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Sunday, 12 July 2015

Trimyristin

Trimyristin

Trimyristin

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.

Name Trimyristin
Synonyms Glycerol trimyristate
Name in Chemical Abstracts Tetradecanoic acid, 1,2,3-propanetriyl ester
CAS No 555-45-3
EINECS No 209-099-7
Molecular formula C45H86O6
Molecular mass 723.18
SMILES code CCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCC
Nutmeg

reacts to

Trimyristin
TRIMYRISTIN.png

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.

1H-NMR

1H NMR
1H-NMR: Trimyristin
300 MHz, CDCl3
delta [ppm] mult. atoms assignment
0.90 m 9 H 14-H (CH3)
1.2-1.4 m 60 H 4-13-H (CH2)
1.5-1.7 m 6 H 3-H
2.33 m 6 H 2-H
4.16 dd 2 H glycerol-C1-Ha
4.31 dd 2 H glycerol-C1-Hb
5.28 m 1 H glycerol-C2-H
7.26

CHCl3
2.11

acetone (impurity)

Isolation of trimyristin from nutmeg
Reaction type: isolation of natural products
Substance classes: carboxylic acid ester, triglyceride, natural product
Techniques: extracting with Soxhlet extractor, evaporating with rotary evaporator, recrystallizing, filtering, heating under reflux, heating with oil bath, stirring with magnetic stir bar
Degree of difficulty: Easy
Batch scale: 25 g Nutmeg

Reaction……….http://kriemhild.uft.uni-bremen.de/nop/en/instructions/pdf/1021_en.pdf

The reaction apparatus consists of a 250 mL round-bottom flask with a magnetic stir bar and a 100 mL soxhlet extraction unit with a reflux condenser. 25 g of finely ground nutmeg are placed into the extraction sleeve and covered with a little glass wool. 150 mL tert-butyl methyl ether are placed into the flask and whilst stirring, the solvent is heated to reflux until the solvent leaving the extraction sleeve is colourless (approximately 5 hours).

Work up

The solvent is evaporated with a final pressure of 20 hPa. The flask containing the residue is cooled in an ice bath or the refrigerator until the contents has crystallized to a thick slurry.
Crude product yield: 12 g;
The crude product is recrystallized from the minimum amount of ethanol. Prior to filtering the crystals, the flask is placed into the refrigerator for at least 30 minutes. The crystalline slurry is filtered and the product is dried in an evacuated desiccator over silica gel. Should the crystals not be colourless after the first recrystallization, a second recrystallization is carried out.
Yield: 6.5 g; melting point 54-55 °C;

Duration of the experiment

Without recrystallization 6 hours

Where can I stop the experiment?

Before and after the evaporation of the solvent

Recycling

The evaporated tert-butyl methyl ether and the evaporated ethanol from the mother liquor are collected and redistilled.

Suggestions for waste disposal
Waste Disposal
residue from mother liquor domestic waste
residue from extraction domestic waste

Operating scheme

Operating scheme

Substances required

Batch scale: 25 g Nutmeg
Educts
Amount Risk Safety
Nutmeg

25 g R S
Solvents
Amount Risk Safety
Ethanol
F F
~ 150 mL R 11 S 2-7-16
tert-Butyl methyl ether
F F Xi Xi
150 mL R 11-38 S 2-9-16-24
Others
Amount Risk Safety
Iodine
Xn Xn N N
0.1 g R 20/21-50 S 2-23.2-23.4-25-61
Solvents for analysis
Amount Risk Safety
Cyclohexane
F F Xn Xn N N
? R 11-38-50/53-65-67 S 2-9-16-33-60-61-62
Acetic acid ethyl ester
F F Xi Xi
? R 11-36-66-67 S 2-16-26-33

Substances produced

Batch scale: 25 g Nutmeg
Products
Amount Risk Safety
Trimyristin

6.5 g R S

Equipment

Batch scale: 25 g Nutmeg
round bottom flask 250 mL round bottom flask 250 mL
Soxhlet extractor 100 mL Soxhlet extractor 100 mL
glass wool glass wool
extraction cone extraction cone
heatable magnetic stirrer with magnetic stir bar heatable magnetic stirrer with magnetic stir bar
oil bath oil bath
reflux condenser reflux condenser
rotary evaporator rotary evaporator
ice bath ice bath
exsiccator with drying agent exsiccator with drying agent
suction filter suction filter
suction flask suction flask

Simple evaluation indices

Batch scale: 25 g Nutmeg
Atom economy
not defined
Yield
not defined
Target product mass
6.5 g
Sum of input masses
250 g
Mass efficiency
26 mg/g
Mass index
39 g input / g product
E factor
38 g waste / g product
Energy input
1500 kJ
Energy efficiency
4.3 mg/kJ

Chromatogram

crude product chromatogram
TLC: crude product
TLC layer Polygram SilG/UV precoated TLC layer; 0.2 mm; silica gel; Macherey & Nagel
mobile phase cyclohexane / EtOAc = 95 : 5
staining reagent Vaughn’s reagent or iodine vapor
Rf (product) 0.51

13C-NMR

13C NMR
13C-NMR: Trimyristin
300 MHz, CDCl3
delta [ppm] assignment
14.08 C14
22.66 C13
24.85-24.89 C3, C17
29.06-31.90 C4-C12
34.04-34.2 C2
62.08 glycerol-C1
68.85 glycerol-C2
172.85 C15
173.26 C1
76.5-77.5 CDCl3


IR

IR
IR: Trimyristin
[KBr, T%, cm-1]
[cm-1] assignment
2950-2850 aliph. C-H valence
1730 C=O valence, ester



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 Yes
ChemSpider 10675 
EC number 209-099-7
Jmol-3D images Image
PubChem 11148
UNII 18L31PSR28 Yes
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)
Boiling point 311 °C (592 °F; 584 K)
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]
Hazards
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no code NFPA 704 four-colored diamond
0
1
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).

    1. References

    2. Merck Index, 11th Edition, 9638.

    4. Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.

    6. 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 Structural Science 57 (3): 372. doi:10.1107/S0108768100019121. edit

    8. Sharma, Someshower Dutt; Kitano, Hiroaki; Sagara, Kazunobu (2004). “Phase Change Materials for Low Temperature Solar Thermal Applications” (PDF). http://www.eng.mie-u.ac.jp. Mie University. Retrieved 2014-06-19.

    10. 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. edit

    12. 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)

“MSDS of Trimyristin”
      .
http://www.fishersci.ca
      . Fisher Scientific. Retrieved 2014-06-19.





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1 comment:

  1. creative peptides23 January 2019 at 07:46

    Myristoyl Pentapeptide-17 is the reaction product of myristic acid and Pentapeptide-17. It promotes the delivery of key ingredients for quicker lash growth, thus stimulates the hair growth at the follicle. Myristoyl Pentapeptide-17

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