Deriving Renewable Squalane from Sugarcane

Jul 1, 2014 | Contact Author | By: Derek McPhee, PhD; Armelle Pin; Lance Kizer, PhD; and Loren Perelman, PhD; Amyris Inc., Emeryville, CA, USA
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Title: Deriving Renewable Squalane from Sugarcane
squalanex squalenex emollientx biotechx fermentationx renewable β-Farnesenex fermentable sugarsx
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Keywords: squalane | squalene | emollient | biotech | fermentation | renewable β-Farnesene | fermentable sugars

Abstract: Commercial use of squalane has been constrained by an inconsistent supply and resulting price volatility, but modern biotechnology has been able to leverage enzyme-catalyzed chemical reactions found in nature coupled with traditional chemical processing steps to create a high-quality source of renewable squalane.

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D McPhee, A Pin, L Kizer and L Perelman, Deriving Renewable Squalane from Sugarcane, Cosm & Toil 129(6) 20-26 (May 2014)

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Squalane (INCI: Squalane; IUPAC name: 2,6,10,15,19,23-hexamethyltetracosane; CAS RN 111-01-3) is a valued cosmetic ingredient due to several of its unique properties. In a pure state, it is a mobile, colorless, odorless and tasteless hydrocarbon oil with good physical and chemical stability; this is illustrated by its high boiling point of 210-215°C (at 1 torr pressure) and notable resistance to chemical oxidation, making the need for preservatives unnecessary. Squalane also naturally occurs in small amounts in the lipid layers of skin, and along with its precursor squalene, it prevents moisture loss while restoring skin’s suppleness and flexibility. The ingredient’s sensorial profile, biocompatibility with skin, robust composition and moisturizing benefits have made it a favorite with cosmetic formulators. From a technical point of view, it is readily emulsifiable, and has excellent dispersion properties and compatibility with other ingredients. It is soluble in all common cosmetic media, and can be used without limits in all types of formulations. Subject to the removal of impurities that vary in type and amount, depending on the source, it is non-toxic and a non-irritant.

Traditional Sources

Traditionally, squalane is manufactured by catalytic hydrogenation of squalene (6E,10E,14E,18E-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene), a natural triterpene hydrocarbon and one of the most important human skin cell lipids. Squalene is synthesized in the sebaceous glands, where it accounts for up to 13% of total lipids. Its concentration varies with skin site and the amount secreted, ranging from 125 mg to 475 mg per day, depending on the individual. It is also found in plants, prokaryotes, yeast and microalgae.

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Table 1. Comparison between squalanes from different sources

Table 1. Comparison between squalanes from different sources

Differences between animal and vegetable squalane (phytosqualane) were reviewed by Gasparoli et al.;24 the complex composition of squalanes from different sources is shown here.

Table 2. Composition of sugar-derived squalane

Table 2. Composition of sugar-derived squalane

Shown here are the major products of the described process and their typical amounts. By summing typical amounts of the first three species, sugar-derived squalane, like high purity shark squalane, is composed of 99% C30 hydrocarbons, and closely matches the performance characteristics of the latter (i.e., odor, density, refractive index and viscosity) while being renewable and environmentally friendly.

Figure 1. Chemical structures of squalane and squalene

Figure 1. Chemical structures of squalane and squalene

Squalane (a) is a valued cosmetic ingredient due to several of its unique properties. Traditionally, squalane is manufactured by catalytic hydrogenation of squalene (b).

Figure 2. Process flow diagram for sugar-derived squalane

Figure 2. Process flow diagram for sugar-derived squalane

β-Farnesene, the natural biosynthetic precursor of squalene, is produced on an industrial scale by fermentation using the common non-pathogenic yeast Saccharomyces cerevisiae. The yeast is then completely removed, followed by a simple chemical coupling that mimics natural processes. This, in turn, avoids the need for isolating lipophilic and oxidatively unstable squalene from the fermentation biomass. Existing hydrogenation and purification technologies can then be used to manufacture high purity squalane.

Figure 3. Compositional variability of 31 consecutive lots of squalane

Figure 3. Compositional variability of 31 consecutive lots of squalane

A tightly controlled manufacturing process ensures consistency from lot to lot, both from a chemical and sensorial (i.e., odor and color) standpoint. Shown here is the compositional data from 31 consecutive lots produced in 2013.

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