Limonene structural formula. Limonene - what it is, what it contains, where it is used
There are many cosmetics, household chemicals, insect repellents with a citrus scent. Have you ever wondered why this is so? What is so remarkable about this aroma of media of a huge number of other possible ones? The thing is that such a smell is produced by the d limonene extract, which manufacturers add to the composition of products. Let's figure out why this is done. And also consider what this substance is, where it comes from and what its properties are.
D limonene is a clear liquid with a pronounced lemon scent. It is one of two limonene isomers. The second L-limonene has a pine needles aroma. Man has found application in both one and the other form. But since we're talking about citrus flavor, let's focus on a compound called limonene d limonene.
The highest concentration of d limonene is found in the essential oils of lemons, oranges, grapefruits and other citrus fruits. A small percentage of this substance is found in pine resin. People have learned to use d limonene in cosmetology and pharmaceuticals. In the first case, it plays the role of a perfume. In the second, it is used as a remedy.
Where do you get d limonene?
The question of where to get the lemon-scented concentrate is solved in two ways - synthetic and natural. Both options are used in industry. If you want to get your limonene at home, you can simply process the citrus fruits. For example, lemon pulp will contain about 90% d limonene. By the way, citrus juice is very healthy. It should be borne in mind that by drinking freshly squeezed juice without pulp, you lose a lot.
The concentrate of interest is available to buy. Of course, if you wonder where to find it. If you are not attracted by the prospect of looking for points of sale in the city, enter a query on the Internet. The iHerb online store offers d limonene at a price of 400 rubles for 60 capsules.
D-limonene is an excellent antioxidant that can inhibit the development of “abnormal” cells in your body, support weakened immune systems and maintain liver health. This supplement should be taken one capsule with food two to three times daily.
Natural component in industrial products
Limonene is far from number one in the list of ingredients for a cosmetic or household product. Its concentration is minimal, about 0.01%. Where can you find the component?
- Household detergents and cleaners, laundry detergents, etc.
- Hygiene products: shower gels, shampoos, conditioners, liquid and solid soaps, shaving foams.
- Skin care cosmetics. Creams for face, body, sun protection, lotions, tonics.
- Decorative cosmetics: lip balms, lipsticks.
- Means that provide protection against insects. Plates, spirals, liquid from flies and mosquitoes. And also what is directly applied to the skin - ointments, sprays, emulsions.
A logical question arises, is it really all for the sake of a pleasant smell? Using any product that contains d limonene, we will get a certain effect. This is due to the properties of this substance.
Multifaceted properties of d limonene
D-limonene in foods works as follows:
- Aromatizes. Citrus freshness pleases the scent receptors. Many people like this smell. People are eager to buy products with lemon on the label;
- Degreases. The degreasing effect allows you to apply the substance in two directions. It is topical to use in the composition of dishwashing gel, liquid powder or window cleaner. And also to remove excess fat from the skin, the component is added to a cream, lotion, tonic and other cosmetic products. Such an ingredient is of great importance in shampoos for oily hair;
- Disinfects. Prevents the development of fungi and bacteria. The first assistant in the fight against mold. The presence of this substance in cosmetics allows you to extend the shelf life;
- Plays the role of a repellent. Helps not only scare away, but also has a deadly effect on insects. It is part of the means for protecting against mosquitoes, midges, ticks, moths, small bugs.
Besides the listed properties, d limonene is used for medicinal purposes. During the research it was found.
D-limonene is a substance found in high concentrations in lemons (hence the name) and many other citrus fruits. Has anti-cancer potential and is considered a fat burner for unclear reasons, despite very limited information on this claim. May be ingested by drinking lemon juice.
reference
D-limonene is a compound known as "lemon extract" that is found in high concentration in lemon juice. D-limonene, like its related "perillic acid", has anti-carcinogenic properties (the ability to fight cancer cells), and also have a beneficial effect on the liver. D-limonene in the form of a preparation, fresh juice or lemonade with pulp can inhibit the development of some types of tumors, as well as slow the accumulation of fatty mass in the liver that occurs as a result of diet. Although the concentration of D-limonene is extremely low in factory-bottled juices, it is much higher in freshly squeezed juices with pulp.
