PRODUCTS

LIMONENE

CAS Number: 138-86-3
EC Number: 205-341-0
Chemical formula: C 10 H 16
Molecular mass: 136.23gmol- 1

Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene and is the main component of the oil in the fruit peels of citrus fruits.
D - isomer is a sweetener used in food production, which occurs in nature mostly as an orange scent.
Limonene is also used as a precursor to carvone in chemical synthesis and as a renewable-based solvent in cleaning products.

Limonene is a chemical found in the peels of citrus fruits and in other plants.
Limonene is used to make medicine.
Limonene is used for obesity, cancer, and bronchitis, but there is no good scientific evidence to support these uses.

In foods, beverages, and chewing gum, limonene is used as a flavoring.
In pharmaceuticals, limonene is added to help medicinal ointments and creams penetrate the skin.
In manufacturing, limonene is used as a fragrance, cleaner (solvent), and as an ingredient in household cleaning products, cosmetics, and personal hygiene products.

Less common L - The isomer is found in peppermint oils and has a pine , turpentine -like odor.
Limonene is one of the main volatile monoterpenes found in the resin of conifers , especially Pinaceae , and orange oil.
Limonene gets its name from the French lemon ("lime").

Limonene is a chiral molecule, and biological sources produce an enantiomer: main industrial source is citrus ( R ) - enantiomer DContains -limonene((+)- limonene).
Limonene is obtained commercially from citrus fruits by two main methods: centrifugal separation or steam distillation.

Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the oil of citrus fruit peels.
The d-isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring agent in food manufacturing.

Limonene is also used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products.
The less common l-isomer has a piny, turpentine-like odor, and is found in the edible parts of such plants as caraway, dill, and bergamot orange plants.

Limonene takes its name from Italian limone ("lemon").
Limonene is a chiral molecule, and biological sources produce one enantiomer: the principal industrial source, citrus fruit, contains d-limonene ((+)-limonene), which is the (R)-enantiomer.

Racemic limonene is known as dipentene.
Limonene is obtained commercially from citrus fruits through two primary methods: centrifugal separation or steam distillation.

Limonene is a mild skin and eye irritant.
Ingestion of 20 g of d-limonene caused diarrhea and a temporary increase in protein in the urine (proteinurea) in five male volunteers.

These data, in addition to the low acute toxicity in animal tests, suggest that d-limonene is not very toxic by ingestion.
Air levels of d-limonene may irritate the eyes and airways of some people, especially when the levels build up indoors (see above for discussion about gas phase reactions between ozone and terpenes which can be a significant source of secondary organic aerosols).
Limonene has been used successfully for the postoperative dissolution of retained cholesterol gallstones.

limonene, a colourless liquid abundant in the essential oils of pine and citrus trees and used as a lemonlike odorant in industrial and household products and as a chemical intermediate.

Limonene exists in two isomeric forms (compounds with the same molecular formula—in this case, C10H16—but with different structures), namely l-limonene, the isomer that rotates the plane of polarized light counterclockwise, and d-limonene, the isomer that causes rotation in the opposite direction.
In the extraction of citrus juices d-limonene is obtained as a by-product, and Limonene also occurs in caraway oil; l-limonene is present in pine needles and cones; dl-limonene, or dipentene, the mixture of equal amounts of the l- and d-isomers, is a component of turpentine.
Dipentene may be sulfurized to produce additives that improve the performance of lubricating oils under heavy loads; d-limonene is commercially converted to l-carvone, which has a caraway-seed flavour.

Limonene: a versatile chemical of the bioeconomy:
Limonene is a renewable chemical with numerous and growing applications.
Limonene traditional uses such as flavor, fragrance and green solvent are rapidly expanding to include Limonene utilization as a platform chemical, extraction solvent for natural products and an active agent for functionalized products.
We anticipate that the expansion in uses for limonene will translate into increasing production and use of this relevant natural product, especially for advanced applications.

Limonene is a chemical found in the peels of citrus fruits and in other plants.
Limonene is used to make medicine.
Limonene is used to promote weight loss, prevent cancer, treat cancer, and treat bronchitis.

Chemical constituent of many natural fragrant ingredients, notably citrus oils such as lemon (d-limonene) and pine trees or species of the mint family (l-limonene).
Topically, limonene can cause sensitivity and is best avoided.

Also, because of Limonene penetration-enhancing effects on skin, Limonene particularly important to avoid products that contain limonene plus other skin sensitizers like denatured alcohol.
Like most volatile fragrance components, limonene also has strong antioxidant benefits and has also been shown to calm skin; however, when exposed to air these highly volatile antioxidant compounds oxidize and become capable of sensitizing skin.

Limonene comes from citrus fruits and is used in many cleaning products:
So you’ve heard about limonene being used in cleaning products, and you want to know what this stuff is and whether Limonene safe.

Limonene is a naturally occurring compound found mainly in the skin of certain plants and fruits, including lemons and oranges.
Limonene is used in cleaning products for two reasons: Limonene has a pleasant, lemon-orange smell, and Limonene acts as a solvent to help clean.
Limonene is from a large family of natural substances called terpenes, and Limonene has no colour and Limonene toxicity is low.

However, you might have heard about Limonene recently because, when Limonene reacts with ozone in the air, Limonene undergoes change which releases tiny amounts of other compounds, including formaldehyde.
Peeling an orange releases orange oil into the air.
As orange oil is 90% limonene you can get more exposure by peeling an orange than from using cleaning products.

Belongs to the class of organic compounds known as menthane monoterpenoids.
These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone.

P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively.
The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Limonene is a hydrocarbon, classed as a terpene.
Limonene is a colourless liquid at room temperatures with an extremely strong smell of oranges.

Limonene takes its name from the lemon, as the rind of the lemon, like other citrus fruits, contains considerable amounts of this chemical compound, which is responsible for much of their smell.
Limonene is a chiral molecule, and as is common with such forms, biological sources produce one specific enantiomer: the principal industrial source, citrus fruit, contains D-limonene ((+)-limonene), which is the (R)-enantiomer (CAS number 5989-27-5, EINECS number 227-813-5).
Racemic limonene is known as dipentene

Limonene is a scent ingredient and solvent naturally ocurring in the rind of citrus fruit.
Upon storage and exposure to sunlight and air, limonene degrades to various oxidation products which act as skin and respiratory irritants and sensitizers.

