Conditions | Yield |
---|---|
With 2,2-dimethylpropanoic anhydride; dmap at 50℃; for 24h; | 93% |
With propylsulfonic acid functionalized rope shaped mesoporous silica at 110℃; for 1h; Catalytic behavior; Reagent/catalyst; | 64.3% |
With dmap; dicyclohexyl-carbodiimide In tetrachloromethane at 20℃; for 6h; | 51% |
oleic anhydride
1,2-dioleoyl-3-O-triisopropylsilyl-sn-glycerol
trioleoylglycerol
Conditions | Yield |
---|---|
With trimethylsilyl bromide; tetrabutylammomium bromide In chloroform for 2h; Heating; | 93% |
Conditions | Yield |
---|---|
With pyridine |
cis-Octadecenoic acid
glycerol
A
trioleoylglycerol
B
1-monooleoyl glycerol
Conditions | Yield |
---|---|
at 35℃; in Gegenwart von entoeltem Chelidoniumsamen; | |
With Sn-EOF In neat (no solvent) for 3h; Reflux; |
Conditions | Yield |
---|---|
With lithium hydroxide unter vermindertem Druck; |
cis-Octadecenoic acid
glycerol
A
trioleoylglycerol
B
1-monooleoyl glycerol
C
1,3-diolein
Conditions | Yield |
---|---|
With lipase PS-Celite at 3℃; for 24h; | A 4 mg B 9 mg C 99 mg |
oleic acid ethyl ester
glycerol
A
trioleoylglycerol
B
1-monooleoyl glycerol
C
1,3-diolein
Conditions | Yield |
---|---|
With lipase PS-Celite In acetonitrile at 30℃; for 96h; | A 5 mg B 100 mg C 17 mg |
cis-Octadecenoic acid
glycerol
A
trioleoylglycerol
B
1-monooleoyl glycerol
C
1,3-diolein
D
1,2-dioleoylglycerol
Conditions | Yield |
---|---|
With lipozyme at 25℃; under 3 Torr; for 12h; Esterification; | A 1.34 % Chromat. B 16.08 % Chromat. C 61.10 % Chromat. D 0.85 % Chromat. |
Conditions | Yield |
---|---|
in Gegenwart von Ricinus-Enzym; | |
in Gegenwart von Chelidonium-Enzym; |
Conditions | Yield |
---|---|
at 240℃; |
Conditions | Yield |
---|---|
mit Pankreas-Lipase; | |
durch entfettete Chelidoniumsamen; |
cis-Octadecenoic acid
glyceroltripalmitate
A
trioleoylglycerol
B
1,2-dipalmitoyl-3-oleoyl-rac-glycerol
C
1,2-dioleoyl-3-palmitoylglycerol
D
1,3-dioleoyl-2-palmitoylglycerol
Conditions | Yield |
---|---|
With Lipase IM 60 In hexane at 50℃; for 24h; Product distribution; Further Variations:; Temperatures; |
Conditions | Yield |
---|---|
With ferrous(II) sulfate heptahydrate; ammonium sulfate; dipotassium hydrogenphosphate; potassium dihydrogenphosphate; sodium molybdate dihydrate; calcium(II) chloride dihydrate; manganese(II) chloride tetrahydrate; magnesium(II) chloride hexahydrate In water at 30℃; for 97h; pH=7; Microbiological reaction; |
Conditions | Yield |
---|---|
Purolite CT276DR at 110℃; for 5h; Product distribution / selectivity; Inert atmosphere; |
Methyl oleate
glycerol
A
trioleoylglycerol
B
2-Oleoylglycerol
C
1-monooleoyl glycerol
D
1,3-diolein
E
1,2-dioleoylglycerol
Conditions | Yield |
---|---|
With lithium doped magnesium oxide at 219.84℃; under 760.051 Torr; Inert atmosphere; chemoselective reaction; |
cis-Octadecenoic acid
glycerol
A
trioleoylglycerol
B
1,3-diolein
C
1,2-dioleoylglycerol
Conditions | Yield |
---|---|
With β‐cyclodextrin Enzymatic reaction; |
Conditions | Yield |
---|---|
With immobilized Candida antarctica lipase B at 23℃; Enzymatic reaction; |
cis-Octadecenoic acid
glycerol
A
trioleoylglycerol
