaeureChEBI
Pentadecanecarboxylic acidChEBI
1-HexyldecanoateGenerator
1-PentadecanecarboxylateGenerator
CetylateGenerator
Hexadecanoic acidGenerator
HexadecoateGenerator
HexadecylateGenerator
HexaectylateGenerator
N-HexadecanoateGenerator
N-HexadecoateGenerator
PalmitinateGenerator
PentadecanecarboxylateGenerator
Edenor C16HMDB
Emersol 140HMDB
Emersol 143HMDB
Glycon p-45HMDB
Hexadecanoate (N-C16:0)HMDB
Hexadecanoic acid palmitic acidHMDB
HydrofolHMDB
Hydrofol acid 1690HMDB
Hystrene 8016HMDB
Hystrene 9016HMDB
Industrene 4516HMDB
Kortacid 1698HMDB
Loxiol ep 278HMDB
Lunac p 95HMDB
Lunac p 95KCHMDB
Lunac p 98HMDB
PalmitoateHMDB
Palmitoic acidHMDB
PAMHMDB
PLMHMDB
Prifac 2960HMDB
Prifrac 2960HMDB
Pristerene 4934HMDB
Univol u332HMDB
Acid, hexadecanoicHMDB
Acid, palmiticHMDB
FA(16:0)HMDB
Aethalic aciddb_source
C16 fatty acidbiospider
FEMA 2832db_source
Glycon P-45HMDB
Hexadecanoic acid (9CI)biospider
Lunac P 95HMDB
Lunac P 95kcHMDB
Lunac P 98HMDB
Palmitic acidbiospider
Palmitic acid, USANdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.00041 g/LALOGPS
logP7.23ALOGPS
logP6.26ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity77.08 m³·mol⁻¹ChemAxon
Polarizability34.36 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H32O2
IUPAC namehexadecanoic acid
InChI IdentifierInChI=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)
InChI KeyIPCSVZSSVZVIGE-UHFFFAOYSA-N
Isomeric SMILESCCCCCCCCCCCCCCCC(O)=O
Average Molecular Weight256.4241
Monoisotopic Molecular Weight256.240230268
Classification
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 74.94%; H 12.58%; O 12.48%DFC
Melting PointMp 63-64°DFC
Boiling PointBp15 215°DFC
Experimental Water Solubility4e-05 mg/mL at 25 oCROBB,ID (1966)
Experimental logP7.17SANGSTER (1993)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-06xx-9100000000-7ac9cd088cb9cb9f75602014-09-20View Spectrum
GC-MSHexadecanoic acid, 1 TMS, GC-MS Spectrumsplash10-014i-0901000000-51ee83f9462d25fa4045Spectrum
GC-MSHexadecanoic acid, 1 TMS, GC-MS Spectrumsplash10-0100-9700000000-3d8b6cf4736afa482b57Spectrum
GC-MSHexadecanoic acid, 1 TMS, GC-MS Spectrumsplash10-0159-2901000000-fb423e89a78708021db1Spectrum
GC-MSHexadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-0abc-9110000000-6d7f0dbe5b588850b941Spectrum
GC-MSHexadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-014i-0901000000-51ee83f9462d25fa4045Spectrum
GC-MSHexadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-0100-9700000000-3d8b6cf4736afa482b57Spectrum
GC-MSHexadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-0159-2901000000-fb423e89a78708021db1Spectrum
GC-MSHexadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-0159-2901000000-fb423e89a78708021db1Spectrum
GC-MSHexadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-014i-1900000000-d7638a578d846871e670Spectrum
Predicted GC-MSHexadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9610000000-f75185fa40c090817f46Spectrum
Predicted GC-MSHexadecanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-022i-9440000000-7d3a81432d58729f9f98Spectrum
Predicted GC-MSHexadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHexadecanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-0090000000-39c3a0e17432781e97602012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-0090000000-8ec1a6953701fc22ce272012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0fba-9200000000-23c995bf81d5ef6094892012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0abc-9110000000-12f1884d67998fb924a52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0091010000-6922411e48d747e592b52017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0091010000-6922411e48d747e592b52017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0091010000-6922411e48d747e592b52017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0091010000-6922411e48d747e592b52017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0091000000-4f6858c1cc0f04cbabf52017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0090000000-14e58eecd83ba52123c22017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0090000000-c3f9f4d5c336137b7fcf2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0090000000-47919da3faa8e0f52bbc2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4i-0090000000-fdd9e98416da12470fe92017-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-26bb4965a56ab0e82b492015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06rj-5790000000-251700f3edf9a5af04cd2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9600000000-5b75a67e276017f221b82015