AFCDB: Hexadecanoic acid (FDB011679)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:46 UTC

Update date

2020-09-17 15:42:18 UTC

Primary ID

FDB011679

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Hexadecanoic 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.

CAS Number

57-10-3

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00041 g/L	ALOGPS
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

Chemical Formula

C16H32O2

IUPAC name

hexadecanoic acid

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

Isomeric SMILES

CCCCCCCCCCCCCCCC(O)=O

Average Molecular Weight

256.4241

Monoisotopic Molecular Weight

256.240230268

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.

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

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 74.94%; H 12.58%; O 12.48%	DFC
Melting Point	Mp 63-64°	DFC
Boiling Point	Bp15 215°	DFC
Experimental Water Solubility	4e-05 mg/mL at 25 oC	ROBB,ID (1966)
Experimental logP	7.17	SANGSTER (1993)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-06xx-9100000000-7ac9cd088cb9cb9f7560	2014-09-20	View Spectrum
GC-MS	Hexadecanoic acid, 1 TMS, GC-MS Spectrum	splash10-014i-0901000000-51ee83f9462d25fa4045	Spectrum
GC-MS	Hexadecanoic acid, 1 TMS, GC-MS Spectrum	splash10-0100-9700000000-3d8b6cf4736afa482b57	Spectrum
GC-MS	Hexadecanoic acid, 1 TMS, GC-MS Spectrum	splash10-0159-2901000000-fb423e89a78708021db1	Spectrum
GC-MS	Hexadecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0abc-9110000000-6d7f0dbe5b588850b941	Spectrum
GC-MS	Hexadecanoic acid, non-derivatized, GC-MS Spectrum	splash10-014i-0901000000-51ee83f9462d25fa4045	Spectrum
GC-MS	Hexadecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0100-9700000000-3d8b6cf4736afa482b57	Spectrum
GC-MS	Hexadecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0159-2901000000-fb423e89a78708021db1	Spectrum
GC-MS	Hexadecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0159-2901000000-fb423e89a78708021db1	Spectrum
GC-MS	Hexadecanoic acid, non-derivatized, GC-MS Spectrum	splash10-014i-1900000000-d7638a578d846871e670	Spectrum
Predicted GC-MS	Hexadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9610000000-f75185fa40c090817f46	Spectrum
Predicted GC-MS	Hexadecanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-022i-9440000000-7d3a81432d58729f9f98	Spectrum
Predicted GC-MS	Hexadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hexadecanoic 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	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-0090000000-8ec1a6953701fc22ce27	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0fba-9200000000-23c995bf81d5ef609489	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0abc-9110000000-12f1884d67998fb924a5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0091010000-6922411e48d747e592b5	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0091010000-6922411e48d747e592b5	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0091010000-6922411e48d747e592b5	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0091010000-6922411e48d747e592b5	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0a4i-0091000000-4f6858c1cc0f04cbabf5	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0a4i-0090000000-14e58eecd83ba52123c2	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0a4i-0090000000-c3f9f4d5c336137b7fcf	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0090000000-47919da3faa8e0f52bbc	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0a4i-0090000000-fdd9e98416da12470fe9	2017-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-26bb4965a56ab0e82b49	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06rj-5790000000-251700f3edf9a5af04cd	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9600000000-5b75a67e276017f221b8	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-26bb4965a56ab0e82b49	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06rj-5790000000-251700f3edf9a5af04cd	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9600000000-5b75a67e276017f221b8	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-e4a4200bd25f8fa480cc	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bti-1090000000-768a48058fc0a2d7a877	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9320000000-c9714c7ffdc804bf9323	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-e4a4200bd25f8fa480cc	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bti-1090000000-768a48058fc0a2d7a877	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9320000000-c9714c7ffdc804bf9323	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15756

Phenol-Explorer ID

Not Available

DrugBank ID

DB03796

HMDB ID

HMDB00220

CRC / DFC (Dictionary of Food Compounds) ID

GXZ18-W:GXZ18-W

EAFUS ID

2858

Dr. Duke ID

HEXADECANOIC-ACID|PALMITIC-ACID

BIGG ID

34386

KNApSAcK ID

C00030479

HET ID

PLM

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1009101

SuperScent ID

Not Available

Wikipedia ID

Palmitic_acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
5alpha-reductase inhibitor	50781	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 alopecic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti androgenic	35497	A compound which inhibits or antagonises the biosynthesis or actions of androgens.	DUKE
anti fibrinolytic			DUKE
antioxidant	22586	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
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
hemolytic			DUKE
hypercholesterolemic			DUKE
lubricant			DUKE
nematicide	25491	A substance used to destroy pests of the phylum Nematoda (roundworms).	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
propecic			DUKE
soap			DUKE