Limonene is one of the most common compounds found in the essential oils of aromatic plants.
The occurrence of this monoterpene hydrocarbon in various plant genera could be attributed to Limonene precursory role in the biosynthesis of other monoterpenes and Limonene defensive role against herbivores.

Due to the medicinal potential and application in the flavor and fragrance industries, limonene has been extensively investigated.
In this paper the biosynthetic, ecological and pharmacological importance of limonene is presented in an attempt to coherently summarize some of the most salient aspects from various studies in a form of a concise review.

Biotechnological production of limonene in microorganisms
This mini review describes novel, biotechnology-based, ways of producing the monoterpene limonene.

Limonene is applied in relatively highly priced products, such as fragrances, and also has applications with lower value but large production volume, such as biomaterials.
Limonene is currently produced as a side product from the citrus juice industry, but the availability and quality are fluctuating and may be insufficient for novel bulk applications.

Therefore, complementary microbial production of limonene would be interesting.
Since limonene can be derivatized to high-value compounds, microbial platforms also have a great potential beyond just producing limonene.

In this review, we discuss the ins and outs of microbial limonene production in comparison with plant-based and chemical production.
Achievements and specific challenges for microbial production of limonene are discussed, especially in the light of bulk applications such as biomaterials.

Limonene is a well-known cyclic monoterpene.
Limonene is an olefin hydrocarbon (C10H16), which can occur in two optical forms.

Limonene is one of the most important and widespread terpenes in the flavor and fragrance industry.
Limonene (in both optical forms) has been found in more than 300 plant essential oils (DNP 2015) from very diverse species including orange, lemon, mint, and fir.

Limonenes biosynthesis has been well described in the plant kingdom.
Limonene has been detected naturally in trace amounts in the headspace of microbes

However, to our knowledge, no corresponding biosynthetic mechanism has been identified.
By transformation with plant limonene synthases, microorganisms such as yeast and bacteria have been engineered to produce limonene.

In this work, biotechnological production of limonene for application as commodity chemical is reviewed.
Others have reviewed general aspects of production of terpenes in microbes and plants.

Recently, Lange (2015) reviewed the biosynthesis and biotechnology of limonene for flavor and fragrance applications.
New applications of limonene for fuel and biomaterials ask for large and stable production volumes.

Metabolic engineering strategies, like overexpressing precursor pathway enzymes, have been applied for the purpose of increasing limonene titers, which are at the moment still far from the maximal theoretical yield.
Crucial in such strategies is the overproduction of geranyl diphosphate (GPP), the direct precursor of limonene.

New opportunities to increase yield will be discussed, including novel strategies for capturing the product from the microbial cultures and possibilities for relieving limonene toxicity.
When successful, these optimization strategies could result in a role for limonene-based products in the bio-based economy

Limonene, a naturally occurring hydrocarbon, is a cyclic monoterpene with the molecular formula C10H16.
Limonene is commonly found in the rinds of citrus fruits such as grapefruit, lemon, lime and, in particular, oranges.

Indeed, limonene constitutes 98% (by weight) of the essential oil obtained from orange peel.
Limonene is also present in the seeds of caraway and dill.
The IUPAC name for limonene is 1-methyl-4-prop-1-en-2-ylcyclohexene.

Summary of Limonene:
Limonene is a useful compound and pleasant to smell.
Limonene is a renewable resource and is considered to have very low toxicity, and is even being studied as a possible dietary supplement to prevent cancer.
Although Limonene can react with ozone in the air to produce tiny amounts of formaldehyde for a short period of time, those amounts are considered by the WHO to present negligible risk.

Isomerism of Limonene:
Carbon number four (labelled with an asterisk) of the cyclohexene ring is chiral.
Limonene therefore has two optical isomers.

The optical isomers are non-superimposable mirror images of each other and their three-dimensional structures can be compared here.
Chiral centres are labelled as R or S using IUPAC nomenclature.

Thus the two isomers of limonene can be named 4(R)-limonene and 4(S)-limonene.
Alternative prefixes to label optical isomers include d and l and more commonly the symbols + and - are used.

The two enantiomers have identical chemical properties but different odours.
Limonene is the isomer that is found in oranges.

And unsurprisingly Limonene smells of oranges.
The smell of (-)-limonene is similar to turpentine, although some people suggest Limonene has a lemon like aroma.

An usual compound of Limonene:
Most naturally occurring chiral compounds are found as a single optical isomer only.
However, limonene is an exception and both enantiomers are produced in nature.
Limonene is an important precursor in the biosynthesis of (-)-menthol the major component of mint and the molecule responsible for the herb's refreshing taste.

Details of the reaction pathway can be found in Simon Cotton’s menthol page.
As mentioned previously (+)-limonene is the isomer found in orange peel.

Limonene is thought that its high abundance in this part of the fruit is connected with the fact that Limonene is an insecticide.
As well as Limonene smell limonene also contributes to the flavour of the fruit and as such has been used as a food additive for many years.

Aside from the food industry limonene has a variety of uses.
Limonene is an ingredient of Orange Guard, a home friendly pest control product that exploits the insecticide properties of limonene.

At room temperature limonene is a liquid and has proven to be a good solvent.
The non-polar nature of limonene means that Limonene has an affinity for petroleum based greases and Limonene has been used as an industrial cleaner for more than thirty years.

One advantage is that limonene is not toxic and is replacing the use of solvents like methyl ethyl ketone (MEK), xylene (dimethylbenzene) and chlorofluorocarbons (CFCs), the use of which has been banned.
Limonene also has the advantage of being biodegradable and can rapidly break down into carbon dioxide and water.

Another benefit of limonene is that Limonene is obtained from a renewable resource.
A by-product of the citrus juicing process is the oil found in the peel of the fruit.
Limonene can be distilled from this oil for both technical and food based uses.

The popularity of limonene based cleaners is growing and Limonene can now be found in many domestic products such as the Mr Muscle Orange Action range of cleaners.
An Australian company, Orange Power, seek to make all of their products from natural, and locally produced, sources.
Their aim is to reduce reliance on fossil fuels and dangerous chemicals which have a cumulative harmful effect on both the population and the environment.

Alternative Parents of Limonene:
Monocyclic monoterpenoids
Branched unsaturated hydrocarbons
Cycloalkenes
Unsaturated aliphatic hydrocarbons

Substituents of Limonene:
P-menthane monoterpenoid
Monocyclic monoterpenoid
Branched unsaturated hydrocarbon
Cycloalkene
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Biochem/physiol Actions of Limonene:
Limonene is a cyclie terpene from Chinese medicinal herb essential oils used in the synthesis of carvone.
Limonene may be used as a shrinking agent to dissolve polystyrene.
Limonene may be used in various insecticidal and insect repellant applications.

