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Squalane
Squalane
Squalane
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Squalane
Skeletal formula of squalane
Skeletal formula of squalane
Names
Preferred IUPAC name
2,6,10,15,19,23-Hexamethyltetracosane[1]
Other names
Perhydrosqualene; Dodecahydrosqualene
Identifiers
3D model (JSmol)
776019
ChemSpider
ECHA InfoCard 100.003.478 Edit this at Wikidata
EC Number
  • 203-825-6
KEGG
MeSH squalane
RTECS number
  • XB6070000
UNII
  • InChI=1S/C30H62/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h25-30H,9-24H2,1-8H3 ☒N
    Key: PRAKJMSDJKAYCZ-UHFFFAOYSA-N ☒N
  • CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C
Properties
C30H62
Molar mass 422.826 g·mol−1
Appearance Colorless liquid
Odor Odorless
Density 810 mg/mL
Melting point −38 °C (−36 °F; 235 K)
Boiling point 176 °C (349 °F; 449 K) at 7 Pa
1.452
Viscosity 31.123 mPa·s[2]
Thermochemistry
886.36 J/(K·mol)
−871.1...−858.3 kJ/mol
−19.8062...−19.7964 MJ/mol
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P305+P351+P338
Flash point 218 °C (424 °F; 491 K)
Related compounds
Related alkanes
 Phytane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Squalane is the organic compound with the formula ((CH3)2CH[CH2]3CH(CH3)[CH2]3CH(CH3)[CH2]2)2. A colorless hydrocarbon, it is the hydrogenated derivative of squalene, although commercial samples are derived from nature.[3] In contrast to squalene, due to the complete saturation of squalane, it is not subject to auto-oxidation. This fact, coupled with its lower costs and desirable physical properties, led to its use as an emollient and moisturizer in cosmetics.[4]

Sources and production

[edit]

Squalene was traditionally sourced from the livers of sharks, with approximately 3000 required to produce one ton of squalane.[5] Due to environmental concerns, other sources such as olive oil, rice and sugar cane have been commercialized, and as of 2014 have been supplying about 40% of the industry total.[5]

In sugar cane squalane manufacturing, farnesene is produced from fermentation of sugarcane sugars using genetically modified Saccharomyces cerevisiae yeast strains.[5] Farnesene is then dimerized to isosqualene and then hydrogenated to squalane.[5][6]

In olive squalane manufacturing, squalene is extracted from olive oil residues in a green chemistry process, and is then hydrogenated into squalane.[7]

Uses in cosmetics

[edit]

Squalane was introduced as an emollient in the 1950s.[5] The unsaturated form of squalene is produced in human sebum and the livers of sharks.[8][9] Squalane has low acute toxicity and is not a significant human skin irritant or sensitizer.[10][11]

Miscellaneous information

[edit]

The hydrogenation of squalene to produce squalane was first reported in 1916.[12][5]

References

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Squalane

View on Grokipedia
from Grokipedia
Squalane is a saturated with the C30H62, known chemically as 2,6,10,15,19,23-hexamethyltetracosane, and exists as a colorless, odorless, at room temperature. It is produced by the of , a naturally occurring found in human sebum, plant sources such as olives and bran, and animal tissues like , rendering it more stable and less prone to oxidation than its precursor. Commercially, modern production favors plant-derived squalane from sources like or to avoid ethical concerns associated with harvesting, though it was historically extracted from deep-sea shark livers. As a key in and , squalane functions primarily as an emollient and -conditioning agent, mimicking the 's natural to enhance moisture retention without clogging pores, making it non-comedogenic and suitable for all types, including oily, acne-prone, and sensitive . Its lightweight texture allows it to absorb quickly, providing hydration that reduces the appearance of fine lines, improves elasticity, and soothes associated with conditions like eczema or post-sun damage. Beyond skincare, squalane offers benefits for by replenishing moisture, increasing shine, and potentially aiding in preventing breakage, while its stability also makes it useful in pharmaceuticals and as a . assessments indicate it is generally well-tolerated, with low potential at typical cosmetic concentrations, though individuals with specific sensitivities should patch-test products.

Chemical overview

Structure and formula

Squalane is a saturated with the molecular C30H62C_{30}H_{62}, consisting of 30 carbon atoms arranged in a branched chain. Its IUPAC name is 2,6,10,15,19,23-hexamethyltetracosane, reflecting the specific positioning of methyl groups along a 24-carbon backbone. The molecular weight of squalane is 422.81 g/mol. As a branched, saturated triterpenoid , squalane is derived from the of and consists of six units (C5H8C_5H_8) linked in a tail-to-tail configuration at the central bond, resulting in a fully saturated structure with no double bonds. In contrast, (C30H50C_{30}H_{50}) features the same carbon but includes six double bonds, making squalane the stable, hydrogenated analog.

