106-72-9

Basic information

• Product Name: 2,6-Dimethyl-5-heptenal
• Synonyms: ,6-Dimethyl hept-5-en-1-al;2,6-dimethyl-5-heptena;2,6-dimethylhept-;2,6-dimethylhept-5-en-1-al;2,6-dimethylhept-5-enal;ai3-33278;nsc78450;Dimethylheptenal
• CAS NO: 106-72-9
• Molecular Formula: C₉H₁₆O
• Molecular Weight: 140.22
• EINECS: 203-427-2
• Mol File: 106-72-9.mol

Chemical Properties

• Boiling Point: 116-124 °C100 mm Hg(lit.)
• Flash Point: 141 °F
• Appearance: /Liquid
• Density: 0.879 g/mL at 25 °C
• Vapor Pressure: 0.622mmHg at 25°C
• Refractive Index: n20/D 1.444(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: Soluble in alcohol, paraffin oil. Insoluble in water.
• Sensitive: Air Sensitive
• CAS DataBase Reference: 2,6-Dimethyl-5-heptenal(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dimethyl-5-heptenal(106-72-9)
• EPA Substance Registry System: 2,6-Dimethyl-5-heptenal(106-72-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 1987
• WGK Germany: 2
• RTECS: MJ8797000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 106-72-9(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
2,6-Dimethyl-5-heptenal is used as a perfuming agent for fragrances designed to have a special fruity note tending towards melon, cucumber, and pumpkin. It is mainly used in creating melon and cucumber notes, adding a fresh and green scent to various fragrance types.
Used in Flavor Industry:
2,6-Dimethyl-5-heptenal is used as a flavoring agent, providing green, melon, watermelon-rind, and cucumber taste characteristics with a waxy, chemical, and floral nuance. It has a taste threshold value of 50 ppm.
Occurrence:
2,6-Dimethyl-5-heptenal has been reported to be found in lemon and lime peel oil, sudachi (Citrus sudachi H. ex. Shirai), and ginger.

Preparation

By condensation of isobutyric aldehyde with α-methylcrotonaldehyde, followed by par tial hydrogenation; also from methylheptenone through Darzen's reaction.

Flammability and Explosibility

Notclassified

Trade name

Melonal (Givaudan), Melomor (Aromor).

Safety Profile

skin and eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C9H16O/c1-8(2)5-4-6-9(3)7-10/h5,7,9H,4,6H2,1-3H3/t9-/m1/s1

Upstream product

• 77963-77-0 2,4,4-trimethyl-1,5-hexadien-3-ol 
• 4434-77-9 2-bromo-6-methylhept-5-ene 
• 68-12-2 N,N-dimethyl-formamide 
• 4234-93-9 2,6-dimethyl-5-hepten-1-ol 
• 266329-33-3 2,6-dimethyl-1-(dimethylphenylsilyl)hept-5-enyl nitrite 
• 75033-21-5 2,3-epoxy-3,7-dimethyl-oct-6-enoic acid ethyl ester 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 96619-86-2 3,4-dimethyl-6-ene-2,3-epoxyoctanoic acid methyl ester 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 65416-36-6 3,7-dimethyl-6-ene-2,3-epoxyoctanoic acid 
• 116-11-0 2-Methoxypropene 
• 105-39-5 chloroacetic acid ethyl ester 
• 122616-29-9 (1S,4R,6R,8R)-4-((R)-1,5-Dimethyl-hex-4-enyl)-11,11-dimethyl-5-oxa-3-thia-tricyclo[6.2.1.0^1,6]undecane 