Limonene may block cancer-forming chemicals and kill cancer cells in the laboratory.
But more research is needed to know if this occurs in humans.

Organs and systems of Limonene:

Respiratory:
Limonene, and possibly linoleic and oleic acids, can have irritative and bronchconstrictive airway effects and can cause reduced vital capacity.
Patients with significant inhalational exposure should be removed from the environment and undergo appropriate decontamination.
Inhaled β2-adrenoceptor agonists can be used for bronchoconstriction.

Urinary tract:
Limonene ingested in sufficient quantity can cause proteinuria.
However, nephropathy and renal tumors are not expected in humans.

Skin:
Contact dermatitis has been attributed to limonene, and a purpuric rash has been attributed to topical exposure to d-limonene.
Autoxidation of d-limonene readily occurs, yielding a variety of oxygenated monocyclic terpenes that are strong contact allergens.

The prevalence of contact allergy after exposure to d-limonene among patients with dermatitis has been studied.
The proportion of positive patch tests to oxidized d-limonene was comparable to that seen with several allergens in the standard series, and patients who reacted to d-limonene often reacted to fragrance mix, balsam of Peru, and colophony.
In a study of patch tests with 3% oxidized R-(+)-limonene in 2273 patients at four dermatology clinics in Europe, there were positive reactions 0.3%, 3.8%, 3.9%, and 6.5%, a total of 63 patients, of whom 57% did not react to fragrance mix or balsam of Peru.

Metabolism/Metabolites of Limonene:
After oral administration, major metabolite in urine was perillic acid 8,9-diol in rats and rabbits, perillyl-beta-d-glucopyranosiduronic acid in hamsters, p-menth-1-ene-8,9-diol in dogs, and 8-hydroxy-p-menth-1-en-9-yl-beta-d-glucopyranosiduronic acid in guinea pigs and man.

Limonene given orally to humans yields the following major plasma metabolites: perillic acid, limonene-1,2-diol, limonene-8,9-diol, and dihydroperillic acid, probably derived from perillic acid.
Limonene (unchanged) and perillic acid artifacts (methyl ester) were also detected as minor plasma metabolites.

Peak plasma levels for all metabolites were achieved 4-6 hours after administration, with the exception of limonene-8,9-diol which reached Limonene peak level one hour after administration.
Phase II glucuronic acid conjugates have been identified in the urine of human volunteers for all major and minor metabolites.
They include the glucuronic acid conjugates of perillic acid, dihydroperillic acid, limonene-8,9-diol, limonene-10- ol, limonene-6-ol, and limonene-7-ol (perillyl alcohol).

Mechanism of Action of Limonene:
The anticarcinogenic effects of monocyclic monoterpenes such as limonene were demonstrated when given during the initiation phase of 7,12-dimethylbenz[a]anthracene induced mammary cancer in Wistar-Furth rats.
The possible mechanisms for this chemoprevention activity including limonene's effects on 7,12-dimethylbenz(a)anthracene-DNA adduct formation and hepatic metabolism of 7,12-dimethylbenz[a]anthracene were investigated.

Twenty four hours after carcinogen administration, there were approx 50% decreases in 7,12-dimethylbenz(a)anthracene-DNA adducts found in control animals formed in the liver, spleen, kidney and lung of limonene fed animals.
While circulating levels of 7,12-dimethylbenz(a)anthracene and/or Limonene metabolites were not different in control and limonene fed rats, there was a 2.3 fold increase in 7,12-dimethylbenz(a)anthracene and/or 7,12-dimethylbenz(a)anthracene derived metabolites in the urine of the limonene fed animals.

Limonene and sobrerol, a hydroxylated monocyclic monoterpenoid with increased chemoprevention activity, modulated cytochrome p450 and epoxide hydrolyase activity.
The 5% limonene diet increased total cytochrome p450 to the same extent as phenobarbital treatment, while 1% sobrerol (isoeffective in chemoprevention to 5% limonene) did not.
However, both 5% limonene and 1% sobrerol diets greatly increased the levels of microsomal epoxide hydrolyase protein and associated hydrating activities towards benzo[a]pyrene 4,5-oxide when compared to control and phenobarbital treatment.

These changes also modified the rate and regioselectivity of in vitro microsomal 7,12-dimethylbenz(a)anthracene metabolism when compared to phenobarbital treatment or control.
Identification of the specific isoforms of cytochrome p450 induced by these terpenoids was performed with antibodies to cytochrome p450 isozymes in Western blot analysis and inhibition studies of microsomal 7,12-dimethylbenz(a)anthracene metabolism.

Five percent limonene was more effective than 1% sobrerol at increasing the levels of members of the cytochrome p450 2B and 2C families but was equally effective at increasing epoxide hydrolyase.
Furthermore, both terpenoid diets caused increased formation of the proximate carcinogen, 7,12-dimethylbenz(a)anthracene 3,4-dihydrodiol.

Limonene is the oil extracted from the peels of oranges and other citrus fruits.
People have been extracting essential oils like limonene from citrus fruits for centuries.

Today, limonene is often used as a natural treatment for a variety of health issues and is a popular ingredient in household items.
However, not all of limonene’s benefits and uses are supported by science.
This article examines limonene’s uses, potential benefits, side effects, and dosage.

Limonene is a chemical found in the rind of citrus fruits, such as lemons, limes, and oranges.
Limonene is especially concentrated in orange peels, comprising around 97% of this rind’s essential oils.
Limonene’s often referred to as d-limonene, which is Limonene main chemical form.

Limonene belongs to a group of compounds known as terpenes, whose strong aromas protect plants by deterring predators.
Limonene is one of the most common terpenes found in nature and may offer several health benefits.
Limonene has been shown to possess anti-inflammatory, antioxidant, anti-stress, and possibly disease-preventing properties.

Linked to several health benefits of Limonene:
Limonene has been studied for its potential anti-inflammatory, antioxidant, anticancer, and heart-disease-fighting properties.
However, most research has been conducted in test tubes or on animals, making Limonene difficult to fully understand the role of limonene in human health and disease prevention.

Anti-inflammatory and antioxidant benefits
Limonene has been shown to reduce inflammation in some studies.
While short-term inflammation is your body’s natural response to stress and is beneficial, chronic inflammation can harm your body and is a major cause of illness.