Useful information
Other names: Lemon extract, D-limonene
Notes:
Limonene is not a stimulant
Limonene is one of the components of citrus fruits, which is responsible, among other things, for the smell
Limonene levels are extremely high in the peel. In juices with pulp, it is much higher than in juices without it.
Limonen instruction
900-1000ml pulp lemonade contains approximately 500mg of D-limonene, which is considered the recommended dosage. However, even 1g of D-limonene taken daily will have noticeable benefits.
Origin and composition
Limonene springs
Limonene gets its name from lemon, the fruit with the highest concentration of this substance, and one of the first fruits in which limonene was found. Limonene is also found in:
Composition
Limonene is known as a monoterpene substance (which contains one isoprene) and as an acyclic terpene (has a cyclic structure of six carbons). Along with limonene, its compound, the metabolite "perilyl alcohol", has been well studied.
Pharmacology
Limonene is a colorless hydrocarbon compound that smells like orange. Despite the smell, its greatest concentration is found in the peel of lemon, from which the substance got its name. After entering the body, limonene is very quickly and almost completely absorbed in the gastrointestinal tract, and then it is divided between various tissues after it passes the stage of metabolism in the liver, where it is metabolized into caveolar or perillyl metabolites using CYP2C enzymes, between which there are interspecific differences. Within 48 hours, 52-83% of the 1.6g limonene dose is excreted from the body, and after the termination of the course of administration for 21 days, the drug does not accumulate in the body. The half-life of D-limonene in the human body is 12 to 24 hours. The main metabolites of limonene are perillic acid, dihydroperyllic acid and limonene-1,2-diol. These metabolites are glucuronidated by the liver and excreted in the urine.
Food Sources of Limonene
Serum limonene and metabolite levels can be increased with food intake. 900-1000ml lemonade (made from whole lemons) contains 447-596mg limonene. The half-life of perillic acid is shorter than that of D-limonene (within 0.82-1.84 hours), and the peak concentration of perilic acid in blood serum is from 2.08 to 13.98 µm. Common citrus juices common in Western countries (without the peel) contain about 100mg of limonene per liter of juice, while juices from the peel contain up to 1027 limonene per liter.
Effects of limonene on liver health
Rats suffering from diet-induced non-alcoholic fatty liver infiltration (caused by diet) were injected with D-limonene and it was noted that hepatic fatty acid accumulation was reversed, as were all the negative effects of liver failure.
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List of used literature:
Perez-Cacho PR, Rouseff RL. Fresh squeezed orange juice odor: a review. Crit Rev Food Sci Nutr. (2008)
Acharya A, et al. Chemopreventive properties of indole-3-carbinol, diindolylmethane and other constituents of cardamom against carcinogenesis. Recent Pat Food Nutr Agric. (2010)
Satomi Y, et al. Production of the monoterpene limonene and modulation of apoptosis-related proteins in embryonic-mouse NIH 3T3 fibroblast cells by introduction of the limonene synthase gene isolated from Japanese catnip (Schizonepeta tenuifolia). Biotechnol Appl Biochem. (2009)
Hyatt DC, et al. Structure of limonene synthase, a simple model for terpenoid cyclase catalysis. Proc Natl Acad Sci U S A. (2007)
L-limonene.
Structural formula
D-limonene.
Structural formula
Limonen- a colorless liquid with a lemon odor. It exists in two forms - the D-limonene isomer and the L-limonene isomer. Essential oils of citrus fruits such as lemon and orange can contain up to 90% D-limonene. Scots pine (Pinus silvestris) turpentine contains 5-6% D-limonene.
