689-89-4

Basic information

• Product Name: Methyl sorbate
• Synonyms: Methyl (2E,4E)-hexa-2,4-dienoate;(2E,4E)-2,4-Hexadienoic acid methyl ester;METHYL 2,4-HEXADIENOATE;METHYL T2 T4 HEXADIENOATE;METHYL SORBATE;FEMA 3714;2,4-HEXADIENOIC ACID METHYL ESTER;SORBIC ACID METHYL ESTER
• CAS NO: 689-89-4
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.15
• EINECS: 211-712-8
• Mol File: 689-89-4.mol
• Article Data: 43

Chemical Properties

• Melting Point: 15°C
• Boiling Point: 180 °C(lit.)
• Flash Point: 158 °F
• Appearance: yellowish liquid
• Density: 0.968 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.915mmHg at 25°C
• Refractive Index: n20/D 1.503(lit.)
• CAS DataBase Reference: Methyl sorbate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl sorbate(689-89-4)
• EPA Substance Registry System: Methyl sorbate(689-89-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 689-89-4(Hazardous Substances Data)

Usage

Description

Methyl sorbate is an organic compound with a fruity, sweet, anise odor. It is characterized by its distinctive taste and aroma, which is reminiscent of a blend of fruits, sweetness, and a hint of brown, vanilla, and nutty notes. Methyl sorbate is known to occur naturally in certain fruits such as guanabana, starfruit, and pineapple.

Uses

Used in Flavor and Fragrance Industry:
Methyl sorbate is used as a flavoring agent for its fruity, sweet, and anise-like taste. Its unique taste profile makes it a valuable addition to the flavor industry, where it can be used to enhance the taste of various food and beverage products.
Methyl sorbate is also used as a fragrance ingredient for its pleasant and distinctive odor. Its fruity, sweet, and anise-like scent can be incorporated into perfumes, cosmetics, and other fragrance products to create a captivating and memorable scent experience.
Used in the Food and Beverage Industry:
Methyl sorbate is used as a flavor enhancer in the food and beverage industry. Its natural occurrence in fruits like guanabana, starfruit, and pineapple makes it an ideal choice for adding a fruity and sweet taste to a wide range of products, from fruit juices and desserts to snacks and confectionery items.
In addition to its flavor-enhancing properties, Methyl sorbate's unique aroma can also be utilized in the development of new and innovative food and beverage products, offering consumers a fresh and exciting taste experience.
Used in the Cosmetics and Personal Care Industry:
Methyl sorbate's pleasant and distinctive scent makes it a valuable ingredient in the cosmetics and personal care industry. It can be used in the formulation of perfumes, body lotions, shower gels, and other fragranced products to provide a long-lasting and enjoyable scent.
Furthermore, its natural occurrence in fruits and its fruity, sweet, anise-like odor can be used to create unique and appealing fragrance profiles for personal care products, setting them apart from competitors and appealing to consumers who are looking for something new and different.

Synthesis Reference(s)

Chemistry Letters, 15, p. 1553, 1986Tetrahedron Letters, 30, p. 843, 1989 DOI: 10.1016/S0040-4039(01)80631-6

InChI:InChI=1/C7H10O2/c1-3-4-5-6-7(8)9-2/h3-6H,1-2H3/b4-3-,6-5+

Synthetic route

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

Conditions	Yield
With thionyl chloride at -10℃; for 2h; Reflux; Inert atmosphere;	99%
With chloro-trimethyl-silane In dichloromethane for 16h;	99%
Stage #1: sorbic Acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere; Stage #2: methanol In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;	95%

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

Conditions	Yield
With iron(III) trifluoromethanesulfonate at 90℃; Schlenk technique;	86%

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

Conditions	Yield
With tributylphosphine; IrH5(P-(i-Pr)3)2 In toluene at 110℃; for 24h;	85%

methanol (67-56-1) + sorbinyl chloride (2614-88-2) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4)

Conditions	Yield
	85%
at 0℃;	81%

methyl (E)-4-oxo-2-butenoate (5837-72-9) + (triphenylphosphoranylidene)acetaldehyde (2136-75-6) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4)

