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3-Oxo-6-heptenoic acid ethyl, also known as ethyl 3-oxo-6-heptenoate, is a chemical compound with a molecular formula C8H12O3. It is an ester of 3-Oxo-6-heptenoic acid, which is a significant intermediate in the biosynthesis of unsaturated fatty acids. 3-Oxo-6-heptenoic acid ethyl is characterized by its fruity, pineapple-like odor and possesses versatile chemical properties.

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  • 17605-06-0 Structure
  • Basic information

    1. Product Name: 3-Oxo-6-heptenoic acid ethyl
    2. Synonyms: 2-Oxo-5-hexene-1-carboxylic acid ethyl ester;3-Oxo-6-heptenoic acid ethyl;3-Oxo-6-heptenoic acid ethyl ester;ETHYL 3-OXO-6-HEPTENOATE;ethyl 3-oxohept-6-enoate
    3. CAS NO:17605-06-0
    4. Molecular Formula: C9H14O3
    5. Molecular Weight: 170.21
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 17605-06-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 227.3 °C at 760 mmHg
    3. Flash Point: 90.989 °C
    4. Appearance: /
    5. Density: 0.985 g/cm3
    6. Vapor Pressure: 0.0781mmHg at 25°C
    7. Refractive Index: 1.437
    8. Storage Temp.: 2-8°C
    9. Solubility: Chloroform, Methanol (Slightly)
    10. CAS DataBase Reference: 3-Oxo-6-heptenoic acid ethyl(CAS DataBase Reference)
    11. NIST Chemistry Reference: 3-Oxo-6-heptenoic acid ethyl(17605-06-0)
    12. EPA Substance Registry System: 3-Oxo-6-heptenoic acid ethyl(17605-06-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 17605-06-0(Hazardous Substances Data)

17605-06-0 Usage

Uses

Used in Food and Beverage Industry:
3-Oxo-6-heptenoic acid ethyl is used as a flavoring agent for its fruity, pineapple-like aroma, enhancing the taste and smell of various food and beverage products.
Used in Perfume and Cosmetics Industry:
Leveraging its pleasant aroma, 3-Oxo-6-heptenoic acid ethyl is utilized in the production of perfumes and cosmetics, contributing to the creation of attractive scents and fragrances.
Used in Pharmaceutical Formulation:
3-Oxo-6-heptenoic acid ethyl is employed in the formulation of pharmaceuticals, capitalizing on its chemical properties to improve the efficacy and delivery of medications.
Used as a Chemical Intermediate in Organic Synthesis:
3-Oxo-6-heptenoic acid ethyl serves as a valuable chemical intermediate in organic synthesis, enabling the development of new chemical products and contributing to advancements in various industries.

Check Digit Verification of cas no

The CAS Registry Mumber 17605-06-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,7,6,0 and 5 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 17605-06:
(7*1)+(6*7)+(5*6)+(4*0)+(3*5)+(2*0)+(1*6)=100
100 % 10 = 0
So 17605-06-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H14O3/c1-3-5-6-8(10)7-9(11)12-4-2/h3H,1,4-7H2,2H3

17605-06-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name ethyl 3-oxohept-6-enoate

1.2 Other means of identification

Product number -
Other names ethyl 2-methyl-3-oxo-hept-6-enoate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:17605-06-0 SDS

17605-06-0Relevant articles and documents

Thermolysis of geminal diazides: Reagent-free synthesis of 3-hydroxypyridines

Erhardt, Hellmuth,Kunz, Kevin A.,Kirsch, Stefan F.

, p. 178 - 181 (2017)

An operationally simple protocol for the rapid and efficient construction of highly substituted 3-hydroxypyridines is presented. The thermally induced cyclization of easily constructed geminal diazides derived from β- ketoesters having an additional olefin moiety affords the title compounds in yields up to 97% under reagent-free conditions. The new method allows for the synthesis of preparative quantities of material. Additionally, the synthetic utility of the pyridine products for the synthesis of valuable heterocycles is described.

Syntheses of both diastereoisomers of 2,8-dioxabicyclo[3.2.1]octane derivatives: Degradation products of Daphniphyllum alkaloids

Kongkathip, Boonsong,Sookkho, Rongsan,Kongkathip, Ngampong,Taylor, Walter C.

, p. 1095 - 1096 (1999)

Both diastereoisomers of 1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octane-4-caboxylic acid ester (3, 4) and the 4-hydroxy methyl analogues (5, 6) were synthesised from ethyl acetoacetate and diethyl malonate respectively. The key step of these process involved intramolecular cyclisation using palladium chloride as catalyst.

Efficient Synthesis of butenolide-medium ring ether hybrids by a [3 + 2] cyclization-ring-closing metathesis strategy

Langer, Peter,Eckardt, Tobias,Stoll, Martin

, p. 2991 - 2993 (2000)

A new strategy for the synthesis of bicyclic γ-alkylidenebutenolides, butenolide-medium ring ether hybrids, is reported which involves Me3-SiOTf-catalyzed cyclization of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with oxalyl chloride, Mitsunobu reaction, and subsequent ring-closing metathesis.

A Suite of “Minimalist” Photo-Crosslinkers for Live-Cell Imaging and Chemical Proteomics: Case Study with BRD4 Inhibitors

Pan, Sijun,Jang, Se-Young,Wang, Danyang,Liew, Si Si,Li, Zhengqiu,Lee, Jun-Seok,Yao, Shao Q.

