929-77-1

Basic information

• Product Name: BEHENIC ACID METHYL ESTER
• Synonyms: Kemester 9022;n-Docosanoic acid methyl ester;METHYL DOCOSANOATE;METHYL BEHENATE;BEHENIC ACID METHYL ESTER;C22;C22:0 METHYL ESTER;DOCOSANOIC ACID METHYL ESTER
• CAS NO: 929-77-1
• Molecular Formula: C₂₃H₄₆O₂
• Molecular Weight: 354.61
• EINECS: 213-207-8
• Mol File: 929-77-1.mol
• Article Data: 25

Chemical Properties

• Melting Point: 54-56 °C(lit.)
• Boiling Point: 393 °C
• Flash Point: 113 °C
• Appearance: /Liquid
• Density: 0.8784 (rough estimate)
• Vapor Pressure: 1.52E-06mmHg at 25°C
• Refractive Index: 1.4339 (589.3 nm 60℃)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Very Slightly, Heated
• Merck: 14,1023
• BRN: 1795147
• CAS DataBase Reference: BEHENIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: BEHENIC ACID METHYL ESTER(929-77-1)
• EPA Substance Registry System: BEHENIC ACID METHYL ESTER(929-77-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 1
• Hazardous Substances Data: 929-77-1(Hazardous Substances Data)

Usage

Description

Docosanoic acid methyl ester is an ester form of docosanoic acid . It has been found in soybean, corn, sunflower, and canola oils, as well as beef fat, used in the production of biodiesel.

Chemical Properties

Wax-like solid. Insoluble in water; soluble in alcohol and ether. Combustible.

Uses

Different sources of media describe the Uses of 929-77-1 differently. You can refer to the following data:
1. Docosanoic Acid Methyl Ester is a long chain fatty acid, existing as a wax and is found in sunflower seeds. It can be used in biodiesel production.
2. Methyl Docosanoate is a long chain fatty acid, existing as a wax and is found in sunflower seeds. It can be used in biodiesel production.

Definition

The methyl ester of behenic acid.

InChI:InChI=1/C23H46O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23(24)25-2/h3-22H2,1-2H3

Synthetic route

methyl erucate → behenic acid methyl ester (929-77-1)

Conditions	Yield
With hydrogen; palladium dichloride In dichloromethane at 20℃; under 760 Torr;	98%

n-docosanoic acid (112-85-6) + carbonic acid dimethyl ester (616-38-6) → behenic acid methyl ester (929-77-1)

Conditions	Yield
With triethylamine at 160℃; for 5h; Autoclave; Green chemistry;	95%
With diiron nonacarbonyl at 180℃; for 1h; Sealed tube;

15-(methoxycarbonyl)pentadecanoic acid (18451-85-9) + Octanoic acid (124-07-2) → tetradecane (629-59-4) + behenic acid methyl ester (929-77-1) + triacontanedioic acid dimethyl ester (24397-43-1)

Conditions	Yield
With sodium methylate In methanol at 27℃; Kolbe coupling; Electrochemical reaction; Pt anode; graphite cathode;	A n/a B 72% C n/a

sebacic acid mono methyl ester (818-88-2) + n-tetradecanoic acid (544-63-8) → behenic acid methyl ester (929-77-1)

Conditions	Yield
With sodium methylate In methanol at 35℃; electrolysis on Pt electrode, 0.05 amps, 50-60 volts;	45.2%

diazomethane (186581-53-3, 908094-01-9) + n-docosanoic acid (112-85-6) → behenic acid methyl ester (929-77-1)

Conditions	Yield
With diethyl ether
In Petroleum ether Acidic conditions;

methanol (67-56-1) + n-docosanoic acid (112-85-6) → behenic acid methyl ester (929-77-1)

Conditions	Yield
With sulfuric acid
With sulfuric acid for 7h; Heating;
With sulfuric acid Heating;

13-docosenoic acid methyl ester (56630-69-4) → behenic acid methyl ester (929-77-1)

