2442-10-6

Basic information

• Product Name: 1-Octen-3-yl acetate
• Synonyms: OCT-1-EN-3-YL ACETATE;OCTENYL ACETATE;1-Octen-3-ol,acetate;1-pentylallylacetate;amylvinylcarbinolacetate;Octen-3-yl acetate;AMYL VINYL CARBINYL ACETATE;FEMA 3582
• CAS NO: 2442-10-6
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.25
• EINECS: 219-474-7
• Product Categories: ester Flavor
• Mol File: 2442-10-6.mol

Chemical Properties

• Melting Point: -89.9°C (estimate)
• Boiling Point: 80 °C15 mm Hg(lit.)
• Flash Point: 165 °F
• Appearance: /
• Density: 0.878 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.213mmHg at 25°C
• Refractive Index: n20/D 1.425(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-Octen-3-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Octen-3-yl acetate(2442-10-6)
• EPA Substance Registry System: 1-Octen-3-yl acetate(2442-10-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36
• WGK Germany: 3
• RTECS: RH3320000
• Hazardous Substances Data: 2442-10-6(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
1-Octen-3-yl acetate is used as a flavoring agent for its green, earthy, and waxy dairy-like taste with unripe fruity nuances. It is particularly useful in the creation of flavors for the food and beverage industry, where it can enhance the natural taste of various products.
1-Octen-3-yl acetate is also used as a fragrance ingredient due to its characteristic odor reminiscent of lavender and lavandin. It is commonly utilized in the perfumery and cosmetics industry to create unique and pleasant scents for perfumes, colognes, and other fragranced products.
Used in the Chemical Industry:
1-Octen-3-yl acetate can be used as a chemical intermediate in the synthesis of various compounds. Its unique chemical properties, such as its metallic, mushroom-like odor, make it a valuable component in the development of new chemicals with specific applications in different industries.

Preparation

By acetylation of amyl vinyl carbinol.

Safety Profile

Moderately toxic by ingestion.Slightly toxic by skin contact. When heated todecomposition it emits acrid smoke and irritating vapors.

InChI:InChI=1/C10H18O2/c1-4-6-7-8-10(5-2)12-9(3)11/h5,10H,2,4,6-8H2,1,3H3

Upstream product

• 3391-86-4 1-octen-3-ol 
• 108-24-7 acetic anhydride 
• 111-67-1 2-octene 
• 64-19-7 acetic acid 
• 111-66-0 oct-1-ene 
• 107-71-1 tert-butyl peroxyacetate 
• 4312-99-6 oct-1-en-3-one 
• 1363906-80-2 1-acetyl-2,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidinium tetraphenylborate 
• 693-25-4 n-pentylmagnesium bromide 
• 66-25-1 hexanal 
• 75-36-5 acetyl chloride 
• 108-22-5 Isopropenyl acetate 
• 3913-80-2 (E)-2-octen-1-yl acetate 
• 26806-12-2 (Z)-oct-2-en-1-yl acetate 

Downstream Products

• 70729-12-3 [Bis-(4-methoxy-phenyl)-methyl]-((E)-oct-2-enyl)-amine 
• 70729-13-4 [Bis-(4-methoxy-phenyl)-methyl]-(1-vinyl-hexyl)-amine 
• 70729-14-5 [Bis-(4-methoxy-phenyl)-methyl]-bis-((E)-oct-2-enyl)-amine 
• 57602-94-5 (E)-4-decenoic acid 
• 55454-06-3 E,Z-2-octen-1-yl phenyl sulfone 
• 76649-16-6 ethyl trans-4-decenoate 
• 109756-10-7 ethyl 3-vinyloctanoate 
• 3391-86-4 (S)-oct-1-en-3-ol 
• 22658-80-6 (R)-(+)-1-pentyl-2-propenyl acetate 
• 26806-12-2 (Z)-oct-2-en-1-yl acetate 
• 3913-80-2 (E)-2-octen-1-yl acetate 
• 3391-86-4 (R)-1-octene-3-ol 
• 4312-99-6 oct-1-en-3-one 
• 3391-86-4 1-octen-3-ol 

Relevant articles and documents

Ozonolysis of acetic acid 1-vinyl-hexyl ester in a falling film microreactor

Ozonolysis of acetic acid 1-vinyl-hexyl ester was carried out in a falling film microreactor in a continuous fashion. The influence of reaction variables (e.g., olefin concentration, ozone initial partial pressure, gas velocity, temperature and liquid flow rate) on the product formation in the liquid phase was studied over a wide range of operating conditions. Based on the obtained results, a formal reaction scheme for the ozonolysis of acetic acid 1-vinylhexyl ester is suggested. The acetic acid 1-formyl-hexyl ester and the corresponding carbonyl oxide are the main products of the cleavage of the primary formed ozonide. The secondary ozonide acetic acid 1-[1,2,4]trioxolan-3-yl-hexyl ester is formed by consecutive reaction of the acetic acid 1-formyl-hexyl ester and the carbonyl oxide.

