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Isoamyl laurate
"Descrizione"
by Al222 (19776 pt)
2023-Jul-13 12:27

Isoamyl laurate is a chemical compound, a fatty latic acid ester obtained by the condensation of dodecanoic acid with 3-methylbutan-1-ol and derived from an isoamylol. It is industrially produced from vegetable oils and sugar.

The name defines the structure of the molecule:

  • "Isoamyl" refers to the isoamyl group, which is a five-carbon alkyl group derived from isopentane. It is often represented as (CH3)2CHCH2-.
  • "Laurate" refers to the laurate group, which is a twelve-carbon alkyl group derived from lauric acid. It is often represented as CH3(CH2)10COO-.

The synthesis of isoamyl laurate typically involves the esterification of isoamyl alcohol and lauric acid. Here is a simplified version of the process:

  • Isoamyl alcohol is reacted with lauric acid in the presence of an acid catalyst, such as sulphuric acid. This reaction is known as esterification.
  • The esterification reaction produces Isoamyl laurate and water. The reaction is reversible, so it is often completed by removing the water that is formed.

The overall process can be summarised as follows:

Isoamyl alcohol + Lauric acid → Isoamyl laurate+ Water

It appears as a colourless transparent liquid. Soluble in ethanol, insoluble in water.

What it is used for and where

Moisturising substitute for silicone oil, of vegetable origin with good compatibility with most epoxy silicone oils, synthetic oils, mineral oils, vegetable oils, silicone oils of various viscosities and sunscreen.

Cosmetics

Used as a solvent, fragrance, as a conditioner in hair conditioners and masks, make-up products for sun protection. Compared to caprylic acid/triglyceride, it has better spreadability, is less sticky and provides a less greasy residual feel on the hands. 

Skin conditioning agent. It is the mainstay of topical skin treatment as it has the function of restoring, increasing or improving skin tolerance to external factors, including melanocyte tolerance. The most important function of the conditioning agent is to prevent skin dehydration, but the subject is rather complex and involves emollients and humectants that can be added in the formulation.

Skin conditioning agent - Emollient. Emollients have the characteristic of enhancing the skin barrier through a source of exogenous lipids that adhere to the skin, improving barrier properties by filling gaps in intercorneocyte clusters to improve hydration while protecting against inflammation. In practice, they have the ability to create a barrier that prevents transepidermal water loss.  Emollients are described as degreasing or refreshing additives that improve the lipid content of the upper layers of the skin by preventing degreasing and drying of the skin. The problem with emollients is that many have a strong lipophilic character and are identified as occlusive ingredients; they are oily and fatty materials that remain on the skin surface and reduce transepidermal water loss. In cosmetics, emollients and moisturisers are often considered synonymous with humectants and occlusives.

Food

Generally used as a flavouring agent in wine, beer.

Typical optimal commercial product characteristics Isoamyl laurate

AppearanceColourless transparent liquid
Density0.856 g/mL at 25 °C(lit.)
Boiling point
170 °C / 2mmHg
Flash Point
>230 °F
Purity99%
Water≤1.0%
Index of Refraction
n20/D 1.436(lit.)
PSA26.30000
LogP5.49660
Heavy metals
≤10 ppm
Residue on ignition
≤0.1%
Total Impurities
≤0.5%
Residue on ignition
≤0.1%
Acidity(mgKOH/g)1.0 Max
Saponification value (mgKOH/g)205.0-215.0



  • Molecular Formula  C17H34O2
  • Linear Formula    CH3(CH2)10CO2CH2CH2CH(CH3)2
  • Molecular Weight    270.5 
  • Exact Mass      270.25600
  • CAS  6309-51-9
  • UNII    M1SLX00M3M
  • EC Number   228-626-1
  • DSSTox Substance ID  DTXSID3064221
  • IUPAC  3-methylbutyl dodecanoate
  • InChI=1S/C17H34O2/c1-4-5-6-7-8-9-10-11-12-13-17(18)19-15-14-16(2)3/h16H,4-15H2,1-3H3  
  • InChl Key      FVKRIDSRWFEQME-UHFFFAOYSA-N
  • SMILES   CCCCCCCCCCCC(=O)OCCC(C)C
  • MDL number  MFCD00048429
  • PubChem Substance ID    24900842
  • JECFA    182
  • FEMA    2077   
  • ChEBI  87343
  • SCHEMBL 120186 
  • NSC   42577
  • Council of Europe no. 379  

Synonyms:

  • 3-Methylbutyl dodecanoate
  • Isopentyl dodecanoate

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