34146-55-9

Usage

Uses

Used in Fragrance and Flavor Industry:
(Z)-hept-4-en-2-ol is used as a key component in the creation of fragrances and flavors due to its pleasant, fruity odor. This makes it a valuable addition to the formulations of various consumer products, such as perfumes, colognes, and food items that require a fruity or floral note.
Used in Organic Synthesis:
(Z)-hept-4-en-2-ol serves as an intermediate in the synthesis of other organic compounds. Its unique chemical structure allows it to be a versatile building block for the development of new molecules with potential applications in various industries, including pharmaceuticals, materials science, and agrochemicals.
Used in Antimicrobial and Insecticidal Applications:
(Z)-hept-4-en-2-ol has been investigated for its potential antimicrobial and insecticidal properties. Its ability to inhibit the growth of certain microorganisms and pests makes it a candidate for use in the development of new antimicrobial and insecticidal products, which could be beneficial in healthcare, agriculture, and other related fields.
Used in Pest Control and Agricultural Applications:
(Z)-hept-4-en-2-ol is known to exhibit pheromone activity in certain species of insects, making it an important chemical in pest control and agricultural applications. By harnessing its pheromone properties, it can be used to disrupt the mating and communication behaviors of pests, leading to more effective and targeted pest management strategies.

InChI:InChI=1/C7H14O/c1-3-4-5-6-7(2)8/h4-5,7-8H,3,6H2,1-2H3/b5-4-

Upstream product

• 3916-64-1 hepta-3,5-dien-2-one 
• 31458-72-7 (3E,5E)-hepta-3,5-dien-2-ol 
• 80186-44-3 4-<(dimethyl-tert-butylsilyl)oxy>-1-pentyne 
• 19781-81-8 (R,S)-4-Heptyn-2-ol 
• 139193-28-5 Acetic acid (1R,2S)-1-ethyl-4-oxo-2-phenylsulfanyl-pentyl ester 
• 2117-11-5 4-pentyn-2-ol 
• 75-56-9 methyloxirane 
• 28832-55-5 2-Chlorobutanal 
• 67-64-1 acetone 
• 139193-36-5 Acetic acid (1R,2S)-1-ethyl-4-hydroxy-2-phenylsulfanyl-pentyl ester 
• 16967-00-3 diethylbutenylaluminum 

Downstream Products

• 90605-45-1 (Z)-4-Hepten-2-one 
• 1006684-47-4 (+/-)-(3Z)-1-methyl-3-hexenyl 4-methylbenzenesulfonate 

Relevant academic research and scientific papers

New volatile sulfur-containing constituents in a simultaneous distillation-extraction extract of red bell peppers (Capsicum annuum)

An extract of red bell peppers (Capsicum annuum) was prepared by simultaneous distillation-extraction (SDE, Likens-Nickerson). In addition to the already known (3E)-hepten-2-one (1), the unsaturated C9-ketones 1-nonen-4-one (2), (2E)-2-nonen-4-one (3), and (2E,5E)-2,5-nonadien-4-one (4), 2-methoxy-3-isobutylpyrazine (5), and heptane-2-thiol (6), we identified 19 new thiols (the aliphatic saturated and unsaturated thiols 14-16, and 22-27, the mercapto-ketones 12 and 13, the mercapto-alcohols 17, 18, and 30, the dithiols 19 and 28, the methylthio-thiols 20 and 21, and the thiophene-thiol 31) and the two new dithiolanes 10 and 29. All of them are structurally related to the unsaturated C7-and C9-ketones 1-4. The free thiols were enriched using Affi-Gel 501 (p-aminophenyl-mercuric acetate grafted on an agarose gel). The new compounds were confirmed by syntheses and were organoleptically evaluated.

Identification of a Novel Moth Sex Pheromone in Eriocrania cicatricella (Zett.) (Lepidoptera: Eriocraniidae) and its Phylogenetic Implications

Extracts from different body parts of adult female Eriocrania cicatricella (Zett.) were tested for electrophysiological activity on conspecific male antennae. Extracts from the Vth abdominal segment, containing a pair of exocrine glands, elicited the largest electroantennographic response when compared to extracts of other body parts. Female extracts were analyzed by gas chromatography with simultaneous flame ionization and electroantennographic detection (EAD). The EAD active peaks were identified as (Z)-4-hepten-2-one, (2R)-heptane-2-ol, and (2R)-(Z)-4-hepten-2-ol by coinjection on a gas chromatography and by comparison of mass spectra with those of synthetic standards. In field tests, a blend of these three pheromone components was highly attractive to conspecific males, and a subtractive assay confirmed that the unsaturated alcohol is the major pheromone component, whereas no definite behavioral activity could be assigned to the ketone or the saturated alcohol. A bait containing the two alcohols with S-configuration was attractive to male E. sparrmanella (Bosc), whereas no males of E. cicatricella were found in these traps. The sex pheromone compounds in E. cicattricella are chemically similar to pheromones reported in Trichoptera and they are produced in homologous glands.

HIGH DIASTEREOFACIAL SELECTIVITY IN THE REACTION OF SILYL ENOL ETHERS WITH CHLOROSULFIDES

The chlorosulfides 1 or 2 react with silyl enol ethers in presence of anhydrous zinc bromide to give mainly the corresponding syn products 4 or 6 respectively.The high syn selectivity of thee reactions is explained by nucleophilic addition to a chelated chiral thionium ion.

COMPOUNDS WITH A HERBAL ODOR 1. CIS-2-PENTENYLCARBINOLS

cis-2-Pentenylcarbinols were synthesized by selective hydrogenation of 1,3-pentadienylcarbinols at chromium hexacarbonyl.The obtained compounds have a herbal odor.

One-Pot Synthesis of Substituted Homoallylic Alcohols (3-Alkenols) and 1-Deuterio-3-alkenols; II. Extension to Ketone Enolates

The reaction of different lithium ketone enolates with α-chloro carbonyl compounds followed by in situ reduction with lithium aluminium hydride or deuteride and final lithiation with lithium powder leads to the corresponding homoallylic or 1-deuterio homoallylic alcohols in a regioselective manner.

Vinyl-copper derivatives-XI1 1 Part X: A. Alexakis, G. Cahiez and J.F. Normant, Synthesis, 826 (1979). Reactivity of Z-alkenyl cuprates towards various electrophiles. Application to the synthesis of some natural products

Z-Alkenylcuprates 1 and 2, prepared in situ by addition of acetylene to alkylcuprates, react with a variety of electrophiles (epoxides, carbon dioxide, aldehydes) and give conjugate addition products with α,β-unsaturated aldehydes, ketones and esters, and with activated cyclopropanes. They also add across the triple bond of some alkynes. The synthesis of natural products (7,9,22) is described.

Preparation of unsaturated alcohols and intermediates therein

This invention relates to the preparation of unsaturated alcohols useful as flavor and fragrance compounds. More specifically, this invention relates to the preparation of predominately cis-unsaturated alcohols by reacting a cis-1-alkenylaluminum dialkyl compound with an epoxide compound followed by hydrolysis. The alkenyl moiety has one or more double bond carbon-to-carbon linkage and from 5 to 20 carbon atoms that can be optionally substituted with the substituents selected from alkyl and aromatic radicals having 1 to 12 carbon atoms.