Myristic acid

Myristic acid

Names
Preferred 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
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 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

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. It is named after the binomial name for nutmeg (Myristica fragrans), from which it was first isolated in 1841 by Lyon Playfair.

Occurrence

Myristica fragrans fruit contains myristic acid

Nutmeg butter has 75% trimyristin, the triglyceride of myristic acid and a source from which it can be synthesised. 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. 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.

Chemical behaviour

Myristic acid acts as a lipid anchor in biomembranes.

Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.

Health effects

Myristic acid consumption raises low-density lipoprotein (LDL) cholesterol.

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