Myristic acid

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Myristic acid[1]
Skeletal formula of myristic acid
Skeletal formula of myristic acid
Ball-and-stick model of myristic acid
Ball-and-stick model of myristic acid
Names
Preferred IUPAC name
Tetradecanoic acid
Other names
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
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EC Number
  • 208-875-2
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RTECS number
  • QH4375000
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • 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
  • CCCCCCCCCCCCCC(=O)O
Properties
C14H28O2
Molar mass 228.376 g·mol−1
Appearance colorless or white solid
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]
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]
−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)[7]
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°
Thermochemistry
432.01 J/mol·K[4][6]
−833.5 kJ/mol[4][6]
8675.9 kJ/mol[6]
Hazards
GHS labelling:
GHS07: Exclamation mark[10]
Warning
H315[10]
NFPA 704 (fire diamond)
[11]

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2
1
0
Flash point > 110 °C (230 °F; 383 K)[11]
Lethal dose or concentration (LD, LC):
>10 g/kg (rats, oral)[11]
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).

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

[edit | edit source]
File:Myristica fragrans.JPG
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

[edit | edit source]
See also: Myristoylation

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

Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.

Health effects

[edit | edit source]

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

See also

[edit | edit source]

References

[edit | edit source]
  1. ^ Merck Index, 11th Edition, 6246
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  6. ^ 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)
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  10. ^ a b Sigma-Aldrich Co., Myristic acid.
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  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
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