141-24-2

Basic information

• Product Name: METHYL RICINOLEATE
• Synonyms: RECINOLEIC ACID METHYL ESTER;RICINOLEIC ACID METHYL ESTER;RICINOLIC ACID METHYL ESTER;DELTA 9 CIS 12 HYDROXY OCTADECENOIC ACID METHYL ESTER;METHYL RICINOLEATE;METHYL RICINOLATE;METHYL 12-HYDROXYOLEATE;9-Octadecenoic acid, 12-hydroxy-, methyl ester, (9Z,12R)-
• CAS NO: 141-24-2
• Molecular Formula: C₁₉H₃₆O₃
• Molecular Weight: 312.49
• EINECS: 205-472-3
• Mol File: 141-24-2.mol
• Article Data: 33

Chemical Properties

• Melting Point: -29°C
• Boiling Point: 170°C 1mm
• Flash Point: 209 °C
• Appearance: /Liquid
• Density: 0,925 g/cm3
• Vapor Pressure: 1.66E-08mmHg at 25°C
• Refractive Index: 1.4638 (589.3 nm 16℃)
• Storage Temp.: −20°C
• PKA: 15.10±0.20(Predicted)
• BRN: 6132055
• CAS DataBase Reference: METHYL RICINOLEATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL RICINOLEATE(141-24-2)
• EPA Substance Registry System: METHYL RICINOLEATE(141-24-2)

Safety Data

• WGK Germany: 3
• F: 8-10-21
• Hazardous Substances Data: 141-24-2(Hazardous Substances Data)

Usage

Uses

Ricinoleic acid, formally called 12-hydroxy-9-cis-octadecenoic acid is a fatty acid. It is an unsaturated omega-9 fatty acid and a hydroxy acid. It is a major component of the seed oil obtained from mature Castor plant (Ricinus communis L., Euphorbiaceae) seeds or in sclerotium of ergot (Claviceps purpurea Tul., Clavicipitaceae). About 90% of the fatty acid content in castor oil is the triglyceride formed from ricinoleic acid.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C19H36O3/c1-3-4-5-12-15-18(20)16-13-10-8-6-7-9-11-14-17-19(21)22-2/h10,13,18,20H,3-9,11-12,14-17H2,1-2H3/b13-10-

Synthetic route

(R,Z)-(R,Z)-18-methoxy-18-oxooctadec-9-en-7-yl 12-hydroxyoctadec-9-enoate → methyl ricinoleate (141-24-2)

Conditions	Yield
With potassium carbonate In methanol at 20℃; for 42h;	100%

sodium methylate (124-41-4) + glyceryl tri-(12R)-hydroxy-((9Z)-octadecanoate) → methyl ricinoleate (141-24-2)

Conditions	Yield
With methanol In tetrahydrofuran at 20℃; for 14h; Inert atmosphere;	100%

methanol (67-56-1) + Ricinoleic acid (141-22-0) → methyl ricinoleate (141-24-2)

Conditions	Yield
With hydrogenchloride at 20℃; for 0.5h;	94.1%
With hydrogenchloride In water at 20℃; for 4h;	90%
With sulfuric acid for 3h; Heating;	66%

glyceryl tri-(12R)-hydroxy-((9Z)-octadecanoate) → methyl ricinoleate (141-24-2) + glycerol (56-81-5)

Conditions	Yield
With potassium hydrogensulfate; silica gel In methanol at 65℃; for 5h;	A 94% B 58%

glyceryl tri-(12R)-hydroxy-((9Z)-octadecanoate) → methyl ricinoleate (141-24-2)

Conditions	Yield
With sodium hydroxide In methanol at 60℃;	90%

methanol (67-56-1) + Ricinoleic acid (141-22-0) → methyl ricinoleate (141-24-2) + (R,Z)-(R,Z)-18-methoxy-18-oxooctadec-9-en-7-yl 12-hydroxyoctadec-9-enoate

