Cannabis Compound Database: Showing Compound Card for Palmitic acid (CDB006153)

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Record Information

Version

1.0

Created at

2020-03-18 23:21:53 UTC

Updated at

2020-12-07 19:06:55 UTC

CannabisDB ID

CDB006153

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Palmitic acid

Description

Palmitic 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‚Äì30% (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‚Äôs 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Hexyldecanoic acid	ChEBI
1-Pentadecanecarboxylic acid	ChEBI
16:00	ChEBI
C16	ChEBI
C16 Fatty acid	ChEBI
C16:0	ChEBI
Cetylic acid	ChEBI
CH3-[CH2]14-COOH	ChEBI
FA 16:0	ChEBI
Hexadecanoate	ChEBI
Hexadecoic acid	ChEBI
Hexadecylic acid	ChEBI
Hexaectylic acid	ChEBI
N-Hexadecanoic acid	ChEBI
N-Hexadecoic acid	ChEBI
Palmitate	ChEBI
Palmitinic acid	ChEBI
Palmitinsaeure	ChEBI
Pentadecanecarboxylic acid	ChEBI
1-Hexyldecanoate	Generator
1-Pentadecanecarboxylate	Generator
Cetylate	Generator
Hexadecanoic acid	Generator
Hexadecoate	Generator
Hexadecylate	Generator
Hexaectylate	Generator
N-Hexadecanoate	Generator
N-Hexadecoate	Generator
Palmitinate	Generator
Pentadecanecarboxylate	Generator
Edenor C16	HMDB
Emersol 140	HMDB
Emersol 143	HMDB
Glycon p-45	HMDB
Hexadecanoate (N-C16:0)	HMDB
Hexadecanoic acid palmitic acid	HMDB
Hydrofol	HMDB
Hydrofol acid 1690	HMDB
Hystrene 8016	HMDB
Hystrene 9016	HMDB
Industrene 4516	HMDB
Kortacid 1698	HMDB
Loxiol ep 278	HMDB
Lunac p 95	HMDB
Lunac p 95KC	HMDB
Lunac p 98	HMDB
Palmitoate	HMDB
Palmitoic acid	HMDB
PAM	HMDB
PLM	HMDB
Prifac 2960	HMDB
Prifrac 2960	HMDB
Pristerene 4934	HMDB
Univol u332	HMDB
Acid, hexadecanoic	HMDB
Acid, palmitic	HMDB
FA(16:0)	HMDB

Chemical Formula

C₁₆H₃₂O₂

Average Molecular Weight

256.42

Monoisotopic Molecular Weight

256.2402

IUPAC Name

hexadecanoic acid

Traditional Name

palmitic acid

CAS Registry Number

67701-02-4

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 Key

IPCSVZSSVZVIGE-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-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 Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:15756 )
straight-chain saturated fatty acid (CHEBI:15756 )
Straight chain fatty acids (C00249 )
Saturated fatty acids (C00249 )
Straight chain fatty acids (LMFA01010001 )

Ontology

Physiological effect

Health effect:

Health condition:

Schizophrenia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	61.8 °C	Not Available
Boiling Point	351–352 °C	Wikipedia
Water Solubility	4.0e-05 mg/mL	Not Available
logP	7.17	SANGSTER (1993)

Predicted Properties

Property	Value	Source
logP	7.23	ALOGPS
logP	6.26	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	77.08 m³·mol⁻¹	ChemAxon
Polarizability	34.36 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-06xx-9100000000-7ac9cd088cb9cb9f7560	Spectrum
GC-MS	Palmitic acid, 1 TMS, GC-MS Spectrum	splash10-014i-0901000000-51ee83f9462d25fa4045	Spectrum
GC-MS	Palmitic acid, 1 TMS, GC-MS Spectrum	splash10-0100-9700000000-3d8b6cf4736afa482b57	Spectrum
GC-MS	Palmitic acid, 1 TMS, GC-MS Spectrum	splash10-0159-2901000000-fb423e89a78708021db1	Spectrum
GC-MS	Palmitic acid, non-derivatized, GC-MS Spectrum	splash10-0abc-9110000000-6d7f0dbe5b588850b941	Spectrum
GC-MS	Palmitic acid, non-derivatized, GC-MS Spectrum	splash10-014i-0901000000-51ee83f9462d25fa4045	Spectrum
GC-MS	Palmitic acid, non-derivatized, GC-MS Spectrum	splash10-0100-9700000000-3d8b6cf4736afa482b57	Spectrum
GC-MS	Palmitic acid, non-derivatized, GC-MS Spectrum	splash10-0159-2901000000-fb423e89a78708021db1	Spectrum
GC-MS	Palmitic acid, non-derivatized, GC-MS Spectrum	splash10-0159-2901000000-fb423e89a78708021db1	Spectrum
GC-MS	Palmitic acid, non-derivatized, GC-MS Spectrum	splash10-014i-1900000000-d7638a578d846871e670	Spectrum
Predicted GC-MS	Palmitic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9610000000-f75185fa40c090817f46	Spectrum
Predicted GC-MS	Palmitic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-022i-9440000000-7d3a81432d58729f9f98	Spectrum
Predicted GC-MS	Palmitic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Palmitic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0a4i-0090000000-39c3a0e17432781e9760	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-0090000000-8ec1a6953701fc22ce27	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0fba-9200000000-23c995bf81d5ef609489	Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0abc-9110000000-12f1884d67998fb924a5	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0091010000-6922411e48d747e592b5	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0091010000-6922411e48d747e592b5	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0091010000-6922411e48d747e592b5	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0091010000-6922411e48d747e592b5	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0a4i-0091000000-4f6858c1cc0f04cbabf5	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0a4i-0090000000-14e58eecd83ba52123c2	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0a4i-0090000000-c3f9f4d5c336137b7fcf	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0090000000-47919da3faa8e0f52bbc	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0a4i-0090000000-fdd9e98416da12470fe9	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-26bb4965a56ab0e82b49	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06rj-5790000000-251700f3edf9a5af04cd	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9600000000-5b75a67e276017f221b8	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-26bb4965a56ab0e82b49	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06rj-5790000000-251700f3edf9a5af04cd	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9600000000-5b75a67e276017f221b8	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-e4a4200bd25f8fa480cc	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bti-1090000000-768a48058fc0a2d7a877	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9320000000-c9714c7ffdc804bf9323	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-e4a4200bd25f8fa480cc	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bti-1090000000-768a48058fc0a2d7a877	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9320000000-c9714c7ffdc804bf9323	Spectrum

NMR

Type	Description	View
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Glycerolipid Metabolism
Fatty acid Metabolism
Fatty Acid Elongation In Mitochondria
Fatty Acid Biosynthesis		Not Available
Long-chain-3-hydroxyacyl-coa dehydrogenase deficiency (LCHAD)		Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000220

DrugBank ID

DB03796

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15756

References

General References

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 ]
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 ]

Showing Compound Card for Palmitic acid (CDB006153)

Structure for CDB006153 (Palmitic acid)