Conditions	Yield
With hydrogen; nickel at 190 - 200℃; Hydrogenation;

adipic acid monomethyl ester (627-91-8) + stearic acid (57-11-4) → behenic acid methyl ester (929-77-1)

Conditions	Yield
With methanol; sodium Electrolysis;

methanol (67-56-1) + oceanapin E → behenic acid methyl ester (929-77-1) + (4E)-2-amino-16-methyloctadec-4-ene-1,3-diol

Conditions	Yield
With sulfuric acid for 6h; Heating;

n-docosanoic acid (112-85-6) → behenic acid methyl ester (929-77-1)

oceanapin E → behenic acid methyl ester (929-77-1) + (4E)-2-amino-16-methyloctadec-4-ene-1,3-diol

Conditions	Yield
With methanol; sulfuric acid for 6h; Heating;

methanol (67-56-1) + C55H111N2O11P → behenic acid methyl ester (929-77-1) + sphinganine (d22:0)

Conditions	Yield
With hydrogenchloride at 90℃; for 2h;

methanol (67-56-1) + N-docosanoyl-1-O-<6-O-(2-trimethylammonioethoxy)phosphinate-β-D-galactopyranosyl>-(4E,8Z,11Z)-docosaspingatrienine → behenic acid methyl ester (929-77-1)

Conditions	Yield
With hydrogenchloride at 90℃; for 1h;

Docosanoic acid ((E)-(1S,2R)-2-hydroxy-1-hydroxymethyl-15-methyl-hexadec-3-enyl)-amide → behenic acid methyl ester (929-77-1) + (E)-(2S,3R)-2-Amino-16-methyl-heptadec-4-ene-1,3-diol

Conditions	Yield
With hydrogenchloride; methanol at 76℃; for 18h;	A n/a B 0.7 mg

methanol (67-56-1) + (2S,3R)-N-(docosanoate)-1,3-dihydroxy-2-amino-octadeca-4-(E)-ene (27888-44-4) → behenic acid methyl ester (929-77-1)

Conditions	Yield
With sulfuric acid In water for 4h; Esterification; methanolysis; Heating;

methanol (67-56-1) + (4E,6E,2S,3R)-2-N-docosanoyl-4,6-tetradecasphingadienine → behenic acid methyl ester (929-77-1)

Conditions	Yield
With hydrogenchloride at 74℃; for 24h;

(2S,3R)-2-(docosanoyl amino)nonadecane-1,3-diol + methanol (67-56-1) → behenic acid methyl ester (929-77-1)

Conditions	Yield
With hydrogenchloride at 90℃; for 15h;

methanol (67-56-1) + ((2S)-1-O-hexadecanoyl-2-O-docosanoyl)-3-O-[6-deoxy-6-amino-α-D-glucopyranoside]glycerol → hexadecanoic acid methyl ester (112-39-0) + behenic acid methyl ester (929-77-1)

Conditions	Yield
With sodium methylate at 20℃; for 3h;

azelaic monomethyl ester (2104-19-0) → behenic acid methyl ester (929-77-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: MeONa / methanol / Electrolysis; Pt anode; graphite cathode 2: Ba(OH)2 3: 72 percent / MeONa / methanol / 27 °C / Electrochemical reaction; Pt anode; graphite cathode View Scheme

dimethyl hexadecanedioate (19102-90-0) → behenic acid methyl ester (929-77-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: Ba(OH)2 2: 72 percent / MeONa / methanol / 27 °C / Electrochemical reaction; Pt anode; graphite cathode View Scheme

n-hexadecylaldehyde (629-80-1) → behenic acid methyl ester (929-77-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) n-BuLi / 1.) THF, hexane, -10 deg C, 45 min, 2.) THF, hexane, room temperature, overnight 2: 86 percent / H2 / Pd/C / methanol / 6 h 3: H2SO4 / 7 h / Heating View Scheme

