Hydroxydecanoic(Decanolactone) is a fatty acid derivative with significant biological activity. Its molecular structure features a hydroxyl group (-OH) attached to a specific carbon atom on the decanoic acid backbone. This modification significantly alters its physical and chemical properties and functions. This compound typically appears as a colorless to pale yellow oily liquid or a low-melting-point solid, being slightly soluble in water but easily soluble in organic solvents. The introduction of the hydroxyl group not only enhances the polarity of the molecule but also makes it more prone to participating in chemical reactions such as esterification.
In biological systems, it often serves as an intermediate in energy metabolism or a precursor for signaling molecules. Studies have shown that decanolactone and its derivatives exhibit potential antibacterial and anti-inflammatory activities in the pharmaceutical field. Additionally, in the fine chemicals industry, they can be used as functional raw materials for synthesizing fragrances or advanced lubricants. Due to its unique structure, it has attracted much attention in the interdisciplinary research of biochemistry and materials science, becoming a valuable model molecule for exploring new biobased chemicals.
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Chemical Formula |
C10H20O3 |
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Exact Mass |
188 |
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Molecular Weight |
188 |
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m/z |
188 (100.0%), 189 (10.8%) |
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Elemental Analysis |
C, 63.80; H, 10.71; O, 25.49 |
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Boiling point 281 ° C, Density 0.948 g/ml at 25 ° C (lit.), FEMA 2360 | GAMMA-DECALACTONE, Refractive index n20/d 1.449, Flash point >230 ° f, Storage condition 2-8 ° C, Morphological neat, Specific gravity 0.950.948, Optical activity[ α] 24/D +34°, neat, ECFA Number231, BRN 117547, InChIKeyIFYYFLINQYPWGJ-UHFFFAOYSA-N, Dangerous goods sign Xi, Hazard category code 36/37/38, Safety instructions 26-37/39-36, WGK Germany 3, RTECS No. lu4600000, Hazard Note Irritant, TSCA Yes.
Hydroxydecanoic (CAS number 706-14-9) is an organic compound with a fruity peach flavor, with a molecular formula of C ₁₀ H ₁₈ O ₂. It is a colorless to light yellow transparent liquid at room temperature, slightly soluble in water, and easily soluble in organic solvents such as alcohols. It naturally exists in fruits such as peaches, apricots, strawberries, and spice tobacco leaves. Due to its unique aroma characteristics and chemical stability, it is widely used in food, daily chemical, feed, pharmaceutical, and industrial fields.
It is an important synthetic flavoring in the food industry, approved as a safe edible flavoring by China's "Food Additive Usage Standard" (GB 2760) and international authoritative organizations such as FEMA in the United States and the European Council. Its core uses include:
Dairy and cream essence
In dairy products such as milk, yogurt, butter, etc., the rich aroma of natural cream can be simulated to enhance the sensory appeal of the product. For example, in ice cream formulas, adding 0.5-2.0mg/kg of propyl decanolactone can significantly enhance the layering of vanilla or caramel flavors.
Fruit essence
As a key component of peach, citrus, coconut and other fruit essence, it gives drinks, candy and baked goods (such as cakes and biscuits) a rich fruit flavor through its characteristic peach and coconut fragrance. FEMA recommends usage limits of 2.0mg/kg for soft drinks, 4.5mg/kg for cold drinks, 5.7mg/kg for candies, and 7.1mg/kg for baked goods.
Artificial butter flavoring agent
In alternatives such as plant-based cream and puff pastry, it can compensate for the lack of natural creamy aroma and make the product taste closer to animal cream. Experiments have shown that the addition of 0.3% propylene decyl lactone can increase the sensory score of margarine by 40%.
Its application in the field of daily chemicals covers multiple market segments, such as perfume, cosmetics and detergents, and its dosage is usually controlled within 10% (IFRA has no restrictions):
Preparation of floral essence
In orange flower, lilac, acacia, jasmine, violet and other floral essence, as a fixative, it can prolong the aroma retention time and enhance the sense of nature. For example, the addition of 5% propyl caprolactone to violet essence can increase the fragrance persistence by 30%.
