Myristic acid
Names | |
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IUPAC name
Tetradecanoic acid
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Other names
C14:0 (Lipid numbers)
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Identifiers | |
544-63-8 | |
ChEBI | CHEBI:28875 |
ChEMBL | ChEMBL111077 |
ChemSpider | 10539 |
EC Number | 208-875-2 |
2806 | |
Jmol 3D model | Interactive image |
PubChem | 11005 |
RTECS number | QH4375000 |
UNII | 0I3V7S25AW |
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Properties | |
C14H28O2 | |
Molar mass | 228.38 g·mol−1 |
Density | 1.03 g/cm3 (−3 °C)[2] 0.99 g/cm3 (24 °C)[3] 0.8622 g/cm3 (54 °C)[4] |
Melting point | 54.4 °C (129.9 °F; 327.5 K) [9] |
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] |
13 mg/L (0 °C) 20 mg/L (20 °C) 24 mg/L (30 °C) 33 mg/L (60 °C)[5] |
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Solubility | Soluble in alcohol, acetates, C6H6, haloalkanes, phenyls, nitros[5] |
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)[5] |
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)[5] |
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)[5] |
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)[5] |
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)[5] |
log P | 6.1[4] |
Vapor pressure | 0.01 kPa (118 °C) 0.27 kPa (160 °C)[6] 1 kPa (186 °C)[4] |
Thermal conductivity | 0.159 W/m·K (70 °C) 0.151 W/m·K (100 °C) 0.138 W/m·K (160 °C)[7] |
Refractive index (nD)
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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)[8] |
Structure | |
Monoclinic (−3 °C)[2] | |
P21/c[2] | |
a = 31.559 Å, b = 4.9652 Å, c = 9.426 Å[2]
α = 90°, β = 94.432°, γ = 90°
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Thermochemistry | |
432.01 J/mol·K[4][6] | |
Std enthalpy of
formation (ΔfH |
−833.5 kJ/mol[4][6] |
Std enthalpy of
combustion (ΔcH |
8675.9 kJ/mol[6] |
Vapor pressure | {{{value}}} |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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verify (what is ?) | |
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.
Contents
Occurrence
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.[9] 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.[10][11]
Uses
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.[citation needed] 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.[citation needed]
The ester isopropyl myristate is used in cosmetic and topical medicinal preparations where good absorption through the skin is desired[citation needed].
Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.
References
- ↑ Merck Index, 11th Edition, 6246
- ↑ 2.0 2.1 2.2 2.3 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 3.0 3.1 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 4.0 4.1 4.2 4.3 4.4 4.5 4.6 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 5.0 5.1 5.2 5.3 5.4 5.5 5.6 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 6.0 6.1 6.2 6.3 Tetradecanoic acid in Linstrom, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov (retrieved 2014-06-17)
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 9.0 9.1 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 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
External links
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