(5-carboxypentyl)triphenylphosphonium bromide (50889-29-7) → behenic acid methyl ester (929-77-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) n-BuLi / 1.) THF, hexane, -10 deg C, 45 min, 2.) THF, hexane, room temperature, overnight 2: 86 percent / H2 / Pd/C / methanol / 6 h 3: H2SO4 / 7 h / Heating View Scheme

6-docosenoic acid (116802-23-4) → behenic acid methyl ester (929-77-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / H2 / Pd/C / methanol / 6 h 2: H2SO4 / 7 h / Heating View Scheme

N-docosanoyl-1-O-<6-O-(2-trimethylammonioethoxy)phosphinate-β-D-galactopyranosyl>-(4E,8Z,11Z)-docosaspingatrienine → behenic acid methyl ester (929-77-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2, 10percent Pd/C 2: HCl / 2 h / 90 °C View Scheme

1,10-decanedioic acid (111-20-6) + lime/chalk/ → behenic acid methyl ester (929-77-1) + heptdecyl magnesium iodide

Conditions	Yield
Multi-step reaction with 2 steps 2: 45.2 percent / MeONa / methanol / 35 °C / electrolysis on Pt electrode, 0.05 amps, 50-60 volts View Scheme

methanol (67-56-1) + soybean oil → methyl trans-2-octadecenoate (14663-11-7) + 5,8,11-Eicosatrienoic acid, methyl ester + heneicosapentaenoic acid methyl ester + eicosadienoic acid methyl ester (88400-02-6) + docosapentaenoic acid methyl ester + docosatetraenoic acid methyl ester + docosadienoic acid methyl ester + palmitelaidic acid methyl ester (10030-74-7) + Methyl oleate (112-62-9) + Methyl linoleate (112-63-0) + methyl cis-13-docosenoate (1120-34-9) + methyl cis-tetracos-15-enate (2733-88-2) + methyl myristoate (124-10-7) + hexadecanoic acid methyl ester (112-39-0) + methyl margarate (1731-92-6) + Methyl stearate (112-61-8) + methyl arachidate (1120-28-1) + behenic acid methyl ester (929-77-1) + methyl tetracosanoate (2442-49-1) + methyl (2E)-eicosenoate (10305-59-6) + methyl (9Z,12Z,15E)-octadeca-9,12,15-trienoate (37929-05-8) + glycerol (56-81-5)

Conditions	Yield
With potassium hydroxide at 48 - 52℃; for 4h;

...Expand

methanol (67-56-1) + canola oil → methyl trans-2-octadecenoate (14663-11-7) + 5,8,11-Eicosatrienoic acid, methyl ester + heneicosapentaenoic acid methyl ester + eicosadienoic acid methyl ester (88400-02-6) + docosapentaenoic acid methyl ester + docosatetraenoic acid methyl ester + docosadienoic acid methyl ester + palmitelaidic acid methyl ester (10030-74-7) + Methyl oleate (112-62-9) + Methyl linoleate (112-63-0) + methyl cis-13-docosenoate (1120-34-9) + methyl cis-tetracos-15-enate (2733-88-2) + methyl myristoate (124-10-7) + hexadecanoic acid methyl ester (112-39-0) + methyl margarate (1731-92-6) + Methyl stearate (112-61-8) + methyl arachidate (1120-28-1) + behenic acid methyl ester (929-77-1) + methyl tetracosanoate (2442-49-1) + methyl (2E)-eicosenoate (10305-59-6) + methyl (9Z,12Z,15E)-octadeca-9,12,15-trienoate (37929-05-8) + glycerol (56-81-5)

Conditions	Yield
With potassium hydroxide at 48 - 52℃; for 4h;