Fruit flavored daily chemical products
In personal care products such as shampoo, shower gel, and body lotion, when combined with ingredients such as citral and geraniol, a refreshing fruity aroma can be created. In the formula of a certain brand of peach flavored shower gel, the proportion of propyl decanolactone is 0.6%, which significantly improves the market acceptance of the product.
Soap and detergent
In the soap industry, by masking alkaline odors, soap is endowed with a soft fruity aroma. At the same time, adding 0.2-0.5% of propyl decanolactone to laundry detergent and fabric softener can enhance the olfactory experience of the product.
Feed flavoring agent: an enhancer that increases animal feed intake
As a feed flavoring agent, propylene glycol lactone can stimulate animal olfactory nerves, improve feed palatability, and promote growth performance:
Pig feed
Adding 10-30mg/kg of propyl decanolactone to piglet feed can increase feed intake by 15-20% and daily weight gain by 8-12%. Its mechanism of action is to simulate the sweet aroma of breast milk and alleviate weaning stress.
Ruminant animal feed
Adding propylene decanolactone to cow concentrate supplements can increase dry matter intake by 5-8% and improve milk fat percentage. Experimental data shows that adding 20mg/kg of caprylic acid can increase milk production in cows by 1.2kg/day.
Pet food
In cat food and dog food, when combined with yeast extract, it can create meat or fish flavors. A certain pet food brand increased its repeat purchase rate by 25% by adding 0.05% propylene glycol lactone.
Pharmaceutical industry: applications as pharmaceutical intermediates or excipients
Although its application in the pharmaceutical field is still in its infancy, hydroxydecanoic has demonstrated potential value:
Drug intermediates
As a key raw material for synthesizing anticancer drugs and antibacterial agents, it can participate in hydroxylation reactions to construct molecular structures with biological activity. For example, in the synthesis of paclitaxel side chains, the use of propyl decyl lactone as a nitroso introducing agent can increase the purity of the product to 99%.
Pharmaceutical excipients
In sustained-release formulations, it can be used as a coating material to control the drug release rate. Its low toxicity and biocompatibility comply with USP (United States Pharmacopeia) standards and are suitable for oral capsules and tablets.
Essence Therapy
In aromatherapy, its peach fragrance can alleviate anxiety. A clinical study showed that inhaling essential oil containing 0.5% propargyrolactone can reduce stress hormone (cortisol) levels in subjects by 22%.
Industrial field: multifunctional solvents and additives
The application in the industrial field is mainly based on its solvent properties and chemical stability:
Coatings and inks
As an environmentally friendly solvent, it can replace some volatile organic compounds (VOCs) and reduce the odor of coatings. Adding 1-3% of propyl decyl lactone to UV cured coatings can improve leveling and reduce pinhole defects.
Adhesive
As a plasticizer in hot melt adhesive and pressure-sensitive adhesive, it can improve the flexibility and adhesive strength of the gel. Experiments have shown that the addition of 2% propyl decyl lactone can increase the peel strength of adhesives by 18%.
Lithium battery electrolyte
As an additive, propyl decyl lactone can inhibit electrolyte decomposition and prolong battery cycle life. A study shows that adding 0.5% of propyl decanolactone can increase the capacity retention rate of lithium-ion batteries to 92% after 500 cycles.
method 1: Artificial synthesis
Use n-heptanol to react with acrylic acid or methyl acrylate in the presence of free radical initiator to prepare propyl decanolactone. This is the synthesis route of propyl decanolactone that can form large-scale production at present.
Using n-heptanol and acrylic acid as starting materials, di tert butyl peroxide as initiator, and adding reaction solvent, the crude product of c-decyl lactone was synthesized by free radical addition in a "one pot" way, and then the reaction solvent was recovered by distillation, and then the c-decyl lactone was prepared by rectification and purification.