, p. 11816 - 11821 (2017)

Affinity-based probes (AfBPs) provide a powerful tool for large-scale chemoproteomic studies of drug–target interactions. The development of high-quality probes capable of recapitulating genuine drug–target engagement, however, could be challenging. “Mini

Photoredox-catalyzed intramolecular cyclopropanation of alkenes with α-bromo-β-keto esters

Furuta, Miyu,Ide, Kohta,Tokuyama, Hidetoshi

supporting information, p. 9172 - 9176 (2021/11/13)

A mild photoredox-catalyzed intramolecular cyclopropanation of alkenes with α-bromo-β-keto esters in an aqueous medium was developed. The sequential reaction process comprising the intramolecular radical addition of α-bromo-β-keto esters to olefins under photoredox catalysis, and subsequent cyclization to form cyclopropane proceeds in one-pot under exceptionally mild conditions at room temperature in the presence of 2,6-lutidine. A broad range of substrates consisting of various alkenes and both base- and acid-sensitive functionalized esters were feasible under the reaction conditions, resulting in a wide range of functionalized bicyclic cyclopropanes. This journal is

Pd(OAc)2-catalyzed orthogonal synthesis of 2-hydroxybenzoates and substituted cyclohexanones from acyclic unsaturated 1,3-carbonyl compounds

Miyagi, Toshinori,Okada, Sho,Tada, Naoya,Sugihara, Masahiro,Kagawa, Natsuko,Takabatake, Tetsuhiko,Toyota, Masahiro

supporting information, p. 1653 - 1657 (2019/05/29)

A Pd-catalyzed orthogonal synthesis of substituted 2-hydroxybenzoates and substituted cyclohexanones was developed for the first time. The substituted 2-hydroxybenzoates were obtained from acyclic unsaturated 1,3-carbonyl compounds using a combination of catalytic Pd(OAc)2 and Cu(OAc)2. On the other hand, the substituted cyclohexanones were produced from similar substrates via catalytic Pd(OAc)2 and hydrogen chloride. Each transformation was clean, easy to work up, provided the desired compounds in good purities, and did not require column chromatography purification.

One-pot, two-step synthesis of unnatural α-amino acids involving the exhaustive aerobic oxidation of 1,2-diols

Inada, Haruki,Furukawa, Keisuke,Shibuya, Masatoshi,Yamamoto, Yoshihiko

supporting information, p. 15105 - 15108 (2019/12/26)

Herein, we report the nor-AZADO-catalyzed exhaustive aerobic oxidations of 1,2-diols to α-keto acids. Combining oxidation with transamination using dl-2-phenylglycine led to the synthesis of free α-amino acids (AAs) in one pot. This method enables the rapid and flexible preparation of a variety of valuable unnatural AAs, such as fluorescent AAs, photoactivatable AAs, and other functional AAs for bioorthogonal reactions.

General [4 + 1] Cyclization Approach to Access 2,2-Disubstituted Tetrahydrofurans Enabled by Electrophilic Bifunctional Peroxides

Gao, Min,Zhao, Yukun,Zhong, Chen,Liu, Shengshu,Liu, Pengkang,Yin, Qi,Hu, Lin

supporting information, p. 5679 - 5684 (2019/08/01)

A general [4 + 1] cyclization reaction of carbonyl nucleophiles with 2-iodomethylallyl peroxides, which function as unique electrophilic oxygen synthons, for the synthesis of a broad range of 2,2-disubstituted tetrahydrofurans is achieved under operationally simple conditions. The unprecedented asymmetric version of such reaction is also realized via chiral auxiliary-assisted cyclization, thus providing a distinct approach to access chiral tetrahydrofurans with high diastereoselectivities. The new method can be applied to the synthesis of core structure of posaconazole drug.

A New Route to Phenols: Palladium-Catalyzed Cyclization and Oxidation of γ,δ-Unsaturated Ketones

Samadi, Sadaf,Orellana, Arturo

, p. 2472 - 2475 (2016/08/25)

We report a new strategy for the synthesis of phenols from acyclic unsaturated ketones in one pot. The reaction proceeds by palladium-catalyzed carbopalladation of an alkene with the enol form of the tethered ketone, generating a substituted cyclohexanone. Upon introduction of a terminal oxidant a palladium-catalyzed oxidation ensues to give the desired phenol. This approach allows the programming of phenol substituents on the acyclic substrate and therefore circumvents the limitations inherent in traditional syntheses of phenols.

Diastereoselective synthesis of the C17-C30 fragment of amphidinol 3

Rival, Nicolas,Hazelard, Damien,Hanquet, Gilles,Kreuzer, Thomas,Bensoussan, Charlelie,Reymond, Sébastien,Cossy, Janine,Colobert, Fran?oise

supporting information, p. 9418 - 9428 (2013/01/15)

The diastereoselective synthesis of the C17-C30 fragment of amphidinol 3 (AM3) 1 was achieved from the enantio-enriched aldehyde 20, Weinreb amide 14 and 2-bromo-3-(trimethylsilyl)propene, which was used as a bifunctional conjunctive reagent. The absolute configuration of the stereogenic centers, in both aldehyde 20 and Weinreb amide 14, were efficiently controlled by using (+)-(R)-methyl-p-tolylsulfoxide as the unique source of chirality.

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