...Expand

methanol (67-56-1) + mustard oil → methyl trans-2-octadecenoate (14663-11-7) + 5,8,11-Eicosatrienoic acid, methyl ester + heneicosapentaenoic acid methyl ester + eicosadienoic acid methyl ester (88400-02-6) + docosapentaenoic acid methyl ester + docosatetraenoic acid methyl ester + docosadienoic acid methyl ester + palmitelaidic acid methyl ester (10030-74-7) + Methyl oleate (112-62-9) + Methyl linoleate (112-63-0) + methyl cis-13-docosenoate (1120-34-9) + methyl cis-tetracos-15-enate (2733-88-2) + methyl myristoate (124-10-7) + hexadecanoic acid methyl ester (112-39-0) + methyl margarate (1731-92-6) + Methyl stearate (112-61-8) + methyl arachidate (1120-28-1) + behenic acid methyl ester (929-77-1) + methyl tetracosanoate (2442-49-1) + methyl (2E)-eicosenoate (10305-59-6) + methyl (9Z,12Z,15E)-octadeca-9,12,15-trienoate (37929-05-8) + glycerol (56-81-5)

Conditions	Yield
With potassium hydroxide at 48 - 52℃; for 4.5h;

...Expand

methanol (67-56-1) + sodium methylate (124-41-4) → methyl (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate (108698-02-8) + methyl vaccenate (1937-63-9, 52380-33-3, 6198-58-9) + methyl linoleate (16326-32-2) + methyl arachidonate (2566-89-4) + (Z)-9-hexadecenoic acid methyl ester (1120-25-8) + Methyl oleate (112-62-9) + Methyl linoleate (112-63-0) + (11Z)-11-icosenoic acid methyl ester (2390-09-2) + methyl linolenate (301-00-8) + methyl n-dodecanoate (111-82-0) + methyl myristoate (124-10-7) + pentadecanoic acid methyl ester (7132-64-1) + hexadecanoic acid methyl ester (112-39-0) + methyl margarate (1731-92-6) + Methyl stearate (112-61-8) + methyl arachidate (1120-28-1) + behenic acid methyl ester (929-77-1) + all-cis-8,11,14-eicosatrienoic acid methyl ester (21061-10-9) + (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester (2734-47-6) + cis,cis,cis,cis-Docosa-7,10,13,16-tetraensaeuremethylester (13487-42-8) + myristoleic acid methyl ester (56219-06-8) + cis,trans-9,11-methyloctadecadienoate (35042-75-2)

Conditions	Yield
at 55℃; for 1.5h; Product distribution / selectivity;

...Expand

D-ribo-phytosphingosine (554-62-1) + behenic acid methyl ester (929-77-1) → (2S,3S,4R)-2-docosanoylamino-1,3,4-octadecanetriol (164576-03-8)

Conditions	Yield
With sodium ethanolate In ethanol at 55℃;	94.1%

2-(morpholin-4-yl)ethanol (622-40-2) + behenic acid methyl ester (929-77-1) → (2-morpholinoethyl) behenate (1021462-80-5)

Conditions	Yield
With sodium methylate In toluene	91%

behenic acid methyl ester (929-77-1) + sodium ethanolate (141-52-6) → 22-tritetracontanone (591-71-9)

Conditions	Yield
at 155 - 160℃; under 15 Torr; Kochen des Reaktionsprodukts mit alkoh.KOH;

behenic acid methyl ester (929-77-1) + phenylmagnesium bromide → 1,1-Diphenyl-1-docosen (96772-77-9)

Conditions	Yield
(i) Et2O, (ii) (heating); Multistep reaction;

behenic acid methyl ester (929-77-1) → n-docosanoic acid (112-85-6)

Conditions	Yield
With potassium hydroxide

behenic acid methyl ester (929-77-1) → 1-docosanol (661-19-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 3h;
With lithium aluminium tetrahydride In tetrahydrofuran

behenic acid methyl ester (929-77-1) + pentadecyl magnesium iodide → 16-pentadecyl-heptatriacontan-16-ol (120747-17-3)

Conditions	Yield
With diethyl ether

behenic acid methyl ester (929-77-1) + tetradecyl magnesium iodide → 15-tetradecyl-hexatriacontan-15-ol (121355-44-0)

Conditions	Yield
With diethyl ether

behenic acid methyl ester (929-77-1) + hexadecyl magnesium iodide → 17-hexadecyl-octatriacontan-17-ol (123935-19-3)

