Trimyristin

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Trimyristin[1]
Skeletal formula of trimyristin
Ball-and-stick model of trimyristin
Space-filling model of trimyristin
Identifiers
CAS number 555-45-3 YesY
PubChem 11148
ChemSpider 10675
UNII 18L31PSR28 YesY
EC number 209-099-7
Jmol-3D images Image 1
Properties
Molecular formula C45H86O6
Molar mass 723.16 g mol−1
Appearance White-yellowish gray solid
Odor Nutmeg-like
Density 0.862 g/cm3 (20 °C)[4]
0.8848 g/cm3 (60 °C)[2]
Melting point 32.3–57 °C (90.1–134.6 °F; 305.4–330.1 K) [4][5]
58.5 °C (137.3 °F; 331.6 K)
at 760 mmHg[2]
Boiling point 311 °C (592 °F; 584 K)
at 760 mmHg[2]
Solubility Slighty soluble in alcohol, ligroin
Soluble in (C2H5)2O, acetone, C6H6,[2] CH2Cl2, CHCl3
Refractive index (nD) 1.4428 (60 °C)[2]
Structure
Crystal structure Triclinic (β-form)[3]
Space group P1 (β-form)[3]
Lattice constant a = 12.0626 Å, b = 41.714 Å, c = 5.4588 Å (β-form)[3]
Lattice constant α = 73.888°, β = 100.408°, γ = 118.274°
Thermochemistry
Specific
heat capacity
C
1013.6 J/mol·K (β-form, 261.9 K)
1555.2 J/mol·K (331.5 K)[5][6]
Std molar
entropy
So298
1246 J/mol·K (liquid)[6]
Std enthalpy of
formation
ΔfHo298
−2355 kJ/mol[6]
Std enthalpy of
combustion
ΔcHo298
27643.7 kJ/mol[6]
Hazards
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point > 110 °C (230 °F; 383 K) [7]
Autoignition temperature 421.1 °C (790.0 °F; 694.2 K) [7]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Trimyristin is an ester with the chemical formula C45H86O6. It is a saturated fat which is the triglyceride of myristic acid. Trimyristin is a white to yellowish-gray solid that is insoluble in water, but soluble in ethanol, benzene, chloroform, dichloromethane, and ether.

Occurrence[edit]

Trimyristin is found naturally in many vegetable fats and oils.

Isolation from nutmeg[edit]

Seed of nutmeg contains trimyristin

The isolation of trimyristin from powdered nutmeg is a common introductory-level college organic chemistry experiment. It is an uncommonly simple natural product extraction because nutmeg oil generally consists of over eighty percent trimyristin. Trimyristin makes up between 20-25% of the overall mass of dried, ground nutmeg. Separation is generally carried out by steam distillation and purification uses extraction from ether followed by distillation or rotary evaporation to remove the volatile solvent. The extraction of trimyristin can also be done with diethyl ether at room temperature, due to its high solubility in the ether. The experiment is frequently included in curricula, both for its relative ease and to provide instruction in these techniques.

See also[edit]

References[edit]

  1. ^ Merck Index, 11th Edition, 9638.
  2. ^ a b c d e f Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0. 
  3. ^ a b c d Van Langevelde, A.; Peschar, R.; Schenk, H. (2001). "Structure of β-trimyristin and β-tristearin from high-resolution X-ray powder diffraction data". Acta Crystallographica Section B Structural Science 57 (3): 372. doi:10.1107/S0108768100019121.  edit
  4. ^ a b Sharma, Someshower Dutt; Kitano, Hiroaki; Sagara, Kazunobu (2004). "Phase Change Materials for Low Temperature Solar Thermal Applications". http://www.eng.mie-u.ac.jp. Mie University. Retrieved 2014-06-19. 
  5. ^ a b Charbonnet, G. H.; Singleton, W. S. (1947). "Thermal properties of fats and oils". Journal of the American Oil Chemists Society 24 (5): 140. doi:10.1007/BF02643296.  edit
  6. ^ a b c d Trimyristin 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 2014-06-19)
  7. ^ a b c "MSDS of Trimyristin". http://www.fishersci.ca. Fisher Scientific. Retrieved 2014-06-19.