1577-19-1

Basic information

• Product Name: 3-OCTENOIC ACID
• Synonyms: TRANS-3-OCTENOIC ACID;3-OCTENOIC ACID;Octenoicacid;oct-3-enoic acid;3-OCTENOIC ACID TECH 85%;3-OCTENOIC ACID 95+%;3-Octenoic acid, tech. 85%
• CAS NO: 1577-19-1
• Molecular Formula: C₈H₁₄O₂
• Molecular Weight: 142.2
• EINECS: 216-418-3
• Product Categories: Fatty & Aliphatic Acids, Esters, Alcohols & Derivatives
• Mol File: 1577-19-1.mol

Chemical Properties

• Melting Point: 1.7°C (estimate)
• Boiling Point: 237-240°C
• Flash Point: >110 °C
• Appearance: /
• Density: 0.9565 (rough estimate)
• Refractive Index: 1.4420-1.4470
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 3-OCTENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-OCTENOIC ACID(1577-19-1)
• EPA Substance Registry System: 3-OCTENOIC ACID(1577-19-1)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: 3265
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 1577-19-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
3-Octenoic acid is used as a synthetic building block for creating various chemical compounds and materials. Its unique structure and properties make it a valuable component in the synthesis of different products.
Used in Pharmaceutical Industry:
3-Octenoic acid is used as an active pharmaceutical ingredient or an intermediate in the development of drugs, taking advantage of its bioactive properties and natural occurrence in certain plant extracts.
Used in Flavor and Fragrance Industry:
3-Octenoic acid is used as a component in the flavor and fragrance industry, leveraging its medium strength, fatty type odor to enhance or create specific scents and flavors in various products.
Used in Cosmetics Industry:
3-Octenoic acid is used as an ingredient in the cosmetics industry, where its fatty nature and bioactive properties can contribute to the formulation of skincare and personal care products, potentially offering benefits such as moisturization and skin conditioning.

Synthesis Reference(s)

Canadian Journal of Chemistry, 44, p. 2241, 1966 DOI: 10.1139/v66-339

Upstream product

• 18185-81-4 cis-3-octen-1-ol 
• 64-19-7 acetic acid 
• 693-02-7 hex-1-yne 
• 141-82-2 malonic acid 
• 142-62-1 hexanoic acid 
• 66-25-1 hexanal 
• 592-76-7 1-Heptene 
• 124-38-9 carbon dioxide 
• 4360-85-4 hexylidene-malonic acid 
• 1117-65-3 ethyl 3-octenoate 
• 103499-82-7 trans-3-octenoic acid nitrile 
• 4938-52-7 1-hepten-3-ol 
• 201230-82-2 carbon monoxide 
• 78693-34-2 (Z)-deca-1,5-dien-3-ol 

Downstream Products

• 30336-14-2 5-butylfuran-2(5H)-one 
• 104-50-7 gamma-octalactone 

Relevant articles and documents

Enantioselective Alkylamination of Unactivated Alkenes under Copper Catalysis

An enantioselective addition reaction of various alkyl groups to unactivated internal alkenes under Cu catalysis has been developed. The reaction uses amide-linked aminoquinoline as the directing group, 4-alkyl Hantzsch esters as the donor of alkyl radicals, and rarely used biaryl diphosphine oxide as a chiral ligand. β-lactams featuring two contiguous stereocenters at Cβ and the β substituent can be obtained in good yield with excellent enantioselectivity. Mechanistic studies indicate that a nucleophilic addition of the alkyl radical to CuII-coordinated alkene is the enantio-determining step.

Palladium-Catalyzed Low Pressure Carbonylation of Allylic Alcohols by Catalytic Anhydride Activation

A direct carbonylation of allylic alcohols has been realized for the first time with high catalyst activity at low pressure of CO (10 bar). The procedure is described in detail for the carbonylation of E-nerolidol, an important step in a new BASF-route to (?)-ambrox. Key to high activities in the allylic alcohol carbonylation is the finding that catalytic amounts of carboxylic anhydride activate the substrate and are constantly regenerated with carbon monoxide under the reaction conditions. The identified reaction conditions are transferrable to other substrates as well.

Iridium-Catalyzed γ-Selective Hydroboration of γ-Substituted Allylic Amides

Reported here for the first time is the Ir-catalyzed γ-selective hydroboration of γ-substituted allylic amides under mild reaction conditions. A variety of functional groups could be compatible with reaction conditions, affording γ-branched amides in good yields with ≤97% γ-selectivity. We have also demonstrated that the obtained borylated products could be used in a series of C-O, C-F, C-Br, and C-C bond-forming reactions.