Conditions	Yield
In dichloromethane for 4h; Heating;	82%

(E)-3-((4S,5S)-5-Methyl-2-oxo-[1,3]dioxolan-4-yl)-acrylic acid methyl ester → (2E,4E)-methylhexa-2,4-dienoate (689-89-4)

Conditions	Yield
With copper(l) iodide; boron trifluoride diethyl etherate; methylmagnesium bromide In tetrahydrofuran at -78℃; for 0.333333h;	82%

(1Z,3E)-1-(t-butyldimethylsilyloxy)-1-methoxyhexa-1,3-diene (287193-97-9) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4)

Conditions	Yield
With chloranil In dichloromethane for 0.00277778h; Elimination;	72%

acrylic acid methyl ester (292638-85-8) + 4,4,5,5-tetramethyl-2-[(1E)-prop-1-en-1-yl]-1,3,2-dioxaborolane (83947-58-4) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4)

Conditions	Yield
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 12h; Inert atmosphere; Sealed tube; stereoselective reaction;	70%

Epoxy-4,5 hexene-2 (E) oate de methyle (51830-12-7) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (+/-)-methyl-E-5-hydroxyhex-3-enoate (113351-26-1)

Conditions	Yield
With maleic anhydride; carbon monoxide; N-ethyl-N,N-diisopropylamine; sodium bromide; Pd2(C4H7)2Cl2 In methanol under 22800 Torr; Ambient temperature;	A 7% B 67%

sorbic Acid (110-44-1) + dimethyl sulfoxide (67-68-5) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4)

Conditions	Yield
With copper(II) chloride monohydrate; dihydrogen peroxide; oxygen; potassium carbonate; calcium chloride at 80℃; for 15h; Sealed tube; Green chemistry;	32%

tributyl-amine (102-82-9) + acrylic acid methyl ester (292638-85-8) + triphenylphosphine (603-35-0) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4)

Conditions	Yield
palladium diacetate	4%

diazomethane (186581-53-3, 908094-01-9) + sorbic Acid (110-44-1) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4)

diazomethane (186581-53-3, 908094-01-9) + hexa-2,4-dienoic acid (110-44-1) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (2Z,4Z)-hexadienoic acid methyl ester (53892-48-1) + (2Z,4E)-hexadienoic acid methyl ester (6932-46-3) + (2E,4Z)-hexadienoic acid methyl ester (30361-31-0)

Conditions	Yield
1.) benzene, irradiation; 2.) MeOH; Yield given. Multistep reaction. Yields of byproduct given;

methanol (67-56-1) + (E)-4-Benzenesulfonyl-2-diethylamino-hepta-2,6-dienenitrile (344890-72-8) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4)

Conditions	Yield
With sulfuric acid; 1,8-diazabicyclo[5.4.0]undec-7-ene 2.) CH2Cl2; Multistep reaction;

2-methylthiophene-5-carboxylic acid (1918-79-2) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4) + Methyl 2,5-Dihydro-5-methyl-2-thiophenecarboxylate (71624-92-5) + methyl (E)-hex-3-enoate (13894-61-6) + methyl (E)-hex-4-enoate (14017-81-3) + methyl (Z)-hex-3-enoate (13894-62-7) + Methyl (Z)-5-Mercapto-3-hexenoate (86610-45-9)

Conditions	Yield
With methanol; sulfuric acid; ammonia; lithium Product distribution; Mechanism; 1) -78 degC, 60 min, 2) room temp., 24 h; other amount of Li: 10 eq.;	A 2 % Spectr. B 71 % Spectr. C 8.5 % Spectr. D n/a E n/a F 18 % Spectr.

trans-Crotonaldehyde (123-73-9) + Malonic acid monomethyl ester (16695-14-0) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (2Z,4E)-hexadienoic acid methyl ester (6932-46-3) + methyl (E)-3,5-hexadienoate (32775-94-3)