Conditions	Yield
With boron trifluoride dimethanol at 50℃;	A 75% B 4%

Ricinoleic acid (141-22-0) → methyl ricinoleate (141-24-2) + (R,Z)-(R,Z)-18-methoxy-18-oxooctadec-9-en-7-yl 12-hydroxyoctadec-9-enoate

Conditions	Yield
With boron trifluoride In methanol at 50℃; for 16h;	A 75% B 4%

methanol (67-56-1) + glyceryl tri-(12R)-hydroxy-((9Z)-octadecanoate) → methyl ricinoleate (141-24-2)

Conditions	Yield
With CaAl layered double hydroxide at 65℃; for 5h;	74%
sodium methylate
With sodium methylate at 80℃; for 2.5h;

methanol (67-56-1) + castor oil → methyl ricinoleate (141-24-2)

Conditions	Yield
With hydrogenchloride
With sodium methylate

sodium methylate (124-41-4) + castor oil → methyl ricinoleate (141-24-2)

Conditions	Yield
With methanol

sodium methylate (124-41-4) + Castor oil → methyl ricinoleate (141-24-2)

Conditions	Yield
In toluene at 50℃; for 0.166667h;	7.8 g

methyl 12-trimethylacetoxyoctadec-9-(Z)-enoate (942062-59-1) → (9Z,11E)-methyl octadeca-9,11-dienoate (822-10-6, 13038-47-6, 17675-24-0, 19295-76-2, 13058-52-1) + Methyl linoleate (112-63-0) + methyl ricinoleate (141-24-2)

Conditions	Yield
With potassium methanolate In methanol at 90 - 100℃; for 3.5h; Product distribution / selectivity;

Ricinoleic acid (141-22-0) → methyl ricinoleate (141-24-2)

Conditions	Yield
In methanol

1,18-octadec-9-enedioic acid (4494-16-0) + methanol (67-56-1) + Ricinoleic acid (141-22-0) → methyl ricinoleate (141-24-2) + dimethyl 9-octadecen-1,18-dioate (13481-97-5)

Conditions	Yield
sulfuric acid Product distribution / selectivity;

methanol (67-56-1) + castor oil → methyl ricinoleate (141-24-2)

Conditions	Yield
With potassium hydroxide at 45℃; for 6h;

methanol (67-56-1) + glyceryl tri-(12R)-hydroxy-((9Z)-octadecanoate) → 1-bromo-2,3-propanediol (4704-77-2) + methyl ricinoleate (141-24-2) + 1,3-dibromo-2-hydroxypropane (96-21-9) + C37H68O5

Conditions	Yield
With trimethylsilyl bromide at 60℃; for 12h; Inert atmosphere;	A 0.042 g B 0.81 g C 0.021 g D 0.115 g

methyl ricinoleate (141-24-2) → methyl (R)-12-hydroxyoctadecanoate (6114-39-2)

Conditions	Yield
With monel; hydrogen at 130℃; under 15001.5 Torr; for 9.5h; Pressure; Temperature; Autoclave; Inert atmosphere;	99%
With ethanol; palladium Hydrogenation;
(hydrogenation);

methyl ricinoleate (141-24-2) → methyl (9Z)-12-oxo-9-octadecenoate (3047-65-2)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane at 20℃; for 12h; Inert atmosphere;	99%
With sodium acetate; pyridinium chlorochromate In dichloromethane	82.6%
With pyridinium chlorochromate In dichloromethane at 18 - 20℃; for 1h; Inert atmosphere;	68%

methyl ricinoleate (141-24-2) + tert-butyldimethylsilyl chloride (18162-48-6) → methyl (9Z,12R)-12-{[tert-butyl(dimethyl)silyl]oxy}octadec-9-enoate (129049-75-8)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	99%
With dmap; triethylamine In dichloromethane at 20℃; for 48h;	87%
With 1H-imidazole In N,N-dimethyl-formamide at 35℃; for 16h;	83.1%
With pyridine; dmap for 72h; Ambient temperature;

diazomethane (186581-53-3, 908094-01-9) + methyl ricinoleate (141-24-2) → methyl (9Z,12R)-12-methoxy-9-octadecenoate

