Dihydromyrcene

Base Information

• Chemical Name: Dihydromyrcene
• CAS No.: 2436-90-0
• Deprecated CAS: 128241-35-0
• Molecular Formula: C10H18
• Molecular Weight: 138.253
• Hs Code.: 2901299090
• European Community (EC) Number: 219-433-3
• UNII: LS5LA2BUG0
• DSSTox Substance ID: DTXSID8029234
• Nikkaji Number: J1.810D
• Wikidata: Q27283156
• ChEMBL ID: CHEMBL2268551
• Mol file: 2436-90-0.mol

Synonyms:beta-citronellene;citronellene

Chemical Property of Dihydromyrcene

Chemical Property:

• Vapor Pressure: 2.19mmHg at 25°C
• Melting Point: -69.6°C (estimate)
• Refractive Index: n20/D 1.437
• Boiling Point: 167.999 °C at 760 mmHg
• Flash Point: 42.345 °C
• PSA: 0.00000
• Density: 0.758 g/cm³
• LogP: 3.55490
• Storage Temp.: 2-8°C
• Water Solubility.: 2.24mg/L at 20℃
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 138.140850574
• Heavy Atom Count: 10
• Complexity: 116

Purity/Quality:

99% ^*data from raw suppliers

(+)-β-Citronellene analytical standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Terpenes
• Canonical SMILES: CC(CCC=C(C)C)C=C
• Uses: Dihydromyrcene is used as a fragrance intermediate and can be used to synthesize dihydromyrcenol.

Technology Process of Dihydromyrcene

There total 83 articles about Dihydromyrcene 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: 95.0%

(3,7-dimethyl-2,6-octadienyl)-triphenylphosphonium bromide (41273-34-1) → dihydromyrcene (2436-90-0)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 20 ℃; for 1h;

DOI:10.1021/jo00195a049

Reference yield: 92.0%

3,7-dimethylocta-2,6-dien-1-yl methyl carbonate (85217-72-7,85217-73-8,91362-68-4) → dihydromyrcene (2436-90-0)

Guidance literature:

With formic acid; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tributylphosphine; In tetrahydrofuran; for 3h; Heating;

DOI:10.1055/s-1986-31723

Reference yield: 87.0%

(+/-)-citronellyl tosylate (41144-01-8) → dihydromyrcene (2436-90-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In 1,2-dimethoxyethane; for 3h; Heating;

DOI:10.1055/s-2003-40210

upstream raw materials:

(E/Z)-3,7-dimethyl-2,6-octadienal

3,7-dimethylocta-1,6-dien-3-ol

Nerol

2,6-Dimethyl-octa-1,3t,7-trien

Downstream raw materials:

3-Hydroxymethyl-2,6-dimethyl-octa-1,7-dien

4,8-dimethyl-7-nonenal

2,6-dimethylocta-2(Z),6-diene

(E)-3,7-dimethyl-2,6-octadien

Refernces

A Convenient access to (All-rac)-α-tocopherol acetate from linalool and dihydromyrcene

10.1246/bcsj.82.829

The study explores a novel synthetic route to produce (All-rac)-α-tocopherol acetate, a form of vitamin E, using linalool and dihydromyrcene as starting materials. The researchers employed trimethylhydroquinone (2) as a key reactant and utilized camphorsulfonic acid as a catalyst to condense it with linalool (3b) in a solvent mixture of dodecane and dichloromethane. The resulting crude product, a mixture of chromanols and tricyclic compounds, was sequentially treated with acetic anhydride (Ac2O) and m-chloroperoxybenzoic acid (m-CPBA) to form a mixture of epoxides. This mixture was then converted to the desired (All-rac)-α-tocopherol acetate through a series of reactions involving aluminum isopropoxide, copper(I) iodide-catalyzed Wurtz coupling with citronellylmagnesium chloride, and hydrogenation. The study aimed to develop a more efficient and cost-effective method for synthesizing this important vitamin E derivative, which is widely used in the feed industry due to its antioxidant properties and health benefits.