Conditions	Yield
dmap In pyridine at 60℃; for 24h; Yields of byproduct given. Title compound not separated from byproducts;

trans-Crotonaldehyde (123-73-9) + trimethyl phosphonoacetate (5927-18-4) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (2Z,4E)-hexadienoic acid methyl ester (6932-46-3) + (E)-3-(6-Methyl-cyclohexa-1,3-dienyl)-acrylic acid methyl ester (95636-75-2) + (E)-3-(2,6-Dimethyl-5,6-dihydro-2H-pyran-3-yl)-acrylic acid methyl ester (95636-76-3)

Conditions	Yield
With potassium tert-butylate DMF, rt; Yield given. Multistep reaction. Yields of byproduct given;

(2E)-5-Hydroxy-2-hexensaeuremethylester (19870-59-8) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4)

Conditions	Yield
With sulfuric acid In methanol Heating;

Methyl (cis,E)-3-(2-Methyl-5,8-dioxaspiro<3.4>oct-1-yl)-2-propenoate (127379-38-8) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (2Z,4E)-hexadienoic acid methyl ester (6932-46-3) + (2E,4Z)-hexadienoic acid methyl ester (30361-31-0)

Conditions	Yield
In benzene-d6 at 189.6℃; Rate constant;
In acetonitrile at 144.4℃; Rate constant;

Methyl (cis,E)-3-(2-Methyl-5,8-dioxaspiro<3.4>oct-1-yl)-2-propenoate (127379-38-8) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (2E,4Z)-hexadienoic acid methyl ester (30361-31-0) + Methyl cis-9-Methyl-1,4-dioxaspiro<4.5>dec-7-ene-6-carboxylate (127281-00-9, 110434-36-1, 110434-37-2, 127281-01-0) + Methyl trans-9-Methyl-1,4-dioxaspiro<4.5>dec-7-ene-6-carboxylate (127281-01-0, 110434-36-1, 110434-37-2, 127281-00-9)

Conditions	Yield
In benzene-d6 at 190℃; Yield given. Further byproducts given. Yields of byproduct given;

Methyl (trans,Z)-3-(2-Methyl-5,8-dioxaspiro<3.4>oct-1-yl)-2-propenoate (127379-37-7) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (2Z,4Z)-hexadienoic acid methyl ester (53892-48-1) + (2Z,4E)-hexadienoic acid methyl ester (6932-46-3) + (2E,4Z)-hexadienoic acid methyl ester (30361-31-0) + Methyl cis-9-Methyl-1,4-dioxaspiro<4.5>dec-7-ene-6-carboxylate (127281-00-9, 110434-36-1, 110434-37-2, 127281-01-0) + Methyl trans-9-Methyl-1,4-dioxaspiro<4.5>dec-7-ene-6-carboxylate (127281-01-0, 110434-36-1, 110434-37-2, 127281-00-9)

Conditions	Yield
In benzene-d6 at 195℃; Thermodynamic data; Mechanism; Kinetics; product yield/distribution, ΔH(excit.)R, ΔS(excit.)R, ΔH(excit.)C, ΔS(excit.)C; other temperature, stereospecificity, stereoselectivity;

Methyl (trans,Z)-3-(2-Methyl-5,8-dioxaspiro<3.4>oct-1-yl)-2-propenoate (127379-37-7) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (2Z,4E)-hexadienoic acid methyl ester (6932-46-3) + (2E,4Z)-hexadienoic acid methyl ester (30361-31-0) + Methyl cis-9-Methyl-1,4-dioxaspiro<4.5>dec-7-ene-6-carboxylate (127281-00-9, 110434-36-1, 110434-37-2, 127281-01-0) + Methyl trans-9-Methyl-1,4-dioxaspiro<4.5>dec-7-ene-6-carboxylate (127281-01-0, 110434-36-1, 110434-37-2, 127281-00-9)

Conditions	Yield
In benzene-d6 at 170.2℃; Thermodynamic data; Mechanism; Kinetics; product yield/distribution, ΔH(excit.)R, ΔS(excit.)R, ΔH(excit.)C, ΔS(excit.)C; stereospecificity, stereoselectivity; other vinylcyclobutanes;

