Myristic acid

Myristic acid (IUPAC systematic name: 1-tetradecanoic acid) is a common saturated fatty acid with the molecular formula CH₃(CH₂)₁₂COOH. Its salts and esters are commonly referred to as myristates or tetradecanoates. It is named after the binomial name for nutmeg (Myristica fragrans), from which it was first isolated in 1841 by Lyon Playfair.[12]

Myristic acid[1]

Names
IUPAC name Tetradecanoic acid
Other names C14:0 (Lipid numbers)
Identifiers
CAS Number	544-63-8^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28875^N
ChEMBL	ChEMBL111077^N
ChemSpider	10539^N
ECHA InfoCard	100.008.069
EC Number	208-875-2
IUPHAR/BPS	2806
PubChem CID	11005
RTECS number	QH4375000
UNII	0I3V7S25AW^N
CompTox Dashboard (EPA)	DTXSID6021666
InChI 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)^N Key: TUNFSRHWOTWDNC-UHFFFAOYSA-N^N InChI=1/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16) Key: TUNFSRHWOTWDNC-UHFFFAOYAZ
SMILES CCCCCCCCCCCCCC(=O)O
Properties
Chemical formula	C14H28O2
Molar mass	228.376 g·mol^−1
Density	1.03 g/cm^3 (−3 °C)[2] 0.99 g/cm^3 (24 °C)[3] 0.8622 g/cm^3 (54 °C)[4]
Melting point	54.4 °C (129.9 °F; 327.5 K) [5]
Boiling point	326.2 °C (619.2 °F; 599.3 K) at 760 mmHg 250 °C (482 °F; 523 K) at 100 mmHg[4] 218.3 °C (424.9 °F; 491.4 K) at 32 mmHg[3]
Solubility in water	13 mg/L (0 °C) 20 mg/L (20 °C) 24 mg/L (30 °C) 33 mg/L (60 °C)[6]
Solubility	Soluble in alcohol, acetates, C6H6, haloalkanes, phenyls, nitros[6]
Solubility in acetone	2.75 g/100 g (0 °C) 15.9 g/100 g (20 °C) 42.5 g/100 g (30 °C) 149 g/100 g (40 °C)[6]
Solubility in benzene	6.95 g/100 g (10 °C) 29.2 g/100 g (20 °C) 87.4 g/100 g (30 °C) 1.29 kg/100 g (50 °C)[6]
Solubility in methanol	2.8 g/100 g (0 °C) 17.3 g/100 g (20 °C) 75 g/100 g (30 °C) 2.67 kg/100 g (50 °C)[6]
Solubility in ethyl acetate	3.4 g/100 g (0 °C) 15.3 g/100 g (20 °C) 44.7 g/100 g (30 °C) 1.35 kg/100 g (40 °C)[6]
Solubility in toluene	0.6 g/100 g (−10 °C) 3.2 g/100 g (0 °C) 30.4 g/100 g (20 °C) 1.35 kg/100 g (50 °C)[6]
log P	6.1[4]
Vapor pressure	0.01 kPa (118 °C) 0.27 kPa (160 °C)[7] 1 kPa (186 °C)[4]
Magnetic susceptibility (χ)	-176·10^−6 cm^3/mol
Thermal conductivity	0.159 W/m·K (70 °C) 0.151 W/m·K (100 °C) 0.138 W/m·K (160 °C)[8]
Refractive index (nD)	1.4723 (70 °C)[4]
Viscosity	7.2161 cP (60 °C) 3.2173 cP (100 °C) 0.8525 cP (200 °C) 0.3164 cP (300 °C)[9]
Structure
Crystal structure	Monoclinic (−3 °C)[2]
Space group	P21/c[2]
Lattice constant	a = 31.559 Å, b = 4.9652 Å, c = 9.426 Å[2] α = 90°, β = 94.432°, γ = 90°
Thermochemistry
Heat capacity (C)	432.01 J/mol·K[4][7]
Std enthalpy of formation (ΔfH^⦵298)	−833.5 kJ/mol[4][7]
Std enthalpy of combustion (ΔcH^⦵298)	8675.9 kJ/mol[7]
Hazards
GHS pictograms	[10]
GHS Signal word	Warning
GHS hazard statements	H315[10]
NFPA 704 (fire diamond)	[11] 1 2 0
Flash point	> 110 °C (230 °F; 383 K) [11]
Lethal dose or concentration (LD, LC):
LD50 (median dose)	>10 g/kg (rats, oral)[11]
Related compounds
Related compounds	Tridecanoic acid, Pentadecanoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Occurrence

