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

Description

1,1-Dimethoxy-3,7-dimethylocta-2,6-diene, also known as Citral dimethyl acetal, is a monoterpenoid that is obtained by the formal condensation of citral with methanol. It has a fresh, lemon-like odor and is characterized by green, citrus, lemon, grapefruit, and lime taste characteristics with a woody and terpy nuance at 10 ppm. The commercial product consists of a mixture of cisand trans-isomers. It has not been reported to occur naturally.

Uses

Used in Flavor and Fragrance Industry:
1,1-Dimethoxy-3,7-dimethylocta-2,6-diene is used as a flavoring agent for its fresh, lemon-like taste and aroma. It is particularly suitable for citrus and fruity flavor profiles.
Used in Perfumery:
1,1-Dimethoxy-3,7-dimethylocta-2,6-diene is used as a fragrance ingredient for its green, citrus, and woody scent. It can be used in various perfume compositions to add a refreshing and uplifting note.
Used in Cosmetics and Personal Care Products:
1,1-Dimethoxy-3,7-dimethylocta-2,6-diene can be used in cosmetics and personal care products for its pleasant scent and flavor. It can be incorporated into products such as soaps, lotions, and shampoos to provide a refreshing and invigorating experience for the user.

Preparation

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

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

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

Downstream Products

• 1588827-74-0 (E)-1-(5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-6-yl)-3-(3-(5-(3-hydroxyphenyl)oxazol-2-yl)phenyl)prop-2-en-1-one 
• 1416512-12-3 4-hydroxy-3-{3-[5-hydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromen-6-yl]-3-oxopropenyl}-benzaldehyde 
• 1416512-13-4 2-hydroxy-5-{3-[5-hydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromen-6-yl]-3-oxopropenyl}-benzaldehyde 
• 1416512-19-0 4-hydroxy-3-{3-[5-hydroxy-2-methyl-8-(3-methyl-but-2-enyl)-2-(4-methyl-pent-3-enyl)-2H-chromen-6-yl]-3-oxo-propenyl}-benzaldehyde 
• 1416512-23-6 3-(3-dimethoxymethyl-4-methoxymethoxy-phenyl)-1-[5-hydroxy-2,8-dimethyl-2,8-bis-(4-methyl-pent-3-enyl)-2H,8H-pyrano[2,3-f]chromen-6-yl]-propenone 
• 1416512-21-4 2-hydroxy-5-{3-[7-hydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromen-8-yl]-3-oxopropenyl}-benzaldehyde 
• 1416512-17-8 1-[2-methyl-2-(4-methyl-pent-3-enyl)-5-(2-piperidin-1-yl-ethoxy)-2H-chromen-6-yl]-3-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-propenone 
• 1416512-16-7 (E)-1-(5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-6-yl)-3-(2-(4-methoxybenzoyl)benzofuran-5-yl)prop-2-en-1-one 
• 1416512-15-6 3-(2-benzoyl-benzofuran-5-yl)-1-[5-hydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromen-6-yl]-propenone 
• 1416512-14-5 5-{3-[5-hydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromen-6-yl]-3-oxo-propenyl}-2-methoxymethoxy-benzaldehyde 
• 871691-29-1 1-[5-hydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromen-6-yl]-3-(3-nitro-phenyl)-propenone 
• 871691-20-2 1-[5-hydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromen-6-yl]-3-(4-nitro-phenyl)-propenone 
• 871691-32-6 4-{3-[5-hydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromen-6-yl]-3-oxo-propenyl}-benzonitrile 
• 871691-27-9 3-(3,5-dichloro-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