Methyl sorbate

Base Information

• Chemical Name: Methyl sorbate
• CAS No.: 689-89-4
• Molecular Formula: C7H10 O2
• Molecular Weight: 126.155
• Hs Code.: H3 MOL WT. 126.15
• European Community (EC) Number: 216-160-1,211-712-8
• UNII: J3048615R1
• DSSTox Substance ID: DTXSID30862370
• Nikkaji Number: J184.214E,J45.089H
• Wikidata: Q27281080
• Metabolomics Workbench ID: 43921
• ChEMBL ID: CHEMBL250421
• Mol file: 689-89-4.mol

Synonyms:Methyl sorbate;689-89-4;methyl (2E,4E)-hexa-2,4-dienoate;Methyl hexa-2,4-dienoate;1515-80-6;Sorbic acid, methyl ester;2,4-HEXADIENOIC ACID, METHYL ESTER;Methyl (2E,4E)-hexadienoate;Methyl (E,E)-sorbate;Methyl-sorbate;Sorbic acid methyl ester;Methyl 2,4-hexadienoate;(2E,4E)-methyl hexa-2,4-dienoate;FEMA No. 3714;METHYLSORBATE;2-trans,4-trans-Methyl sorbate;Methyl (E,E)-hexa-2,4-dienoate;Sorbic acid, methyl ester, (E,E)-;Methyl trans,trans-sorbate;Methyl sorbate, (E,E)-;2,4-HEXADIENOIC ACID, METHYL ESTER, (E,E)-;2-trans-4-trans-Methyl sorbate;Methyl (E,E)-2,4-hexadienoate;2,4-Hexadienoic acid,methyl ester, (2E,4E)-;2,4-Hexadienoic acid, methyl ester, (2E,4E)-;UNII-J3048615R1;EINECS 211-712-8;EINECS 216-160-1;Methyl 2,4-hexadienoate, (E,E)-;NSC 33701;(E,E)-2,4-hexadienoic acid methyl ester;2,4-HEXADIENOIC ACID METHYL ESTER;AI3-30202;J3048615R1;Methyl (2E,4E)-2,4-hexadienoate;MFCD00038319;(e,e)-Methyl sorbate;2,4-Hexadienoic acid methyl;METHYL SORBATE [FHFI];SCHEMBL166359;Methyl ester(e,e)-Sorbic acid;CHEMBL250421;FEMA 3714;(E,E)-Methyl 2,4-hexadienoate;2,4-Hexadienoic acid methylester;DTXSID30862370;CHEBI:184593;2,4-Hexadienoic acid,methyl ester;LMFA07010967;AKOS015836368;AT35159;HY-W068700;3-(3-THIENYL)-ACRYLOYLCHLORIDE;BS-44927;Methyl ester(E,E)-2,4-Hexadienoic acid;2,4-Hexadienoic acid, methyl ester (9CI);CS-0069857;Methyl ester(2E,4E)-2,4-Hexadienoic acid;EN300-343813;H10763;trans-trans-hexa-2,4-dienoic acid methyl ester;A884085;A934962;W-104643;(2E,4E)-HEXA-2,4-DIENOIC ACID METHYL ESTER;Q27281080;InChI=1/C7H10O2/c1-3-4-5-6-7(8)9-2/h3-6H,1-2H3/b4-3+,6-5

Chemical Property of Methyl sorbate

Chemical Property:

• Appearance/Colour: yellowish liquid
• Vapor Pressure: 0.915mmHg at 25°C
• Melting Point: 15oC
• Refractive Index: 1.501 - 1.505
• Boiling Point: 180 C
• Flash Point: 158 ºF
• PSA: 26.30000
• Density: 0.968
• LogP: 1.29170
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 126.068079557
• Heavy Atom Count: 9
• Complexity: 134

Purity/Quality:

99%, ^*data from raw suppliers

SorbicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC=CC(=O)OC
• Isomeric SMILES: C/C=C/C=C/C(=O)OC
• Description: Methyl sorbate has a fruity, sweet, anise odor.

Technology Process of Methyl sorbate

There total 47 articles about Methyl 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: 99.0%

methanol (67-56-1) + sorbic Acid (110-44-1,91751-55-2) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4)

Guidance literature:

With thionyl chloride; at -10 ℃; for 2h; Reflux; Inert atmosphere;

DOI:10.1002/chem.201303435

Reference yield: 86.0%

sorbic Acid (110-44-1,91751-55-2) + tert-butyl methyl ether (1634-04-4) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4)

Guidance literature:

With iron(III) trifluoromethanesulfonate; at 90 ℃; Schlenk technique;

DOI:10.1039/c8gc00037a

Reference yield: 85.0%

methyl 2-hexynoate (18937-79-6) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4)

Guidance literature:

With tributylphosphine; IrH₅(P-(i-Pr)3)2; In toluene; at 110 ℃; for 24h;

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

upstream raw materials:

diazomethane

sorbic Acid

methanol

hexa-2,4-dienoic acid

Downstream raw materials:

methyl (2E,4E)-6-bromo-2,4-hexadienoate

3,6-dihydro-6-methoxycarbonyl-3-methyl-2H-1,2-oxazine

methyl (E)-4-oxo-2-butenoate

(+/-)-aucantene

Refernces

• 1、 Dethe, Dattatraya H.,Beeralingappa, Nagabhushana C.,Uike, Amar. "Ruthenium-Catalyzed Oxidative Cross-Coupling Reaction of Activated Olefins with Vinyl Boronates for the Synthesis of (E, E)-1,3-Dienes". . p. 3444 - 3455. Retrieved 2021/02/16.
• 2、 Zhu, Xiaotao,Qian, Bo,Wei, Rongbiao,Huang, Jian-Dong,Bao, Hongli. "Protection of COOH and OH groups in acid, base and salt free reactions". supporting information. p. 1444 - 1447. Retrieved 2018/04/12.