Methyl (trans,Z)-3-(2-Methyl-5,8-dioxaspiro<3.4>oct-1-yl)-2-propenoate (127379-37-7) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (2Z,4E)-hexadienoic acid methyl ester (6932-46-3) + Methyl cis-9-Methyl-1,4-dioxaspiro<4.5>dec-7-ene-6-carboxylate (127281-00-9, 110434-36-1, 110434-37-2, 127281-01-0) + Methyl trans-9-Methyl-1,4-dioxaspiro<4.5>dec-7-ene-6-carboxylate (127281-01-0, 110434-36-1, 110434-37-2, 127281-00-9)

Conditions	Yield
In benzene-d6 at 170℃; other temperatures; Yield given. Further byproducts given. Yields of byproduct given;

Methyl (trans,E)-3-(2-Methyl-5,8-dioxaspiro<3.4>oct-1-yl)-2-propenoate (127280-96-0) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (2Z,4E)-hexadienoic acid methyl ester (6932-46-3) + (2E,4Z)-hexadienoic acid methyl ester (30361-31-0) + Methyl cis-9-Methyl-1,4-dioxaspiro<4.5>dec-7-ene-6-carboxylate (127281-00-9, 110434-36-1, 110434-37-2, 127281-01-0)

Conditions	Yield
In benzene-d6 at 190℃; other temperatures; Yield given;	A n/a B n/a C n/a D 61 % Spectr.
In benzene-d6 at 179.8℃; Thermodynamic data; Kinetics; Mechanism; product yield/distribution; ΔH(excit.)R, ΔS(excit.)R, ΔH(excit.)C, ΔS(excit.)C; stereospecificity, stereoselectivity; other temperature;	A n/a B n/a C n/a D 65 % Spectr.

Methyl (trans,E)-3-(2-Methyl-5,8-dioxaspiro<3.4>oct-1-yl)-2-propenoate (127280-96-0) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (2E,4Z)-hexadienoic acid methyl ester (30361-31-0) + Methyl cis-9-Methyl-1,4-dioxaspiro<4.5>dec-7-ene-6-carboxylate (127281-00-9, 110434-36-1, 110434-37-2, 127281-01-0)

Conditions	Yield
In benzene-d6 at 170.8℃; Thermodynamic data; Kinetics; Mechanism; product yield/distribution; ΔH(excit.)R, ΔS(excit.)R, ΔH(excit.)C, ΔS(excit.)C; stereospecificity, stereoselectivity;	A n/a B n/a C 70 % Spectr.

Methyl (trans,E)-3-(2-Methyl-5,8-dioxaspiro<3.4>oct-1-yl)-2-propenoate (127280-96-0) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4) + Methyl cis-9-Methyl-1,4-dioxaspiro<4.5>dec-7-ene-6-carboxylate (127281-00-9, 110434-36-1, 110434-37-2, 127281-01-0)

Conditions	Yield
In benzene-d6 at 160.2℃; Thermodynamic data; Kinetics; Mechanism; product yield/distribution; ΔG(excit.), ΔH(excit.)R, ΔS(excit.)R, ΔH(excit.)C, ΔS(excit.)C; stereospecificity, stereoselectivity;	A 25 % Spectr. B 75 % Spectr.

(E)-4-(4-Chloro-benzenesulfinyl)-hex-2-enoic acid methyl ester → (2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (2E,4Z)-hexadienoic acid methyl ester (30361-31-0)

Conditions	Yield
In xylene for 2h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(E)-(2S,3S)-2-Hydroxy-3-trimethylsilanyl-hex-4-enoic acid methyl ester (108965-77-1, 108965-78-2) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (2Z,4Z)-hexadienoic acid methyl ester (53892-48-1) + (2Z,4E)-hexadienoic acid methyl ester (6932-46-3)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at -20℃; Yield given. Yields of byproduct given;

(E)-(2S,3S)-2-Hydroxy-3-trimethylsilanyl-hex-4-enoic acid methyl ester (108965-77-1, 108965-78-2) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (2E,4Z)-hexadienoic acid methyl ester (30361-31-0)

Conditions	Yield
With potassium hydride In tetrahydrofuran at -78 - -40℃; Yield given. Yields of byproduct given;

5-methyl-2-carbomethoxy-2,5-dihydrothiophene-1,1-dioxide (88418-76-2) → (2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (2E,4Z)-hexadienoic acid methyl ester (30361-31-0)