Enzymes

Name	Gene Name	UniProt ID
Bile acid-CoA:amino acid N-acyltransferase	BAAT	Q14032
Liver carboxylesterase 1	CES1	P23141
Pancreatic triacylglycerol lipase	PNLIP	P16233
Hepatic triacylglycerol lipase	LIPC	P11150
Inactive pancreatic lipase-related protein 1	PNLIPRP1	P54315
Patatin-like phospholipase domain-containing protein 3	PNPLA3	Q9NST1
Gastric triacylglycerol lipase	LIPF	P07098
Endothelial lipase	LIPG	Q9Y5X9
Pancreatic lipase-related protein 2	PNLIPRP2	P54317
Lipoprotein lipase	LPL	P06858
Patatin-like phospholipase domain-containing protein 4	PNPLA4	P41247
Patatin-like phospholipase domain-containing protein 2	PNPLA2	Q96AD5
Pancreatic lipase-related protein 3	PNLIPRP3	Q17RR3
Cholinesterase	BCHE	P06276
Carboxylesterase 5A	CES5A	Q6NT32
60 kDa lysophospholipase	ASPG	Q86U10
Fatty acid synthase	FASN	P49327
Galactoside-binding soluble lectin 13	LGALS13	Q9UHV8
Eosinophil lysophospholipase	CLC	Q05315
Cocaine esterase	CES2	O00748
Acylphosphatase-2	ACYP2	P14621
Acylphosphatase-1	ACYP1	P07311
Aspartoacylase	ASPA	P45381
Aspartoacylase-2	ACY3	Q96HD9
Lysosomal thioesterase PPT2	PPT2	Q9UMR5
Acid ceramidase	ASAH1	Q13510
Homeodomain-interacting protein kinase 1	HIPK1	Q86Z02
Peroxisome proliferator-activated receptor gamma	PPARG	P37231
Long-chain fatty acid transport protein 6	SLC27A6	Q9Y2P4
Long-chain fatty acid transport protein 3	SLC27A3	Q5K4L6
Long-chain fatty acid transport protein 4	SLC27A4	Q6P1M0
Putative neutral ceramidase C	ASAH2C	P0C7U2
Alkaline ceramidase 2	ACER2	Q5QJU3
Neutral ceramidase	ASAH2	Q9NR71
Alkaline ceramidase 1	ACER1	Q8TDN7
Neuropathy target esterase	PNPLA6	Q8IY17
Carboxylesterase 3	CES3	Q6UWW8
S-acyl fatty acid synthase thioesterase, medium chain	OLAH	Q9NV23
Cytosolic acyl coenzyme A thioester hydrolase	ACOT7	O00154
Acyl-coenzyme A thioesterase 2, mitochondrial	ACOT2	P49753
Acyl-coenzyme A thioesterase 4	ACOT4	Q8N9L9
Acyl-coenzyme A thioesterase 8	ACOT8	O14734
Acyl-coenzyme A thioesterase 1	ACOT1	Q86TX2
Acyl-protein thioesterase 1	LYPLA1	O75608
Acyl-protein thioesterase 2	LYPLA2	O95372
Palmitoyl-protein thioesterase 1	PPT1	P50897
Cytosolic acyl coenzyme A thioester hydrolase-like	ACOT7L	Q6ZUV0
Long-chain-fatty-acid--CoA ligase ACSBG2	ACSBG2	Q5FVE4
Long-chain-fatty-acid--CoA ligase ACSBG1	ACSBG1	Q96GR2

Pathways

Name	SMPDB Link	KEGG Link
Fatty Acid Biosynthesis	SMP00456	Not Available
Fatty Acid Elongation In Mitochondria	SMP00054	map00062
Fatty acid Metabolism	SMP00051	map00071
Glycerolipid Metabolism	SMP00039	map00561

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
slightly waxy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not 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.

Hexadecanoic acid (FDB011679)

Structure for FDB011679 (Hexadecanoic acid)