Conditions	Yield
With cobalt(II) tetrafluoroborate In pentane for 2h;	98%
With tetrafluoroboric acid

methyl ricinoleate (141-24-2) + acetyl chloride (75-36-5) → [R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4)

Conditions	Yield
With pyridine In benzene for 2h; Heating;	98%
With pyridine In benzene

methyl ricinoleate (141-24-2) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → (Z)-(R)-12-(2,2,2-Trichloro-ethoxycarbonyloxy)-octadec-9-enoic acid methyl ester (404861-01-4)

Conditions	Yield
With pyridine In diethyl ether at 5 - 20℃;	97.1%

methyl ricinoleate (141-24-2) + dimethyl amine (124-40-3) + 1,1'-Thiocarbonyldiimidazole (6160-65-2) → methyl (Z)-12-(dimethylthiocarbamoyloxy)octadec-9-enoate

Conditions	Yield
Stage #1: methyl ricinoleate; 1,1'-Thiocarbonyldiimidazole With dmap In dichloromethane Stage #2: dimethyl amine In tetrahydrofuran	96%

methyl ricinoleate (141-24-2) + hexanoic acid (142-62-1) → methyl (12R)-hexanoyloxyoleate

Conditions	Yield
Stage #1: hexanoic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: methyl ricinoleate With dmap In dichloromethane at 20℃; for 14h; Cooling with ice;	96%

methyl ricinoleate (141-24-2) + acetic anhydride (108-24-7) → [R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4)

Conditions	Yield
With [Hmim][HSO4] at 80℃; for 4h; Concentration; Temperature;	94.47%
With pyridine at 20℃;

methyl ricinoleate (141-24-2) → (9Z,12R)-12-hydroxyoctadec-9-enoic acid hydrazide (55732-66-6)

Conditions	Yield
With hydrazine hydrate In ethanol for 4h; Reflux;	94%
With hydrazine hydrate In methanol

methyl ricinoleate (141-24-2) + tert-butylchlorodiphenylsilane (58479-61-1) → (R,Z)-methyl 12-(tert-butyldiphenylsilyloxy)octadec-9-enoate (1346933-32-1)

Conditions	Yield
With pyridine; silver nitrate In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere;	93%

methyl ricinoleate (141-24-2) + tert-butyldimethylsilyl chloride (18162-48-6) → (R,Z)-methyl 12-(tert-butyldiphenylsilyloxy)octadec-9-enoate (1346933-32-1)

Conditions	Yield
With pyridine; silver nitrate In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere;	93%

linoleic acid (60-33-3) + methyl ricinoleate (141-24-2) → methyl (12R)-linoleoyloxyoleate

Conditions	Yield
Stage #1: linoleic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Cooling with ice; Inert atmosphere; Stage #2: methyl ricinoleate With dmap In dichloromethane at 20℃; for 16h; Cooling with ice; Inert atmosphere;	93%

methyl ricinoleate (141-24-2) + methanesulfonyl chloride (124-63-0) → (Z)-(R)-12-methanesulfonyloksyoctadec-9-enoic acid methyl ester (57884-97-6)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 1h;	92%
With triethylamine In dichloromethane at -40 - -10℃; for 4h; Inert atmosphere;	65%
With triethylamine In dichloromethane for 0.75h;	2.2 g
With hydrogenchloride; triethylamine In 1,2-dichloro-ethane at -5 - 20℃; for 3h; Temperature;	0.41 g

methyl ricinoleate (141-24-2) + allyl alcohol (107-18-6) → C22H40O3 (1426060-81-2)

Conditions	Yield
With [RuCp(DPPSA)(η3-propenyl)] at 45 - 100℃; regioselective reaction;	92%

methyl ricinoleate (141-24-2) + carbonic acid dimethyl ester (616-38-6) → (Z)-methyl 12-(methoxy carbonyloxy)octadec-9-enoate