Limonene’s important to prevent or reduce this type of inflammation as much as possible.
Limonene has been shown to reduce inflammatory markers that relate to osteoarthritis, a condition characterized by chronic inflammation.

A test-tube study in human cartilage cells noted that limonene reduced nitric oxide production.
Nitric oxide is a signaling molecule that plays a key role in inflammatory pathways.

In a study in rats with ulcerative colitis — another disease characterized by inflammation — treatment with limonene significantly decreased inflammation and colon damage, as well as common inflammatory markers.
Limonene has demonstrated antioxidant effects as well.
Antioxidants help reduce cell damage caused by unstable molecules called free radicals.

Free radical accumulation can lead to oxidative stress, which may trigger inflammation and disease.
One test-tube study revealed that limonene may inhibit free radicals in leukemia cells, suggesting a decrease in inflammation and cellular damage that would normally contribute to disease.
Although promising, these effects need to be confirmed by human studies.

May boost heart health of Limonene:
Heart disease remains the leading cause of death in the United States, accounting for nearly one in four deaths.
Limonene may lower your risk of heart disease by reducing certain risk factors, such as elevated cholesterol, blood sugar, and triglyceride levels.

In one study, mice given 0.27 grams of limonene per pound of body weight (0.6 grams/kg) showed reduced triglycerides, LDL (bad) cholesterol, fasting blood sugar, and fat accumulation in the liver, compared to a control group.
In another study, stroke-prone rats given 0.04 grams of limonene per pound of body weight (20 mg/kg) exhibited significant reductions in blood pressure compared to rats of similar health status that did not receive the supplement.
Keep in mind that human studies are needed before strong conclusions can be drawn.

Safety and research of Limonene:
Limonene and its oxidation products are skin irritants, and limonene-1,2-oxide (formed by aerial oxidation) is a known skin sensitizer.
Most reported cases of irritation have involved long-term industrial exposure to the pure compound, e.g. during degreasing or the preparation of paints.

However a study of patients presenting dermatitis showed that 3% were sensitized to limonene.
Limonene causes renal cancer in male rats, but not in female rats or in mice of either sex, due to binding of the metabolite limonene-1,2-oxide to α2u-globulin, a protein produced only by male rats.
There is no evidence for carcinogenicity or genotoxicity in humans. The IARC classifies d-limonene under Class 3: not classifiable as to Limonene carcinogenicity to humans.

Limonene applied to skin may cause irritation from contact dermatitis, but otherwise appears to be safe for human uses.
Limonene is flammable as a liquid or vapor and Limonene is toxic to aquatic life.

Other benefits of Limonene:
Aside from the benefits listed above, limonene may:
Reduce appetite.

The scent of limonene has been shown to significantly reduce appetite in blowflies.
However, this effect has not been studied in humans.

Decrease stress and anxiety.
Rodent studies suggest that limonene could be used in aromatherapy as an anti-stress and anti-anxiety agent.
Support healthy digestion.

Limonene may protect against stomach ulcers.
In a study in rats, citrus aurantium oil, which is 97% limonene, protected nearly all of the rodents against ulcers caused by medication use.

Potentially effective dosages:
Because few limonene studies exist in humans, Limonene difficult to provide a dosage recommendation.
Nonetheless, dosages of up to 2 grams daily have been safely used in studies.

Capsule supplements that can be purchased online contain dosages of 250–1,000 mg.
Limonene is also available in liquid form with typical dosages of 0.05 ml per serving.

However, supplements aren’t always necessary.
You can easily obtain this compound by eating citrus fruits and peels.

For example, fresh orange, lime, or lemon zest can be used to add limonene to baked goods, drinks, and other items.
What’s more, pulpy citrus juices, such as lemon or orange juice, boast limonene, too.

Common uses of limonene:
Limonene is a popular additive in foods, cosmetics, cleaning products, and natural insect repellants.
For example, Limonene is used in foods like sodas, desserts, and candies to provide a lemony flavor.
Limonene is extracted through hydrodistillation, a process in which fruit peels are soaked in water and heated until the volatile molecules are released via steam, condensed, and separated.

Due to Limonene strong aroma, limonene is utilized as a botanical insecticide.
Limonene an active ingredient in multiple pesticide products, such as eco-friendly insect repellents.

Other household products containing this compound include soaps, shampoos, lotions, perfumes, laundry detergents, and air fresheners.
Additionally, limonene is available in concentrated supplements in capsule and liquid form.

These are often marketed for their supposed health benefits.
This citrus compound is also used as an aromatic oil for Limonene calming and therapeutic properties.

Industrial of Limonene:
There have been some reported cases of skin sensitisation, but these have usually developed in those involved regularly with pure limonene in an industrial setting for paint preparation or degreasing machinery.

Use and Manufacturing of Limonene:
Limonene is a naturally occurring chemical which is used in many food products, soaps and perfumes for Limonene lemon-like flavor and odor.
Limonene also is a registered active ingredient in 15 pesticide products used as insecticides, insect repellents, and dog and cat repellents.

Pesticide products containing limonene are used for flea and tick control on pets, as an insecticide spray, an outdoor dog and cat repellent, a fly repellent tablecloth, a mosquito larvicide, and an insect repellent for use on humans.
Formulations include ready-to-use solutions, emulsifiable concentrates, granulars and impregnated material.

Limonene is applied by hand as needed, both indoors and outdoors.
Use practice limitations include a label prohibition against use on weanling kittens and a caution against use of undiluted product.

As the main odour constituent of citrus (plant family Rutaceae), d-limonene is used in food manufacturing and some medicines, e.g., bitter alkaloids, as a flavoring, and added to cleaning products such as hand cleansers to give a lemon-orange fragrance.
Limonene is increasingly being used as a solvent for cleaning purposes, such as the removal of oil from machine parts, as Limonene is produced from a renewable source (citrus oil, as a byproduct of orange juice manufacture.)

Limonene works as paint stripper when applied to painted wood.
The (R)-enantiomer is also used as botanical insecticide.

The (S)-enantiomer, also known as l-limonene (CAS number 5989-54-8, EINECS number 227-815-6), is used as a fragrance in some cleaning products.
In contrast to the citrus (orange-lemon) scent (see above) of d-limonene, the enantiomer l-limonene has a piney, turpentine-like odor.

Limonene is very common in cosmetic products.
Due to Limonene combustible nature, d-limonene has also seen limited use as an experimental biofuel.

