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Trimyristin

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Trimyristin
Skeletal formula of trimyristin
Ball-and-stick model of trimyristin
Space-filling model of trimyristin
Names
Systematic IUPAC name Propane-1,2,3-triyl tri(tetradecanoate)
Other names Glyceryl trimyristate; Glycerol tritetradecanoate; 1,2,3-Tritetradecanoylglycerol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.273 Edit this at Wikidata
EC Number
  • 209-099-7
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C45H86O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-43(46)49-40-42(51-45(48)39-36-33-30-27-24-21-18-15-12-9-6-3)41-50-44(47)38-35-32-29-26-23-20-17-14-11-8-5-2/h42H,4-41H2,1-3H3Key: DUXYWXYOBMKGIN-UHFFFAOYSA-N
  • InChI=1/C45H86O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-43(46)49-40-42(51-45(48)39-36-33-30-27-24-21-18-15-12-9-6-3)41-50-44(47)38-35-32-29-26-23-20-17-14-11-8-5-2/h42H,4-41H2,1-3H3Key: DUXYWXYOBMKGIN-UHFFFAOYAC
SMILES
  • CCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC
Properties
Chemical formula C45H86O6
Molar mass 723.177 g·mol
Appearance White-yellowish gray solid
Odor Odorless
Density 0.862 g/cm (20 °C)
0.8848 g/cm (60 °C)
Melting point 56–57 °C (133–135 °F; 329–330 K)
at 760 mmHg
Boiling point 311 °C (592 °F; 584 K) at 760 mmHg
Solubility Slightly soluble in alcohol, ligroin
Soluble in diethyl ether, acetone, benzene, dichloromethane, chloroform, TBME
Refractive index (nD) 1.4428 (60 °C)
Structure
Crystal structure Triclinic (β-form)
Space group P1 (β-form)
Lattice constant a = 12.0626 Å, b = 41.714 Å, c = 5.4588 Å (β-form)α = 73.888°, β = 100.408°, γ = 118.274°
Thermochemistry
Heat capacity (C) 1013.6 J/mol·K (β-form, 261.9 K)
1555.2 J/mol·K (331.5 K)
Std molar
entropy (S298) 		1246 J/mol·K (liquid)
Std enthalpy of
formation (ΔfH298) 		−2355 kJ/mol
Std enthalpy of
combustion (ΔcH298) 		27643.7 kJ/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1 0 0
Flash point > 110 °C (230 °F; 383 K)
Autoignition
temperature 		421.1 °C (790.0 °F; 694.2 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

Occurrence

Trimyristin is found naturally in many vegetable fats and oils.

Isolation from nutmeg

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. Trimyristin can then be used to prepare myristic acid or one of its salts as an example of saponification.

See also

References

  1. Merck Index, 11th Edition, 9638.
  2. ^ 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. ^ 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. 57 (3): 372–377. doi:10.1107/S0108768100019121. PMID 11373397.
  4. ^ Sharma, Someshower Dutt; Kitano, Hiroaki; Sagara, Kazunobu (2004). "Phase Change Materials for Low Temperature Solar Thermal Applications" (PDF). Res. Rep. Fac. Eng. Mie Univ. 29. Mie University: 31–64. Retrieved 2014-06-19.
  5. ^ 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. S2CID 101805872.
  6. ^ Trimyristin 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) (retrieved 2014-06-19)
  7. ^ "MSDS of Trimyristin". fishersci.ca. Fisher Scientific. Retrieved 2014-06-19.
  8. Frank, Forrest; Roberts, Theodore; Snell, Jane; Yates, Christy; Collins, Joseph (1971). "Trimyristin from nutmeg". Journal of Chemical Education. 48 (4): 255. Bibcode:1971JChEd..48..255F. doi:10.1021/ed048p255.
  9. Vestling, Martha M (1990). "Isolation of trimyristin and cholesterol: Two microscale extractions for one laboratory period". Journal of Chemical Education. 67 (3): 274. Bibcode:1990JChEd..67..274V. doi:10.1021/ed067p274.
  10. Beal, G. D. (1926). "Myristic Acid". Organic Syntheses. 6: 66. doi:10.15227/orgsyn.006.0066.
  11. De Mattos, Marcio C. S; Nicodem, David E (2002). "Soap from Nutmeg: An Integrated Introductory Organic Chemistry Laboratory Experiment". Journal of Chemical Education. 79 (1): 94. Bibcode:2002JChEd..79...94D. doi:10.1021/ed079p94.
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