25601-41-6

Basic information

• Product Name: 9-Decenoic acid, methyl ester
• Synonyms: 9-Decenoic acid, methyl ester;methyl Sdecenoate;9-Decenoic acid, methyl;methyl dec-9-enoate
• CAS NO: 25601-41-6
• Molecular Formula: C₁₁H₂₀O₂
• Molecular Weight: 184.2753
• Mol File: 25601-41-6.mol
• Article Data: 90

Chemical Properties

• Boiling Point: 123 °C(Press: 21 Torr)
• Appearance: white crystalline powder
• Density: 0.883±0.06 g/cm3(Predicted)
• Vapor Pressure: 13.37Pa at 25℃
• CAS DataBase Reference: 9-Decenoic acid, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Decenoic acid, methyl ester(25601-41-6)
• EPA Substance Registry System: 9-Decenoic acid, methyl ester(25601-41-6)

Safety Data

• Hazardous Substances Data: 25601-41-6(Hazardous Substances Data)

Usage

General Description

9-Decenoic acid, methyl ester is a chemical compound with the molecular formula C11H20O2. Also known as methyl 9-decenoate, it is a colorless liquid with a fruity, waxy odor. 9-Decenoic acid, methyl ester is commonly used as a flavoring agent and fragrance ingredient in the food and cosmetics industries. It is also utilized in the production of pharmaceuticals and other chemical products. Moreover, it can be found naturally in various plants and food sources, such as apples, bananas, and strawberries. The chemical's properties make it an important component in the creation of various scents and flavors, adding a pleasant and distinctive aroma to products.

Synthetic route

methanol (67-56-1) + dec-9-enoic acid (14436-32-9) → methyl 9-decenoate (25601-41-6)

Conditions	Yield
With hydrogenchloride In water at 20℃; for 48h; Inert atmosphere;	100%
sulfuric acid for 4h; Heating;	98%
With sulfuric acid	98%

dec-9-enoic acid (14436-32-9) + methyl iodide (74-88-4) → methyl 9-decenoate (25601-41-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 23h;	93%

ethene (74-85-1) + dimethyl 9-octadecen-1,18-dioate (13481-97-5) → methyl 9-decenoate (25601-41-6)

Conditions	Yield
With C50H60Br2MoN2O2 In pentane at 20℃; under 8625.86 Torr; for 12.5h; Reagent/catalyst; Concentration; Autoclave; Glovebox;	86%
With C29H47Cl2OPRu In carbonic acid dimethyl ester at 20℃; under 750.075 Torr; for 3h; Inert atmosphere;
With Hoveyda-Grubbs catalyst first generation In carbonic acid dimethyl ester at 20℃; under 750.075 Torr; for 3h; Inert atmosphere;

10-(2-Nitro-phenylselanyl)-decanoic acid methyl ester (95259-35-1) → methyl 9-decenoate (25601-41-6)

Conditions	Yield
With dihydrogen peroxide In tetrahydrofuran for 15h;	84%
With dihydrogen peroxide In tetrahydrofuran for 24h;	84%

dimethyl (Z)-octadec-9-ene-1,18-dioate (13481-97-5, 24753-49-9, 40393-46-2) + acrylonitrile (107-13-1) → methyl 9-decenoate (25601-41-6) + methyl 10-cyano-dec-9-enoate (1046470-12-5)

Conditions	Yield
With Hoveyda-Grubbs catalyst second generation In toluene at 100℃; for 1h; Cross-metathesis; Inert atmosphere;	A n/a B 82%

Methyl oleate (112-62-9) + ethene (74-85-1) → methyl 9-decenoate (25601-41-6)

Conditions	Yield
Stage #1: Methyl oleate With tetraethylammonium iodide In toluene at 20℃; for 1h; Inert atmosphere; Glovebox; Stage #2: ethene With C50H59Br2Cl2N3O2SiW In toluene; benzene at 50℃; under 7600.51 Torr; for 18h; Reagent/catalyst; Concentration; Autoclave; Inert atmosphere;	78%
Grubbs catalyst first generation In dichloromethane at 40℃; under 7757.43 Torr; for 4h; Product distribution / selectivity;
1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene-dichloro(3-methyl-2-buteneylidene)-(tricyclohexylphosphine)ruthenium In dichloromethane at 40 - 60℃; under 7757.43 Torr; for 2 - 4h; Product distribution / selectivity;

octadec-9-enoic acid methyl ester (112-62-9) + ethene (74-85-1) → 1-Decene (872-05-9) + methyl 9-decenoate (25601-41-6) + 9-octadecene (5557-31-3) + dimethyl 9-octadecen-1,18-dioate (13481-97-5)