Conditions	Yield
In toluene for 3h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → methyl 3,4-hexadienoate (81981-05-7)

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 36h; Irradiation;	100%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → methyl (Z)-hex-3-enoate (13894-62-7)

Conditions	Yield
With hydrogen; tricarbonyl(η(6)-1,2,3-trimethoxybenzene)chromium In tetrahydrofuran at 80℃; under 45600 Torr; for 5h; different catalysts, different temperatures;	100%
With hydrogen; tricarbonyl(η(6)-1,2,3-trimethoxybenzene)chromium In tetrahydrofuran at 100℃; under 45600 Torr; for 5h; various catalysts, other temperatures;	100%
With hydrogen; methyl benzoate*Cr(CO)3 In acetone at 100℃; under 53200 Torr; for 16h;	94%
With hydrogen; (η(6)-benzene)(η(2)-methylacrylate)dicarbonylchromium In tetrahydrofuran at 23℃; under 750.06 Torr; for 54h;	87%
With hydrogen; chromium(0) hexacarbonyl

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → methyl (E)-3,5-hexadienoate (32775-94-3)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 1h;	99%
With n-butyllithium; diisopropylamine In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -78℃; for 1.5h;	76.6%
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 1.25h; Inert atmosphere;	70%
With lithium diisopropyl amide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide
With n-butyllithium; diisopropylamine; Hexamethylphosphorous triamide In tetrahydrofuran; hexane at -78 - 0℃; for 1h; Schlenk technique;

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → 1,4-trans-threo-disyndiotactic poly((E,E)-methyl sorbate), Mn = 5.4E4 Da, Mw/Mn = 1.4; monomer(s): methyl 2,4-hexadienoate

Conditions	Yield
With tert.-butyl lithium; bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum In toluene; pentane at -20℃; for 72h;	98%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → methyl (E)-hex-2-enoate (13894-63-8)

Conditions	Yield
With hydrogen; montmorillonit-bipyridinpalladium(II)-acetate In tetrahydrofuran Ambient temperature;	97%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (η6-7β-methyl-1,3,5-cycloheptatriene)tricarbonylchromium(0) → 10α,11β-dimethyl-7α-(methoxycarbonyl)-(1Hβ,6Hβ)-bicyclo[4.4.1]undeca-2,4,8-triene (129000-89-1)

Conditions	Yield
In hexane for 3h; Irradiation;	97%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) + benzaldehyde (100-52-7) → (2E,4E)-7-Hydroxy-7-phenyl-hepta-2,4-dienoic acid methyl ester

Conditions	Yield
Stage #1: (2E,4E)-methylhexa-2,4-dienoate; benzaldehyde With aluminium tris(2,6-diphenylphenoxide) In toluene at -78℃; for 0.333333h; Complexation; Stage #2: With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; hexane; toluene at -78℃; for 0.5h; Crossed aldol condensation;	97%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (E)-(1-methoxyprop-1-enyloxy)trimethylsilane (72658-09-4) → methyl 5-methoxy-2-methyl-3-(1-propenyl)-5-trimethylsiloxy-4-pentenoate

Conditions	Yield
aluminum ion-exchanged montmorillonite In dichloromethane at -50℃; for 0.5h;	96%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (η6-1,3,5-cycloheptatriene)tricarbonylchromium(0) → 7α-(methoxycarbonyl)-10α-methyl-(1Hβ,6Hβ)-bicyclo[4.4.1]undeca-2,4,8-triene (86067-63-2, 143428-66-4)

Conditions	Yield
In hexane for 0.5h; Irradiation;	96%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → 1,4-trans-threo-disyndiotactic poly((E,E)-methyl sorbate), Mn = 3.1E4 Da, Mw/Mn = 1.2; monomer(s): methyl 2,4-hexadienoate