Found in a vast array of cleaning products, cosmetics, food flavourings and even aromatherapy, Limonene comes in two forms: d-limonene and l-limonene.
These are like “different handed” versions of the same molecule, with only subtle differences.
The d-limonene form is used in food-grade products, as well as cleaning and beauty products, and is prized mainly for Limonene smell.

Limonene is also used in hospital laboratories when cleaning tissue samples for analysis.
The l-limonene version has a more pine-like scent but is used mainly as a solvent in industrial cleaning products.

Apart from these well-known uses, researchers now also believe limonene could be used as a dietary supplement to prevent cancer.
Limonene even turns up in some 3D printing processes.

Limonene has been produced since 1995 and has been used as a flavor and fragrance additive in cleaning and cosmetic products, food, beverages, and pharmaceuticals.
Limonene is also increasingly used as a solvent.

Limonene is used in the manufacturing of resins, as a wetting and dispersing agent, and in insect control.
Limonene is present in most of the essential oils commonly used in Australia, particularly citrus oils.
In the workplace, products such as hand cleaners, industrial cleaners, degreasers, and strippers may also contain limonene as a solvent.

Industrial limonene is produced by alkaline extraction of citrus residues and steam distillation.
This distillate contains more than 90% d-limonene.

Limonene is used as a substitute for chlorinated hydrocarbons, chlorofluorocarbons, and other solvents.
Limonene is used in degreasing metals (30% limonene) prior to industrial painting, for cleaning in the electronics industry (50–100% limonene), for cleaning in the printing industry (30–100% limonene), and in paint as a solvent.

Limonene is also used as a solvent in histology laboratories and as a flavor and fragrance additive in food, household cleaning products, and perfumes.
Limonene has been used as a gallstone solubilizer in humans.

Limonene has also been used as a sorption promoter or accelerant for improving transdermal drug delivery and works by penetrating the skin to reversibly decrease barrier resistance.
Commercial mixtures of d-limonene molecules may contain other forms of limonene (l-limonene and d,l-limonene), which are called terpenes, and related compounds such as p-cumene.

Some studies have indicated that limonene has anticancer effects.
Limonene increase the levels of liver enzymes involved in detoxifying carcinogens.

The glutathione-S-transferase (GST) system eliminates carcinogens.
The GST system can be promoted by limonene in the liver and small bowel leading to a decrease in the damaging effects of carcinogens.
Animal studies demonstrated that dietary limonene reduced mammary tumor growth.

Limonene is common as a dietary supplement and as a fragrance ingredient for cosmetics products.
As the main fragrance of citrus peels, d-limonene is used in food manufacturing and some medicines, such as a flavoring to mask the bitter taste of alkaloids, and as a fragrance in perfumery, aftershave lotions, bath products, and other personal care products.

Limonene is also used as a botanical insecticide.
Limonene is used in the organic herbicide, Avenger.

Limonene is added to cleaning products, such as hand cleansers to give a lemon or orange fragrance (see orange oil) and for Limonene ability to dissolve oils.
In contrast, l-limonene has a piny, turpentine-like odor.

Limonene is used as a solvent for cleaning purposes, such as adhesive remover, or the removal of oil from machine parts, as Limonene is produced from a renewable source (citrus essential oil, as a byproduct of orange juice manufacture).
Limonene is used as a paint stripper and is also useful as a fragrant alternative to turpentine.

Limonene is also used as a solvent in some model airplane glues and as a constituent in some paints.
Commercial air fresheners, with air propellants, containing limonene are used by stamp collectors to remove self-adhesive postage stamps from envelope paper.
Limonene is also used as a solvent for fused filament fabrication based 3D printing.

Printers can print the plastic of choice for the model, but erect supports and binders from High Impact Polystyrene (HIPS), a polystyrene plastic that is easily soluble in limonene.
In preparing tissues for histology or histopathology, d-limonene is often used as a less toxic substitute for xylene when clearing dehydrated specimens.

Clearing agents are liquids miscible with alcohols (such as ethanol or isopropanol) and with melted paraffin wax, in which specimens are embedded to facilitate cutting of thin sections for microscopy.
Limonene is also combustible and has been considered as a biofuel.

Limonene is used for cleaning or safety in an occupational or industrial setting (e.g. industrial cleaning supplies or laundry detergent, eye wash, spill kits)
Cleaning and household care products that can not be placed in a more refined category

Home air fresheners, including candles with a fragrance
Bathtub, tile, and toilet surface cleaners antiseptic

Carpet-cleaning products that may be used directly (or require dilution), includes solutions that may be used by hand or in mechanical carpet cleaners
Hard floor cleaners, including pre-moistened wipes

Limonene that impart a shine to solid floors
Detergent based products used during the hand washing of dishes
Cleaning products for general household cleaning, which do not fit into a more refined category

Limonene is used to control microbial pests on hard surfaces or laundry
Limonene is used to clean glass, mirrors, and windows

Limonene is used to clean hard surfaces in the home, including kitchen specific hard surface cleaners
Heavy duty hard surface cleaning products that may require dilution prior to use (i.e., may be concentrated)

Limonene is used in washing machines to clean fabrics
Limonene is used to clean grills, ovens, or range cooktops

Limonene is applied to footwear to color, polish, clean, or add a protective surface.
Contains fragrance allergens.

Limonene for removing grease and other hydrophobic materials from hard surfaces:
fragrance allergen
fragrance component
fragrance ingredient
fragrances

Paint or stain related products that do not fit into a more refined category,
Limonene is used on wooden surfaces, including decks, to impart transparent or semitransparent color,

Limonene is for coating and protecting household surfaces other than glass, stone, or grout,
General personal care products which do not fit into a more refined category,

Facial cleansing products (excluding scrubs), for acne treatment
Multicomponent body care or bath set for which individual products are not designated,

Products related to body hygiene which do not fit into a more refined category,
Bar and other solid soaps,

Body cleaners containing abrasives or exfoliants,
Body cleaners, washes, shower gels,

Antibacterial products for application to hands,
Liquid hand soaps,

Lipophilic products applied to skin (excluding baby oils),
Personal care products intended for use by children, which do not fit into a more specific category,

Toothpastes and dentrifices,
Deodorants and antiperspirants,

Facial cleansing and moisturizing products which do not fit into a more refined category,
Products specifically marketed for application to hands or body to moisturize or improve skin characteristics (excluding baby lotion),

General hair styling or hair care products which do not fit into a more refined category,
Products for removing oil and dirt from hair,

Rinse-out everyday hair conditioners (excluding combo shampoo/conditioner products),
Leave-in everyday hair conditioners and detanglers,

Spray fixatives for hair,
Styling Products for imparting hold, shine, or texture to hair

Shampoos, including dual shampoo/conditioner products,
Make-up or cosmetic products which do not fit into a more refined category,

Eye liners or brow coloring products,
Foundation make-up and concealers,

Lip products primarily for protection,
Colored lip products, excluding glosses,

Adhesives for reparing fingernails or attaching artificial nails.
Chemistry of Limonene:

Limonene is a relatively stable terpene, which can be distilled without decomposition, though Limonene forms isoprene when passed over a hot metal filament.
Limonene is easily oxidised in moist air to carveol and carvone.
Oxidation using sulfur leads to p-cymene and a sulfide.