Physical properties

Squalane is a colorless, odorless liquid at , appearing as a transparent, oily viscous substance that remains stable under ambient conditions. Its density is approximately 0.81 g/cm³ at 20°C, making it lighter than and suitable for applications requiring low-mass formulations. The is -38°C, allowing it to remain fluid well below typical storage temperatures, while the is around 350°C at . Squalane exhibits low solubility in water, rendering it insoluble and non-miscible, but it is highly soluble in most organic solvents such as , , , , and oils, as well as slightly soluble in alcohols like and acetone. Its viscosity ranges from 20 to 34 cP at 25°C to 20°C, respectively, contributing to its smooth, non-greasy texture in practical uses. The refractive index is 1.452 at 20°C, indicative of its optical clarity in liquid form.

Chemical properties

Squalane exhibits high owing to its fully saturated structure, which provides resistance to oxidation in marked contrast to the unsaturated precursor . This saturation prevents the formation of peroxides and minimizes degradation under exposure to air, light, or normal environmental conditions, making it suitable for long-term storage and use without significant breakdown. Unlike , squalane does not readily polymerize or undergo auto-oxidation, contributing to its inert nature in typical applications. As a branched , squalane displays low reactivity under ambient conditions, behaving as a substance with no hydrolyzable functional groups or tendency for spontaneous reactions. It can participate in standard alkane reactions, such as complete combustion to and : \ce2C30H62+91O2−>60CO2+62H2O\ce{2 C30H62 + 91 O2 -> 60 CO2 + 62 H2O} or under irradiation, but these processes are seldom relevant outside specialized settings. Squalane's purely composition renders it non-polar, with a low constant of approximately 1.91 and negligible ionic conductivity, properties that align with its role as a non-conductive and . Thermally, it remains stable up to around 300°C, as evidenced by its use in high-temperature analytical techniques without , enabling applications in environments requiring heat resistance.

Natural occurrence and

Biosynthesis pathway

The biosynthesis of squalene, the direct precursor to squalane, occurs primarily through the in eukaryotic organisms. This pathway begins with , which is converted to 3-hydroxy-3-methylglutaryl-CoA () by HMG-CoA synthase. is then reduced to mevalonate by the rate-limiting enzyme . Mevalonate undergoes phosphorylation and to form isopentenyl (IPP), the fundamental five-carbon building block of isoprenoids. IPP isomerizes to (), and through sequential condensations, these units form () and finally () catalyzed by farnesyl pyrophosphate synthase. The final committed step in squalene biosynthesis involves the head-to-head condensation of two FPP molecules. This process first generates presqualene diphosphate, an unstable intermediate, which is then rearranged and reduced to using NADPH as a cofactor, a reaction catalyzed by squalene synthase (also known as farnesyl-diphosphate farnesyltransferase). Squalene synthase is an of the and represents a key regulatory point in the pathway, as it diverts FPP from other isoprenoid branches toward production. Squalene serves as a crucial intermediate in the of , such as in animals and phytosterols in , where it is subsequently epoxidized to 2,3-oxidosqualene by squalene epoxidase before cyclization into sterol precursors. In humans, endogenous squalene production is estimated at approximately 1 g per day, reflecting the overall flux through the cholesterol synthesis pathway, with the majority occurring in the liver and intestines. The enzymes in this pathway are encoded by specific genes, with squalene synthase expressed from the FDFT1 gene located on chromosome 8p23.1 in humans. Genetic variations in FDFT1 can lead to squalene synthase deficiency (SQSD), a rare autosomal recessive disorder characterized by profound developmental delay, brain malformations, , and dysmorphic features due to disrupted sterol biosynthesis.

Sources in nature

Squalene, the primary natural precursor to , is abundantly present in animal tissues, particularly in the liver oil of deep-sea . In species such as those of the Centrophorus, comprises 27-61% of the liver oil, serving as a low-density that contributes to in the deep ocean environment. Trace amounts of squalane, the saturated derivative, occur naturally in human sebum as an endogenous component of skin lipids, typically constituting less than 0.5% of total sebaceous lipids. In , squalene is found at lower concentrations compared to marine animals, primarily in various seed oils. contains 0.1-0.7% squalene (1000-7000 mg/kg), while seed oil has notably higher levels, up to 8% of the total content. Other sources include and , where squalene levels range from 0.2-0.5%. Microbial organisms also produce squalene as an intermediate in pathways. Yeasts like and oleaginous species such as Yarrowia lipolytica, along with certain and , synthesize squalene naturally, though yields are generally low without . Overall, squalene abundance is highest in marine animals, where it functions in and energy storage, whereas concentrations in terrestrial and microbes are substantially lower, reflecting its role as a biosynthetic precursor to sterols like across organisms.