Protection of COOH and OH groups in acid, base and salt free reactions

We report an iron-catalyzed general functional group protection method with inexpensive reagents. This environmentally benign process does not use acids or bases, and does not produce waste products. Further purification beyond filtration and evaporation is, in most cases, unnecessary. Free COOH and OH groups can be protected in a one-pot reaction.

Proton-gradient-transfer acid complexes and their catalytic performance for the synthesis of geranyl acetate

Special proton-gradient-transfer acid complexes (PGTACs) in which the bonded protons are not equivalent and have gradients in transfer ability, acidity, and reactivity were reported. The acidity gradient of the protons gave the PGTACs excellent catalytic activity and selectivity in the esterification of terpenols. These PGTACs are “reaction-induced self-separation catalysts” and can be easily reused. The kinetics with PGTACs as catalyst in the esterification of geraniol were also studied for use in engineering design.

Branch-selective allylic C-H carboxylation of terminal alkenes by pd/sox catalyst

A ligand-controlled branch-selective allylic C-H carboxylation through Pd catalysis is described. The developed catalytic system, which consists of Pd(OAc)2, sulfoxide-oxazoline (sox) as a ligand and benzoquinone as an oxidant, couples terminal alkenes and carboxylic acids to furnish the corresponding branched allylic esters with high regioselectivity.

Palladium-catalyzed selective anti-markovnikov oxidation of allylic esters

An aldol alternative: The palladium(II)-catalyzed anti-Markovnikov oxidation of allylic esters to aldehydes at room temperature provides a viable alternative to valuable cross aldol products. High regioselectivity towards the aldehyde product was achieved using the ester protecting group for the allylic alcohol. Rapid isomerization and the much higher rate of oxidation of the branched isomer result in the same product forming from both linear and branched allylic esters. Copyright

Syntheses of enantiopure aliphatic secondary alcohols and acetates by bioresolution with lipase B from candida antarctica

The lipase B from Candida antarctica (Novozym 435, CALB) efficiently catalyzed the kinetic resolution of some aliphatic secondary alcohols: (±)-4-methylpentan- 2-ol (1), (±)-5-methylhexan-2-ol (3), (±)-octan-2-ol (4), (±)-heptan-3-ol (5) and (±)-oct-1- en-3-ol (6). The lipase showed excellent enantioselectivities in the transesterifications of racemic aliphatic secondary alcohols producing the enantiopure alcohols (>99% ee) and acetates (>99% ee) with good yields. Kinetic resolution of rac-alcohols was successfully achieved with CALB lipase using simple conditions, vinyl acetate as acylating agent, and hexane as non-polar solvent.

N-acyl 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) tetraphenylborate salts as O-acylating agents

Air-stable and crystalline N-acyl DBN tetraphenylborate salts have been shown to be effective O-acylating agents, reacting with both primary and secondary alcohols to give the corresponding esters in good yields. In the case of diols, the N-acyl DBN·BPh4 salts have been shown to acylate regioselectively the primary alcohol functionality in the presence of a secondary alcohol. The DBN hydrotetraphenylborate side product can be readily removed by filtration, providing the ester products without the need for further purification.

Highly efficient kinetic resolution of allylic alcohols with terminal double bond

In this study, the lipase-catalyzed kinetic resolution (Novozyme 435) was employed to prepare chiral allylic alcohols and acetates with terminal double bonds in enantiomeric excesses ranging from 94 to >99 %.

o-benzenedisulfonimide as a soft, efficient, and recyclable catalyst for the acylation of alcohols, phenols, and thiols under solvent-free conditions: Advantages and limitations

o-Benzenedisulfonimide turns out to be a highly efficient Bransted acid catalyst for the acylation of a number of alcohols, phenols, and thiols under a metal- and solvent-free procedure; reaction conditions are mild and yields very good. After the workup, the catalyst can be easily recovered and purified, ready to be reused, with economic and ecological advantages. Georg Thieme Verlag Stuttgart · New York.

Unified, radical-based approach for the synthesis of spiroketals

Functionalization of S-(3-chloro-2-oxo-propyl)-O-ethyl xanthate 1 by two consecutive xanthate transfer reactions, followed by spirocyclization of the resulting dihydroxy ketones, provides a flexible and highly convergent access to diversely substituted spiroketals, containing five-, six-, and seven-membered rings.