Trimyristin

From Infogalactic: the planetary knowledge core
Jump to: navigation, search
Trimyristin[1]
Skeletal formula of trimyristin
Ball-and-stick model of trimyristin
Space-filling model of trimyristin
Names
IUPAC name
1,3-Di(tetradecanoyloxy)propan-2-yl tetradecanoate
Other names
Glyceryl trimyristate; Glycerol tritetradecanoate;[2] 1,2,3-Tritetradecanoylglycerol[3]
Identifiers
555-45-3 YesY
ChemSpider 10675 N
EC Number 209-099-7
Jmol 3D model Interactive image
PubChem 11148
UNII 18L31PSR28 YesY
  • 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 723.18 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 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 Slighty soluble in alcohol, ligroin
Soluble in (C2H5)2O, acetone, C6H6,[2] CH2Cl2, CHCl3
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]
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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

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.

See also

References

  1. ↑ Merck Index, 11th Edition, 9638.
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ 3.0 3.1 3.2 3.3 Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ 4.0 4.1 Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ 5.0 5.1 Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ 6.0 6.1 6.2 6.3 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)


<templatestyles src="Asbox/styles.css"></templatestyles>

Stub icon

This biochemistry article is a stub. You can help Wikipedia by expanding it.
Retrieved from "https://infogalactic.com/w/index.php?title=Trimyristin&oldid=688382"