Limonene

Base Information

• Chemical Name: Limonene
• CAS No.: 138-86-3
• Deprecated CAS: 555-08-8,7705-14-8,8022-90-0,8050-32-6,7705-14-8,8022-90-0,8050-32-6
• Molecular Formula: C10H16
• Molecular Weight: 136.237
• Hs Code.: 2902.19
• European Community (EC) Number: 205-341-0,231-732-0,642-944-1
• NSC Number: 757069,21446,844
• UN Number: 2052
• UNII: 9MC3I34447
• DSSTox Substance ID: DTXSID2029612
• Nikkaji Number: J2.532A
• Wikipedia: Limonene
• Wikidata: Q278809
• NCI Thesaurus Code: C61709
• RXCUI: 1426477
• Metabolomics Workbench ID: 123668
• ChEMBL ID: CHEMBL15799
• Mol file: 138-86-3.mol

Synonyms:(+)-(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

Chemical Property of Limonene

Chemical Property:

• Appearance/Colour: colourless or light yellow liquid
• Vapor Pressure: <3 mm Hg ( 14.4 °C)
• Melting Point: -84 - -104 °C
• Refractive Index: 1.4750
• Boiling Point: 175.44 °C at 760 mmHg
• Flash Point: 42.778 °C
• PSA: 0.00000
• Density: 0.834 g/cm³
• LogP: 3.30890
• Storage Temp.: 2-8°C
• Water Solubility.: <1 g/100mL
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 136.125200510
• Heavy Atom Count: 10
• Complexity: 163
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

D-Limonene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 10-38-43-50/53
• Safety Statements: 24-37-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Terpenes
• Canonical SMILES: CC1=CCC(CC1)C(=C)C
• Recent ClinicalTrials: Limonene for Pulmonary Nodule Chemoprevention
• Description: D-limonene, which is a volatile oil, constitutes approximately 98% of orange peel oil by weight and has moderately good knockdown activity against ectoparasites of companion animals. The insecticidal activity of both d-limonene and linalool is enhanced when synergized by piperonyl butoxide. Apart from toxicoses reported in cats (65), d-limonene generally has a high margin of safety. (±)-Limonene is a cyclic monoterpene that has been found in various plant oils and Cannabis and has antifungal activity. It completely inhibits mycelial growth and aflatoxin B1 production in A. flavus when used at concentrations of 500 and 250 ppm, respectively. (±)-Limonene also inhibits the growth of various additional fungi in vitro, including S. cerevisiae, R. glutinis, and K. thermotolerans (MICs = 500-4,000 μg/ml). It has been identified as a contact dermatitis allergen in honing oil, paint thinner, and turpentine. Formulations containing (±)-limonene have been used as fragrance and flavoring ingredients.
• Uses: d-Limonene is a flavoring agent that is a liquid, colorless with a pleasant odor resembling mild citrus. It is miscible in alcohol, most fixed oils, and mineral oil; soluble in glycerin; and insoluble in water and propylene glycol. It is obtained from citrus oil. It is also termed d-p-mentha-1,8,diene and cinene. Limonene is an antioxidant and flavoring agent that occurs in lemons, oranges, and pineapple juice, being obtained from the oils. It is a colorless liquid which is insoluble in water and propylene glycol, very slightly soluble in glycerin, and miscible with alcohol, most fixed oils, and mineral oil. It prevents or delays enzymatic browning-type oxidation.

