Limonene

Base Information

• Chemical Name: Limonene
• CAS No.: 5989-27-5
• 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.: 2902199012
• 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: 5989-27-5.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: Colorless oily liquid
• Vapor Pressure: 1.54mmHg at 25°C
• Melting Point: -75--73 °C
• Refractive Index: n20/D 1.473(lit.)
• Boiling Point: 175.4 °C at 760 mmHg
• Flash Point: 42.8 °C
• PSA: 0.00000
• Density: 0.834 g/cm³
• LogP: 3.30890
• 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

Safty Information:

• Pictogram(s): Xi, N
• Hazard Codes: Xi:Irritant;; <
• Statements: R10:Flammable.; R38:Irritating to skin.; R43:May cause sensitization by skin contact.; R50/53:Very toxic to
• Safety Statements: S24:Avoid contact with skin.; S37:Wear suitable gloves.; S60:This material and its container must be disposed of a

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

Technology Process of Limonene

There total 74 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: 80.0%

Phosphoric acid diethyl ester (R)-5-isopropenyl-2-methyl-cyclohex-1-enyl ester → D-limonene (5989-27-5,555-08-8,8022-90-0,9003-73-0,95327-98-3)

Guidance literature:

With ammonia; lithium;

DOI:10.1021/jo00281a002

Reference yield: 78.0%

L-carveol (308363-12-4,22567-18-6,20307-86-2) → D-limonene (5989-27-5,555-08-8,8022-90-0,9003-73-0,95327-98-3)

Guidance literature:

With 2-nitrobenzenesulfonyl hydrazide; triphenylphosphine; diethylazodicarboxylate; In various solvent(s); -30 deg, 1 h; 23 deg C 30 min;

DOI:10.1016/0040-4039(96)00965-3

Reference yield: 68.0%

(+)-trans-carveol (2102-58-1,22567-18-6,20307-86-2) → D-limonene (5989-27-5,555-08-8,8022-90-0,9003-73-0,95327-98-3)

Guidance literature:

With triethylsilane; lithium perchlorate; In diethyl ether; for 16h; Ambient temperature;

DOI:10.1016/0040-4039(94)88162-6

upstream raw materials:

(+)-α-pinene

Pinene

2,4,6-Trinitrophenol

benzene

Downstream raw materials:

4-methylisopropylbenzene

(R)-(+)-3-(4-methyl-3-cyclohexen-1-yl)-3-buten-1-ol

2-Hydroxymethyl-4-isopropenyl-1-methyl-cyclohexanol

4-acetoxy-2-((R)-4-methyl-cyclohex-3-enyl)-but-1-ene

Refernces

Protecting group free enantiospecific total syntheses of structurally diverse natural products of the tetrahydrocannabinoid family

10.1039/c4cc08562k

The study presents a protecting group-free enantiospecific total synthesis of structurally diverse natural products belonging to the tetrahydrocannabinoid family. The researchers developed a simple, highly diastereoselective method using Lewis acid catalyzed Friedel-Crafts coupling of cyclic allylic alcohol with resorcinol derivatives. Key chemicals used in the study include R-(+) and S-(-) limonene as starting materials, allylic alcohol 14 and electron-rich aromatic moiety 15 for coupling, and BF3·OEt2 as the best catalyst for the cyclization reaction. The purpose of these chemicals was to achieve the synthesis of natural products like machaeriol-D, Δ8-THC, Δ9-THC, epi-perrottetinene, and their analogues with high atom economy, without the need for protecting groups, and in a short sequence of less than six steps, starting from readily available and inexpensive materials.