Myristic acid

Myristic acid^[1]
Names
	Preferred IUPAC name Tetradecanoic acid
	Other names C14:0 (Lipid numbers)
Identifiers
CAS Number	544-63-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28875 ;
ChEMBL	ChEMBL111077 ;
ChemSpider	10539 ;
ECHA InfoCard	100.008.069
EC Number	208-875-2;
IUPHAR/BPS	2806;
PubChem CID	11005;
RTECS number	QH4375000;
UNII	0I3V7S25AW ;
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) Key: TUNFSRHWOTWDNC-UHFFFAOYSA-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
Appearance	colorless or white solid
Density	1.03 g/cm3 (−3 °C); 0.99 g/cm3 (24 °C); 0.8622 g/cm3 (54 °C)
Melting point	54.4 °C (129.9 °F; 327.5 K)
Boiling point	326.2 °C (619.2 °F; 599.3 K) at 760 mmHg; 250 °C (482 °F; 523 K); at 100 mmHg; 218.3 °C (424.9 °F; 491.4 K); at 32 mmHg
Solubility in water	13 mg/L (0 °C); 20 mg/L (20 °C); 24 mg/L (30 °C); 33 mg/L (60 °C)
Solubility	Soluble in alcohol, acetates, C6H6, haloalkanes, phenyls, nitros
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)
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)
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)
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)
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)
log P	6.1
Vapor pressure	0.01 kPa (118 °C); 0.27 kPa (160 °C); 1 kPa (186 °C)
Magnetic susceptibility (χ)	-176·10−6 cm3/mol
Thermal conductivity	0.159 W/m·K (70 °C); 0.151 W/m·K (100 °C); 0.138 W/m·K (160 °C)
Refractive index (nD)	1.4723 (70 °C)
Viscosity	7.2161 cP (60 °C); 3.2173 cP (100 °C); 0.8525 cP (200 °C); 0.3164 cP (300 °C)
Structure
Crystal structure	Monoclinic (−3 °C)
Space group	P21/c
Lattice constant	a = 31.559 Å, b = 4.9652 Å, c = 9.426 Å α = 90°, β = 94.432°, γ = 90°
Thermochemistry
Heat capacity (C)	432.01 J/mol·K
Std enthalpy of; formation (ΔfH⦵298)	−833.5 kJ/mol
Std enthalpy of; combustion (ΔcH⦵298)	8675.9 kJ/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315
NFPA 704 (fire diamond)	2 1 0
Flash point	> 110 °C (230 °F; 383 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	>10 g/kg (rats, oral)
Related compounds
Related esters of myristic acid	Isopropyl myristate; Phorbol myristate acetate; Myristylbenzylmorphine; Dimyristoylphosphatidylethanolamine
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). verify (what is ?) Infobox references

Myristic acid (IUPAC name: 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. The name of the acyl group derived from myristic acid is myristoyl or tetradecanoyl. The acid is named after the binomial name for nutmeg (Myristica fragrans), from which it was first isolated in 1841 by Lyon Playfair.^[12]

Occurrence

Myristica fragrans (nutmeg) fruit contains myristic acid

Nutmeg butter has 75% trimyristin, the triglyceride of myristic acid and a source from which it can be synthesised.^[13] Besides nutmeg, myristic acid is 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.^[9] It is 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.^[14]^[15]

Chemical behaviour

Myristic acid acts as a lipid anchor in biomembranes.^[16]

Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.