Conditions	Yield
With dichloro[(2-(tert-butyl)-6-propylphenoxy)(pyrrolidin-1-ium-1-ylidene)methanide](2-isopropoxyphenylmethylene)ruthenium(II) at 40℃; under 7757.43 Torr; Reagent/catalyst;	A 73% B n/a C n/a D n/a
With RuCl2(CN2C2H4(C6H3(CH(CH3)2)2)(C7H8(CH3)3))(CHC6H4OCH(CH3)2) In dichloromethane at 40℃; under 7757.43 Torr; for 6h; Inert atmosphere;
Stage #1: octadec-9-enoic acid methyl ester; ethene With [1 ,3-bis-(2,4,6-trimethylpheuyl)-2-imidazolidinylidene]dichloro(phenylindenylidene)(acetonitrile)ruthenium(II) at 40℃; under 8517.48 Torr; for 4h; Glovebox; Sealed tube; Inert atmosphere; Stage #2: With tris(hydroxymethyl)phosphine In isopropyl alcohol at 70℃; for 1h; Catalytic behavior;
With Grubbs catalyst first generation In toluene for 0.333333h; Reagent/catalyst; Flow reactor;

methanol (67-56-1) + (2-nitrophenyl)(undec-10-en-1-yl)selane → methyl 9-decenoate (25601-41-6)

Conditions	Yield
Stage #1: methanol; (2-nitrophenyl)(undec-10-en-1-yl)selane With ozone; sodium hydroxide In dichloromethane at -78℃; Stage #2: With oxygen In dichloromethane at -78℃; Stage #3: In dichloromethane at -78 - 20℃;	65%

octadec-9-enoic acid methyl ester (112-62-9) + ethene (74-85-1) → 1-Decene (872-05-9) + methyl 9-decenoate (25601-41-6)

Conditions	Yield
With F6P(1-)*C48H51Br2Cl2N4O2W(1+)	A n/a B 62%
silica gel In dichloromethane under 5250.4 Torr; for 2h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With Grubbs catalyst first generation In toluene for 0.333333h; Flow reactor;

methyl (9E)-octadec-9-enoate (2462-84-2) + but-3-enenitrile (109-75-1) → methyl 9-decenoate (25601-41-6) + methyl 11-cyano-9-undecenoate (1395034-03-3)

Conditions	Yield
With Hoveyda-Grubbs catalyst second generation; p-benzoquinone In chlorobenzene for 7h;	A 9.2 %Chromat. B 55%

Methyl oleate (112-62-9) + ethene (74-85-1) → 1-Decene (872-05-9) + methyl 9-decenoate (25601-41-6) + 9-octadecene (5557-31-3) + dimethyl 9-octadecen-1,18-dioate (13481-97-5)

Conditions	Yield
Cl2(PCy3)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC6H5 at 20℃; for 12h; Product distribution / selectivity;	A 43% B 46% C 3% D 2%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In toluene at 20 - 23℃; under 11103.3 - 26618.1 Torr; Autoclave; Inert atmosphere;
With BerEt In toluene at 40℃; under 3102.97 Torr; for 1h; microfluidic reactor;

octadec-9-enoic acid methyl ester (112-62-9) + ethene (74-85-1) → 1-Decene (872-05-9) + methyl 9-decenoate (25601-41-6) + dimethyl 9-octadecen-1,18-dioate (13481-97-5)

Conditions	Yield
With C29H47Cl2OPRu In carbonic acid dimethyl ester at 20℃; under 750.075 Torr; Inert atmosphere;	A 42% B 43% C 2%

methyl (9E)-octadec-9-enoate (2462-84-2) + 4-Pentenenitrile (592-51-8) → methyl 9-decenoate (25601-41-6) + 12-cyano-9-dodecenoic acid methyl ester

Conditions	Yield
With Hoveyda-Grubbs catalyst second generation; p-benzoquinone In chlorobenzene at 110℃; for 4h;	A 16.2 %Chromat. B 42.9%

undecanedioic acid monomethyl ester (3927-60-4) → methyl 9-decenoate (25601-41-6)

