(-)-Limonene

Base Information

• Chemical Name: (-)-Limonene
• CAS No.: 5989-54-8
• Deprecated CAS: 7721-11-1
• Molecular Formula: C10H16
• Molecular Weight: 136.237
• Hs Code.: 29029090
• European Community (EC) Number: 227-815-6
• UNII: 47MAJ1Y2NE
• DSSTox Substance ID: DTXSID6047078
• Nikkaji Number: J85.992C
• Wikidata: Q27089405
• Metabolomics Workbench ID: 28092
• ChEMBL ID: CHEMBL236688
• Mol file: 5989-54-8.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 liquid with lemon odour
• Vapor Pressure: <3 mm Hg ( 14.4 °C)
• Melting Point: -74°C
• Refractive Index: n20/D 1.471(lit.)
• Boiling Point: 175.4 °C at 760 mmHg
• Flash Point: 48 ºC
• Density: 0.842
• Storage Temp.: Flammables area
• Water Solubility.: Insoluble
• 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

Purity/Quality:

99.0% ^*data from raw suppliers

(-)-Limonene ^*data from reagent suppliers

Safty Information:

• 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
• Isomeric SMILES: CC1=CC[C@H](CC1)C(=C)C
• Description: (S)-(-)-Limonene is one of the most popular natural occurring cyclic terpenes and its chemical name is D-Limonene. It is a colorless liquid at room temperature with a characteristic lemon-like odor. Although it is insoluble in ether and alcohol, (S)-(-)-Limonene is soluble in water and has a boiling point of 74oC. (S)-(-)-Limonene can be recovered from orange peel from the conversion of press liquor to molasses. It is a major constituent of numerous citrus oils such as lemon, orange, lime, mandarin, and grapefruit, which are fruits from the Rutaceae family. (S)-(-)-Limonene can be obtained by stream distillation of pulp and citrus peels resulting from production of cold-pressed oils and juice or from deterpenation of citrus oils. The compound also occurs in other essences and oils obtained during the processing of citrus juice, including deoiler, essence oil, aroma, and juice oil. ι-Limonene has a pleasant, lemon-like odor free from camphora ceous and turpentine-like notes. The most important and wide spread terpene; it is known in the d- and ι- optically active forms and in the optically inactive dl-form (known as dipentene); it has been reported found in more than 300 essential oils in amounts ranging from 90 - 95% (lemon, orange, mandarin) to as low as 1% (palmarosa);1 the most widespread form is the d-limonene, followed by the racemic form, and then ι-limonene.
• Uses: (S)-(-)-Limonene is used to inhibit the proliferation of colon cancer cells. It is also used in artificial essential oils in order to produce (+)-carvone. It is an active component of turpentine. Further, it is used in flavorings, fragrances, and cosmetics. It finds application as a solvent and wetting agent. In addition to this it is used to produce resins.

Technology Process of (-)-Limonene

There total 59 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: 72.0%

beta-pinene (18172-67-3,19902-08-0,25719-60-2) → 7-methyl-3-methene-1,6-octadiene (123-35-3) + pseudolimonene (499-97-8) + (-)-(S)-limonene (5989-54-8,555-08-8,8022-90-0,9003-73-0,95327-98-3)

Guidance literature:

In ethanol; at 400 ℃; for 0.0194444h; under 91206.1 Torr; Further Variations:; Temperatures; Product distribution;

DOI:10.1007/s11172-007-0186-x

Reference yield:

(+)-α-pinene (7785-70-8,25766-18-1) → 4-methylisopropylbenzene (99-87-6) + tricyclene (508-32-7) + camphene (5794-04-7) + C12H20O2 (1361143-31-8) + (-)-(S)-limonene (5989-54-8,555-08-8,8022-90-0,9003-73-0,95327-98-3) + α-fenchene (7378-37-2) + (1R)-(-)-myrtenyl acetate (35670-93-0,36203-31-3,1079-01-2) + bornyl acetate (5655-61-8)

Guidance literature:

With Co(2,6-Me₂C₅H₃N)2Br₂; oxygen; In carbon dioxide; ethyl acetate; at 280 ℃; under 95006.4 Torr; tubular reactor; Supercritical conditions;

DOI:10.1134/S0036024412010049

Reference yield:

(+)-α-pinene (7785-70-8,25766-18-1) → 4-methylisopropylbenzene (99-87-6) + camphene (5794-04-7) + (-)-(S)-limonene (5989-54-8,555-08-8,8022-90-0,9003-73-0,95327-98-3)

Guidance literature:

With Co(2,6-Me₂C₅H₃N)2Br₂; oxygen; In carbon dioxide; ethyl acetate; at 320 ℃; under 83605.6 Torr; tubular reactor; Supercritical conditions;

DOI:10.1134/S0036024412010049

upstream raw materials:

(-)-α-pinene

beta-pinene

(4S)-(-)-α-terpinyl acetate

(1S,2S,5S)-5-isopropenyl-2-methylcyclohexan-1-ol

Downstream raw materials:

(4S)-1-methyl-4-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]-heptane

(S)-carvomenthene

2-Bromo-4-isopropenyl-1-methoxy-1-methyl-cyclohexane

Trimethyl-[2-((S)-4-methyl-cyclohex-3-enyl)-allyl]-silane

Refernces

• 1、 Kutateladze, Dennis A.,Strassfeld, Daniel A.,Jacobsen, Eric N.. "Enantioselective Tail-to-Head Cyclizations Catalyzed by Dual-Hydrogen-Bond Donors". supporting information. p. 6951 - 6956. Retrieved 2020/05/19.
• 2、 Xu, Jinkun,Ai, Ying,Wang, Jianhui,Xu, Jingwei,Zhang, Yongkang,Yang, Dong. "Converting S-limonene synthase to pinene or phellandrene synthases reveals the plasticity of the active site". . p. 34 - 41. Retrieved 2017/03/27.