Conditions	Yield
With diethyl ether

behenic acid methyl ester (929-77-1) + heptdecyl magnesium iodide → 18-heptadecyl-nonatriacontan-18-ol (122218-04-6)

Conditions	Yield
With diethyl ether

behenic acid methyl ester (929-77-1) + octadecyl magnesium iodide → 19-octadecyl-tetracontan-19-ol (120579-98-8)

Conditions	Yield
With diethyl ether

behenic acid methyl ester (929-77-1) + 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) → 3-(4'-hydroxyphenyl)propyl docosanoate

Conditions	Yield
With sodium hydrogen sulfate; silica gel In hexane at 70℃; for 1h;

behenic acid methyl ester (929-77-1) + rac-rhododendrol (69617-84-1) → 4-(4'-hydroxyphenyl)-2-butyl docosanoate

Conditions	Yield
With sodium hydrogen sulfate; silica gel In hexane at 70℃; for 1h;

Upstream product

• 186581-53-3 diazomethane 
• 112-85-6 n-docosanoic acid 
• 67-56-1 methanol 
• 56630-69-4 13-docosenoic acid methyl ester 
• 116802-23-4 6-docosenoic acid 
• 50889-29-7 (5-carboxypentyl)triphenylphosphonium bromide 
• 629-80-1 n-hexadecylaldehyde 
• 19102-90-0 dimethyl hexadecanedioate 
• 2104-19-0 azelaic monomethyl ester 
• 18451-85-9 15-(methoxycarbonyl)pentadecanoic acid 
• 124-07-2 Octanoic acid 
• 27888-44-4 (2S,3R)-N-(docosanoate)-1,3-dihydroxy-2-amino-octadeca-4-(E)-ene 
• 818-88-2 sebacic acid mono methyl ester 
• 544-63-8 n-tetradecanoic acid 

Downstream Products

• 591-71-9 22-tritetracontanone 
• 7211-53-2 potassium Behenate 
• 629-83-4 methyl 1-triacontanoate 
• 593-50-0 melissyl alcohol 
• 661-19-8 1-docosanol 
• 112-85-6 n-docosanoic acid 
• 96772-77-9 1,1-Diphenyl-1-docosen 

Relevant articles and documents

New sphingosines from a gorgonian, Pseudopterogorgia australiensis Ridley, of the Indian Ocean

Two new sphingosines, (2S,3R)-2-(docosanoyl amino)nonadecane-1,3-diol (1) and (2S,3S,4R)-2-[(2′R)-2′-hydroxynonadecanoylamino]nonadecane-1,3, 4-triol (3), along with the known (2S,3R,4E)-2-(heptadecanoylamino)octadec-4- ene-1,3-diol, have been isolated from Pseudopterogorgia australiensis, of the Indian Ocean. The structures were deduced from spectral and chemical methods. Compounds 1-3 showed moderate antibacterial activity.

Methylation of Aliphatic and Aromatic Carboxylic Acids with Dimethyl Carbonate under the Influence of Manganese and Iron Carbonyls

The synthesis of methyl esters has been carried out via the reaction of aliphatic and aromatic carboxylic acids with dimethyl carbonate in the presence of manganese and iron carbonyls. The optimal ratio of catalyst and reagents and other conditions for the synthesis of methyl esters of carboxylic acids with high yield have been found.

Methylation of mono- and dicarboxylic acids with dimethyl carbonate catalyzed with binder-free zeolite NaY

Synthesis of methyl mono- and dicarboxylates was developed consisting in treating the corresponding acids with dimethyl carbonate in the presence of a heterogenic catalyst, crystalline aluminosilicate whose mechanically strong granules to 90–95% were built of crystal aggregates of zeolite Y with modulus of about 5.0 in the Na-form. Optimum catalyst and reagents ratio and the reaction conditions were found for the preparation in high yields of methyl esters of mono- and dicarboxylic acids.