Conditions	Yield
With pyridine; lead(IV) acetate; copper diacetate In benzene for 3h; Heating;	36.3%

methanol (67-56-1) + Methyl 10-undecenoate (111-81-9) → methyl 9-decenoate (25601-41-6)

Conditions	Yield
Multistep reaction;

1-butylene (106-98-9) + octadec-9-enoic acid methyl ester (112-62-9) → 1-Decene (872-05-9) + methyl 9-decenoate (25601-41-6) + dodec-3-ene (2030-83-3) + 9-dodecenoic acid methyl ester (39202-17-0)

Conditions	Yield
With tetramethylstannane; tungsten(VI) chloride at 20 - 100℃; Kinetics; Product distribution; Mechanism;

1-Heptene (592-76-7) + octadec-9-enoic acid methyl ester (112-62-9) → 1-Decene (872-05-9) + methyl 9-decenoate (25601-41-6) + 6-pentadecene (42714-72-7) + methyl 6-pentadecenoate

Conditions	Yield
With tetramethylstannane; tungsten(VI) chloride at 20 - 100℃; Kinetics; Product distribution; Mechanism;

1-hexene (592-41-6) + octadec-9-enoic acid methyl ester (112-62-9) → 1-Decene (872-05-9) + methyl 9-decenoate (25601-41-6) + myristelaidic acid methyl ester (72025-18-4) + 1-tetradecene (4084-07-5)

Conditions	Yield
With tetramethylstannane; tungsten(VI) chloride at 20 - 100℃; Kinetics; Product distribution; Mechanism;

Methyl oleate (112-62-9) + ethene (74-85-1) → trans-9-octadecene (7206-25-9) + Dimethyl (E)-octadec-9-enedioate (24753-49-9) + 1-Decene (872-05-9) + methyl 9-decenoate (25601-41-6)

Conditions	Yield
aluminum oxide; tetramethylstannane; rhenium(VII) oxide In chlorobenzene at 19.9℃; under 1500.1 Torr; for 20h; Product distribution; var. of catalyst, ratio substrate : catalyst, solvent, temp., pressure;

10-bromodecanoic acid methyl ester (26825-94-5) → methyl 9-decenoate (25601-41-6)

Conditions	Yield
With sodium tetrahydroborate; ortho-nitrophenyl selenocyanate; dihydrogen peroxide 1) EtOH, THF, 8h, RT 2) 6h, RT; Yield given. Multistep reaction;
Multi-step reaction with 3 steps 1: 1.) aq. NaOH / 1.) 50 deg C 2: 76 percent / tributylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 3: 84 percent / aq. H2O2 / tetrahydrofuran / 24 h View Scheme
Multi-step reaction with 3 steps 1: 1.) 20percent KOH / 1.) water, 50 deg C 2: 78 percent / tri-n-butylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 3: 84 percent / 30percent H2O2 / tetrahydrofuran / 15 h View Scheme
Multi-step reaction with 2 steps 1: 76 percent / NaBH4 / ethanol / 13 h / Ambient temperature 2: 84 percent / 30percent H2O2 / tetrahydrofuran / 15 h View Scheme

θ.ι-dibromo-capric acid methyl ester → methyl 9-decenoate (25601-41-6)

Conditions	Yield
With hydrogenchloride; zinc

Methyl oleate (112-62-9) + ethene (74-85-1) → 1-Decene (872-05-9) + methyl 9-decenoate (25601-41-6)

Conditions	Yield
Grubbs catalyst first generation In dichloromethane at 50℃; under 7500.6 Torr; for 2h; metathesis;
phoban-indenylidene ruhenium catalyst at 50℃; for 2h; Product distribution; Further Variations:; Catalysts;
Grubbs catalyst first generation In toluene at 30℃; under 3102.97 Torr; for 4h;	A 19.9 %Chromat. B 18 %Chromat.

