75983-36-7

Basic information

• Product Name: 4,8-dimethyldecanal
• Synonyms: 4,8-dimethyldecanal
• CAS NO: 75983-36-7
• Molecular Formula: C₁₂H₂₄O
• Molecular Weight: 184.31836
• EINECS: 278-356-3
• Mol File: 75983-36-7.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 235.5°C at 760 mmHg
• Flash Point: 102.1°C
• Appearance: /
• Density: 0.82g/cm³
• Vapor Pressure: 0.0498mmHg at 25°C
• Refractive Index: 1.427
• CAS DataBase Reference: 4,8-dimethyldecanal(CAS DataBase Reference)
• NIST Chemistry Reference: 4,8-dimethyldecanal(75983-36-7)
• EPA Substance Registry System: 4,8-dimethyldecanal(75983-36-7)

Safety Data

• Hazardous Substances Data: 75983-36-7(Hazardous Substances Data)

Usage

General Description

4,8-dimethyldecanal is a naturally occurring organic compound primarily found in citrus fruits, characterized by its strong, sweet, and citrus-like aroma. 4,8-dimethyldecanal belongs to the family of Aldehydes, specifically the Aliphatic Acyclic Aldehydes. 4,8-dimethyldecanal is used in the food and beverage industry to give a fruity and citrus flavor, while in the cosmetic industry, it's used as a fragrance ingredient. This substance is typically synthesized in a laboratory setting for industrial usage, but it is also naturally formed during the ripening process of certain citrus fruits, including oranges and mandarins. Despite its common usage, there are concerns about its potential toxicity and allergenic effects, and therefore its usage is regulated in cosmetics and food products.

InChI:InChI=1/C12H24O/c1-4-11(2)7-5-8-12(3)9-6-10-13/h10-12H,4-9H2,1-3H3

Synthetic route

4,8-dimethyl-1,1-dimethoxydecane (106445-80-1) → 4,8-dimethyldecan-1-al (75983-36-7)

Conditions	Yield
With water; pyridinium p-toluenesulfonate In acetone Heating;	80%

2,6,10-trimethyldodecane-2,3-diol (114088-43-6) → 4,8-dimethyldecan-1-al (75983-36-7)

Conditions	Yield
With periodic acid dihydrate In tetrahydrofuran at 0 - 5℃; for 0.333333h;	73%

4,8-Dimethyldecan-1-ol (28339-05-1) → 4,8-dimethyldecan-1-al (75983-36-7)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane for 1h; Ambient temperature;	68%
With pyridinium chlorochromate In dichloromethane at 20 - 22℃; for 3h;	67%
With pyridinium chlorochromate In dichloromethane for 1h; Ambient temperature; Yield given;
With pyridinium chlorochromate In dichloromethane

Upstream product

• 28339-05-1 4,8-Dimethyldecan-1-ol 
• 19198-88-0 4-methyl-3-hexenyl bromide 
• 114088-43-6 2,6,10-trimethyldodecane-2,3-diol 
• 63526-71-6 p-toluenesulfonic acid 2-methylbutyl ester 
• 106-23-0 3,7-dimethyl-oct-6-enal 
• 28339-05-1 4,8-dimethyldecan-1-ol 
• 106445-80-1 4,8-dimethyl-1,1-dimethoxydecane 
• 105485-71-0 ethyl 2-carbethoxy-4,8-dimethyldecanoate 
• 105485-68-5 ethyl 4,8-dimethyldecanoate 
• 105485-65-2 rhodinal 
• 245118-38-1 (2R/S,6S)-(+)-2,6-dimethyl-1-octanol 
• 105500-65-0 1-bromo-2,6-dimethyloctane 
• 105485-66-3 2,6-dimethyl-1-octene 
• 110659-29-5 (R)-2-methyl-3-buten-2-yl tosylate 

Downstream Products

• 87106-39-6 4(RS),8(S)-dimethyldecanal dimethyl acetal 

Relevant articles and documents

PHEROMONES OF INSECTS AND THEIR ANALOGS. XXVII. SYNTHESIS OF 10-HYDROXY-4,8-DIMETHYLDECA-4E,8E-DIENOIC ACID AND OF RACEMIC 4,8-DIMETHYLDECANAL FROM GERANYL ACETATE

10-Hydroxy-4,8-dimethyldeca-4E,8E-dienoic acid and racemic 4,8-dimethyldecanal (components of beetle pheromones) have been synthesized from geranyl acetate.

Deuterated analogues of 4,8-dimethyldecanal, the aggregation pheromone of Tribolium castaneum: Synthesis and pheromonal activity

To elucidate the deuterium isotope effect (DIE) in pheromonal activity and to investigate the biosynthetic pathway of 4,8-dimethyldecanal (4,8-DMD; 1), the aggregation pheromone of the red flour beetle (Tribolium castaneum), deuterated analogues of 4,8-DMDs (2, 3, 4, and 5), were synthesized and their pheromonal activities were tested using a two-hole pitfall olfactometer. Although no apparent DIE was observed in their pheromonal activities, 4,8-DMD-1-d 1 (2) was less attractive than other analogues, which suggested that the bond distance between the formyl group of 1 and its receptor was critical in pheromone recognition by T. castaneum. Copyright 2004 John Wiley & Sons, Ltd.

OZONOLYSIS OF ALKENES AND THE REACTIONS OF POLYFUNCTIONAL COMPOUNDS LII. SELECTIVE OZONOLYSIS OF (E)-2,7-OCTADIENAL AND (E)-3,7-DIMETHYL-2,6-OCTADIENAL IN THE SYNTHESIS OF INSECT PHEROMONES

The partial ozonolysis of (E)-2,7-octadienal and (E)-3,7-dimethyl-2,6-octadienal led to (E)-7,7-dimethoxy-2-heptenal and (E)-1,6-diacetoxy-3-methyl-2-hexene.The products were used for the synthesis of (5E,7Z)-5,7-dodecadienal and the corresponding alcohol and acetate , 4,8-dimethyldecanal , and (E)-4-methyl-1,1-dimethoxy-8-oxo-4-nonene .