Myristica fragrans fruit contains myristic acid

Nutmeg butter has 75% trimyristin, the triglyceride of myristic acid. Besides nutmeg, myristic acid is also found in palm kernel oil, coconut oil, butterfat, 8–14% of bovine milk, and 8.6% of breast milk as well as being a minor component of many other animal fats.[5] It is also found in spermaceti, the crystallized fraction of oil from the sperm whale. It is also found in the rhizomes of the Iris, including Orris root.[13][14] It also comprises 14.49% of the fats from the fruit of the Durian species Durio graveolens.[15]

Uses

See also: Myristoylation

Myristic acid is commonly added to the N-terminus glycine in receptor-associated kinases to confer the membrane localization of the enzyme. The myristic acid has a sufficiently high hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell. In this way, myristic acid acts as a lipid anchor in biomembranes.[16]

Various "human epidemiological studies have shown that myristic acid and lauric acid were the saturated fatty acids most strongly related to the average serum cholesterol concentrations in humans",[17] meaning they were positively correlated with higher cholesterol levels as well as raising triglycerides in plasma by some 20% increasing the risk for cardiovascular disease, although some research points to myristic acid's positive effects on HDL cholesterol and hence improving HDL (good cholesterol) to total cholesterol ratio.[18]

Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.

References

1. Merck Index, 11th Edition, 6246
2. Bond, Andrew D. (2003). "On the crystal structures and melting point alternation of the n-alkyl carboxylic acids" (PDF). RSC.org. Royal Society of Chemistry. Retrieved 17 June 2014.
3. G., Chuah T.; D., Rozanna; A., Salmiah; Y., Thomas Choong S.; M., Sa'ari (2006). "Fatty Acids used as Phase Change Materials (PCMs) for Thermal Energy Storage in Building Material Applications" (PDF). University Putra Malaysia. Retrieved 17 June 2014.
4. Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
5. Beare-Rogers, J. L; Dieffenbacher, A; Holm, J. V (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. doi:10.1351/pac200173040685.
6. Seidell, Atherton; Linke, William F. (1940). Solubilities of Inorganic and Organic Compounds (3rd ed.). New York: D. Van Nostrand Company. pp. 762–763.
7. Tetradecanoic acid in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD), http://webbook.nist.gov
8. Vargaftik, Natan B.; et al. (1993). Handbook of Thermal Conductivity of Liquids and Gases (illustrated ed.). CRC Press. p. 305. ISBN 978-0-8493-9345-7.
9. Yaws, Carl L. (2009). Transport Properties of Chemicals and Hydrocarbons. New York: William Andrew Inc. p. 177. ISBN 978-0-8155-2039-9.
10. Sigma-Aldrich Co., Myristic acid.
11. "MYRISTIC ACID". ChemicalLand21.com. AroKor Holdings Inc. Retrieved 17 June 2014.
12. Playfair, Lyon (2009). "XX. On a new fat acid in the butter of nutmegs". Philosophical Magazine. Series 3. 18 (115): 102–113. doi:10.1080/14786444108650255. ISSN 1941-5966.
13. Council of Europe, August 2007 Natural Sources of Flavourings, Volume 2, p. 103, at Google Books
14. John Charles Sawer Odorographia a natural history of raw materials and drugs used in the perfume industry intended to serve growers, manufacturers and consumers, p. 108, at Google Books
15. Nasaruddin, Mohd hanif; Noor, Noor Qhairul Izzreen Mohd; Mamat, Hasmadi (2013). "Komposisi Proksimat dan Komponen Asid Lemak Durian Kuning (Durio graveolens) Sabah" [Proximate and Fatty Acid Composition of Sabah Yellow Durian (Durio graveolens)] (PDF). Sains Malaysiana (in Malay). 42 (9): 1283–1288. ISSN 0126-6039. OCLC 857479186. Retrieved 28 November 2017.
16. Cox, David L. Nelson, Michael M. (2005). Lehninger principles of biochemistry (4th ed.). New York: W.H. Freeman. ISBN 978-0716743392.
17. German JB, Dillard CJ. (2010). "Saturated fats: a perspective from lactation and milk composition". Lipids. 45 (10): 915–923. doi:10.1007/s11745-010-3445-9. PMC 2950926. PMID 20652757.
18. Kromhout, Daan; et al. (1995). "Dietary Saturated and transFatty Acids and Cholesterol and 25-Year Mortality from Coronary Heart Disease: The Seven Countries Study". Preventive Medicine. 24 (3): 308–315. doi:10.1006/pmed.1995.1049. PMID 7644455.