Trimyristin

Trimyristin
Names



IUPAC name 1,3-Di(tetradecanoyloxy)propan-2-yl tetradecanoate
Other names Glyceryl trimyristate; Glycerol tritetradecanoate; 1,2,3-Tritetradecanoylglycerol
Identifiers
CAS Number	555-45-3^Y
3D model (Jmol)	Interactive image
ChemSpider	10675^N
ECHA InfoCard	100.008.273
EC Number	209-099-7
PubChem CID	11148
UNII	18L31PSR28^Y
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^N Key: DUXYWXYOBMKGIN-UHFFFAOYSA-N^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	723.18 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 (C₂H₅)₂O, acetone, C₆H₆,CH₂Cl₂, CHCl₃
Refractive index (n_D)	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
Specific 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^o₂₉₈)	1246 J/mol·K (liquid)
Std enthalpy of formation (Δ_fH^o₂₉₈)	−2355 kJ/mol
Std enthalpy of combustion (Δ_cH^o₂₉₈)	27643.7 kJ/mol
Hazards
NFPA 704	0 1 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).
N (what is ^YN ?)
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.

Trimyristin is found naturally in many vegetable fats and oils.

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.

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