Conditions	Yield
With tert.-butyl lithium; bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum; (-)-sparteine In toluene; pentane at -20℃; for 72h;	96%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → Sorbyl alcohol (17102-64-6)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In methanol at 50℃; under 45004.5 Torr; for 12h; Temperature; Pressure; Autoclave; Green chemistry;	94.95%
With strain of the zygomycete fungus S. racemosum MUT 770 In dimethyl sulfoxide for 72h; Enzymatic reaction;	23%
With lithium aluminium tetrahydride
With diisobutylaluminium hydride In toluene at -40℃; for 2h; Inert atmosphere;

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → methyl (E)-4-oxo-2-butenoate (5837-72-9)

Conditions	Yield
With ozone In methanol; dichloromethane at -30℃;	90%
With dimethylsulfide; ozone In dichloromethane	90%
With sodium perchlorate In water; acetonitrile (electrolysis);

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → (3E,7E)-5,6-Dimethyl-deca-3,7-dienedioic acid dimethyl ester (29653-35-8, 138823-73-1, 138823-74-2)

Conditions	Yield
With methanol; samarium diiodide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide Ambient temperature;	90%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) + lithium (R)-N-3,4-dimethoxybenzyl-N-(α-methylbenzyl)amide → (E)-(S)-3-[(3,4-Dimethoxy-benzyl)-((R)-1-phenyl-ethyl)-amino]-hex-4-enoic acid methyl ester (213467-20-0)

Conditions	Yield
	90%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) + benzaldehyde (100-52-7) → (Z)-methyl 2-[hydroxy(phenyl)methyl]hex-3-enoate

Conditions	Yield
With [Rh(OH)(cod)]2; triethyl borane In tetrahydrofuran at 20 - 50℃; Inert atmosphere; stereoselective reaction;	90%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) + N-p-Anisylmonothiomaleimide (167258-61-9) → rel-(5S,7R,10S)-Methyl 7-methyl-1-p-methoxyphenyl-2-oxo-6-thia-1-azaspiro<4.5>deca-3,8-diene-10-carboxylate

Conditions	Yield
In benzene for 15h; Ambient temperature;	89%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → (E)-(4S,5S)-4,5-Dihydroxy-hex-2-enoic acid methyl ester (143289-07-0)

Conditions	Yield
With AD-mix-α Sharpless reaction;	88%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → 1,4-trans-threo-disyndiotactic poly((E,E)-methyl sorbate), Mn = 4.2E4 Da, Mw/Mn = 1.6; monomer(s): methyl 2,4-hexadienoate

Conditions	Yield
With tert.-butyl lithium; bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum; (-)-sparteine In toluene; pentane at -50℃; for 72h;	88%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → 1,4-trans-threo-disyndiotactic poly((E,E)-methyl sorbate), Mn = 4.4E4 Da, Mw/Mn = 1.6; monomer(s): methyl 2,4-hexadienoate

Conditions	Yield
With menthyl ethyl ether; tert.-butyl lithium; bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum In toluene; pentane at -50℃; for 72h;	88%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → 1,4-trans-threo-disyndiotactic poly((E,E)-methyl sorbate), Mn = 3.3E4 Da, Mw/Mn = 1.4; monomer(s): methyl 2,4-hexadienoate

Conditions	Yield
With tert.-butyl lithium; bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum; (-)-sparteine In toluene; pentane at -60℃; for 168h;	87%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) + 2-diazopropane (2684-60-8) → 5,5-Dimethyl-4-((E)-propenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid methyl ester (96685-07-3)

Conditions	Yield
In diethyl ether; ethylbenzene at -5℃;	85%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → (+/-) methyl (4,5)-trans-epoxy-(2E)-hexenoate (14202-27-8, 51830-12-7, 67315-16-6, 70095-87-3, 70494-79-0, 139686-29-6, 139686-31-0, 139686-32-1)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 24h; Ambient temperature;	85%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane Yield given;

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → <1-2H2>2,4-hexadien-1-ol

Conditions	Yield
With lithium aluminium deuteride In diethyl ether at -78 - 20℃;	85%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) + 7-exo-nethylcyclopentatriene complex → 10α,11β-dimethyl-7α-(methoxycarbonyl)-(1Hβ,6Hβ)-bicyclo[4.4.1]undeca-2,4,8-triene (129000-89-1)