Downstream Products

• 542-30-3 1,2-dihydrolinalool 
• 82009-61-8 (+/-)-1r-methyl-3c-isopropyl-cyclopentanol-(2t) 
• 66575-33-5 trans-2-Isopropyl-5-methyl-cyclopentanon 
• 81980-09-8 (1R,2S,5S)-2-(1,1-Dimethyl-propyl)-5-methyl-cyclopentanol 
• 66575-34-6 (2R,5R)-2-Isopropyl-5-methyl-cyclopentanone 
• 131929-41-4 (E)-4,8-dimethyl-1-(phenylsulfonyl)-1,7-nonadien-3-ol 
• 118268-20-5 C₁₇H₂₆FNO₂S 
• 142505-23-5 1-(4-tertiobutyl)phenyl-3,7-dimethyl-6-octen-2-ol 
• 75265-33-7 4-methyl-4-(4-methylpent-3-en-1-yl)cyclohex-2-en-1-one 
• 227624-37-5 2,6-dimethyl-1-(dimethylphenylsilyl)hept-5-en-1-ol 

Relevant articles and documents

Stereochemistry of female-specific normonoterpenes, sex pheromone candidates from the acarid mite, Tyreophagus sp. (Astigmata: Acaridae)

Two normonoterpenes were detected from an unidentified Tyreophagus sp. as new female-specific components. Both planar structures were identified to be 2,6-dimethyl-5-heptenal (1) and 2,6-dimethyl-5-hepten- 1-ol (2) by GC/MS co-chromatography with synthetic 1 and 2. The stereochemistry of 2 was determined to be R by a GC analysis with a chiral column, while that of 1 was presumed to be similar to 2 based on the biosynthetic aspects.

Aromatic aldols and 1,5-diketones as optimized fragrance photocages

Aromatic aldols and 1,5-diketones with abstractable γ-hydrogen atoms are highly photoactive cage molecules for the release of fragrance carbonyl compounds (aldehydes and Michael ketones, respectively). Aldols 3a-d are easily accessible by Mukaiyama addition and are cleaved to form the substrates with high quantum yields under solar radiation. By tuning the properties of the chromophores, a series of δ-damascone cages 5 were developed that can be used for selective and fast (5a,e) or slow (5b,d) release of fragrances under air and solar irradiation. The intermediates of the Norrish II process were observed by laser transient absorption spectroscopy.

Semiochemicals of the scarabaeinae. VII: Identification and synthesis of ead-active constituents of abdominal sex attracting secretion of the male dung beetle, Kheper subaeneus

Using gas chromatography with flame ionization detection (FID) and electroantennographic detection (EAD) in parallel, butanoic acid, skatole, and (E)-2,6-dimethyl-6-octen-2-ol were identified as constituents of the abdominal sex-attracting secretion of the male dung beetle, Kheper subaeneus, which reproducibly elicited EAD responses in male and female antennae. This is the first report of the occurrence of (E)-2,6-dimethyl-6-octen-2-ol as a natural product, for which the name (E)-subaeneol is proposed. In some experiments, a few other constituents of the secretion also gave reproducible responses in specific male and female antennae but did not elicit responses when the analyses were repeated with other antennae. The major volatile constituent of the secretion, identified as (S)-(+)-2,6-dimethyl-5-heptenoic acid, is one of these EAD-active compounds. Both this compound and (E)-2,6-dimethyl-6-octen-2-ol were synthesized from authentic starting materials for comparison with the natural products.

A New Family of Rigid Dienone Musks Challenges the Perceptive Range of the Human Olfactory Receptor OR5AN1

A new family of dienone musks was discovered by alkylation of different aldehydes with but-3-en-1-yn-1-yllithium and subsequent domino reaction of a Saucy-Marbet transfer vinylation-Claisen rearrangement with an intramolecular Diels-Alder reaction, and concluding Lewis acid catalyzed double-bond isomerization. The newly synthesized dienone structures possess pleasant musk odors displaying fatty, slightly fruity and green facets. Although the dienone musks were predicted in silico to bind to the OR5AN1 receptor based on QM/MM calculations, they were found to be inactive in the in vitro assay. The latter results suggest that the OR5AN1 receptor is not the prime musk receptor but primarily responsible for the animalic character of certain macrocyclic ketones and nitro musks.