Application in cosmetics:
D-limonene has a strong citrus scent. L-limonene has a piney odor. Both are widely used in cosmetics as a fragrance. D-limonene is more popular and when limonene is mentioned it is the D-isomer that is generally referred to.
But aromatization isn't its only use. Limonene is used as a repellent - it not only effectively repels, but also kills many insects.
Limonene dissolves fats quite well, making them easier to mix. In this respect, it is an excellent alternative to toxic solvents such as alcohol or acetone.
Harm and benefit:
Limonene is produced chemically. It is synthesized from geranyl phosphate by cyclization of the intermediate carbocation. Such "chemosis" causes mistrust among consumers and accusations are thrown at limonene, one more terrible than the other - from allergenicity to carcinogenicity.
There is nothing to argue about allergenicity. Like any other flavoring, limonene can cause allergies. However, it must be borne in mind that allergy is an atypical reaction of the immune system to the most harmless substances. With the same success, an allergy can manifest itself on the fruits of a date or the wool of a Daurian hedgehog. Limonene has no particular allergenicity.
With regard to carcinogenicity, none of the studies carried out have established the slightest carcinogenic properties. On the contrary, there is evidence that D-limonene may help in the treatment of cancer (especially breast cancer) due to its ability to increase liver enzymes. The first experiments on rats are already encouraging, but research is still a long way off.
Output: limonene is an excellent example of how scientific and technological progress has brought chemistry and cosmetology to a new level, creating the most useful and safe products in a synthetic way.
Scientific and technological progress has led, on the one hand, to a significant improvement in the comfort of human life, and on the other hand, has had a negative impact on the environment and human health. As a result, a scientific direction called "green chemistry" arose, designed to make chemical industries and their products as safe as possible for human health and the environment.
Nature has truly endless resources of substances and compounds that can influence human life. Some of them become real sources of new ideas in the production of household and industrial chemicals, perfumery and cosmetics, food and pharmaceutical industries.
One such substance is d-limonene. It is a widespread terpene hydrocarbon and is the main component of orange peel oil (up to 80-90%). It is also found in almost all citrus fruits and many other essential oils: lemon, mandarin, lime, grapefruit, bergamot, neroli, petitgrain, elemi, cumin, dill, fennel, parsley, erigeron, orthodon. d-Limonene is obtained by fractional distillation of terpene mixtures formed during their extraction from citrus essential oils. At present, the annual production of d-limonene in the world reaches 70 thousand tons and continues to grow rapidly.
INCI: Limonene
CAS No: 5989-27-5
EINECS-No .: 5989-27-5
FEMA: 2633
Gross formula: С10H16
Molecular mass: 136.24
Evaporating temperature: 175.5 ° C
Density: 0.84 g / cm3 (at 20 ° C,)
Appearance: Transparent, colorless liquid
with a pleasant citrus scent.
Let's dissolve in alcohol, fatty and mineral oils, kerosene, acetone, dimethyl sulfoxide, diethyl ether, insoluble in water, propylene glycol, glycerin.
D-Limonene is widely used in production due to its various chemical properties and pleasant orange aroma:
d-Limonene is used in a wide variety of industries due to its varied properties. It is a part of many perfumery products, shampoos, detergents and cleaners, solvents - in everyday life and at work. It has perhaps no competitor in removing gum or sticker marks from metal, wood or plastic surfaces. d-Limonene is used for degreasing metal before industrial painting, in household chemicals, for example, for cleaning wooden coatings, for removing grease from the skin of the hands. It is an excellent environmentally friendly alternative to toxic and hazardous solvents and petroleum products such as acetone, benzene, butyl cellosolve, toluene, trichlorethylene, xylene, methyl ethyl ketone, white spirit, etc.
D-limonene-based cleaners have a natural citrus scent, leave behind a fresh scent and, importantly, are biodegradable. In addition to the field of household chemicals, it is widely used in perfumery and cosmetics. The current trend of using environmentally friendly products contributes to the growing popularity of natural citrus scents. It has long been recognized that the scent of citrus fruits is very beneficial for creating a good mood and in general has a calming effect on the nervous system.
