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Myristic acid









Myristic acid


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Myristic acid[1]

Skeletal formula of myristic acid

Ball-and-stick model of myristic acid
Names

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





Properties

Chemical formula


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]

Solubility in water

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]


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)[7]


Refractive index (nD)

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

Crystal structure


Monoclinic (−3 °C)[2]

Space group

P21/c[2]

Lattice constant



a = 31.559 Å, b = 4.9652 Å, c = 9.426 Å[2]

α = 90°, β = 94.432°, γ = 90°

Thermochemistry


Heat capacity (C)

432.01 J/mol·K[4][6]


Std enthalpy of
formation (ΔfHo298)

−833.5 kJ/mol[4][6]


Std enthalpy of
combustion (ΔcHo298)

8675.9 kJ/mol[6]
Hazards

GHS pictograms

The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)[10]

GHS signal word
Warning

GHS hazard statements


H315[10]

NFPA 704


[11]



Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil
Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform
Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen
Special hazards (white): no code
NFPA 704 four-colored diamond


1


2


0




Flash point
> 110 °C (230 °F; 383 K) [11]
Lethal dose or concentration (LD, LC):


LD50 (median dose)

>10 g/kg (rats, oral)[11]
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 ☑Y☒N ?)

Infobox references



Myristic acid (IUPAC systematic name: 1-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. It is named after the binomial name for nutmeg (Myristica fragrans), from which it was first isolated in 1841 by Lyon Playfair.[12]




Contents






  • 1 Occurrence


  • 2 Uses


  • 3 See also


  • 4 References





Occurrence[edit]





Myristica fragrans fruit contains myristic acid


Nutmeg butter has 75% trimyristin, the triglyceride of myristic acid. Besides nutmeg, myristic acid is also 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 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.[13][14] It also comprises 14.49% of the fats from the fruit of the Durian species Durio graveolens.[15]



Uses[edit]


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


Various "human epidemiological studies have shown that myristic acid and lauric acid were the saturated fatty acids most strongly related to the average serum cholesterol concentrations in humans",[16] meaning they were positively correlated with higher cholesterol levels as well as raising triglycerides in plasma by some 20% increasing the risk for cardiovascular disease, although some research points to myristic acid's positive effects on HDL cholesterol and hence improving HDL (good cholesterol) to total cholesterol ratio.[17]


Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.



See also[edit]




  • 1-Tetradecanol – the corresponding alcohol


  • Myristyl aldehyde – the corresponding aldehyde



References[edit]





  1. ^ Merck Index, 11th Edition, 6246


  2. ^ abcd 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..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output q{quotes:"""""""'""'"}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}


  3. ^ ab G., Chuah T.; D., Rozanna; A., Salmiah; Y., Thomas Choong S.; M., Sa'ari (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.


  4. ^ abcdefg Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.


  5. ^ abcdefg Seidell, Atherton; Linke, William F. (1940). Solubilities of Inorganic and Organic Compounds (3rd ed.). New York: D. Van Nostrand Company. pp. 762–763.


  6. ^ abcd 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), http://webbook.nist.gov


  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.


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


  9. ^ ab 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.


  10. ^ ab Sigma-Aldrich Co., Myristic acid.


  11. ^ abc "MYRISTIC ACID". ChemicalLand21.com. AroKor Holdings Inc. Retrieved 17 June 2014.


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


  14. ^ 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


  15. ^ Nasaruddin, Mohd hanif; Noor, Noor Qhairul Izzreen Mohd; Mamat, Hasmadi (2013). "Komposisi Proksimat dan Komponen Asid Lemak Durian Kuning (Durio graveolens) Sabah" [Proximate and Fatty Acid Composition of Sabah Yellow Durian (Durio graveolens)] (PDF). Sains Malaysiana (in Malay). 42 (9): 1283–1288. ISSN 0126-6039. OCLC 857479186. Retrieved 28 November 2017.


  16. ^ German JB, Dillard CJ. (2010). "Saturated fats: a perspective from lactation and milk composition". Lipids. 45 (10): 915–923. doi:10.1007/s11745-010-3445-9. PMC 2950926. PMID 20652757.


  17. ^ Kromhout, Daan; et al. (1995). "Dietary Saturated and transFatty Acids and Cholesterol and 25-Year Mortality from Coronary Heart Disease: The Seven Countries Study". Preventive Medicine. 24 (3): 308–315. doi:10.1006/pmed.1995.1049. PMID 7644455.
















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