Preparation method of epoxy caprylate and preparation method of melonal

The invention relates to a preparation method of epoxy caprylate and a preparation method of melonal. The preparation method of the epoxy caprylate comprises the steps of in a solvent, in the presence of a first alkaline substance and a first catalyst, carrying out a Darzens reaction on methyl heptenone and alpha-halogenated acetate to obtain a first reaction solution; and separating the first reaction solution to obtain epoxy caprylate, wherein the first catalyst comprises transition metal ions and a Schiff base ligand combined with the transition metal ions, and the structure of the Schiff base ligand is shown in a formula I defined in the description. According to the preparation method of the epoxy caprylate, the raw materials are good in safety, the reaction conditions are mild, melonal is prepared on the basis of the preparation method of the epoxy caprylate, the first reaction solution can be directly subjected to saponification, acidification and decarboxylation reactions without purification, and the prepared melonal has excellent purity and yield.

A study towards the synthesis of (-)-atrop-abyssomicin C core

An attempt to synthesize the cyclohexane core of antibiotic abyssomicin C is described. The initial, protecting group-free approach (relying on internal protection) failed and had to be modified, in order to allow for efficient deprotection of the acid-sensitive cyclization precursor in the penultimate synthetic step. Thus, a pyranoside structural unit was used as a latent lactone/ester functionality, which was deprotected via thioacetalization/hydrolysis/oxidation sequence, to give the δ-valerolactone-type cyclization precursor. Unfortunately, the key cyclization reaction was not feasible, even after structural modification of the cyclization precursor. Reluctance towards cyclization turned out to be a general property of (at least some) Δ7-unsaturated esters, which required the development of a new strategy for this type of transformation.

Preparation method of muskmelon aldehyde, muskmelon aldehyde and application thereof

The invention relates to a preparation method of muskmelon aldehyde, muskmelon aldehyde and an application thereof, the preparation method comprises the following steps: carrying out a Darzen condensation reaction on 6-methyl-5-heptene-2-ketone, chloroacetate and an acid-binding agent under the condition of adding a solvent and a phase transfer catalyst to obtain epoxy caprylate; and saponifying the obtained epoxy caprylate in an aqueous solution of alkali to generate corresponding salt, acidifying with acid to obtain 3, 7-dimethyl-6-ene-2, 3-epoxy caprylic acid, carrying out a reduced pressure decarboxylation reaction on 3, 7-dimethyl-6-ene-2, 3-epoxy caprylic acid, and adding a mixture composed of an antioxidant and a polymerization inhibitor to obtain the muskmelon aldehyde product. Theconditions of the preparation method are easier to control, the production is safer, the yield is higher, and the product purity is high.

Process for industrially producing muskmelon aldehyde

The invention discloses a process for industrially producing muskmelon aldehyde. 1-methyl-3-propylimidazolium hexafluorophosphate ionic liquid is used as a catalyst and a solvent, methyl 3,7-dimethyl-6-ene-2,3-epoxy caprylate is used for obtaining the melonal in one step, and meanwhile, through sectional heating reaction control, the reaction selectivity and the catalytic reaction rate can be improved, the reaction is effectively promoted, and the yield of the melonal is increased and can reach 95% or above. According to the process provided by the invention, the use of hydrogen bromide or hydroiodic acid with strong corrosivity is avoided, the requirements on equipment materials are reduced, the product is easy to separate, the operation is simple and convenient, and the industrial production is facilitated.

PROCESS FOR THE MANUFACTURE OF 2,6-DIMETHYL-5-HEPTEN-1-AL

The present invention relates to an improved process for the manufacture of 2,6-dimethyl-5-hepten-1-al.

Method for preparing melonal

The invention discloses a method for preparing melonal. Under the action of hydroiodic acid or hydrobromic acid, 3,7-dimethyl-6-alkene-2,3-epoxy methyl caprylate reacts, thereby acquiring the melonal. According to the invention, hydroiodic acid or hydrobromic acid is used for replacing the alkaline condition in the prior art, the hydrolysis is directly performed and the melonal is acquired in one step through epoxy acid methyl ester, and the steps of acidification and decarboxylation are omitted, so that the operation is simple, the waste salt problem of the prior art is avoided, the equipment investment is lowered and the method is convenient for industrial production.