Commercial production

Traditional methods

, the primary precursor to squalane, was first isolated in 1906 from by Japanese chemist Mitsumaru Tsujimoto, who identified it as an unsaturated through fractional . Commercial production of squalane via of this squalene began in the mid-20th century, with its initial adoption in during the due to its emollient properties and stability. The conventional industrial process starts with harvesting livers from deep-sea sharks, such as those in the genus , where squalene constitutes 40-80% of the liver oil. Extraction involves grinding the livers and using organic solvents like to separate the oil, followed by purification of squalene through or adsorption with molecular sieves to achieve high purity. The squalene is then hydrogenated to squalane using a nickel or catalyst under elevated conditions of 100-200 atm pressure and 100-150°C temperature, typically in a , yielding over 95% conversion and resulting in 99% pure squalane suitable for commercial use. On a production scale, approximately 50-100 kg of squalene can be extracted from one ton of livers, depending on the and oil content, though this requires processing thousands of animals annually to meet demand. This method faced significant challenges, including seasonal variability in shark availability tied to cycles and growing ethical concerns over and , which contributed to its decline after the 1990s as conservation efforts intensified.

Modern sustainable methods

Modern sustainable methods for squalane production emphasize renewable plant and microbial feedstocks to replace animal-derived sources, focusing on biotechnological and green extraction techniques developed primarily since the . These approaches leverage , , and eco-friendly solvents to produce , which is then hydrogenated to stable squalane, similar in principle to traditional but applied to bio-based precursors. The squalane produced from these methods is chemically identical to that from animal sources, both being fully saturated C30H62 hydrocarbons with the same composition, stability, physical properties, and suitability for commercial applications regardless of the precursor source. The primary differences lie in ethical sourcing and environmental impact, with modern methods providing sustainable, vegan, and cruelty-free alternatives that avoid contributing to overfishing and marine biodiversity loss. Plant-derived methods include extraction from , where comprises about 0.1-0.7% of the unsaponifiable fraction, obtained through solvent extraction or molecular of by-products, followed by purification and . This process utilizes agricultural waste from olive production in regions like the Mediterranean, minimizing environmental impact through sustainable farming practices. Another innovative plant-based route involves sugarcane-derived squalane, pioneered by in the 2010s; converts sugarcane sugars into farnesene, which undergoes oligomerization to form and subsequent to squalane, yielding a high-purity product compliant with USP standards. In 2023, acquired Amyris' squalane portfolio, including Neossance, and established a manufacturing to continue production. Microbial biotechnology offers scalable alternatives through genetically engineered yeasts that overexpress key enzymes in the , such as . For instance, the oleaginous yeast Yarrowia lipolytica has been engineered by overexpressing , ATP-citrate lyase, and NADPH-supplying enzymes like mannitol dehydrogenase, alongside CRISPR-Cas9 optimizations to enhance flux toward biosynthesis during glucose or . These strains achieve yields of up to 502 mg/L in shake-flask cultures under optimized conditions (e.g., C/N ratio of 40:1, pH 6.0), with further improvements like cerulenin addition to inhibit competing pathways; the is then extracted and hydrogenated to squalane. Additional plant sources include seeds and , where supercritical CO₂ extraction enables efficient isolation of without harsh solvents. In , SC-CO₂ at 10-30 MPa and 30-130°C extracts oil containing up to 8% , allowing into enriched streams for subsequent . Similarly, rice deodorization distillates, a by-product of oil refining, yield (around 8%) via SC-CO₂ combined with complexation or adsorption, providing a valorization route for agro-industrial waste. These methods are renewable and scalable, drawing from abundant feedstocks like agricultural residues and sugars, and by 2023, plant-based sources already accounted for over 82% of the global squalene market, driving a significant decline in shark-derived harvesting through ethical alternatives that preserve marine biodiversity.

Applications

Cosmetics and personal care

Squalane serves as a key ingredient in cosmetics and personal care products, primarily functioning as an emollient and moisturizer that provides lightweight hydration without greasiness. Its saturated hydrocarbon structure allows it to closely mimic the lipid profile of human sebum, where squalene constitutes about 12% of the natural oils produced by sebaceous glands, enabling seamless integration with the skin's barrier. This similarity makes squalane non-comedogenic and suitable for all skin types, including oily, dry, and sensitive, as it absorbs rapidly without clogging pores or causing irritation. Additionally, squalane enhances the penetration of other active ingredients in formulations by improving their delivery through the skin's lipid layers, thereby boosting overall efficacy. In common skincare products, squalane is typically incorporated at concentrations of 5-20% to balance hydration and texture, though pure oils can reach 100%. It appears in moisturizers, serums, sunscreens, and lip balms, where it helps maintain product stability and spreadability. These applications leverage squalane's versatility in both oil-based and formulas. Squalane benefits skin by strengthening the and reducing (TEWL), with studies showing improvements in hydration and moisture retention in compromised skin. Its inherent stability as a hydrogenated form of also confers properties, helping to neutralize free radicals and support long-term skin health without oxidizing in formulations. Approximately 70% of global squalane production is directed toward the sector, driven by demand for clean, plant-derived emollients in personal care. The overall market for and its derivatives, including squalane, reached around 2,500 metric tons annually as of 2024, with accounting for the largest share due to rising consumer preference for sustainable hydration ingredients.

