Myristic acid

Myristic acid
Names


IUPAC name Tetradecanoic acid
Other names C14:0 (Lipid numbers)
Identifiers
CAS Number	544-63-8^Y
3D model (Jmol)	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	11005
RTECS number	QH4375000
UNII	0I3V7S25AW^N
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	228.38 g·mol⁻¹
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 (n_D)	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
Specific heat capacity (C)	432.01 J/mol·K
Std enthalpy of formation (Δ_fH^o₂₉₈)	−833.5 kJ/mol
Std enthalpy of combustion (Δ_cH^o₂₉₈)	8675.9 kJ/mol
Hazards
GHS pictograms
GHS signal word	Warning
GHS hazard statements	H315
EU classification (DSD)	Xi
R-phrases	R36/37/38
NFPA 704	1 2 0
Flash point	> 110 °C (230 °F; 383 K)
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	>10 g/kg (rats, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

Myristic acid, also called tetradecanoic acid, is a common saturated fatty acid with the molecular formula CH₃(CH₂)₁₂COOH. A myristate is a salt or ester of myristic acid. Myristic acid is named after the nutmeg Myristica fragrans.

Nutmeg butter has 75% trimyristin, the triglyceride of myristic acid. Besides nutmeg, myristic acid is also found in palm kernel oil, coconut oil, butter fat and is a minor component of many other animal fats. 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.

Myristic acid is commonly added co-translationally to the penultimate, nitrogen-terminus, glycine in receptor-associated kinases to confer the membrane localisation 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.

The ester isopropyl myristate is used in cosmetic and topical medicinal preparations where good absorption through the skin is desired.

Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.

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