2436-90-0

Basic information

• Product Name: Dihydromyrcene
• Synonyms: 3,7-DIMETHYL-1,6-OCTADIENE;(+)-BETA-CITRONELLENE;DIHYDROMYRCENE;(+)-β-citronellene;1,6-Octadiene, 3,7-dimethyl-;1,6-octadiene,3,7-dimethyl-,S(+)-;3,7-dimethyl-6-octadiene;3,7-Dimethyl-octa-1,6-diene
• CAS NO: 2436-90-0
• Molecular Formula: C₁₀H₁₈
• Molecular Weight: 138.25
• EINECS: 219-433-3
• Mol File: 2436-90-0.mol
• Article Data: 47

Chemical Properties

• Melting Point: -69.6°C (estimate)
• Boiling Point: 154-155 °C(lit.)
• Flash Point: 38 °C
• Appearance: /
• Density: 0.760 g/mL at 20 °C(lit.)
• Vapor Pressure: 2.19mmHg at 25°C
• Refractive Index: n20/D 1.437
• Storage Temp.: 2-8°C
• Water Solubility: 2.24mg/L at 20℃
• CAS DataBase Reference: Dihydromyrcene(CAS DataBase Reference)
• NIST Chemistry Reference: Dihydromyrcene(2436-90-0)
• EPA Substance Registry System: Dihydromyrcene(2436-90-0)

Safety Data

• RIDADR: UN 2319 3/PG 3
• WGK Germany: 2
• RTECS: RG5340000
• F: 10
• Hazardous Substances Data: 2436-90-0(Hazardous Substances Data)

Usage

Uses

Dihydromyrcene is used as a fragrance intermediate and can be used to synthesize dihydromyrcenol.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 2126, 1986 DOI: 10.1021/jo00361a038

Safety Profile

A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C10H18/c1-5-10(4)8-6-7-9(2)3/h5,7,10H,1,6,8H2,2-4H3/t10-/m1/s1

Upstream product

• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 123-35-3 7-methyl-3-methene-1,6-octadiene 
• 141-12-8 neryl acetate 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 105-86-2 (E)-3,7-dimethyl-2,6-octadien-1-ol, formate 
• 65071-54-7 3,7-dimethyl-1,2,6-octatriene 
• 60699-29-8 (Z)-3,7-dimethylocta-2,6-dien-1-yl diethyl phosphate 
• 60699-32-3 (E)-3,7-dimethylocta-2,6-dien-1-yl diethyl phosphate 
• 106-25-2 Nerol 
• 106-24-1 Geraniol 
• 85217-72-7 3,7-dimethylocta-2,6-dien-1-yl methyl carbonate 
• 624-15-7 geraniol 
• 473-55-2 2,6,6-trimethylbicyclo[3.1.1]heptane 
• 85217-72-7 geranyl methyl carbonate 

Downstream Products

• 53767-93-4 2,6-dimethyl-7-octene-2-yl acetate 
• 80-26-2 terpinyl acetate 
• 59019-90-8 3-(2-Isopropyl-5-methyl-cyclopentyl)-1-phenyl-propan-1-one 
• 61099-47-6 3-(2-Isopropenyl-5-methyl-cyclopentyl)-1-phenyl-propan-1-one 
• 18479-58-8 Dihydromyrcenol 
• 7712-75-6 1-Isopropyliden-2,3-dimethylcyclopentan 
• 6876-05-7 (1S,2S,3R)-1-Isopropenyl-2,3-dimethyl-cyclopentane 
• 6876-05-7 1r-Isopropenyl-2t,3t-dimethylcyclopentane 
• 6876-05-7 1r-Isopropenyl-2c,3c-dimethylcyclopentane 
• 6876-05-7 1r-Isopropenyl-2c,3t-dimethylcyclopentane 
• 93904-58-6 (S)-4-methyl-5-hexenal 
• 7540-51-4 (S)-3,7-dimethyl-6-octen-1-ol 
• 53767-86-5 7-methoxy-3,7-dimethyloct-1-ene 
• 76343-94-7 latrunculin B 

Relevant articles and documents

Regiodivergent reduction of allylic esters with Samarium(II) iodide by tuning ester groups and proton sources

Samarium(II) iodide reduced allylic esters in the presence or the absence of palladium(0) catalyst to give α- and γ-protonated products in a regiodivergent fashion by tuning ester functionality and proton sources.

Total Synthesis and Biological Investigation of (?)-Artemisinin: The Antimalarial Activity of Artemisinin Is not Stereospecific

Here, we describe an efficient and diversity-oriented entry to both (?)-artemisinin (1) and its natural antipode (+)-artemisinin, starting from commercially and readily available S-(+)- and R-(?)-citronellene, respectively. Subsequently, we answered the still open question regarding the specificity of artemisinins action. By using a drug-sensitive Plasmodium falciparum NF54 strain, we showed that the antimalarial activity of artemisinin is not stereospecific. Our straightforward and biomimetic approach to this natural endoperoxide enables the synthesis of artemisinin derivatives that are not accessible through applying current methods and may help to address the problem of emerging resistance of Plasmodium falciparum towards artemisinin.

Transition metal triflate catalyzed conversion of alcohols, ethers and esters to olefins

Herein, we report an efficient transition metal triflate catalyzed approach to convert biomass-based compounds, such as monoterpene alcohols, sugar alcohols, octyl acetate and tea tree oil, to their corresponding olefins in high yields. The reaction proceeds through C-O bond cleavage under solvent-free conditions, where the catalytic activity is determined by the oxophilicity and the Lewis acidity of the metal catalyst. In addition, we demonstrate how the oxygen containing functionality affects the formation of the olefins. Furthermore, the robustness of the used metal triflate catalysts, Fe(OTf)3 and Hf(OTf)4, is highlighted by their ability to convert an over 2400-fold excess of 2-octanol to octenes in high isolated yields.

Process for the Catalytic Reversible Alkene-Nitrile Interconversion

The present invention refers to processes for catalytic reversible alkene-nitrile interconversion through controllable HCN-free transfer hydrocyanation.