(9Z,11E)-methyl octadeca-9,11-dienoate (822-10-6, 13038-47-6, 17675-24-0, 19295-76-2, 13058-52-1) + ethene (74-85-1) → deca-1,3-diene (2051-25-4) + oct-1-ene (111-66-0) + methyl 9-decenoate (25601-41-6) + tetradec-7-ene (10374-74-0) + methyl dodeca-9,11-dienoate (256235-74-2) + dimethyl 9-octadecen-1,18-dioate (13481-97-5)

Conditions	Yield
RuCl2(sIMes)(CHPh)(pyridine)2 In dichloromethane at 30℃; under 7757.43 Torr; for 0.5 - 17.45h; Product distribution / selectivity;
Mol's catalyst In dichloromethane at 30℃; under 7757.43 Torr; for 0.5 - 17.45h; Product distribution / selectivity;
C34H44Cl2N2ORu In dichloromethane at 30℃; under 7757.43 Torr; for 0.5 - 17.45h; Product distribution / selectivity;

dec-9-enoic acid (14436-32-9) + diazomethyl-trimethyl-silane (18107-18-1) → methyl 9-decenoate (25601-41-6)

Conditions	Yield
In methanol; hexane; benzene at 25℃; for 0.5h;

9-Decen-1-ol (13019-22-2) + [4-(chloro-diphenyl-methyl)phenoxy]-poly[styrene-co-divinylbenzene] → methyl 9-decenoate (25601-41-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / CrO3; H2SO4 / acetone 2: 98 percent / H2SO4 View Scheme

1,10-Decanediol (112-47-0) + carbon monoxide → methyl 9-decenoate (25601-41-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) 48 percent HBr, concd. H2SO4; 2.) KMnO4 / 1.) 3 h, reflux; 2.) 20percent H2SO4, 15-20 deg C 3: 1.) aq. NaOH / 1.) 50 deg C 4: 76 percent / tributylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 5: 84 percent / aq. H2O2 / tetrahydrofuran / 24 h View Scheme
Multi-step reaction with 4 steps 2: 1.) 20percent KOH / 1.) water, 50 deg C 3: 78 percent / tri-n-butylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 4: 84 percent / 30percent H2O2 / tetrahydrofuran / 15 h View Scheme
Multi-step reaction with 3 steps 2: 76 percent / NaBH4 / ethanol / 13 h / Ambient temperature 3: 84 percent / 30percent H2O2 / tetrahydrofuran / 15 h View Scheme

10-bromodecanoic acid (50530-12-6) → methyl 9-decenoate (25601-41-6)

Conditions	Yield
Multi-step reaction with 4 steps 2: 1.) aq. NaOH / 1.) 50 deg C 3: 76 percent / tributylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 4: 84 percent / aq. H2O2 / tetrahydrofuran / 24 h View Scheme
Multi-step reaction with 2 steps 1: 94 percent / TsOH / 24 h / Ambient temperature 2: 1) o-Nitrophenyl selenocyanate, NaBH4 2) 30percent H2O2 / 1) EtOH, THF, 8h, RT 2) 6h, RT View Scheme

methyl 10-hydroxydecanoate (2640-94-0) → methyl 9-decenoate (25601-41-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / tributylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 2: 84 percent / aq. H2O2 / tetrahydrofuran / 24 h View Scheme
Multi-step reaction with 2 steps 1: 78 percent / tri-n-butylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 2: 84 percent / 30percent H2O2 / tetrahydrofuran / 15 h View Scheme

Methyl 10-undecenoate (111-81-9) → methyl 9-decenoate (25601-41-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) BF3*THF, 2) Jones' reagent / 1a) 0 deg C, 2 h, b) r.t., 2 h, 2) acetone, r.t., 3 h 2: 36.3 percent / Pb(OAc)4, pyridine, Cu(OAc)2 / benzene / 3 h / Heating View Scheme

9-Decen-1-ol (13019-22-2) → methyl 9-decenoate (25601-41-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / CrO3 / acetone; aq. H2SO4 / 20 h / Ambient temperature 2: 1.) SOCl2 / 1.) methylene dichloride, 4.0 h reflux; 2.) room temp., 2.0 h View Scheme
Multi-step reaction with 2 steps 1: chromium(VI) oxide; sulfuric acid / acetone / 0.25 h / 0 °C 2: diethyl ether View Scheme

methyl 9-decenoate (25601-41-6) → 9-Decen-1-ol (13019-22-2)

Conditions	Yield
Stage #1: methyl 9-decenoate With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 5.5h; Cooling; Stage #2: With sodium hydroxide In tetrahydrofuran; water at 20℃; Reagent/catalyst; Concentration; Solvent; Temperature; Time;	98.3%
With lithium aluminium tetrahydride In tetrahydrofuran at 15 - 20℃; for 5.5h; Inert atmosphere;	98.3%
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 15 - 20℃; for 2h; Sealed tube; Cooling with ice; Inert atmosphere;	97.14%

methyl 9-decenoate (25601-41-6) + 2,2'-iminobis[ethanol] (111-42-2) → N,N-dihydroxyethyl-9-decenamide