During this synthesis process, the by-product could not be separated from the reaction system in time, resulting in a decrease in the reaction yield and an extension of the reaction time, Moreover, the product contains oil odor of low boiling point impurities, high boiling point impurities and poor oil consumption odor of isomers, which affect the aroma quality of the final product of c-decanolactone.
method 2: Biocatalysis method
GDL enzyme has catalytic activity in non-aqueous phase and is widely used in organic synthesis. Lipase is the most widely used one. It is cheap, does not need coenzyme, and has strong substrate adaptability.
Lipase can catalyze not only the hydrolysis of lipids, but also esterification and transesterification in organic phase, including the formation of lactones from hydroxyl fatty acids.
However, it is very difficult to cyclize these hydroxyl acids by conventional methods, and the yield is very low. It is much easier to complete the cyclization process by enzymatic method in organic media, which undoubtedly provides a good way for the large-scale market of these aromatic lactones.
Sometimes, if conditions permit, other biotechnological enzyme catalysis methods can also be used. It may also become one of the important means to solve the problem of marketization of lactone bioactive substances in the near future.
I. Optical and Surface-Active Properties
Natural and conventionally synthesized hydroxydecanoic mostly exists as racemates with no optical activity. Monomers substituted at chiral positions are optically active and can be resolved into levorotatory and dextrorotatory isomers. This compound features an amphipathic structure: the long hydrocarbon chain acts as the hydrophobic end, while the carboxyl and hydroxyl groups serve as the hydrophilic ends. It exhibits surface activity and can reduce the surface tension of solutions, making it an excellent intermediate for nonionic surfactants with favorable emulsifying and dispersing capacities.
II. Crystallization and Rheological Properties
The pure product forms regular crystals and tends to precipitate as needle-like or flaky crystals during cooling. It shows good fluidity in the molten state, and its melt viscosity decreases gradually with rising temperature, followed by rapid solidification upon cooling. The crystals are non-hygroscopic and hardly agglomerate at room temperature. The powder maintains stable flowability, facilitating material conveying and batching processes.
III. Compatibility and Reaction Compatibility
It is miscible and compatible with most alcohols, carboxylic acids and esters, and remains stable in weakly acidic and weakly alkaline systems. Long-term blending with strong oxidants, concentrated strong acids or concentrated strong alkalis is not recommended, as it may trigger oxidative decomposition and dehydrative cyclization. It can undergo amidation with amines and step-growth polymerization with polyols, serving as a high-quality monomer for synthesizing long-chain functional polyesters and polyamides.
IV. Biological and Toxicological Properties
It possesses good biocompatibility and low toxicity, with slight skin irritation. The compound can be gradually biodegraded in the natural environment and is not classified as a persistent pollutant. Microorganisms can decompose and metabolize its carbon chain, so it is suitable for applications in daily chemicals and biomaterials. High concentrations may exert mild adverse effects on aquatic organisms, hence production wastewater shall be treated conventionally before discharge.
In 1921, German scientist D.J. Lange first detected decanolactone substances in the secretions from the mandibular glands of worker bees.
In 1940, Townsend and Lucas successfully isolated such components from bees and preliminarily confirmed their properties as fatty acids.
In 1957, German scholars Adolf Butenandt and Heinz Rembold precisely separated 10-decanolactone from royal jelly and identified its chemical structure using infrared spectroscopy and other analytical methods, laying a foundation for scientific research on this compound.
During the same period, 3-decanolactone, also known as Myrmicacin, was discovered in South American leafcutter ants, proving that decanolactone is widely present in insects and natural products.
Subsequent studies gradually clarified the distribution and biological functions of isomers with hydroxyl groups at different substitution positions.
FAQ
Is hydroxystearic acid good for skin?
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Overall, Hydroxystearic Acid is quite useful in improving skin health by leaving it clean, nourished, supple, and soft.
Is hydroxystearic acid good for lips?
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It is created from hydroxystearic acid, a modified fatty acid derived from castor oil, and appears as a soft, pliable, wax-like solid. In our lip care formulas, it plays an essential role in helping us create smooth, creamy, high-performance vegan lip balm without using beeswax or any animal-derived ingredients.
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