7549-37-3

Basic information

• Product Name: 1,1-Dimethoxy-3,7-dimethylocta-2,6-diene
• Synonyms: FEMA 2305;CITRAL DIMETHYL ACETAL;3,7-DIMETHYL-2,6-OCTADIENAL DIMETHYL ACETAL;2,6-DIMETHYL-2,6-OCTADIEN-8-ALIMETHYL ACETAL;1,1-DIMETHOXY-3,7-DIMETHYL-2,6-OCTADIENE;1,1-dimethoxy-3,7-dimethylocta-2,6-diene;CITRAL DIMETHYL ACETAL 95+%;CITRAL DIMETHYL ACETAL, 95%, MIXTURE OF CIS AND TRANS
• CAS NO: 7549-37-3
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.3
• EINECS: 231-434-0
• Product Categories: Acyclic Monoterpenes;Biochemistry;Terpenes
• Mol File: 7549-37-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 105-106 °C10 mm Hg(lit.)
• Flash Point: 180 °F
• Appearance: /
• Density: 0.89 g/mL at 25 °C(lit.)
• Vapor Density: 6.8 (vs air)
• Vapor Pressure: 9 mm Hg ( 102.7 °C)
• Refractive Index: n20/D 1.454(lit.)
• CAS DataBase Reference: 1,1-Dimethoxy-3,7-dimethylocta-2,6-diene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-Dimethoxy-3,7-dimethylocta-2,6-diene(7549-37-3)
• EPA Substance Registry System: 1,1-Dimethoxy-3,7-dimethylocta-2,6-diene(7549-37-3)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 2
• RTECS: RG5330000
• Hazardous Substances Data: 7549-37-3(Hazardous Substances Data)

Usage

Chemical Properties

Citral dimethyl acetal has a fresh, lemon-like odor. The commercial product consists of a mixture of cis- and trans-isomers.

Occurrence

Apparently has not been reported to occur in nature.

Preparation

From citral and methyl alcohol in the presence of a catalyst, or by reacting citral with trimethyl orthoformate.

Definition

ChEBI: A monoterpenoid that is the acetal obtained by formal condensation of citral with methanol.

Taste threshold values

Taste characteristics at 10 ppm: green, citrus, lemon, grapefruit, lime with woody and terpy nuance.

InChI:InChI=1/C12H22O2/c1-10(2)7-6-8-11(3)9-12(13-4)14-5/h7,9,12H,6,8H2,1-5H3/b11-9-

Upstream product

• 681-84-5 tetramethylorthosilicate 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 149-73-5 trimethyl orthoformate 
• 67-56-1 methanol 

Downstream Products

• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 7479-28-9 2,3,5-trimethyl-1,4-hydroquinone diacetate 
• 476214-12-7 (RS)-2,5,7,8-tetramethyl-2-(4-methylpent-3-en-1-yl)-6-acetoxy-3-chromene 
• 123164-53-4 cordiachromene 
• 1416512-45-2 C₂₆H₂₈O₅ 
• 1416511-90-4 1-[5-hydroxy-2-methyl-2-(4-methyl-pentyl)-chroman-6-yl]-3-(4-hydroxy-phenyl)propenone 
• 1416511-91-5 1-[5-hydroxy-2-methyl-2-(4-methyl-pentyl)-chroman-6-yl]-3-(4-methoxy-phenyl)-propenone 
• 871691-30-4 1-(5-hydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromen-6-yl)-3-(2-methoxy-phenyl)-propenone 
• 871691-19-9 1-[5-hydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromen-6-yl]-3-(4-methoxy-phenyl)-propenone 
• 871691-31-5 3-(4-ethoxy-phenyl)-1-[5-hydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromen-6-yl]-propenone 
• 871691-24-6 3-(4-dimethylamino-phenyl)-1-[5-hydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromen-6-yl]-propenone 
• 1416512-09-8 1-(3,4-dimethyl-phenyl)-3-[5-hydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromen-6-yl]-propenone 
• 1416512-10-1 3-(3,4-dimethoxy-phenyl)-1-[5-hydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromen-6-yl]-propenone 
• 871691-22-4 3-(4-fluoro-phenyl)-1-[5-hydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromen-6-yl]-propenone 

Relevant articles and documents

Method for the selective formation of dimethyl acetals in the presence of hydroxylamine

An inexpensive and mild method for the formation of dimethyl acetals from the corresponding aldehydes is achieved using hydroxylamine and methanol under neutral conditions at room temperature. Notably, the reaction is selective for aldehydes in the presence of ketones, rendering this an example of a chemoselective acetalization. For saturated, sterically accessible aldehydes, catalytic amounts of hydroxylamine may be employed to attain the corresponding dimethyl acetal as the sole product in good to excellent yield. Unsaturated and hindered aldehydes required stoichiometric amounts of hydroxylamine but provided dimethyl acetals as the major product in typically excellent yield. In some cases, the corresponding oxime was also observed but may be separated from the acetal by flash column chromatography or distillation. The involvement of an intermediate oxime compound is postulated. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Taylor & Francis Group, LLC.

A facile procedure for acetalization of aldehydes and ketones catalyzed by cerium(III) trifluoromethanesulfonate

Aldehydes and ketones are readily protected in the presence of trialkyl orthoformate and a catalytic amount of cerium(III) trifluoromethanesulfonate under mild conditions to give the corresponding acetals in good to excellent yields. Due to the mild reaction conditions, this method is compatible with acid-sensitive substrates. Copyright