75983-36-7

Usage

Uses

Used in Food and Beverage Industry:
4,8-dimethyldecanal is used as a flavoring agent to impart a fruity and citrus taste to various food and beverage products. Its natural occurrence in citrus fruits makes it a popular choice for enhancing the flavor of these types of products.
Used in Cosmetic Industry:
In the cosmetic industry, 4,8-dimethyldecanal is utilized as a fragrance ingredient. Its strong, sweet, and citrus-like aroma makes it a desirable component in the formulation of various cosmetic products.
However, it is important to note that due to concerns about its potential toxicity and allergenic effects, the use of 4,8-dimethyldecanal is regulated in both the cosmetics and food products industries. This ensures that its application is safe and does not pose any health risks to consumers.

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 
• 78774-68-2 (6R/S,10R/S)-2,6,10-trimethyl-2-dodecene 
• 106445-80-1 4,8-dimethyl-1,1-dimethoxydecane 
• 86414-51-9 1-bromo-3,7-dimethylnonane 
• 68-12-2 N,N-dimethyl-formamide 
• 80699-61-2 2,3-epoxy-2,6,10-trimethyldodecane 
• 63284-81-1 1,1-dimethoxy-4-methyl-8-oxonon-4Z-ene 
• 106-22-9 Citronellol 
• 4895-14-1 citronellylbromide 
• 19198-88-0 4-methyl-3-hexenyl bromide 
• 4433-36-7 6,10-dimethyl-9-undecen-2-one 
• 155504-36-2 ethyl 4,8-dimethyldecanoate 
• 22661-89-8 ethyl 3,7,11-trimethyl-2,10-dodecadienoate 
• 137-32-6 (+/-)-2-methyl-1-butanol 

Downstream Products

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

Relevant academic research and scientific papers

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.

Pheromone synthesis. Part 259: Synthesis of seven methyl-branched hydrocarbons as the pheromone candidates for female Korean apricot wasp, Eurytoma maslovskii

Seven new methyl-branched hydrocarbons were synthesized, which were the pheromone candidates of the female Korean apricot wasp (Eurytoma maslovskii). They are (Z)-15-methyl-7-nonacosene (1), (Z)-17-methyl-7-hentriacontene (2), 3,7-dimethylheptacosane (3), 8,12-dimethyltriacontane (4), 8,18-dimethyltriacontane (5), 3,7,11-trimethylnonacosane (6), and 3,7,17-trimethylnonacosane (7). All of them were synthesized as stereoisomeric mixtures, employing short and simple routes. Hydrocarbon 7 was synthesized via 4,8-dimethyldecanal (71, tribolure), the red flour beetle pheromone. The hydrocarbons 1,2,3 and 6 were identified by GC–MS analysis as the components (with unknown stereochemistry) of the female-specific secretion of E. maslovskii.

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.

A CONVENIENT SYNTHESIS OF RACEMIC 4,8-DIMETHYLDECANAL, THE AGGREGATION PHEROMONE OF Tribolium castaneum AND Tribolium confusum

A convenient synthesis of racemic 4,8-dimethyldecanal, which is the aggregation pheromone of Tribolium castaneum and Tribolium confusum, by hydrolytic cleavage of 1-furyl-3-methyl-1-pentanol is described.

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 .

PHEROMONES OF INSECTS AND THEIR ANALOGS. XX. METHYL-BRANCHED PHEROMONES BASED ON 4-METHYLTETRAHYDROPYRAN. I. SYNTHESIS OF RACEMIC 4,8-DIMETHYLDECANAL - THE PHEROMONE OF THE FLOUR BEETLES Tribolium confusum AND Tribolium castaneum

A synthesis is proposed of 4,8-dimethyldecanal (VIII) - a pheromone of the flour beetles Tribolium confusum and T. castaneum.By heating 71.2 g of 4-methyltetrahydropyran (I), 83.2 g of AcBr and 1.57 g ZnCl2 (45 deg C , then 120 deg C, 2h), 1-acetoxy-5-bromo-3-methylpentane (II) was obtained.The hydrolysis of 19.8 g of (II) ( MeOH-H2O, TsOH, 20 deg C, 15h) gave 5-bromo-3-methylpentan-1-ol (III).From 18.1 g of (III) and 38.9 ml of 2,3-dihydropyran (Et2O, TsOH, 20 deg C, 20h) was obtained the 2-THPL ester of (III), (IV), which was converted into 3-methyloct-7-en-1-ol (V) by the treatment of the corresponding Grignard reagent with allyl bromide (THF, CuI-bi-2-pyridyl, 2 deg C, 4 h, Ar).The interaction of 1.42 g of (V) with Et3Al (hexane, 20 deg C, Cp2ZrCl2, Ar) gave 3,7-dimethylnonan-1-ol (VI), boiling which with 48percent HBr in the presence of concentrated H2SO4 gave 1-bromo-3,7-dimethylnonane (VII) which was then converted into the desired (VIII) by the reaction of the corresponding Grignard reagent with DMFA ( 0-2 deg C, 1 h; 20 deg C, 2h; Ar).The characteristics of the compounds - yield (percent), nD (deg C): (I), 79, 1.4340 (22); (III) 89, 1.4660 (23); (IV), 82, 1.4739 (23); (V), 85, -; (VI) , 90, 1.4483 (20); (VII), 88, 1.4409 (22); (VIII), 88, 1.4589 (22).Details of the IR and PMR spectra of the compounds (II) - (VII) are given.

A NEW SYNTHESIS OF (4R,8R)-4,8-DIMETHYLDECANAL - THE PHEROMONE OF THE MEAL WORMS Tribolium confusum AND Tribolium castaneum

A method of synthesis was developed for (4R,8R)-4,8-dimethyldecanal - the aggregation pheromone of the meal worms Tribolium confusum and T. castaneum.It contains altogether 12 stages and uses (R)-(+)-5-acetoxy-4-ethylpentanoic acid and (S)-(+)-3,7-dimethyl-1,6-octadiene as the initial chiral compounds.The overall yield of the pheromone amounted to 27percent on the initial acid or 15percent on the initial diene.The optical purity of the chiral centers C-4 and C-8 in the molecule of the pheromone was estimated as ca. 55 and ca. 97percent respectively.

OZONOLYSIS OF ALKENES AND REACTIONS OF POLYFUNCTIONAL COMPOUNDS. XXVIII. SYNTHESIS OF RACEMIC HOMO- AND BISHOMODIHYDROCITRONELLALS

A five-stage synthesis was developed for racemic 4,8-dimethylnonanal and diastereomeric 4,8-dimethyldecanal (attractants of meal worms Tribolium castaneum, T. confusum) from dimethylcyclooctadiene.

Synthesis of 4(RS),8(S)-Dimethyldecanal: An Aggrigation Pheromone of Red Flour Beetles

A simple and straight forward synthesis of the pheromone 4(RS),8(S)-dimethyldecanal (IX) has been described starting from 7-hydroxycitronellal (I).