Limonene occurs naturally as the (R)-enantiomer, but Limonene can be racemised to dipentene simply by heating at 300 °C.
When warmed with mineral acid, limonene forms the conjugated diene terpinene, which can itself easily be oxidised to p-cymene, an aromatic hydrocarbon.
Evidence for this includes the formation of Diels-Alder α-terpinene adducts when limonene is heated with maleic anhydride.

In both cases the second C=C double bond can be made to react if desired.
In another synthetic method Markovnikov addition of trifluoroacetic acid followed by hydrolysis of the acetate gives terpineol

Uses & Effectiveness of Limonene:
Insufficient Evidence to Rate Effectiveness for.
Cancer treatment.

One form of limonene (D-limonene) seems to build up in tumors in people with advanced cancer, when Limonene is taken by mouth in 21-day cycles.
The high levels of limonene in the tumors may slow down the progress of the cancer, but their effect on the person's survival is uncertain.

Cancer prevention.
Weight loss.
Bronchitis.
Other conditions.

Sources/Uses of Limonene:
Used in flavorings, fragrances, cosmetics and as a solvent and wetting agent; Also used to make resins, insecticides, insect repellants, and animal repellants; [HSDB] Used as a dissolving agent for gallstones and gutta-percha; [ChemIDplus] Used in floor waxes and furniture polishes; [CAMEO] Occurs naturally in essential oils of many plants and is a minor constituent of turpentine; [CHEMINFO]

Household Products of Limonene:

Household & Commercial/Institutional Products of Limonene:
Information on 6 consumer products that contain 1-Methyl-4-Methylvinyl-Cyclohexene in the following categories is provided:

Auto Products of Limonene:

Household & Commercial/Institutional Products
Information on 126 consumer products that contain Dipentene in the following categories is provided:

Auto Products
Commercial / Institutional
Inside the Home
Personal Care

Household & Commercial/Institutional Products
Information on 31 consumer products that contain Grapefruit oil in the following categories is provided:

Auto Products
Inside the Home
Personal Care

Household & Commercial/Institutional Products of Limonene:
Information on 3 consumer products that contain Limonene fraction terpenes in the following categories is provided:

Inside the Home of Limonene:

Methods of Manufacturing of Limonene:
Extraction from Southeastern pine stumps, and citrus fruits (especially from the peels of oranges and lemons); from pyrolysis of alpha-pinene.
As a by-product in the manufacture of terpineol and in various synthetic products made from alpha-pinene or turpentine oil.
Derivation: Lemon, bergamot, caraway, orange, and other oils, peppermint and spearmint oils.

The richest sources are the oils contained in the peel of citrus fruits, which contain levels up to 90%.
The major source of limonene is from citrus peel, largely as a by-product of the fruit juice industry.
Citrus fruit produce the (R)-enantiomer and so the bulk of commercially available limonene is dextrorotatory.
The levorotatory enantiomer is available, but in much more restricted supply and at a higher price.

Chemical products for tanning, staining, or coloring the skin
Limonene applied to the skin following shaving to provide scent, or improve skin characteristics

Cleanin and lubricating products for hair clippers
Shaving creams, foams, balms and soaps

Solid or powdered products added to bathwater including bath salts, soaks, and fizzes
Limonene added to bath water to create bubbles, may provide cleaning, fragrance, or improve skin characteristics (including bubble bath marketed to babies or children)

Limonene applied to the skin to block harmful effects of sunlight
Limonene for repelling insects from skin

Insecticides, for interior or exterior use solvent
Products for masking odors or adding fragrance to car cabin air
Auto body waxes and coatings, excluding combo wash/wax products

Pharmacology and Biochemistry of Limonene:

Absorption, Distribution and Excretion of Limonene:
The data suggest that monoterpenes are poorly resorbed in the GI tract.
The resorbed portion of hydrocarbons accumulates in the lipophilic body compartments and is metabolized and then excreted by the kidneys.

Percutaneous absorption of radioactive limonene from foam bath was measured in animals.
Maximum blood level reached after 10 min of exposure and the concentration was proportional to the skin exposed.

SKH-1 mice received topical or oral administration of limonene in the form of orange oil every day for 4 weeks.
Plasma and mammary pads were collected 4 hr after the final dosing.

The mouse disposition study showed that topical and oral orange oil administration resulted in similar mammary tissue disposition of limonene with no clinical signs of toxicity.
Our studies showed that limonene is bio available in mammary tissue after topical orange oil application in mice

Physical Description of Limonene:
Dipentene appears as a colorless liquid with an odor of lemon.
Flash point 113°F.

Density about 7.2 lb /gal and insoluble in water.
Hence floats on water.

Vapors heavier than air.
Limonene is used as a solvent for rosin, waxes, rubber; as a dispersing agent for oils, resins, paints, lacquers, varnishes, and in floor waxes and furniture polishes.

Chemical reactions of Limonene:
Limonene is a relatively stable monoterpene and can be distilled without decomposition, although at elevated temperatures Limonene cracks to form isoprene.
Limonene oxidizes easily in moist air to produce carveol, carvone, and limonene oxide.
With sulfur, Limonene undergoes dehydrogenation to p-cymene.

Limonene occurs commonly as the (R)-enantiomer, but racemizes to dipentene at 300 °C.
When warmed with mineral acid, limonene isomerizes to the conjugated diene α-terpinene (which can also easily be converted to p-cymene).
Evidence for this isomerization includes the formation of Diels–Alder adducts between α-terpinene adducts and maleic anhydride.

