Trimyristin

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
Trimyristin[1]
Skeletal formula of trimyristin
Skeletal formula of trimyristin
Ball-and-stick model of trimyristin
Ball-and-stick model of trimyristin
Space-filling 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;[2] 1,2,3-Tritetradecanoylglycerol[3]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.273 Edit this at Wikidata
EC Number
  • 209-099-7
UNII
  • 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
  • CCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC
Properties
C45H86O6
Molar mass 723.177 g·mol−1
Appearance White-yellowish gray solid
Odor Odorless
Density 0.862 g/cm3 (20 °C)[4]
0.8848 g/cm3 (60 °C)[2]
Melting point 56–57 °C (133–135 °F; 329–330 K)
at 760 mmHg[2][4][5]
Boiling point 311 °C (592 °F; 584 K) at 760 mmHg[2]
Solubility Slightly soluble in alcohol, ligroin
Soluble in diethyl ether, acetone, benzene,[2] dichloromethane, chloroform, TBME
1.4428 (60 °C)[2]
Structure
Triclinic (β-form)[3]
P1 (β-form)[3]
a = 12.0626 Å, b = 41.714 Å, c = 5.4588 Å (β-form)[3]
α = 73.888°, β = 100.408°, γ = 118.274°
Thermochemistry
1013.6 J/mol·K (β-form, 261.9 K)
1555.2 J/mol·K (331.5 K)[5][6]
1246 J/mol·K (liquid)[6]
−2355 kJ/mol[6]
27643.7 kJ/mol[6]
Hazards
NFPA 704 (fire diamond)
[7]
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)[7]
421.1 °C (790.0 °F; 694.2 K)[7]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 exercise in organic chemistry courses.[8][9] It is an uncommonly simple natural product extraction because nutmeg oil generally consists of over 80% trimyristin. Trimyristin makes up between 20–25% of the 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.

See also

References

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