2385-77-5

Basic information

• Product Name: (+)-CITRONELLAL
• Synonyms: 7-dimethyl-(theta)-6-octena;D-Citronellal;R-3,7-dimethyl-oct-6-enal;(R)-(+)-CITRONELLAL;(R)-(+)-3,7-DIMETHYL-6-OCTENAL;(3R)-3,7-DIMETHYL-6-OCTENAL;(R)-(+)-CITRONELLAL, TECH., 90%;CITRONELLAL(D-)
• CAS NO: 2385-77-5
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25
• EINECS: 219-194-5
• Product Categories: Acyclic Monoterpenes;Biochemistry;Terpenes
• Mol File: 2385-77-5.mol
• Article Data: 83

Chemical Properties

• Melting Point: 25°C
• Boiling Point: 207 °C(lit.)
• Flash Point: 185 °F
• Appearance: Colourless to slightly yellow liquid with intense lemon-citronella-rose aroma
• Density: 0.851 g/mL at 25 °C(lit.)
• Vapor Pressure: 33.9Pa at 25℃
• Refractive Index: n20/D 1.448(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• Water Solubility: 88mg/L
• Merck: 2329
• BRN: 1720791
• CAS DataBase Reference: (+)-CITRONELLAL(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-CITRONELLAL(2385-77-5)
• EPA Substance Registry System: (+)-CITRONELLAL(2385-77-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 2385-77-5(Hazardous Substances Data)

Usage

Description

(+)-Citronellal, also known as the (3R)-stereoisomer of 3,7-dimethyloct-6-enal, is a monoterpene compound derived from the metabolism of plants. It is a clear colorless liquid and is recognized for its natural insect repellent properties, being the main component of citronellal oil.

Uses

Used in Insect Repellent Industry:
(+)-Citronellal is used as a natural insect repellant for its ability to ward off insects without causing harm to humans or the environment. Its natural properties make it a preferred choice over synthetic repellants.
Used in Perfumery and Flavor Industry:
(+)-Citronellal is used as a key ingredient in the production of perfumes and flavors due to its distinct and pleasant aroma. Its natural scent adds a unique touch to various fragrances and flavorings.
Used in Pharmaceutical Industry:
(+)-Citronellal is used as a starting material in the one-pot synthesis of (-)-Menthol, a compound with various pharmaceutical applications, including its use as a cooling agent and in the treatment of respiratory conditions.
Used in Chemical Synthesis:
(+)-Citronellal serves as an important intermediate in the synthesis of various chemical compounds, contributing to the development of new products and innovations in the chemical industry.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3/t10-/m1/s1

Upstream product

• 106-22-9 Citronellol 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 106-23-0 3,7-dimethyl-oct-6-enal 
• 37586-57-5 4-methyl-3-pentenylmagnesium bromide 
• 123-73-9 crotonaldehyde 
• 502-47-6 racemic citronellic acid 
• 82215-37-0 (2R,4R,5S)-3,4-Dimethyl-5-phenyl-2-((E)-styryl)-oxazolidine 
• 67392-56-7 (R)-(-)-N,N-diethyl-3,7-dimethyl-1(E),6-octadienylamine 
• 20763-19-3 (methoxymethylene)triphenylphosphorane 
• 106-72-9 (R)-(-)-2,6-dimethyl-5-heptenal 
• 114784-88-2 4,8-dimethyl-non-7-ene-1,2-diol 
• 546-67-8 lead(IV) tetraacetate 
• 64-19-7 acetic acid 
• 71-43-2 benzene 

Downstream Products

• 89-79-2 Isopulegol 
• 1117-61-9 (3R)-citronellol 
• 82850-74-6 cyclohexyl-((R)-3.7-dimethyl-octen-⁽⁶⁾-yliden)-amine 
• 89-49-6 Isopulegol acetate 
• 95891-86-4 2-((3R)-1-hydroxy-3,7-dimethyloct-7-enyl)phenol 
• 120229-88-1 benzyl (5R)-2-(benzyloxycarbonyl)-5,9-dimethyldeca-2,8-dienoate 
• 95891-90-0 2-((3R)-1-hydroxy-3,7-dimethyloct-7-enyl)bis(O-methoxymethyl)resorcinol 
• 143538-22-1 (R)-1-(2,6-Bis-methoxymethoxy-4-pentyl-phenyl)-3,7-dimethyl-oct-6-en-1-ol 
• 156256-43-8 (1'R,2'R,5R)-2'-hydroxycyclohexyl (E)-5,9-dimethyl-2,8-decadienoate 
• 62192-80-7 (R)-p-mentha-3,8-diene 
• 144541-38-8 <1R-(1α,2α,5α)>-5-Methyl-2-(1-methylethenyl)cyclohexanol 
• 7786-67-6 isopulegol 
• 96612-21-4 <1S-(1α,2β,5β)>-5-Methyl-2-(1-methylethenyl)cyclohexanol 
• 91739-72-9 Trans-p-Menthane-3,8-diol 

Relevant articles and documents

Synthesis of Citronellal by RhI-Catalysed Asymmetric Isomerization of N,N-Diethyl-Substituted Geranyl- and Nerylamines or Geraniol and Nerol in the Presence of Chiral Diphosphino Ligands, under Homogeneous and Supported Conditions

For the asymmetric isomerization of geranyl- or neryldiethylamine (( E)- or(Z)-1, resp.) and allyl alcohols geraniol or nerol ((E)- or (Z)-2, resp.) to citronellal (4) in the presence of a [RhI(ligand)cycloocta-1,5-diene)]- catalyst, the atropic ligands 5-11 are compared under homogeneous and polymer-supported conditions with the non-C2-symmetrical diphosphino ferrocene ligands 12-16. The tBu-josiphos ligand 13 or daniphos ligand 19, available in both antipodal series, already catalyse the reaction of (E)-1 at 20 deg (97 percent e.e.) and favourably compare with the binap ligand 5 (see Table 1). Silica-gel- or polymer-supported diphosphino ligands usually afford similar selectivity as compared to the corresponding ligands applied under homogeneous conditions, but are generally less reactive. In this context, a polymer-supported ligand of interest is the polymer-anchored binap (R)-6, in terms of reactivity, selectivity, and recoverability, with a turnover of more than 14400.

Asymmetric cleavage of chiral α,β-ethylenic acetals by organolithium reagents

,β-Ethylenic chiral acetals react regio- and stereoselectively with organolithium reagents. The obtained enol ether may be hydrolyzed into a chiral β-disubstituted aldehyde.

Multicatalytic approach to one-pot stereoselective synthesis of secondary benzylic alcohols

One-pot procedures bear the potential to rapidly build up molecular complexity without isolation and purification of consecutive intermediates. Here, we report multicatalytic protocols that convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities (typically >95:5 er) under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Prochiral allylic alcohols can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er, >20:1 dr).

Chiral amorphous metal–organic polyhedra used as the stationary phase for high-resolution gas chromatography separations

Herein, we describe a new chiral amorphous metal–organic polyhedra used as the stationary phase for high-resolution gas chromatography (GC). The chiral stationary phase was coated onto a capillary column via a dynamic coating process and investigated for a variety of compounds. The experimental results showed that the chiral stationary phase exhibits good selectivity for linear alkanes, linear alcohols, polycyclic aromatic hydrocarbons, isomers, and chiral compounds. In addition, the column has the advantages of high column efficiency and short analysis time. The present work indicated that amorphous metal–organic polyhedra have great potential for application as a new type of stationary phase for GC.