Conditions	Yield
With potassium carbonate for 35h; Reflux;	90%

trimethyl phosphite (512-56-1) + methyl ricinoleate (141-24-2) → methyl (9Z,12R)-12-methoxy-9-octadecenoate

Conditions	Yield
With Aquivion PW98 at 110℃; for 18h;	90%

methyl ricinoleate (141-24-2) → (11R)-methyl 8,9-epoxy-11-hydroxyoctadecanoate

Conditions	Yield
With Oxone; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In butanone for 1h; Product distribution; other epoxidizing agents, var. distereoselectivity of epoxidation;	89.4%
With titanium(IV) isopropylate; tert.-butylhydroperoxide; DIPT; 3 A molecular sieve In dichloromethane for 24h; Ambient temperature;

methyl ricinoleate (141-24-2) + Diethyl carbonate (105-58-8) → (Z)-methyl 12-(ethoxycarbonyloxy)octadec-9-enoate

Conditions	Yield
With potassium carbonate for 35h; Reflux;	89%

phenylacetic acid (103-82-2) + methyl ricinoleate (141-24-2) → methyl 12-phenylacetylricinoleate (1108200-40-3)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Reflux;	88.5%

methyl ricinoleate (141-24-2) → (9Z,12R)-12-hydroxyoctadec-9-enal (101885-21-6)

Conditions	Yield
With diisobutylaluminium hydride In dichloromethane; toluene at -70℃; for 3h; Inert atmosphere;	87%

methyl ricinoleate (141-24-2) → (9Z,12R)-octadec-9-ene-1,12-diol (540-11-4)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 24h;	86%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2.33333h;	62%
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride In tetrahydrofuran for 14h; Cooling with ice; Inert atmosphere;

methyl ricinoleate (141-24-2) + ethanolamine (141-43-5) → (Z)-(R)-12-hydroxyoctadec-9-enoic acid (2-hydroxyethyl)amide

Conditions	Yield
In neat (no solvent) at 130 - 140℃; for 2h; Green chemistry;	84%
at 130 - 140℃; for 2h;	84%
In acetonitrile for 24h;

pyrrolidine (123-75-1) + methyl ricinoleate (141-24-2) → (Z)-(R)-12-hydroxy-1-pyrrolidin-1-yl-octadec-9-en-1-one (1246776-23-7)

Conditions	Yield
In neat (no solvent) at 80 - 90℃; for 10h; Green chemistry;	83%
at 80 - 90℃; for 10h;	83%
In acetonitrile for 24h;

methyl ricinoleate (141-24-2) → 1,10-decanedioic acid (111-20-6)

Conditions	Yield
With sodium hydroxide; sodium nitrate In water	81.7%

Upstream product

• 67-56-1 methanol 
• 141-22-0 Ricinoleic acid 
• 4494-16-0 1,18-octadec-9-enedioic acid 
• 124-41-4 sodium methylate 
• 942062-59-1 methyl 12-trimethylacetoxyoctadec-9-(Z)-enoate 
• 111-71-7 heptanal 
• 111-81-9 Methyl 10-undecenoate 

Downstream Products

• 123-99-9 azelaic acid 
• 111-71-7 heptanal 
• 111-81-9 Methyl 10-undecenoate 
• 1577-55-5 octadec-9-ene-1,12-diol 
• 106-14-9 12-Hydroxystearic acid 
• 6114-39-2 methyl 12-hydroxyoctadecanoate 
• 112-61-8 Methyl stearate 
• 875892-95-8 methyl (Z)-11-acetoxyundec-9-enoate 
• 540-13-6 (R)-12-hydroxy-octadec-9-ynoic acid 
• 141-08-2 glycerol monoricinoleate 
• 540-11-4 (9Z,12R)-octadec-9-ene-1,12-diol 
• 35732-94-6 (R,Z)-12-hydroxyoctadec-9-enamide 
• 822-10-6 octadeca-9,11-dienoic acid methyl ester 
• 140-03-4 [R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester 

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