B
1-monooleoyl glycerol
C
1,2-dioleoylglycerol
Conditions | Yield |
---|---|
With 1.05HO3P*0.95C6H5O3P(2-)*0.1H2O*Zr(2+) at 180℃; for 1h; Reagent/catalyst; |
Conditions | Yield |
---|---|
With methanesulfonic acid at 80℃; | 98% |
With SO3H and NH2+ functional carbon-based solid acid at 100℃; under 760.051 Torr; for 8h; Catalytic behavior; Temperature; Sealed tube; | 95% |
With sulfuric acid at 30℃; Kinetics; |
trioleoylglycerol
Conditions | Yield |
---|---|
With bromine In chloroform at 0℃; | 97% |
With bromine; sodium hydrogencarbonate In dichloromethane at 0 - 20℃; for 0.0833333h; | 85% |
With bromine In dichloromethane at -10 - 20℃; for 4.33333h; | 50% |
Conditions | Yield |
---|---|
With dihydrogen peroxide In diethyl ether; water at 20℃; for 0.5h; | 96.7% |
trioleoylglycerol
isopropyl alcohol
isopropyl oleate
Conditions | Yield |
---|---|
With SO3H and NH2+ functional carbon-based solid acid at 100℃; for 8h; Sealed tube; | 94% |
With sulfuric acid at 30℃; Kinetics; |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In 1,4-dioxane; water at 70℃; for 4h; | A 93% B n/a |
Conditions | Yield |
---|---|
With sulfonated carbonized β-cyclodextrin CD-3 at 80℃; under 15001.5 Torr; for 12h; Catalytic behavior; Pressure; Autoclave; | A 90% B n/a |
vanadia at 150℃; for 24h; Product distribution / selectivity; | A 88% B 32% |
With manganese titanate at 200℃; under 37503.8 Torr; for 24h; Mechanism; Reagent/catalyst; Temperature; Flow reactor; | A 87% B 49% |
Conditions | Yield |
---|---|
With Candida antarctica lipase B immobilized on acrylic resin In hexane; butanone at 35℃; for 48h; Catalytic behavior; Molecular sieve; Enzymatic reaction; | 87% |
Conditions | Yield |
---|---|
With zirconocene bis(perfluorooctanesulfonate) trihydrate*(tetrahydrofuran) In neat (no solvent) at 80℃; for 24h; Sealed tube; Green chemistry; chemoselective reaction; | 85% |
With immobilized lipase from Rhizomucor miehei at 40℃; for 24h; | 80% |
With sulfuric acid at 30℃; Kinetics; | |
sulfonate derived amorphous carbon at 80℃; for 12h; Rate constant; | 0% |
With C2F6NO4S2(1-)*C20H39N2(1+) at 60℃; Enzymatic reaction; |
trioleoylglycerol
Conditions | Yield |
---|---|
With sulfuryl dichloride In chloroform for 3h; Cooling with ice; | 84% |
Conditions | Yield |
---|---|
With 2C33H37N*H2O7S2; water at 80℃; for 24h; Concentration; | 82% |
Stage #1: trioleoylglycerol With sulfuric acid; dimethylsulfoxonium methylide In tetrahydrofuran for 3h; Reflux; Inert atmosphere; Stage #2: With hydrogenchloride; water In ethyl acetate pH=2; Inert atmosphere; | 80% |
With 2C33H37N*H2O7S2; water at 80℃; | 86 %Spectr. |
With Yarrowia lipolytica lipase Lip2 In aq. phosphate buffer at 35℃; for 0.0833333h; pH=8; Kinetics; Reagent/catalyst; Concentration; Enzymatic reaction; | |
With lipase from Candida rugose In aq. buffer at 37℃; for 12h; Enzymatic reaction; |
trioleoylglycerol
2-Oleoylglycerol
Conditions | Yield |
---|---|
With lipase from Rhizopus oryzae; ethanol; water In n-heptane at 37℃; for 6h; Catalytic behavior; Reagent/catalyst; Sealed tube; Enzymatic reaction; regioselective reaction; | 76% |
