Ethyl sorbate

Base Information

• Chemical Name: Ethyl sorbate
• CAS No.: 2396-84-1
• Deprecated CAS: 5941-48-0,91660-95-6
• Molecular Formula: C8H12O2
• Molecular Weight: 140.182
• Hs Code.: H5 MOL WT. 140.18
• European Community (EC) Number: 219-258-2
• NSC Number: 8874
• UNII: HSR16USG4D
• DSSTox Substance ID: DTXSID80883712
• Nikkaji Number: J432.515J,J342.433B,J114.256I
• Wikidata: Q27140166,Q63398535
• Metabolomics Workbench ID: 49060
• ChEMBL ID: CHEMBL398921
• Mol file: 2396-84-1.mol

Synonyms:ETHYL SORBATE;2396-84-1;Ethyl hexa-2,4-dienoate;Ethyl 2,4-hexadienoate;Sorbic acid, ethyl ester;2,4-Hexadienoic acid, ethyl ester;ethyl (2E,4E)-hexa-2,4-dienoate;2,4-Hexadienoic acid, ethyl ester, (2E,4E)-;FEMA No. 2459;Sorbic Acid Ethyl Ester;Ethyl (E,E)-2,4-hexadienoate;Hexa-2,4-dienoic acid ethyl ester;NSC 8874;Ethyl 2,4-hexadienoate, (E,E)-;EINECS 219-258-2;UNII-HSR16USG4D;HSR16USG4D;AI3-11732;2,4-Hexadienoic acid, ethyl ester, (E,E)-;Ethyl (2E,4E)-2,4-hexadienoate;Ethyl trans,trans-2,4-hexadienoate;NSC-8874;(2E,4E)-ethyl hexa-2,4-dienoate;2,4-Hexadienoic acid, ethyl ester, (E,E)-);ethylsorbate;MFCD00009296;Ethyl sorbate, 98%;ETHYL SORBATE [FHFI];SCHEMBL345935;CHEMBL398921;Ethyl sorbate, >=97%, FG;(E,E)-Ethyl 2,4-hexadienoate;CHEBI:72819;FEMA 2459;OZZYKXXGCOLLLO-TWTPFVCWSA-;DTXSID80883712;NSC8874;CAA39684;LMFA07010882;AKOS015915299;CS-W014374;LS-2749;(4E)-2,4-Hexadienoic acid ethyl ester;Ethyl ester(E,E)-2,4-Hexadienoic acid;AS-56445;2,4-Hexadienoic acid, ethyl ester (9CI);Ethyl ester(2E,4E)-2,4-Hexadienoic acid;S0055;trans,trans-hexa-2,4-dienoic acid ethyl ester;(E,E)-2,4-HEXADIENOIC ACID ETHYL ESTER;A817011;W-107365;2,4-Hexadienoic acid, ethyl ester, (E,E)- (9CI);Ethyl 2,4-dimethyl-2,4-hexadienoate, not E,E, # 1;Q27140166

Chemical Property of Ethyl sorbate

Chemical Property:

• Appearance/Colour: clear colorless to yellowish liquid
• Vapor Pressure: 0.418mmHg at 25°C
• Melting Point: 95-98℃
• Refractive Index: 1.486 - 1.498
• Boiling Point: 195.5 °C at 760 mmHg
• Flash Point: 69.4 °C
• PSA: 26.30000
• Density: 0.926 g/cm³
• LogP: 1.68180
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in alcohol.
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 140.083729621
• Heavy Atom Count: 10
• Complexity: 145

Purity/Quality:

98%,99%, ^*data from raw suppliers

SorbicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CC=CC
• Isomeric SMILES: CCOC(=O)/C=C/C=C/C
• Uses: The addition of chlorine and bromine to ethyl sorbate (la) gave 1, 2-and 1, a-dihalo products derived from attack of the halogen. Chlorination of la under ionic conditions proceeds through a tightly bridged chloronium ion intermediate. Ethyl Sorbate is a synthetic flavoring agent that is a moderately sta- ble, light yellow liquid of fruity odor. it should be stored in glass or tin containers. it is used in flavors such as pineapple, papaya, and passion fruit with applications in ice cream, beverages, candy, and baked goods at 6–18 ppm. it is also termed ethyl-2,4-hexadienoate.

Technology Process of Ethyl sorbate

There total 51 articles about Ethyl sorbate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

sorbic Acid (110-44-1,91751-55-2) + ethanol (64-17-5) → (2E,4E)-ethyl hexa-2,4-dienoate (2396-84-1)

Guidance literature:

With carbon tetrabromide; for 72h; Heating;

Reference yield: 88.0%

ethyl 2-hexynoate (16205-90-6) → (2E,4E)-ethyl hexa-2,4-dienoate (2396-84-1)

Guidance literature:

With tributylphosphine; dihydridotetrakis(triphenylphosphine)ruthenium; In toluene; at 110 ℃; for 30h;

DOI:10.1016/S0040-4020(01)85458-2 DOI:10.1016/S0040-4039(01)80631-6

Reference yield: 87.0%

sorbic Acid (110-44-1,91751-55-2) + (2,2-diethoxyvinylidene)triphenylphosphorane (21882-77-9,53472-13-2) → (2E,4E)-ethyl hexa-2,4-dienoate (2396-84-1) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2)

Guidance literature:

In tetrahydrofuran; for 3h; Ambient temperature;

DOI:10.1055/s-1981-29678

upstream raw materials:

sorbic Acid

ethanol

hexa-2,4-dienoyl chloride

parasorbic acid

Downstream raw materials:

4-oxo-but-2-enoic acid ethyl ester

(1R,2S,5S,6S,7S)-1,6,7-Trichloro-7-fluoro-5-methyl-bicyclo[4.1.0]hept-3-ene-2-carboxylic acid ethyl ester

ethyl 3-<5,7-dichloro-3,4-dihydro-3-methyl-4-(4-nitrobenzoyl)-2H-1,4-benzoxazin-2-yl>-2-propenoate

4-carbethoxy-2-cyclohex-1'-enyl-3(E)-prop-1'-enylpyrrole

Refernces

• 1、 Stork,Tomasz. "". . p. 310. Retrieved 1962.
• 2、 Ma, Dawei,Lu, Xiyan. "FACILE SYNTHESIS OF (2E,4E)-DIENOIC ESTERS VIA STEREOSELECTIVE ISOMERIZATION OF 2-YNOIC ESTERS". . p. 843 - 844. Retrieved 1989.
• 3、 Yu, Jingxun,Zhou, Yu,Lin, Zhenyang,Tong, Rongbiao. "Regioselective and Stereospecific Copper-Catalyzed Deoxygenation of Epoxides to Alkenes". supporting information. p. 4734 - 4737. Retrieved 2016/09/28.
• 4、 Kumar, Davinder,Narang, Rakesh,Judge, Vikramjeet,Kumar, Devinder,Narasimhan, Balasubramanian. "Antimicrobial evaluation of 4-methylsulfanyl benzylidene/3-hydroxy benzylidene hydrazides and QSAR studies". experimental part. p. 382 - 394. Retrieved 2012/08/27.