AFCDB: Tetradecanoic acid (FDB002890)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:34 UTC

Update date

2020-09-17 15:42:29 UTC

Primary ID

FDB002890

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Tetradecanoic acid

Description

Myristic acid, also known as tetradecanoic acid or C14:0, 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.. Myristic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It has a waxy, fatty or soapy odor and a fatty, creamy or cheesy taste. Myristic acid exists in all living species, ranging from bacteria to humans. Myristic acid is a naturally occurring saturated fatty acid found in most animal and vegetable fats. Some of the highest levels of myristic acid are found in nutmeg. In particular, nutmeg butter has 75% trimyristin, the triglyceride of myristic acid. Besides nutmeg, myristic acid is also found in palm kernel oil, coconut oil, butterfat, 8‚Äì14% of bovine milk, and 8.6% of breast milk as well as being a minor component of many other animal fats. It also comprises 14.49% of the fats from the fruit of the Durian species. Industrially myristic acid is used as an ingredient in soaps and cosmetics (From Dorland, 28th ed). In many eukaryotes (including humans), myristic acid is commonly added to the N-terminal glycine residue in receptor-associated kinases to confer membrane localization of the enzyme. This is achieved by the myristic acid having a high enough hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell (Wikipedia). Some research has pointed to myristic acid's positive effects on regulating HDL cholesterol and hence improving the HDL (good cholesterol) to total cholesterol ratio (PMID: 7644455).

CAS Number

544-63-8

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	0.0017 g/L	ALOGPS
logP	6.1	ALOGPS
logP	5.37	ChemAxon
logS	-5.1	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	12	ChemAxon
Refractivity	67.88 m³·mol⁻¹	ChemAxon
Polarizability	30.1 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C14H28O2

IUPAC name

tetradecanoic acid

InChI Identifier

InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)

InChI Key

TUNFSRHWOTWDNC-UHFFFAOYSA-N

Isomeric SMILES

CCCCCCCCCCCCCC(O)=O

Average Molecular Weight

228.3709

Monoisotopic Molecular Weight

228.20893014

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:28875 )
straight-chain saturated fatty acid (CHEBI:28875 )
Straight chain fatty acids (C06424 )
Saturated fatty acids (C06424 )
Straight chain fatty acids (LMFA01010014 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 73.63%; H 12.36%; O 14.01%	DFC
Melting Point	Mp 54°	DFC
Boiling Point	Bp16 199°	DFC
Experimental Water Solubility	0.00107 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	6.11	SANGSTER (1993)
Experimental pKa	4.9
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-9200000000-4fdd41f0461ff5186901	2014-09-20	View Spectrum
GC-MS	Tetradecanoic acid, 1 TMS, GC-MS Spectrum	splash10-017i-2910000000-66b35fb8449ba9de9cd6	Spectrum
GC-MS	Tetradecanoic acid, non-derivatized, GC-MS Spectrum	splash10-017i-2910000000-66b35fb8449ba9de9cd6	Spectrum
GC-MS	Tetradecanoic acid, non-derivatized, GC-MS Spectrum	splash10-0159-0910000000-f45703c464ca75f98f26	Spectrum
Predicted GC-MS	Tetradecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9700000000-ec8d81e37bc3b8531c99	Spectrum
Predicted GC-MS	Tetradecanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0079-9330000000-5ec01705dfacc992be28	Spectrum
Predicted GC-MS	Tetradecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetradecanoic 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)	splash10-004i-0090000000-73ac1cfb8731e6318cc5	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-004i-1090000000-3aa768974da0ea81c1c9	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0090000000-22cd107a87b9acf058c5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-0090000000-2f7bb32e4b42206d851d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-2090000000-d45cffc15e2efbd45cd6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-001i-9200000000-dbca68238dfebab35251	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004r-9000000000-26827be8f8c2a4fbfd75	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0006-0090000000-110165b889d231d09d59	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0006-0090000000-110165b889d231d09d59	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0006-0090000000-110165b889d231d09d59	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0006-0090000000-110165b889d231d09d59	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0090000000-91f4f874b25705464fb0	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0090000000-15225a799e0a0bcff7c7	2017-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0290000000-b88426a2003ceec57e30	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-5940000000-6c73dc0032502abe4fc4	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9300000000-bde9bfcd2889066fc853	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0290000000-b88426a2003ceec57e30	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-5940000000-6c73dc0032502abe4fc4	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9300000000-bde9bfcd2889066fc853	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0190000000-a32f141c7b5af0bc4de1	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-057i-1490000000-14bfb0d0344d7cf63443	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9400000000-512abb1322963024336f	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0190000000-a32f141c7b5af0bc4de1	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-057i-1490000000-14bfb0d0344d7cf63443	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9400000000-512abb1322963024336f	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

28875

Phenol-Explorer ID

Not Available

DrugBank ID

DB08231

HMDB ID

HMDB00806

CRC / DFC (Dictionary of Food Compounds) ID

CPB50-O:CPB50-O

EAFUS ID

2626

Dr. Duke ID

N-TETRADECANOIC-ACID|MYRISTIC-ACID|TETRADECANOIC-ACID

BIGG ID

215851

KNApSAcK ID

C00001228

HET ID

MYR

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1009061

SuperScent ID

Not Available

Wikipedia ID

Myristic 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
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
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cosmetic	64857	The role played by a substance in enhancing the appearance or odour of the human body; a name given to the substance itself or to a component of it.	DUKE
hypercholesterolemic			DUKE
lubricant			DUKE
nematicide	25491	A substance used to destroy pests of the phylum Nematoda (roundworms).	DUKE

Enzymes

Name	Gene Name	UniProt ID
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
Dehydrogenase/reductase SDR family member 4	DHRS4	Q9BTZ2
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

Pathways

Name	SMPDB Link	KEGG Link
Fatty Acid Biosynthesis	SMP00456	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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

Tetradecanoic acid (FDB002890)

Structure for FDB002890 (Tetradecanoic acid)