The use of d-limonene as an insecticide is interesting. It came about when Ohio University entomology professor Fred Hink discovered flea-lethal poisons in orange peels. "These are possibly the only natural insecticides available that kill adult insects, their larvae and eggs," he says.
Russian scientists have protected a patent on the use of an additive in the alcoholic beverage industry to improve the quality of alcoholic beverages in the form of a complex of essential oils, which includes d-limonene. According to the authors, the use of such an additive makes it possible to obtain vodka with an increased stimulating and tonic effect, without an unpleasant "fume" smell after consumption, reduces the severity of the hangover syndrome and, in general, weakens the harmful effect of alcohol on the body.
With the help of d-limonene, domestic pharmacologists have developed a method for reducing the hepatotoxicity of drugs such as paracetamol, caffeine, phenacitin, which are metabolized in the human liver to active metabolites, i.e. substances that are easily processed by the liver. As a result of medical and biochemical studies, data have been obtained on the hormone-regulating effect of d-limonene, which contributes to the detoxification of estrogens by inducing the synthesis of the corresponding enzymes in the liver. This suggests that this substance may be effective in the prevention and treatment of breast and other tissue cancers.
The tables below highlight several popular applications for d-limonene. The information on its recommended dosages can be used as a guide for developing effective mixtures.
Carcinogenicity and genotoxicity studies of d-limonene have shown that it is located in the “zone of stable safety”. Its effect is approximately equal to that of caffeic acid from daily coffee consumption. The International Agency for Research on Cancer (IARC) classifies d-limonene as class-3, that is, it does not classify it as a carcinogen.
Due to its unique properties, d-limonene is widely used in various industries. Through the efforts of chemists, biologists, physicians and scientists of other specialties, the range of application of this amazing natural substance will undoubtedly be expanded and our world around us will become more pleasant, harmonious and safe.
ATTENTION We do not ship this product to cities with air delivery (8-9 tariff zones, for example, to the cities of Vladivostok, Petropavlovsk-Kamchatsky, Yuzhno-Sakhalinsk, Elizovo, Norilsk, Magadan, Yakutsk).
For security reasons, we send this product only as a separate parcel at the rates of delivery services
d-Limonene (d-Limonene) is a colorless liquid with a pronounced citrus odor.
This is a technical type of oil. Does not dissolve in water. It dissolves fats well, in this respect it acts as a wonderful alternative to toxic solvents such as alcohol or acetone.
Perfectly dissolves HIPS, PS polystyrene.
Does not dissolve ABS, PLA, PC, POM
Limonene is used in various fields, especially in the production of cosmetics, cleaning products and perfumery.
In undiluted form it is mainly used as an alternative to products: acetone, toluene, glycol ether, fluorine and chlorine-containing organic solvents, mineral solvent, methyl ethyl ketone. Unlike the aforementioned solvents, it does not contain butyl, alkali, solvents, phosphates.
It is non-toxic and biodegradable. However, be careful, limonene in concentrated form can be a powerful irritant to the skin and mucous membranes.
After processing the part with limonene, it must be thoroughly rinsed. It is recommended to use gloves when working.
Limonene vapors, despite the pleasant orange scent, can cause irritation of the eyes, respiratory tract and headache symptoms. It is recommended to carry out work in a ventilated area.
DO NOT HEAT the limonene in an attempt to speed up the process - this greatly increases the hazard of exposure to vapors and may discolor the model, and the heated solution can make bright colors pale when interacting with the dye.
Limonene is reusable.
Considered a hazardous waste category due to its low flash point (vapor ignition). To dispose of limonene, just make sure you place it wisely in a container that won't dissolve. For example: metal, glass, ceramics, PE (polyethylene), PP (polypropylene).