Limonene is possible to effect reaction at one of the double bonds selectively.
Anhydrous hydrogen chloride reacts preferentially at the disubstituted alkene, whereas epoxidation with mCPBA occurs at the trisubstituted alkene.
In another synthetic method Markovnikov addition of trifluoroacetic acid followed by hydrolysis of the acetate gives terpineol.

Limonene is a relatively stable mono- terpene and can be distilled without decomposition, although Limonene cracks at high temperatures to form isoprene.
Carveol is easily oxidized in humid air to produce carvone and limonene oxide.
Limonene undergoes dehydrogenation with sulfur in the form of "p" - cemen.

Biosynthesis of Limonene:
In nature, limonene is formed from geranyl pyrophosphate, via cyclization of a neryl carbocation or Limonene equivalent as shown.
The final step involves loss of a proton from the cation to form the alkene.

The most widely practiced conversion of limonene is to carvone.
The three-step reaction begins with the regioselective addition of nitrosyl chloride across the trisubstituted double bond.
This species is then converted to the oxime with a base, and the hydroxylamine is removed to give the ketone-containing carvone.

In plants of Limonene:
Limonene is a major component of the aromatic scents and resins characteristic of numerous coniferous and broadleaved trees: red and silver maple, cottonwoods, aspens (Populus grandidentata, Populus tremuloides) sumac (Rhus glabra), spruce (Picea spp.), various pines (e.g., Pinus echinata, Pinus ponderosa), Douglas fir (Pseudotsuga menziesii), larches (Larix spp.), true firs (Abies spp.), hemlocks (Tsuga spp.), cannabis (Cannabis sativa spp.),[10] cedars (Cedrus spp.), various Cupressaceae, and juniper bush (Juniperus spp.).[1] It contributes to the characteristic odor of orange peel, orange juice and other citrus fruits.
To optimize recovery of valued components from citrus peel waste, Limonene is typically removed.

Specifications of Limonene:
Assay (GC, area%): ≥ 95.0 % (a/a)
Density (d 20 °C/ 4 °C): 0.841 - 0.845
Identity (IR): passes test

Identifiers of Limonene:
CAS Number:
138-86-3 (R/S)
5989-27-5 (R)
5989-54-8 (S)
ChEBI: CHEBI:15384
ChEMBL: ChEMBL449062 (R)
ECHA InfoCard: 100.028.848
KEGG: D00194
UNII:
9MC3I34447 (R/S)
GFD7C86Q1W (R)
47MAJ1Y2NE (S)
CompTox Dashboard (EPA): DTXSID2029612
InChI:
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3 check
Key: XMGQYMWWDOXHJM-UHFFFAOYSA-N check
InChI=1/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3
Key: XMGQYMWWDOXHJM-UHFFFAOYAC
SMILES: CC1=CCC(CC1)C(=C)C

Properties of Limonene:
Chemical formula: C10H16
Molar mass: 136.238 g·mol−1
Appearance: colorless liquid
Odor: Orange
Density: 0.8411 g/cm3
Melting point: −74.35 °C (−101.83 °F; 198.80 K)
Boiling point: 176 °C (349 °F; 449 K)
Solubility in water: Insoluble
Chiral rotation ([α]D): 87–102°
Refractive index (nD): 1.4727

Features of Limonene:
Chemical formula: C 10 H 16
molecular mass: 136.23gmol- 1
Appearance: colorless to pale-yellow liquid
Smell: Orange
Intensity: 0.8411 g / cm 3
Melting point: -74.35
Boiling point: 176

Molecular Weight: 136.23
XLogP3-AA: 3.4
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Rotatable Bond Count: 1
Exact Mass: 136.125200510
Monoisotopic Mass: 136.125200510
Topological Polar Surface Area: 0 Å²
Heavy Atom Count: 10
Complexity: 163
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Preferred IUPAC name of Limonene:
1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene

Other names of Limonene:
1-Methyl-4-(1-methylethenyl)cyclohexene
4-Isopropenyl-1-methylcyclohexene
p-Menth-1,8-diene
Racemic: dl-Limonene; Dipentene