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-26bb4965a56ab0e82b492015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06rj-5790000000-251700f3edf9a5af04cd2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9600000000-5b75a67e276017f221b82015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-e4a4200bd25f8fa480cc2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bti-1090000000-768a48058fc0a2d7a8772015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9320000000-c9714c7ffdc804bf93232015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-e4a4200bd25f8fa480cc2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bti-1090000000-768a48058fc0a2d7a8772015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9320000000-c9714c7ffdc804bf93232015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
ChemSpider ID960
ChEMBL IDCHEMBL82293
KEGG Compound IDC00249
Pubchem Compound ID985
Pubchem Substance IDNot Available
ChEBI ID15756
Phenol-Explorer IDNot Available
DrugBank IDDB03796
HMDB IDHMDB00220
CRC / DFC (Dictionary of Food Compounds) IDGXZ18-W:GXZ18-W
EAFUS ID2858
Dr. Duke IDHEXADECANOIC-ACID|PALMITIC-ACID
BIGG ID34386
KNApSAcK IDC00030479
HET IDPLM
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1009101
SuperScent IDNot Available
Wikipedia IDPalmitic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
5alpha-reductase inhibitor50781 An EC 1.3.1.* (oxidoreductase acting on CH-CH group of donor, NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of of 3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+)), EC 1.3.1.22, the enzyme which converts testosterone (CHEBI:17347) into the more potent androgen 5alpha-dihydrotestosterone.DUKE
anti alopecic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti androgenic35497 A compound which inhibits or antagonises the biosynthesis or actions of androgens.DUKE
anti fibrinolyticDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
hemolyticDUKE
hypercholesterolemicDUKE
lubricantDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
propecicDUKE
soapDUKE
Enzymes
NameGene NameUniProt ID
Bile acid-CoA:amino acid N-acyltransferaseBAATQ14032
Liver carboxylesterase 1CES1P23141
Pancreatic triacylglycerol lipasePNLIPP16233
Hepatic triacylglycerol lipaseLIPCP11150
Inactive pancreatic lipase-related protein 1PNLIPRP1P54315
Patatin-like phospholipase domain-containing protein 3PNPLA3Q9NST1
Gastric triacylglycerol lipaseLIPFP07098
Endothelial lipaseLIPGQ9Y5X9
Pancreatic lipase-related protein 2PNLIPRP2P54317
Lipoprotein lipaseLPLP06858
Patatin-like phospholipase domain-containing protein 4PNPLA4P41247
Patatin-like phospholipase domain-containing protein 2PNPLA2Q96AD5
Pancreatic lipase-related protein 3PNLIPRP3Q17RR3
CholinesteraseBCHEP06276
Carboxylesterase 5ACES5AQ6NT32
60 kDa lysophospholipaseASPGQ86U10
Fatty acid synthaseFASNP49327
Galactoside-binding soluble lectin 13LGALS13Q9UHV8
Eosinophil lysophospholipaseCLCQ05315
Cocaine esteraseCES2O00748
Acylphosphatase-2ACYP2P14621
Acylphosphatase-1ACYP1P07311
AspartoacylaseASPAP45381
Aspartoacylase-2ACY3Q96HD9
Lysosomal thioesterase PPT2PPT2Q9UMR5
Acid ceramidaseASAH1Q13510
Homeodomain-interacting protein kinase 1HIPK1Q86Z02
Peroxisome proliferator-activated receptor gammaPPARGP37231
Long-chain fatty acid transport protein 6SLC27A6Q9Y2P4
Long-chain fatty acid transport protein 3SLC27A3Q5K4L6
Long-chain fatty acid transport protein 4SLC27A4Q6P1M0
Putative neutral ceramidase CASAH2CP0C7U2
Alkaline ceramidase 2ACER2Q5QJU3
Neutral ceramidaseASAH2Q9NR71
Alkaline ceramidase 1ACER1Q8TDN7
Neuropathy target esterasePNPLA6Q8IY17
Carboxylesterase 3CES3Q6UWW8
S-acyl fatty acid synthase thioesterase, medium chainOLAHQ9NV23
Cytosolic acyl coenzyme A thioester hydrolaseACOT7O00154
Acyl-coenzyme A thioesterase 2, mitochondrialACOT2P49753
Acyl-coenzyme A thioesterase 4ACOT4Q8N9L9
Acyl-coenzyme A thioesterase 8ACOT8O14734
Acyl-coenzyme A thioesterase 1ACOT1Q86TX2
Acyl-protein thioesterase 1LYPLA1O75608
Acyl-protein thioesterase 2LYPLA2O95372
Palmitoyl-protein thioesterase 1PPT1P50897
Cytosolic acyl coenzyme A thioester hydrolase-likeACOT7LQ6ZUV0
Long-chain-fatty-acid--CoA ligase ACSBG2ACSBG2Q5FVE4
Long-chain-fatty-acid--CoA ligase ACSBG1ACSBG1Q96GR2
Pathways
NameSMPDB LinkKEGG Link
Fatty Acid BiosynthesisSMP00456 Not Available
Fatty Acid Elongation In MitochondriaSMP00054 map00062
Fatty acid MetabolismSMP00051 map00071
Glycerolipid MetabolismSMP00039 map00561
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
slightly waxy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.