Conditions	Yield
Stage #1: methyl 9-decenoate; 2,2'-iminobis[ethanol] at 100℃; for 5h; Inert atmosphere; Stage #2: With sodium methylate In methanol	98%

methyl 9-decenoate (25601-41-6) → methyl E-8-decenoate (62472-91-7)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 10h; Heating;	97%
With toluene-4-sulfonic acid

methyl 9-decenoate (25601-41-6) → dec-9-enoic acid (14436-32-9)

Conditions	Yield
With potassium hydroxide In water; isopropyl alcohol at 20 - 54℃; under 760.051 Torr; for 4.5h; Inert atmosphere; Large scale;	97%
With potassium hydroxide In tetrahydrofuran; water for 14h; Ambient temperature;	90%
Stage #1: methyl 9-decenoate With potassium hydroxide In glycerol at 100 - 140℃; Stage #2: With sulfuric acid In water; glycerol at 90℃;
With water; sodium hydroxide at 50℃; for 1h;	26.3 g
With water; potassium hydroxide In isopropyl alcohol at 30 - 55℃; for 4h;	957 g

methyl 9-decenoate (25601-41-6) → 9,10-Dihydroxy-decanoic acid methyl ester

Conditions	Yield
With potassium osmate(VI) dihydrate; potassium hexacyanoferrate(III); sodium hydrogencarbonate; potassium carbonate; hydroquinine (anthraquinone-1,4-diyl) diether In water; tert-butyl alcohol at -20℃; for 48h; Sharpless asymmetric dihydroxylation;	97%

methyl 9-decenoate (25601-41-6) + ethanolamine (141-43-5) → N-hydroxyethyl-9-decenamide

Conditions	Yield
Stage #1: methyl 9-decenoate; ethanolamine at 110℃; for 6h; Inert atmosphere; Stage #2: With potassium hydroxide In methanol	97%

methyl 9-decenoate (25601-41-6) → methyl 8-(oxiran-2-yl)octanoate (87321-84-4)

Conditions	Yield
With ethylbenzene hydroperoxide; molybdenum naphthenate In ethylbenzene at 200℃; for 3.5h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	96.4%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 1h;	86.4%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane Cooling with ice;

methyl 9-decenoate (25601-41-6) → methyl 2-(7-octenyl)-3-oxo-11-dodecenoate

Conditions	Yield
With tributyl-amine; titanium tetrachloride In toluene at 0 - 5℃; for 1h; Condensation;	93%

methyl 9-decenoate (25601-41-6) + 3-methyl-5H-1,4,2-dioxazol-5-one → methyl 8-acetamidodec-9-enoate

Conditions	Yield
With silver hexafluoroantimonate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) acetate In dichloromethane at 40℃; for 18h; Schlenk technique; Inert atmosphere; Sealed tube; regioselective reaction;	91%

methyl 9-decenoate (25601-41-6) + (E)-1,4-hexadiene (7319-00-8) → (9Z,12E)-9,12-Tetradecadiensaeure-methylester (53143-98-9)

Conditions	Yield
With C35H47N3O4Ru In tetrahydrofuran at 20℃; for 5h; Glovebox; Inert atmosphere; chemoselective reaction;	82%

methyl 9-decenoate (25601-41-6) → dimethyl 9-octadecen-1,18-dioate (13481-97-5)

Conditions	Yield
With Mo(N-2,6-’Pr2-C5H3)(CHCMe2Ph)(2,5-dimeth-ylpyrrolide)(O-2,6-Ph2C5H3) at 50℃; Reagent/catalyst; Temperature; Inert atmosphere; Molecular sieve; Glovebox;	80.9%
With [1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene][2-isopropoxy-5-(2,2,2-trifluoroacetamido)benzylidene]ruthenium(II) dichloride In toluene at 110℃; for 2h; Inert atmosphere;	63%
Grubbs catalyst first generation at 50℃; under 3.7503 Torr; for 2h;

methyl 9-decenoate (25601-41-6) + C35H48N2O6Si → C44H64N2O8Si

Conditions	Yield
With Hoveyda-Grubbs catalyst second generation; p-benzoquinone In dichloromethane for 3.5h; Reflux;	79%

methyl 9-decenoate (25601-41-6) + 2,4,6-tris-(2-fluorophenyl)boroxine → C17H23FO2

