5989-54-8 Usage
Description
(S)-(-)-Limonene, also known as D-Limonene, is a popular natural occurring cyclic terpene with the chemical name D-Limonene. It is a colorless liquid at room temperature, characterized by a distinct lemon-like odor. This monoterpenoid compound is insoluble in ether and alcohol but soluble in water, with a boiling point of 74°C. It is a major constituent in numerous citrus oils such as lemon, orange, lime, mandarin, and grapefruit, which are fruits from the Rutaceae family. (S)-(-)-Limonene can be obtained through steam distillation of pulp and citrus peels or from the deterpenation of citrus oils. It is also known for its potent antimicrobial activity and is used in various applications across different industries.
Uses
Used in Clinical Applications:
(S)-(-)-Limonene is used as a cholesterol solvent for dissolving cholesterol-containing gallstones. It also aids in relieving heartburn and gastroesophageal reflux disorder (GERD) due to its gastric acid neutralizing properties and support for normal peristalsis. Additionally, it has chemo-preventive activity against various types of cancers, as demonstrated in phase 1 clinical trials for breast and colorectal cancer patients. Furthermore, it is used to maintain regular bowel movements, particularly in cases caused by Candida albicans infection, and as a mild appetite suppressant to help manage weight, especially in individuals with unhealthy blood sugar levels.
Used in Personal Care:
(S)-(-)-Limonene serves as a flavoring agent to mask the bitter taste of alkaloids and as a fragrance in perfumery. It is also used in bath products, aftershave lotions, and other personal care products. (S)-(-)-LIMONENE is commonly added to cleaning products, such as hand wash solutions, to provide an orange or lemon fragrance.
Used in the Food Industry:
(S)-(-)-Limonene is utilized as a fragrance and flavoring agent in the manufacture of foods, chewing gums, and beverages.
Used in Agricultural Applications:
(S)-(-)-Limonene is employed as a botanical insecticide and is also a component of the organic herbicide "Aenger."
Used in Industrial Purposes:
As a natural product derived from citrus oil and byproducts during orange juice manufacturing, (S)-(-)-Limonene is used as a solvent for cleaning purposes, such as removing oil from machine parts. It is also used as a paint stripper, an alternative fragrance to turpentine, a solvent in glues and paints for some airplane models, and in commercial air fresheners. Additionally, it is used to remove self-adhesive postage stamps from envelopes by philatelists and has been considered as a biofuel due to its combustibility.
Used in Printing:
(S)-(-)-Limonene is used as a solvent for filament in 3D printing, allowing printers to erect binders and supports from HIPS, a polystyrene plastic that can easily dissolve in (S)-(-)-Limonene.
Used in Therapeutic Applications:
(S)-(-)-Limonene possesses therapeutic properties such as antimicrobial, antianaemic, antiseptic, and anti-sclerotic. It also has carminative, bactericidal, depurative, cicatrizant, diuretic, rubefacient, hyposensitive, vermifuge, and tonic characteristics.
Used in Histology:
Due to its less toxic nature compared to xylene, (S)-(-)-Limonene is often used in preparing tissues, particularly when cleaning dehydrated specimens, for histology.
Other Applications:
(S)-(-)-Limonene is also used for treating wounds and sores, in aromatherapy, douching, cataract treatment, mouth ulcers, varicose veins, and spots. Furthermore, it is used to inhibit the proliferation of colon cancer cells and in the production of artificial essential oils, such as (+)-carvone. It is an active component of turpentine and finds application as a solvent and wetting agent, as well as in the production of resins.
Chemical Composition and Reactions
The main D-Limonene’s compositions include camphene, a-pinene, a-terpene, b-pinene, b-bisabolene, trans-a-bergamotene, limonene, neral, and nerol. It chemically belongs to the family of cycloalkane known as terpenes. Notably, its IUPAC name is 4-isopropeny–1–methylcyclohexane.
D-limonene can be distilled without decomposing and is a typically stable monoterpene, but can crack in high temperatures to form isoprene. D-limonene oxidizes easily in moist air to generate limonene oxide, carvone, and carveol. It dehydrates when reacted with Sulphur to form p-cymene. D-limonene isomerizes to conjugated diene α-terpinene when heated with mineral acid.
