Showing Compound Card for Palmitic acid (CDB006153)

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Record Information
Version1.0
Created at2020-03-18 23:21:53 UTC
Updated at2020-12-07 19:06:55 UTC
CannabisDB IDCDB006153
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePalmitic 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. Palmitic acid is also a constituent of cannabis plant and cannabis smoke. It is volatilized during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
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
Chemical FormulaC16H32O2
Average Molecular Weight256.42
Monoisotopic Molecular Weight256.2402
IUPAC Namehexadecanoic acid
Traditional Namepalmitic acid
CAS Registry Number67701-02-4
SMILES
CCCCCCCCCCCCCCCC(O)=O
InChI Identifier
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)
InChI KeyIPCSVZSSVZVIGE-UHFFFAOYSA-N
Chemical Taxonomy
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point61.8 °CNot Available
Boiling Point351–352 °CWikipedia
Water Solubility4.0e-05 mg/mLNot Available
logP7.17SANGSTER (1993)
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-06xx-9100000000-7ac9cd088cb9cb9f75602014-09-20View Spectrum
GC-MSPalmitic acid, 1 TMS, GC-MS Spectrumsplash10-014i-0901000000-51ee83f9462d25fa4045Spectrum
GC-MSPalmitic acid, 1 TMS, GC-MS Spectrumsplash10-0100-9700000000-3d8b6cf4736afa482b57Spectrum
GC-MSPalmitic acid, 1 TMS, GC-MS Spectrumsplash10-0159-2901000000-fb423e89a78708021db1Spectrum
GC-MSPalmitic acid, non-derivatized, GC-MS Spectrumsplash10-0abc-9110000000-6d7f0dbe5b588850b941Spectrum
GC-MSPalmitic acid, non-derivatized, GC-MS Spectrumsplash10-014i-0901000000-51ee83f9462d25fa4045Spectrum
GC-MSPalmitic acid, non-derivatized, GC-MS Spectrumsplash10-0100-9700000000-3d8b6cf4736afa482b57Spectrum
GC-MSPalmitic acid, non-derivatized, GC-MS Spectrumsplash10-0159-2901000000-fb423e89a78708021db1Spectrum
GC-MSPalmitic acid, non-derivatized, GC-MS Spectrumsplash10-0159-2901000000-fb423e89a78708021db1Spectrum
GC-MSPalmitic acid, non-derivatized, GC-MS Spectrumsplash10-014i-1900000000-d7638a578d846871e670Spectrum
Predicted GC-MSPalmitic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9610000000-f75185fa40c090817f46Spectrum
Predicted GC-MSPalmitic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-022i-9440000000-7d3a81432d58729f9f98Spectrum
Predicted GC-MSPalmitic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPalmitic 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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000220
DrugBank IDDB03796
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031084
KNApSAcK IDC00030479
Chemspider ID960
KEGG Compound IDC00249
BioCyc IDPALMITATE
BiGG ID34386
Wikipedia LinkPalmitic_acid
METLIN ID187
PubChem Compound985
PDB IDNot Available
ChEBI ID15756
References
General References
  1. KINGSBURY KJ, PAUL S, CROSSLEY A, MORGAN DM: The fatty acid composition of human depot fat. Biochem J. 1961 Mar;78:541-50. doi: 10.1042/bj0780541. [PubMed:13756126 ]
  2. Jensen RG, Hagerty MM, McMahon KE: Lipids of human milk and infant formulas: a review. Am J Clin Nutr. 1978 Jun;31(6):990-1016. doi: 10.1093/ajcn/31.6.990. [PubMed:352132 ]