Conditions	Yield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In 1,2-dichloro-ethane at 60℃; for 4h; Suzuki-Miyaura Coupling;	77%

methyl 9-decenoate (25601-41-6) + 1-bromo-2-(triisopropylsilyl)acetylene (111409-79-1) → C22H40O2Si + methyl (E)-12-(triisopropylsilyl)dodec-8-en-11-ynoate

Conditions	Yield
With silver tetrafluoroborate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium acetate at 60℃; for 12h; Schlenk technique; Glovebox; Inert atmosphere; Sealed tube; Overall yield = 45 percent; Overall yield = 25.2 mg; regioselective reaction;	A n/a B 75%

methyl 9-decenoate (25601-41-6) → methyl ester of azelaic acid aldehyde (1931-63-1)

Conditions	Yield
Stage #1: methyl 9-decenoate With ozone In dichloromethane at -78℃; Stage #2: With acetic acid; zinc Further stages.;	72%
Stage #1: methyl 9-decenoate With oxygen; ozone; acetic acid for 7h; Cooling with water bath; Industry scale; Stage #2: With zinc In diethyl ether; water Product distribution / selectivity; Industry scale;
Multi-step reaction with 2 steps 1: ozone / dichloromethane / -78 °C / Inert atmosphere 2: dimethylsulfide / 20 °C / Inert atmosphere View Scheme
With potassium osmate(VI) dihydrate; sodium periodate In tetrahydrofuran; water for 5h;

methyl 9-decenoate (25601-41-6) + di(4-tosyl)amine (3695-00-9) → methyl 10,11-bis(4-methyl-N-tosylphenylsulfonamido)undecanoate (1374869-71-2)

Conditions	Yield
With [bis(acetoxy)iodo]benzene In dichloromethane at 50℃; for 12h;	70%

methyl 9-decenoate (25601-41-6) + carbon monoxide (201230-82-2) → methyl 11-hydroxyundecanoate (24724-07-0)

Conditions	Yield
Stage #1: methyl 9-decenoate; carbon monoxide With hydrogen; 1,1'-[2,7-bis(1,1-dimethylethyl)-9,9-dimethyl-9H-xanthene-4,5-diyl]bis[1,1-diphenylphosphine]; Rh(acac)(CO)2 at 20 - 100℃; under 23272.3 Torr; for 20h; Stage #2: 5 % platinum on carbon In 1,4-dioxane at 150℃; under 25858.1 Torr; for 20h;	65%

methyl 9-decenoate (25601-41-6) + (S)-dec-9-en-2-ol (142288-39-9) → (S,Z)-methyl 17-hydroxyoctadece-9-enoate (114127-64-9)

Conditions	Yield
With C35H47N3O4Ru In dichloromethane at 20℃; for 24h; Inert atmosphere; diastereoselective reaction;	59%

methyl 9-decenoate (25601-41-6) + 3-(methoxymethoxy)-5-(triisopropylsilyl)pent-1-en-4-yne → methyl (9Z)-11-(methoxymethoxy)-13-(triisopropylsilyl)tridec-9-en-12-ynoate

Conditions	Yield
With C35H47N3O4Ru In dichloromethane at 60℃; Catalytic behavior; Reagent/catalyst; Temperature; Cross Metathesis; Sealed tube;	59%
With C35H47N3O4Ru In dichloromethane at 60℃; Catalytic behavior; Reagent/catalyst; Temperature; Cross Metathesis; Sealed tube;	43%
With C35H47N3O4Ru In dichloromethane at 60℃; Catalytic behavior; Reagent/catalyst; Temperature; Cross Metathesis; Sealed tube;	40%

methyl 9-decenoate (25601-41-6) + 2,4,6,8-tetramethylcyclotetrasiloxane (2370-88-9) → 1,3,5,7-tetrakis(9-carboxynonyl)-1,3,5,7-tetramethylcyclotetrasiloxane tetramethyl ester

Conditions	Yield
Stage #1: methyl 9-decenoate With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 20℃; for 0.0833333h; Stage #2: 2,4,6,8-tetramethylcyclotetrasiloxane In toluene for 2h; Reflux;	58%
In ethyl acetate; toluene

