Myrcene

Base Information

• Chemical Name: Myrcene
• CAS No.: 123-35-3
• Deprecated CAS: 2153-31-3
• Molecular Formula: C10H16
• Molecular Weight: 136.237
• Hs Code.: 2901.29 Oral rat LD50: 5000 mg/kg
• European Community (EC) Number: 204-622-5
• NSC Number: 406264
• UN Number: 2319
• UNII: 3M39CZS25B
• DSSTox Substance ID: DTXSID6025692
• Nikkaji Number: J2.010I
• Wikipedia: Myrcene
• Wikidata: Q424577
• RXCUI: 2166047
• Metabolomics Workbench ID: 28004
• ChEMBL ID: CHEMBL455491
• Mol file: 123-35-3.mol

Synonyms:2-methyl-6-methylene-1,7-octadiene;alpha-myrcene;beta-myrcene

Chemical Property of Myrcene

Chemical Property:

• Appearance/Colour: clear to pale yellow liquid
• Vapor Pressure: ~7 mm Hg ( 20 °C)
• Melting Point: <-10 °C
• Refractive Index: 1.4690
• Boiling Point: 167 °C at 760 mmHg
• Flash Point: 44.4 °C
• PSA: 0.00000
• Density: 0.769 g/cm³
• LogP: 3.47500
• Storage Temp.: 2-8°C
• Solubility.: water: soluble0.00109g/L at 20°C
• Water Solubility.: practically insoluble
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 136.125200510
• Heavy Atom Count: 10
• Complexity: 145
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Myrcene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 10-36/37/38-R36/37/38-R10-65-38
• Safety Statements: 16-26-36-37/39-S37/39-S26-S16-62

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Terpenes
• Canonical SMILES: CC(=CCCC(=C)C=C)C
• Recent ClinicalTrials: Analgesic and Subjective Effects of Terpenes
• Description: Myrcene has a pleasant odor. Prepared from linalool. β-Myrcene is a terpene that has been found in Cannabis and has antioxidative properties. It reduces thiobarbituric acid reactive substance (TBARS) and increases glutathione (GSH), catalase, GSH peroxidase, and CuZn superoxide dismutase levels in a rat model of persistent environmental pollutant-induced oxidative stress when administered at a dose of 200 mg/kg per day.
• Uses: Found in oil of bay, verbena, hop, etc. Used as an intermediate in the manufacturing of perfume chemicals. Myrcene is the suitable synthetic standard used in the identification of E-myrcenol (2-methyl-6-methylene-E-2,7-octadien-1-01) as a major hindgut constituent in Eurasian bark beetle Ips duplicatus by GC-MS.

Technology Process of Myrcene

There total 124 articles about Myrcene 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: 36.0%

2-(geranyloxy)-3,5,7-trimethyltropone → 7-methyl-3-methene-1,6-octadiene (123-35-3) + (Z)-ocimene (3338-55-4,1856-63-9) + trans ocimene (3779-61-1,1856-63-9) + 3,5,7-trimethyltropolone (2885-58-7)

Guidance literature:

at 180 ℃; pyrolysis;

DOI:10.1246/cl.1982.1061

Reference yield: 29.0%

3,5,7-trimethyl-2-(neryloxy)tropone → 7-methyl-3-methene-1,6-octadiene (123-35-3) + (Z)-ocimene (3338-55-4,1856-63-9) + trans ocimene (3779-61-1,1856-63-9)

Guidance literature:

at 140 ℃;

DOI:10.1246/cl.1982.1061

upstream raw materials:

linalool

linalool acetate

γ-geraniol

beta-pinene

Downstream raw materials:

6,7-epoxymyrcene

1,2;5,6-diepoxy-6-methyl-2-vinyl-heptane

ethyl-4-(4'-methyl-3'-pentenyl)-3-cyclohexenyl ketone

3-(4-methylpent-3-en-1-yl)-2,5-dihydrothiophene-1,1-dioxide

Refernces

• 1、 Skouroumounis, George K.,Sefton, Mark A.. "Acid-catalyzed hydrolysis of alcohols and their β-D-glucopyranosides". . p. 2033 - 2039. Retrieved 2000.
• 2、 Matsushita, Hajime,Negishi, Ei-ichi. "Palladium-Catalyzed Reactions of Allylic Electrophiles with Organometallic Reagents. A Regioselective 1,4-Elimination and a Regio- and Stereoselective Reduction of Allylic Derivatives". . p. 4161 - 4165. Retrieved 1982.
• 3、 Yasuda,A. et al.. "-". . p. 1752 - 1756. Retrieved 1979.
• 4、 Bhati. "". . p. 376,380. Retrieved 1963.
• 5、 Tsuji, Jiro,Minami, Ichiro,Shimizu, Isao. "Preparation of 1-Alkenes by the Palladium-Catalyzed Hydrogenolysis of Terminal Allylic Carbonates and Acetates with Formic Acid-Triethylamine". . p. 623 - 627. Retrieved 1986.
• 6、 Stolle, Achim,Brauns, Claudia,Nuechter, Matthias,Ondruschka, Bernd,Bonrath, Werner,Findeisen, Matthias. "Thermal behaviour of selected C10H16 monoterpenes". . p. 3317 - 3325. Retrieved 2006.
• 7、 Kallen, Heilbronner. "". . p. 489,490. Retrieved 1960.
• 8、 Tsuji,J. et al.. "". . p. 2075 - 2078. Retrieved 1978.
• 9、 Liu,R.S.H.,Hammond,G.S.. "-". . p. 1892 - 1893. Retrieved 1964.
• 10、 Eisenacher, Matthias,Beschnitt, Stefan,H?lderich, Wolfgang. "Novel route to a fruitful mixture of terpene fragrances in particular phellandrene starting from natural feedstock geraniol using weak acidic boron based catalyst". . p. 214 - 217. Retrieved 2012.