Conditions	Yield
Irradiation;	83%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → Epoxy-4,5 hexene-2 (E) oate de methyle (51830-12-7) + methyl (E)-4-oxo-2-butenoate (5837-72-9) + methyl (E,E)-5-formyl-2,4-pentadienoate (40188-21-4)

Conditions	Yield
With tert.-butylhydroperoxide; chloroperoxidase In phosphate buffer pH=6; Enzymatic reaction;	A 4% B 13% C 83%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) + (R)-N-allyl (1-phenylethyl)amine (126275-19-2) → methyl (3S,4E,αR)-3-[N-allyl-N-(α-methylbenzyl)amino]hex-4-enoate (1202039-13-1)

Conditions	Yield
Stage #1: (R)-N-allyl (1-phenylethyl)amine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: (2E,4E)-methylhexa-2,4-dienoate In tetrahydrofuran; hexane at -78℃; for 2h; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water at -78 - 20℃; for 0.25h; optical yield given as %de; diastereoselective reaction;	83%

Upstream product

• 186581-53-3 diazomethane 
• 110-44-1 sorbic Acid 
• 67-56-1 methanol 
• 110-44-1 hexa-2,4-dienoic acid 
• 344890-72-8 (E)-4-Benzenesulfonyl-2-diethylamino-hepta-2,6-dienenitrile 
• 1918-79-2 2-methylthiophene-5-carboxylic acid 
• 123-73-9 trans-Crotonaldehyde 
• 16695-14-0 Malonic acid monomethyl ester 
• 5927-18-4 trimethyl phosphonoacetate 
• 18937-79-6 methyl 2-hexynoate 
• 19870-59-8 (2E)-5-Hydroxy-2-hexensaeuremethylester 
• 127379-38-8 Methyl (cis,E)-3-(2-Methyl-5,8-dioxaspiro<3.4>oct-1-yl)-2-propenoate 
• 127379-37-7 Methyl (trans,Z)-3-(2-Methyl-5,8-dioxaspiro<3.4>oct-1-yl)-2-propenoate 
• 127280-96-0 Methyl (trans,E)-3-(2-Methyl-5,8-dioxaspiro<3.4>oct-1-yl)-2-propenoate 

Downstream Products

• 51010-88-9 methyl (2E,4E)-6-bromo-2,4-hexadienoate 
• 412338-32-0 3,6-dihydro-6-methoxycarbonyl-3-methyl-2H-1,2-oxazine 
• 5837-72-9 methyl (E)-4-oxo-2-butenoate 
• 52811-30-0 (+/-)-aucantene 
• 74312-60-0 methyl (2Z,4E)-3-phenyl-2,4-hexadienoate 
• 74312-59-7 methyl (2E,4Z)-5-phenylhexa-2,4-dienoate 
• 110317-86-7 cis-2-Hydroxy-3,4-dimethyl-1,5-cyclohexadien-1-carbonsaeure-methylester 
• 110317-87-8 trans-2-Hydroxy-3,4-dimethyl-1,5-cyclohexadien-1-carbonsaeure-methylester 
• 110317-84-5 cis-4,5-Dimethyl-6-oxo-1-cyclohexen-1-carbonsaeure-methylester 
• 110317-85-6 trans-4,5-Dimethyl-6-oxo-1-cyclohexen-1-carbonsaeure-methylester 
• 110486-03-8 cis-2-Hydroxy-3-ethyl-4-methyl-1,5-cyclohexadien-1-carbonsaeure-methylester 
• 110317-89-0 trans-2-Hydroxy-3-ethyl-4-methyl-1,5-cyclohexadien-1-carbonsaeure-methylester 
• 110318-28-0 cis-5-Ethyl-4-methyl-6-oxo-1-cyclohexen-1-carbonsaeure-methylester 
• 110317-88-9 trans-5-Ethyl-4-methyl-6-oxo-1-cyclohexen-1-carbonsaeure-methylester 

Relevant articles and documents

Ruthenium-Catalyzed Oxidative Cross-Coupling Reaction of Activated Olefins with Vinyl Boronates for the Synthesis of (E, E)-1,3-Dienes

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