Safety and Side Effects
D-limonene is considered to have low toxicity; therefore, does not pose a carcinogenic, mutagenic, or nephrotoxic risk to humans. In proportional food amounts, d-limonene is safe. When taken orally for up to one year in correct medical amounts, d-limonene appears safe for most people.
However, there is no enough information or research regarding the effect of d-limonene on pregnant and breast feeding women when taken in larger medical amounts. As such, it is vital to stay on the safer side until more research is done.
Dosing
The correct dosage for d-limonene is dependent on numerous factors, such as user’s health, age, as well as other conditions.
Flammability and Explosibility
Flammable
Contact allergens
Limonene is a racemic form of dand l-limonene.
d-Limonene is contained in Citrus species such as citrus,
orange, mandarin, and bergamot. l-Limonene is
contained in Pinus pinea.
Safety Profile
A skin irritant. When
heated to decomposition it emits acrid
smoke and irritating fumes.
Check Digit Verification of cas no
The CAS Registry Mumber 5989-54-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,9,8 and 9 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 5989-54:
(6*5)+(5*9)+(4*8)+(3*9)+(2*5)+(1*4)=148
148 % 10 = 8
So 5989-54-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3
5989-54-8Relevant articles and documents
Electro-mediated PhotoRedox Catalysis for Selective C(sp3)–O Cleavages of Phosphinated Alcohols to Carbanions
Barham, Joshua P.,K?nig, Burkhard,Karl, Tobias A.,Reiter, Sebastian,Tian, Xianhai,Yakubov, Shahboz,de Vivie-Riedle, Regina
supporting information, p. 20817 - 20825 (2021/08/18)
We report a novel example of electro-mediated photoredox catalysis (e-PRC) in the reductive cleavage of C(sp3)?O bonds of phosphinated alcohols to alkyl carbanions. As well as deoxygenations, olefinations are reported which are E-selective and can be made Z-selective in a tandem reduction/photosensitization process where both steps are photoelectrochemically promoted. Spectroscopy, computation, and catalyst structural variations reveal that our new naphthalene monoimide-type catalyst allows for an intimate dispersive precomplexation of its radical anion form with the phosphinate substrate, facilitating a reactivity-determining C(sp3)?O cleavage. Surprisingly and in contrast to previously reported photoexcited radical anion chemistries, our conditions tolerate aryl chlorides/bromides and do not give rise to Birch-type reductions.
Upcycling a plastic cup: One-pot synthesis of lactate containing metal organic frameworks from polylactic acid
Slater, Benjamin,Wong, So-On,Duckworth, Andrew,White, Andrew J. P.,Hill, Matthew R.,Ladewig, Bradley P.
supporting information, p. 7319 - 7322 (2019/06/27)
Waste PLA can be upcycled to metal organic frameworks of potential high value in a one-pot synthesis scheme, where PLA depolymerisation occurs in situ. Three homochiral lactate based frameworks were successfully synthesised and characterised from PLA as a feed source, including ZnBLD. The chiral separation ability of ZnBLD was maintained.
Converting S-limonene synthase to pinene or phellandrene synthases reveals the plasticity of the active site
Xu, Jinkun,Ai, Ying,Wang, Jianhui,Xu, Jingwei,Zhang, Yongkang,Yang, Dong
, p. 34 - 41 (2017/03/27)
S-limonene synthase is a model monoterpene synthase that cyclizes geranyl pyrophosphate (GPP) to form S-limonene. It is a relatively specific enzyme as the majority of its products are composed of limonene. In this study, we converted it to pinene or phellandrene synthases after introducing N345A/L423A/S454A or N345I mutations. Further studies on N345 suggest the polarity of this residue plays a critical role in limonene production by stabilizing the terpinyl cation intermediate. If it is mutated to a non-polar residue, further cyclization or hydride shifts occurs so the carbocation migrates towards the pyrophosphate, leading to the production of pinene or phellandrene. On the other hand, mutant enzymes that still possess a polar residue at this position produce limonene as the major product. N345 is not the only polar residue that may stabilize the terpinyl cation because it is not strictly conserved among limonene synthases across species and there are also several other polar residues in this area. These residues could form a “polar pocket” that may collectively play this stabilizing role. Our study provides important insights into the catalytic mechanism of limonene synthases. Furthermore, it also has wider implications on the evolution of terpene synthases.
