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Trimyristin^[1]
Names
	Systematic IUPAC name Propane-1,2,3-triyl tri(tetradecanoate)
	Other names Glyceryl trimyristate; Glycerol tritetradecanoate; 1,2,3-Tritetradecanoylglycerol
Identifiers
CAS Number	555-45-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	10675 ;
ECHA InfoCard	100.008.273
EC Number	209-099-7;
PubChem CID	11148;
UNII	18L31PSR28 ;
CompTox Dashboard (EPA)	DTXSID701014651 ;
	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,4-41H2,1-3H3 Key: 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,4-41H2,1-3H3 Key: DUXYWXYOBMKGIN-UHFFFAOYAC;
	SMILES CCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC;
Properties
Chemical formula	C45H86O6
Molar mass	723.177 g·mol−1
Appearance	White-yellowish gray solid
Odor	Odorless
Density	0.862 g/cm3 (20 °C); 0.8848 g/cm3 (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 (S⦵298)	1246 J/mol·K (liquid)
Std enthalpy of; formation (ΔfH⦵298)	−2355 kJ/mol
Std enthalpy of; combustion (ΔcH⦵298)	27643.7 kJ/mol
Hazards
NFPA 704 (fire diamond)	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 [77 °F], 100 kPa). verify (what is ?) Infobox references

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

The isolation of trimyristin from powdered nutmeg is a common introductory-level college organic chemistry experiment.^[8]^[9] 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^[10] or one of its salts^[11] as an example of saponification.

References

^ Merck Index, 11th Edition, 9638.
^ ^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.
^ ^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. 57 (3): 372–377. doi:10.1107/S0108768100019121. PMID 11373397.
^ ^a ^b 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.
^ ^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. S2CID 101805872.
^ ^a ^b ^c ^d 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)
^ ^a ^b ^c "MSDS of Trimyristin". fishersci.ca. Fisher Scientific. Retrieved 2014-06-19.
^ 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.
^ 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.
^ Beal, G. D. (1926). "Myristic Acid". Organic Syntheses. 6: 66. doi:10.15227/orgsyn.006.0066.
^ 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.