Technology Process of Limonene

There total 382 articles about Limonene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Acid Orange 7 → ethylbenzene (100-41-4,27536-89-6) + (1S)-camphor (464-48-2,68546-28-1) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 2-benzylpropionaldehyde (5445-77-2) + 1,3-bis(3-phenoxyphenoxy)benzene (2455-71-2) + (+)-isothujone (471-15-8) + acetic acid (64-19-7,77671-22-8) + acrylic acid (79-10-7) + limonene. (138-86-3,555-08-8,8022-90-0,9003-73-0,95327-98-3)

Guidance literature:

With zinc(II) oxide; Reagent/catalyst; Concentration; pH-value; Sonication; Darkness;

DOI:10.1016/j.ultsonch.2014.08.023

Reference yield:

wood → Beta-pinene (177698-19-0,25719-60-2) + limonene. (138-86-3,555-08-8,8022-90-0,9003-73-0,95327-98-3) + 3-carene (13466-78-9,19079-29-9) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With air; Further byproducts given. Title compound not separated from byproducts; Formation of xenobiotics;

DOI:10.1021/es9909632

Reference yield:

Pinene (80-56-8,177698-18-9,25766-18-1) → Beta-pinene (177698-19-0,25719-60-2) + Terpinolene (586-62-9,69073-38-7) + 4-methylisopropylbenzene (99-87-6) + camphene (79-92-5) + limonene. (138-86-3,555-08-8,8022-90-0,9003-73-0,95327-98-3) + 3-carene (13466-78-9,19079-29-9)

Guidance literature:

With Zr⁴⁺/natural zeolite (concentration of Zr 11%); at 150 ℃; for 3h; Temperature; Reagent/catalyst; Catalytic behavior;

DOI:10.14233/ajchem.2017.20552

upstream raw materials:

pyridine

geranyl bromide

1,8-Cineole

benzoyl chloride

Downstream raw materials:

4-(2-methoxypropan-2-yl)-1-methylcyclohex-1-ene

optically inactive bis-(1-chloro-p-menth-8-en-2-yl)-diazene-N,N'-dioxide

maleic anhydride

maleic acid

Refernces

A new approach for bio-jet fuel generation from palm oil and limonene in the absence of hydrogen

10.1039/c5cc06601h

The research aims to develop a novel approach for generating bio-jet fuel from palm oil and limonene without the need for external hydrogen, addressing the challenges faced by the aviation industry in seeking sustainable fuel sources. The study proposes a "carbon-chain filling strategy" (CFS) that utilizes a one-pot process to convert C10 terpene and lipids into jet fuel-ranged hydrocarbons, including aromatic hydrocarbons, without external hydrogen. The process involves the use of limonene as a C10 terpene, which releases aromatic hydrocarbons and hydrogen, and a PdNi/HZSM-5 catalyst to facilitate the conversion of palm oil to C14-C18 alkanes through hydrodeoxygenation. The in-situ generated hydrogen from limonene dehydroaromatization enables the hydrodeoxygenation of lipids, and the resulting hydrocarbon mixture resembles the composition and properties of commercial bio-jet fuel. The study concludes that this integrated process is a simple, efficient, and green method for producing bio-jet fuel, offering a high yield and addressing the high-demand issues for hydrogen, aromatics, and light alkanes in a single-step process.

tert-Butyl Hydroperoxide-Pyridinium Dichromate: A Convenient Reagent System for Allylic and Benzylic Oxidations

10.1021/jo00231a046

The research focuses on the development of a more efficient and convenient method for allylic and benzylic oxidations using a reagent system comprised of tert-butyl hydroperoxide and pyridinium dichromate. The purpose of this study was to address the drawbacks of traditional chromium(VI)-based oxidation methods, such as the use of large excess reagents, large volumes of solvents, and long reaction times. The researchers found that the combination of these two reagents in a 1:1 molar ratio effectively facilitated the oxidation process under mild conditions, yielding high conversion rates and product yields. The chemicals used in the process included tert-butyl hydroperoxide, pyridinium dichromate, and various substrates such as cholesteryl acetate, dicyclopentadiene, citronellol acetate, 1-phenylcyclohexene, α-pinene, A3-carene, cycloheptene, limonene, fluorene, diphenylmethane, and tetralin, among others. The conclusions of the research highlighted the utility and simplicity of the tert-butyl hydroperoxide-pyridinium dichromate method, suggesting its potential for wide application in organic synthesis.