Upstream product

• 112-62-9 Methyl oleate 
• 74-85-1 ethene 
• 141-24-2 methyl ricinoleate 
• 401630-64-6 methyl ricinoleate acetate 
• 124-41-4 sodium methylate 
• 187737-37-7 propene 
• 6651-33-8 1-(trimethylsiloxy)but-1-ene 
• 39202-17-0 9-dodecenoic acid methyl ester 
• 20701-68-2 (9Z)-octadec-9-enedioic acid 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 107-13-1 acrylonitrile 
• 13481-97-5 dimethyl (Z)-octadec-9-ene-1,18-dioate 
• 2462-84-2 methyl (9E)-octadec-9-enoate 
• 67-56-1 methanol 

Downstream Products

• 123-99-9 azelaic acid 
• 64-18-6 formic acid 
• 13481-97-5 dimethyl 9-octadecen-1,18-dioate 
• 676335-59-4 (E)-(12S,13S)-13-Benzyloxycarbonylamino-12-hydroxy-9-oxo-tetradec-10-enoic acid methyl ester 
• 676335-57-2 (E)-(12S,13S)-13-Benzyloxycarbonylamino-9-oxo-12-trimethylsilanyloxy-tetradec-10-enoic acid methyl ester 
• 13481-97-5 dimethyl (Z)-octadec-9-ene-1,18-dioate 
• 24753-49-9 Dimethyl (E)-octadec-9-enedioate 
• 1191950-43-2 methyl 11-[(acetyloxy)(phenyl)methyl]dodeca-9,11-dienoate 
• 1417996-20-3 methyl tridec-9-enoate 
• 58257-45-7 methyl tridec-9-enoate 
• 22915-49-7 11-cyanoundecanoic acid methyl ester 
• 53005-24-6 methyl 12-aminododecanoate 
• 74-85-1 ethene 
• 1046470-12-5 methyl 10-cyano-dec-9-enoate 

Relevant articles and documents

Solubility in CO2 and carbonation studies of epoxidized fatty acid diesters: Towards novel precursors for polyurethane synthesis

Novel linear polyurethanes were synthesized by bulk polyaddition of diamines with two vegetable-based biscarbonates produced from oleic acid methyl ester. Internal carbonated fatty acid diester (ICFAD) and terminal carbonated fatty acid diester (TCFAD) were obtained by the reaction of their epoxide precursors with CO2. Terminal epoxy fatty acid diester (TEFAD) was found to be more soluble and more reactive in CO2 than internal epoxy fatty acid diester (IEFAD). Polyurethanes obtained by polyaddition of TCFAD and ICFAD with diamines exhibit molecular weights up to 13500 g mol-1 and glass transitions around -15 °C. Amide linkages were not observed when secondary diamine was used as the comonomer.

Identification of novel decenoic acids in heated butter

Novel decenoic acids such as (E)-4-decenoic acid and (E)- and (Z)-5-,6-decenoic acid were detected as minor components in heated butter using GC and GC/MS. The formation mechanism of these novel decenoic acids is discussed on the basis of the result of the reaction of δ-decalactone with active clay in a model experiment.

EXTRAHEPATIC DELIVERY

One aspect of the present invention relates to a compound comprising an antisense strand which is complementary to a target gene; a sense strand which is complementary to said antisense strand; and one or more lipophilic monomers, containing one or more lipophilic moieties, conjugated to one or more positions on at least one strand, optionally via a linker or carrier. Another aspect of the invention relates to a method of gene silencing, comprising administering to a cell or a subject in need thereof a therapeutically effective amount of the lipophilic monomer-conjugated compound.

Direct and Tandem Routes for the Copolymerization of Ethylene with Polar Functionalized Internal Olefins

Transition metal catalyzed ethylene copolymerization with polar monomers is a highly challenging reaction. After decades of research, the scope of suitable comonomer substrates has expanded from special to fundamental polar monomers and, recently, to 1,1-disubstituted ethylenes. Described in this contribution is a direct and tandem strategy to realize ethylene copolymerization with various 1,2-disubstituted ethylenes. The direct route is sensitive to sterics of both the comonomers and the catalyst. In the tandem route, ruthenium-catalyzed ethenolysis can convert 1,2-disubstituted ethylenes into terminal olefins, which can be subsequently copolymerized with ethylene to afford polar functionalized polyolefins. The one-pot, two-step tandem route is highly versatile and efficient in dealing with challenging substrates. This work is a step forward in terms of expanding the substrate scope for transition metal catalyzed ethylene copolymerization with polar-functionalized comonomers.