PROCESS FOR THE PREPARATION OF UNSATURATED CARBOXYLIC ACIDS BY CARBONYLATION OF ALLYL ALCOHOLS AND THEIR ACYLATION PRODUCTS

The present invention relates to a process for carbonylating allyl alcohols at low temperature, low pressure and/or low catalyst loading. In an alternative embodiment, an acylation product of the allyl alcohol is used for the carbonylation. The present invention likewise relates to the preparation of conversion products of these carbonylation products and specifically of (?)-ambrox.

Iridium-Catalyzed Distal Hydroboration of Aliphatic Internal Alkenes

The regioselective hydroboration of aliphatic internal alkenes remains a great challenge. Reported herein is an iridium-catalyzed hydroboration of aliphatic internal alkenes, providing distal-borylated products in good to excellent yields with high regioselectivity (up to 99:1). We also demonstrate that the C?B bond of the distal-borylated product can be readily converted into other functional groups. DFT calculations indicate that the reaction proceeds through an unexpected IrIII/IrV cycle.

Structure-Odor Relationships of (Z)-3-Alken-1-ols, (Z)-3-Alkenals, and (Z)-3-Alkenoic Acids

(Z)-3-Unsaturated volatile acids, alcohols, and aldehydes are commonly found in foods and other natural sources, playing a vital role in the attractiveness of foods but also as compounds with chemocommunicative function in entomology. However, a systematic investigation of their smell properties, especially regarding humans, has not been carried out until today. To close this gap, the odor thresholds in air and odor qualities of homologous series of (Z)-3-alken-1-ols, (Z)-3-alkenals, and (Z)-3-alkenoic acids were determined by gas chromatography-olfactometry. It was found that the odor qualities in the series of the (Z)-3-alken-1-ols and (Z)-3-alkenals changed, with increasing chain length, from grassy, green to an overall fatty and citrus-like, soapy character. On the other hand, the odor qualities of the (Z)-3-alkenoic acids changed successively from cheesy, sweaty via plastic-like, to waxy in their homologous series. With regard to their odor potencies, the lowest thresholds in air were found for (Z)-3-hexenal, (Z)-3-octenoic acid, and (Z)-3-octenal.

A Light/Ketone/Copper System for Carboxylation of Allylic C-H Bonds of Alkenes with CO2

A photo-induced carboxylation reaction of allylic C-H bonds of simple alkenes with CO2 is prompted by means of a ketone and a copper complex. The unique carboxylation reaction proceeds through a sequence of an endergonic photoreaction of ketones with alkenes forming homoallyl alcohol intermediates and a thermal copper-catalyzed allyl transfer reaction from the homoallyl alcohols to CO2 through C-C bond cleavage. An allylic C-H bond of simple alkenes is carboxylated with CO2 in the presence of a substoichiometric amount of a ketone and a catalytic amount of a copper complex under UV irradiation (see scheme).

Enantiodivergent and γ-selective asymmetric allylic amination

Double agent: The title reaction using the guanidine catalyst 1 can deliver both enantiomers of the product with excellent enantioselectivity by judicious choice of the double bond geometry of the the β,γ-unsaturated carbonyl compound. Computational studies reveal the possible origin of the inversed enantioselectivity, and the potential for enantiodivergent synthesis chiral amine-containing substrates is attractive. Copyright

Practical synthesis of (E)-α,β-unsaturated carboxylic acids using a one-pot hydroformylation/decarboxylative Knoevenagel reaction sequence

Combining the regioselective room temperature/ambient pressure hydroformylation and a modification of the Doebner-Knoevenagel reaction allowed for the development of an efficient, one-pot procedure for the synthesis of (E)-α,β-unsaturated carboxylic acids. The reaction proceeds under mild conditions, tolerates a variety of functional groups and gives (E)-α,β-unsaturated carboxylic acids in good yields and with excellent regio-and stereocontrol. The practicability of this process has been demonstrated by a short protecting group-free synthesis of the queen honeybee pheromones 9-ODA[( E)-9-oxodec-2-enoic acid] and 9-HDA[( E)-9-hydroxydec-2-enoic acid].

A simple method for the alkaline hydrolysis of esters

A very mild and rapid procedure for the efficient alkaline hydrolysis of esters in non-aqueous conditions has been developed, by the use of dichloromethane/methanol (9:1) as solvent. This method conveniently provides both carboxylic acids and alcohols from the corresponding esters and sodium hydroxide in a few minutes at room temperature. A plausible reaction mechanism is proposed.