Synonyms of Limonene:
LIMONENE
Dipentene
138-86-3
Cinene
Cajeputene
DL-Limonene
Kautschin
p-Mentha-1,8-diene
Dipenten
Eulimen
Nesol
1,8-p-Menthadiene
Cajeputen
Limonen
Cinen
Cyclohexene, 1-methyl-4-(1-methylethenyl)-
Inactive limonene
Acintene DP dipentene
1-Methyl-4-(1-methylethenyl)cyclohexene
Polylimonene
Dipanol
Unitene
alpha-Limonene
Flavor orange
Orange flavor
Goldflush II
Acintene DP
Di-p-mentha-1,8-diene
1,8(9)-p-Menthadiene
4-Isopropenyl-1-methyl-1-cyclohexene
4-Isopropenyl-1-methylcyclohexene
1-methyl-4-prop-1-en-2-ylcyclohexene
p-Mentha-1,8-diene, dl-
(+/-)-Limonene
DL-4-Isopropenyl-1-methylcyclohexene
1-Methyl-4-isopropenyl-1-cyclohexene
MENTHA-1,8-DIENE (DL)
Dipentene, technical grade
.alpha.-Limonene
NSC 21446
PC 560
1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
.delta.-1,8-Terpodiene
7705-14-8
CHEBI:15384
1-Methyl-4-isopropenylcyclohexene
Limonene, dl-
65996-98-7
NCGC00163742-03
Polydipentene
Limonene polymer
DSSTox_CID_9612
d,l-Limonene
Dipentene polymer
DSSTox_RID_78787
DSSTox_GSID_29612
Dipentene 200
Terpenes and Terpenoids, limonene fraction
(+-)-Dipentene
(+-)-Linonene
Caswell No. 526
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (.+/-.)-
delta-1,8-Terpodiene
(+-)-alpha-Limonene
d-Limonene (JAN)
Dipentene, crude
CAS-138-86-3
HSDB 1809
NSC 844
p-Mentha-1,8-diene, (+-)-
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)-
EINECS 205-341-0
EINECS 231-732-0
UN2052
1-Methyl-p-isopropenyl-1-cyclohexene
DIPENTENE (+-)
EPA Pesticide Chemical Code 079701
NSC-844
Terpodiene
Ciene
Cyclil decene
AI3-00739
NSC-21446
Achilles dipentene
NSC-757069
Dipentene, tech.
4-isopropenyl-1-methyl-cyclohexene
Dipentene, technical, for use as solvent (for the paint industry), mixture of various terpenes
c0626
Mentha-1,8-diene
p-Mentha-1, dl-
Dipentene, homopolymer
d(R)-4-Isopropenyl-1-methylcyclohexene
(.+-.)-Limonene
(.+-.)-Dipentene
(.+/-.)-Dipentene
(.+/-.)-Limonene
DIPENTENE 38 PF
Limonene, (+/-)-
ESSENCE DE PIN PF
(1)-1-Methyl-4-(1-methylvinyl)cyclohexene
DL-p-mentha-1,8-diene
Mentha-1,8-diene, DL
(+-)-(RS)-limonene
Cyclohexene, (.+-.)-
Dipentene, p.a., 95%
p-Mentha-1,8(9)-diene
8016-20-4
Dipentene, mixture of isomers
CHEMBL15799
Monocyclic terpene hydrocarbons
Methyl-4-isopropenylcyclohexene
NSC844
(.+/-.)-.alpha.-Limonene
DTXSID2029612
(+/-)-p-Mentha-1,8-diene
p-Mentha-1, (.+-.)-
HMS3264E05
Pharmakon1600-00307080
Methyl-4-isopropenyl-1-cyclohexene
HY-N0544
NSC21446
Tox21_112068
Tox21_201818
Tox21_303409
MFCD00062992
NSC757069
STK801934
1-methyl-4-isopropenylcyclohex-1-ene
AKOS009031280
Cyclohexene, 4-Isopropenyl-1-methyl-
Methyl-4-(1-methylethenyl)cyclohexene
WLN: L6UTJ A1 DY1 & U1
CCG-214016
MCULE-2462317444
p-Mentha-1,8-diene, (.+/-.)-
p-Mentha-1,8-diene, polymers (8CI)
SB44847
UN 2052
(+/-)-p-Mentha-1,8-diene homopolymer
Limonene 1000 microg/mL in Isopropanol
NCGC00163742-01
NCGC00163742-02
NCGC00163742-04
NCGC00163742-05
NCGC00257291-01
NCGC00259367-01
Terpenes andTerpenoids, limonene fraction
8050-32-6
NCI60_041856
p-Mentha-1,8-diene, homopolymer (7CI)
1-methyl-4-(1-methylethenyl) cylcohexene
1-methyl-4-(prop-1-en-2-yl)cyclohexene
4-(1-methylethenyl)-1-methyl-cyclohexene
Dipentene [UN2052] [Flammable liquid]
Cyclohexene, 1-methyl-4-(1-methylethynyl)
DB-053490
DB-072716
CS-0009072
FT-0600409
FT-0603053
FT-0605227
L0046
EN300-21627
C06078
D00194
1-METHYL-4-PROP-1-EN-2-YL-CYCLOHEXENE
AB01563249_01
Q278809
SR-01000872759
J-007186
J-520048
SR-01000872759-1
4B4F06FC-8293-455D-8FD5-C970CDB001EE
Dipentene, mixt. of limonene, 56-64%, and terpinolene, 20-25%
555-08-8
8022-90-0
(+)-(R)-limonene
(R)-(+)-Limonene
(+)-(4R)-Limonene
(+)-4-isopropenyl-1-methylcyclohexene
(+)-a-Limonene
(+)-carvene
(+)-Limonene
(+)-p-Mentha-1,8-diene
(+)-α-Limonene
(4R)-1-Méthyl-4-(1-propèn-2-yl)cyclohexène
(4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohexen
(4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohexene
(4R)-4-Isopropenyl-1-methylcyclohexen
(4R)-4-Isopropenyl-1-methylcyclohexene
(4R)-4-Isopropényl-1-méthylcyclohexène
(4R)-limonene
(R)-4-isopropenyl-1-methyl-1-cyclohexene
(R)-4-Isopropenyl-1-methyl-cyclohexene
(R)-limonene
2204754
227-813-5
5989-27-5
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-
D-(+)-limonene
D-Limonen
d-limonene
MFCD00062991
p-Mentha-1,8-diene, (R)-(+)-
R-(+)-limonene
()-Carvene
(+)-1,8-para-Menthadiene
(+)-Dipentene
(+)-Mentha-1,8-diene
(+)-p-Mentha-1,8-diene, (R)-(+)-4-Isopropenyl-1-methyl-1-cyclohexene
(+)-r-limonene
(4R)-1-methyl-4-(1-methylethenyl)cyclohexene
(4R)-1-methyl-4-(1-methylvinyl)cyclohex-1-ene
(4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
(4R)-1-methyl-4-isopropenylcyclohex-1-ene
(4R)-1-methyl-4-prop-1-en-2-ylcyclohexene
(4R)-1-methyl-4-prop-1-en-2-yl-cyclohexene
(4R)-4-isopropenyl-1-methyl-cyclohexene
(D)-Limonene
(R)-()-Limonene
(R)-(+)-4-Isopropenyl-1-methylcyclohexene
(R)-(+)-P-MENTHA-1,8-DIENE
(R)-1-Methyl-4-(1-methylethenyl)cyclohexene
(R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
(R)-p-mentha-1,8-diene
1-Methyl-4-(1-methylethenyl)cyclohexene
1-Methyl-4-prop-1-en-2-yl-cyclohexene
1-methyl-4R-(1-methylethenyl)-cyclohexene
205-341-0
95327-98-3
Biogenic SE 374
Carvene
citrene
Cyclohexene, 1-methyl-4-(1-methylethenyl)-
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)-
D-1,8-p-Menthadiene
Dextro-limonene
Dipentene
D-p-mentha-1,8-diene
EC 7
Glidesafe
Glidsafe
Hemo-sol
Limonene, (+)-
PARA-MENTHA-1,8-DIENE
p-mentha-1,8-diene
Refchole
α-limonene

MeSH of Limonene:
(+)-(R)-4-isopropenyl-1-methylcyclohexene
(+)-limonene
(-)-limonene
(4R)-1-methyl-4-(1-methylethenyl)cyclohexene
(4S)-1-methyl-4-isopropenylcyclohex-1-ene
(D)-limonene
(R)-(+)-limonene
(R)-4-isopropenyl-1-methylcyclohexene
1-methyl-4-(1-methylethenyl)cyclohexene
4 Mentha 1,8 diene
4-mentha-1,8-diene
AISA 5203-L (+)limonene
cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-
d Limonene
d-limonene
dipentene
limonene
limonene, (+)-
limonene, (+-)-
limonene, (+-)-isomer
limonene, (R)-isomer
limonene, (S)-isomer