Industrial uses

Squalane, particularly in high-purity grades, serves as a sustainable in industrial lubricants, offering a biodegradable alternative to synthetic options like polyalphaolefin for applications requiring low and high performance. Its saturated structure provides excellent thermal stability, enabling use in demanding high-temperature environments, while low volatility minimizes evaporation and maintenance needs in precision instruments such as watches and components. In pharmaceuticals, squalane functions as a carrier in systems, including oil-in-water emulsions that act as alternative adjuvants to enhance immune responses in . It is also incorporated into topical formulations to support by stimulating migration and aiding tissue repair processes. Recent research as of 2025 indicates squalane protects against UV-induced inhibition of biosynthesis, further supporting its role in and repair. Beyond these, squalane finds application as a component in sample preparation for electron microscopy, where it aids in embedding and stabilizing hydrogels or nanostructures for high-resolution imaging. In research, squalane supports studies by influencing the organization of lipid monolayers and is increasingly employed in biotech for liposomal delivery systems to enhance vesicular integrity and protection. These niche markets represent a growing portion of squalane production, driven by demand in technical and biotechnological sectors.

Safety and environmental impact

Toxicity and safety profile

Squalane exhibits low , with an oral LD50 exceeding 2 g/kg in rats, indicating it is not harmful when ingested in moderate amounts. It is non-irritating to and eyes, as demonstrated in standardized tests following guidelines 404 and 405, respectively. Regarding chronic effects, squalane shows no evidence of carcinogenicity, mutagenicity, or in available studies, supporting its recognition by the U.S. (FDA) as an approved inactive ingredient for oral and topical pharmaceutical applications. Additionally, it is biodegradable under aerobic conditions, further contributing to its favorable safety profile. Allergic reactions to squalane are rare, and it is well-tolerated on sensitive due to its non-sensitizing nature. The Cosmetic Ingredient Review (CIR) Expert Panel has deemed squalane safe for use in cosmetics at concentrations up to approximately 97% in leave-on products. Regulatory bodies affirm its safety for human use; it is exempt from restrictions in the European Union's Annex II list of prohibited cosmetic substances and is permitted without limits in cosmetic formulations under EU Regulation (EC) No 1223/2009. Squalane's stability also minimizes potential irritation in formulations, aligning with its overall low-risk profile.

Sustainability concerns

The historical reliance on shark-derived squalene for squalane production, predominant before the 2000s, contributed significantly to of deep-sea such as gulper sharks, leading to substantial declines; for instance, global abundance of oceanic and rays decreased by 71% between 1970 and 2018 due to intensified exploitation. This overharvesting prompted international regulatory responses, including Appendix II listings for several deep-sea starting in the to control trade in squalene-rich livers and promote . In 2025, proposals at CoP20 seek to include additional deep-sea , such as gulper sharks, in Appendix II to further regulate squalene trade. The shift toward plant-based alternatives like olive oil residues and sugarcane-derived squalane has mitigated biodiversity threats to marine ecosystems by reducing demand for shark livers, though it introduces terrestrial concerns such as the environmental costs of monoculture agriculture. Sugarcane cultivation, a common source for bio-fermented squalane, demands high water inputs—approximately 2,500 liters per liter of bioethanol—potentially straining resources in water-scarce regions and affecting local ecosystems through intensive farming practices. Olive-derived squalane, while leveraging agricultural byproducts to lessen waste, still faces challenges from climate-dependent yields and land use expansion. Biotechnological production methods, such as microbial using feedstocks, offer a lower compared to traditional sourcing, with reports indicating reductions in production waste by 60% and water consumption by nearly 50%. These approaches position plant- and biotech-derived squalane as net-positive for environmental when evaluated across full supply chains. The squalane industry is increasingly committing to sustainable sourcing, driven by commitments to certifications like the (RSPO) for any palm-derived variants, alongside broader adoption of biotech and plant alternatives to eliminate animal sourcing entirely. This trajectory aligns with global efforts to balance cosmetic demand with ecological preservation.

References

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