Health effects

Myristic acid consumption raises low-density lipoprotein (LDL) cholesterol.^[17]^[18]

References

^ Merck Index, 11th Edition, 6246
^ ^a ^b ^c ^d 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.
^ ^a ^b Chuah, T.G.; Rozanna, D.; Salmiah, A.; Thomas, Choong S.Y.; Sa’ari, M. (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.
^ ^a ^b ^c ^d ^e ^f ^g Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
^ ^a ^b ^c ^d ^e ^f ^g Seidell, Atherton; Linke, William F. (1940). Solubilities of Inorganic and Organic Compounds (3rd ed.). New York: D. Van Nostrand Company. pp. 762–763.
^ ^a ^b ^c ^d 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)
^ 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.
^ Yaws, Carl L. (2009). Transport Properties of Chemicals and Hydrocarbons. New York: William Andrew Inc. p. 177. ISBN 978-0-8155-2039-9.
^ ^a ^b 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. S2CID 84492006.
^ ^a ^b Sigma-Aldrich Co., Myristic acid.
^ ^a ^b ^c "Myristic Acid". ChemicalLand21.com. AroKor Holdings Inc. Retrieved 17 June 2014.
^ 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.
^ Beal, G. D. (1926). "Myristic Acid". Organic Syntheses. 6: 66. doi:10.15227/orgsyn.006.0066.
^ Council of Europe, August 2007 Natural Sources of Flavourings, Volume 2, p. 103, at Google Books
^ 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
^ Cox, David L. Nelson, Michael M. (2005). Lehninger principles of biochemistry (4th ed.). New York: W.H. Freeman. ISBN 978-0716743392.{{cite book}}: CS1 maint: multiple names: authors list (link)
^ Mensink, Ronald P. (2016). "Effects of saturated fatty acids on serum lipids and lipoproteins: a systematic review and regression analysis" (PDF). World Health Organization.
^ Schwingshackl L, Bogensberger B, Benčič A, Knüppel S, Boeing H, Hoffmann G (2018). "Effects of oils and solid fats on blood lipids: a systematic review and network meta-analysis". J Lipid Res. 59 (9): 1771–1782. doi:10.1194/jlr.P085522. PMC 6121943. PMID 30006369.

[1] Merck Index, 11th Edition, 6246

[adb-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.

[dspace-3] Chuah, T.G.; Rozanna, D.; Salmiah, A.; Thomas, Choong S.Y.; Sa’ari, M. (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.

[crc-4] ^ ^a ^b ^c ^d ^e ^f ^g Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.

[sioc-5] ^ ^a ^b ^c ^d ^e ^f ^g Seidell, Atherton; Linke, William F. (1940). Solubilities of Inorganic and Organic Compounds (3rd ed.). New York: D. Van Nostrand Company. pp. 762–763.

[nist-6] 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)

[7] 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.

[trp-8] Yaws, Carl L. (2009). Transport Properties of Chemicals and Hydrocarbons. New York: William Andrew Inc. p. 177. ISBN 978-0-8155-2039-9.

[lexicon-9] 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. S2CID 84492006.

[sigma-10] Sigma-Aldrich Co., Myristic acid.

[fca-11] "Myristic Acid". ChemicalLand21.com. AroKor Holdings Inc. Retrieved 17 June 2014.

[Playfair2009-12] 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] Beal, G. D. (1926). "Myristic Acid". Organic Syntheses. 6: 66. doi:10.15227/orgsyn.006.0066.

[14] Council of Europe, August 2007 Natural Sources of Flavourings, Volume 2, p. 103, at Google Books

[15] 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

[Lehninger_Textbook-16] Cox, David L. Nelson, Michael M. (2005). Lehninger principles of biochemistry (4th ed.). New York: W.H. Freeman. ISBN 978-0716743392.{{cite book}}: CS1 maint: multiple names: authors list (link)

[17] Mensink, Ronald P. (2016). "Effects of saturated fatty acids on serum lipids and lipoproteins: a systematic review and regression analysis" (PDF). World Health Organization.

[18] Schwingshackl L, Bogensberger B, Benčič A, Knüppel S, Boeing H, Hoffmann G (2018). "Effects of oils and solid fats on blood lipids: a systematic review and network meta-analysis". J Lipid Res. 59 (9): 1771–1782. doi:10.1194/jlr.P085522. PMC 6121943. PMID 30006369.

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Myristic acid

Contents

Occurrence

Chemical behaviour

Health effects

See also

References