Milk Composition Database: Showing metabocard for Myristic acid (BMDB0000806)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:36:51 UTC

Update Date

2020-06-04 22:55:30 UTC

MCDB ID

BMDB0000806

Secondary Accession Numbers

BMDB00806

Metabolite Identification

Common Name

Myristic acid

Description

Myristic acid, also known as 14 or tetradecanoate, 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 exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Myristic acid exists in all living species, ranging from bacteria to humans. Myristic acid participates in a number of enzymatic reactions, within cattle. In particular, Myristic acid can be biosynthesized from trans-tetra-dec-2-enoic acid through the action of the enzyme fatty acid synthase. enoyl reductase domain. In addition, Myristic acid and malonic acid can be converted into 3-oxohexadecanoic acid through the action of the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In cattle, myristic acid is involved in the metabolic pathway called fatty acid biosynthesis pathway. Myristic acid is a potentially toxic compound.

Structure

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

Synonyms

Value	Source
1-Tetradecanecarboxylic acid	ChEBI
14	ChEBI
14:0	ChEBI
14:00	ChEBI
Acide tetradecanoique	ChEBI
C14	ChEBI
CH3-[CH2]12-COOH	ChEBI
Myristinsaeure	ChEBI
N-Tetradecan-1-Oic acid	ChEBI
N-Tetradecanoic acid	ChEBI
N-Tetradecoic acid	ChEBI
Tetradecoic acid	ChEBI
Tetradecanoate	Kegg
1-Tetradecanecarboxylate	Generator
N-Tetradecan-1-Oate	Generator
N-Tetradecanoate	Generator
N-Tetradecoate	Generator
Tetradecoate	Generator
Tetradecanoic acid	Generator
Myristate	Generator
1-Tridecanecarboxylate	HMDB
1-Tridecanecarboxylic acid	HMDB
Crodacid	HMDB
Myristic acid pure	HMDB
Myristoate	HMDB
Myristoic acid	HMDB
Tetradecanoic (myristic) acid	HMDB
Acid, tetradecanoic	HMDB
Acid, myristic	HMDB
FA(14:0)	HMDB

Chemical Formula

C₁₄H₂₈O₂

Average Molecular Weight

228.3709

Monoisotopic Molecular Weight

228.20893014

IUPAC Name

tetradecanoic acid

Traditional Name

myristic acid

CAS Registry Number

544-63-8

SMILES

CCCCCCCCCCCCCC(O)=O

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

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

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	53.9 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0011 mg/mL	Not Available
LogP	6.11	SANGSTER (1993)

Predicted Properties

Property	Value	Source
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	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-017i-2910000000-66b35fb8449ba9de9cd6	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-017i-2910000000-66b35fb8449ba9de9cd6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0910000000-f45703c464ca75f98f26	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9700000000-ec8d81e37bc3b8531c99	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0079-9330000000-5ec01705dfacc992be28	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-004i-0090000000-73ac1cfb8731e6318cc5	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-004i-1090000000-3aa768974da0ea81c1c9	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0090000000-22cd107a87b9acf058c5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-0090000000-2f7bb32e4b42206d851d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-2090000000-d45cffc15e2efbd45cd6	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-001i-9200000000-dbca68238dfebab35251	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004r-9000000000-26827be8f8c2a4fbfd75	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0006-0090000000-110165b889d231d09d59	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0006-0090000000-110165b889d231d09d59	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0006-0090000000-110165b889d231d09d59	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0006-0090000000-110165b889d231d09d59	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0090000000-91f4f874b25705464fb0	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0090000000-15225a799e0a0bcff7c7	2017-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0290000000-b88426a2003ceec57e30	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-5940000000-6c73dc0032502abe4fc4	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9300000000-bde9bfcd2889066fc853	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0290000000-b88426a2003ceec57e30	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-5940000000-6c73dc0032502abe4fc4	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9300000000-bde9bfcd2889066fc853	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0190000000-a32f141c7b5af0bc4de1	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-057i-1490000000-14bfb0d0344d7cf63443	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9400000000-512abb1322963024336f	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0190000000-a32f141c7b5af0bc4de1	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-057i-1490000000-14bfb0d0344d7cf63443	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9400000000-512abb1322963024336f	2015-05-27	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-06xx-9200000000-4fdd41f0461ff5186901	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, CDCl₃, experimental)	Not Available	2016-10-22	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected and Quantified	17953 +/- 5254 uM	Total fatty acid	PMID: 16899705	details
Detected but not Quantified	Not Applicable		Kurt J. Boudonck,...	details
Detected and Quantified	19661 +/- 4291 uM	Total fatty acid	M. Ferrand et al....	details
Detected and Quantified	19004 +/- 3809 uM	Total fatty acid	M. Ferrand et al....	details
Detected but not Quantified	Not Applicable		PMID: 14168161	details
Detected but not Quantified	Not Applicable		PMID: 11913692	details
Detected and Quantified	6875 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	6568 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	1445 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	1927 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	1445 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	16814 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	16158 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	15107 uM	Total fatty acid	Fooddata+, T...	details
Detected but not Quantified	Not Applicable		Kurt J. Boudonck,...	details
Detected but not Quantified	Not Applicable		Lawrence K. Cream...	details
Detected and Quantified	35.64 +/- 6.48 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	41.48 +/- 6.48 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	17.52 +/- 1.14 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	7.14 +/- 0.65 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	30.39 +/- 0.20 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	39 +/- 1 uM	Free fatty acid	Catrienus De Jong...	details
Detected and Quantified	84.5 +/- 26.1 uM	Free fatty acid	PMID: 11754544	details
Detected and Quantified	53.5 +/- 15.7 uM	Free fatty acid	PMID: 11754544	details
Detected and Quantified	10.5 +/- 0.1 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	14.4 +/- 0.3 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	17.5 +/- 0.3 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	19 +/- 1 uM	Free fatty acid	PMID: 30994344	details

External Links

HMDB ID

HMDB0000806

DrugBank ID

DB08231

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

28875

References

Synthesis Reference

Greaves, W. S.; Linstead, R. P.; Shephard, B. R.; Thomas, S. L. S.; Weedon, B. C. L. Anodic syntheses. I. New syntheses of stearic, myristic, and other acids. Journal of the Chemical Society (1950), 3326-30.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. [PubMed:16899705 ]
Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]
van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.
Lawrence K. Creamer, Alastair K.H. MacGibbon (1996). Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X. International Dairy Journal.
Fooddata+, The Technical University of Denmark (DTU) [Link]

Showing metabocard for Myristic acid (BMDB0000806)

Structure for BMDB0000806 (Myristic acid)