With Novozym 435; ethanol at 25℃; for 4h; Enzymatic reaction; | 63% |
With pancreas lipase type II (EC 3.1.1.3); Tris buffer; calcium chloride; Difco bile salt No.3 In water at 40℃; for 0.75h; pH=8.0; |
trioleoylglycerol
diglycerol
3-(2,3-dihydroxypropoxy)-2-hydroxypropyl oleate
Conditions | Yield |
---|---|
at 200℃; for 48h; Catalytic behavior; Solvent; Inert atmosphere; | 63% |
trioleoylglycerol
Conditions | Yield |
---|---|
With lipase from Pseudomonas fluorescens; ethanol; water In n-heptane at 37℃; for 6h; Catalytic behavior; Reagent/catalyst; Sealed tube; Enzymatic reaction; regioselective reaction; | 58% |
mit Hilfe Pankreas-Lipase-Praeparat; | |
for 2h; Ambient temperature; phosphate buffer pH 7.00; Rhizopus oryzae lipase; | |
With acetic acid In methanol; chloroform |
trioleoylglycerol
glycerol
A
1-monooleoyl glycerol
B
1,3-diolein
C
1,2-dioleoylglycerol
Conditions | Yield |
---|---|
at 200℃; for 48h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; | A 51% B n/a C n/a |
trioleoylglycerol
A
2-Oleoylglycerol
B
1,2-dioleoylglycerol
Conditions | Yield |
---|---|
With ethanol; lipase from Pseudomonas sp.; water In n-heptane at 37℃; for 6h; Catalytic behavior; Reagent/catalyst; Sealed tube; Enzymatic reaction; regioselective reaction; | A 38.7% B n/a |
trioleoylglycerol
A
octadec-9-enoic acid propane-1,2,3-triyl ester
B
18-bis(1,3-bis(octadec-9-enoyloxy)propan-2-yl)-1,1-3-(octadec-9-enoyloxy)propane-1,2-diyl dioctadec-9-enedioate
C
1-(21,43-bis((octadec-9-enoyloxy)methyl)-18,23,40,45,62,68-hexaoxo-19,22,41,44,63,67-hexaoxapentaoctaconta-9,31,53,76-tetraen-65-yl) 18-(1,3-bis(octadec-9-enoyloxy)propan-2-yl) octadec-9-enedioate
E
bis(1,3-bis(octadec-9-enoyloxy)propan-2-yl) octadec-9-enedioate
Conditions | Yield |
---|---|
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In neat (no solvent) at 38℃; for 6h; Inert atmosphere; Overall yield = 21.4 %; | A 21.1% B 16.3% C 11.2% D 8.9% E 12.4% |
trioleoylglycerol
A
octadec-9-enoic acid propane-1,2,3-triyl ester
B
18-bis(1,3-bis(octadec-9-enoyloxy)propan-2-yl)-1,1-3-(octadec-9-enoyloxy)propane-1,2-diyl dioctadec-9-enedioate
E
bis(1,3-bis(octadec-9-enoyloxy)propan-2-yl) octadec-9-enedioate
Conditions | Yield |
---|---|
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 38℃; for 6h; Inert atmosphere; Overall yield = 26.7 %; | A 12.8% B 2.2% C n/a D n/a E 13.1% F n/a G n/a |
trioleoylglycerol
A
octadec-9-enoic acid propane-1,2,3-triyl ester
D
bis(1,3-bis(octadec-9-enoyloxy)propan-2-yl) octadec-9-enedioate
G
bis (6,23-dioxo-1,5-dioxacyclotricos-14-en-3-yl) octadec-9-enedioate
H
18-bis (6,23-dioxo-1,5-dioxacyclotricos-14-en-3-yl)-1,1-2(octadec-9-enoyloxy)propane-1,3-diyl dioctadec-9-enedioate
Conditions | Yield |
---|---|
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 38℃; for 6h; Inert atmosphere; Overall yield = 28.3 %; | A 8.1% B n/a C n/a D 2.8% E n/a F n/a G 8.8% H 5% |
Conditions | Yield |
---|---|
With hydrogenchloride ethyl ester of/the/ oleic acid; |
trioleoylglycerol
Conditions | Yield |
---|---|
With potassium permanganate |
Conditions | Yield |
---|---|
With mercurous nitrate; nitric acid | |
at 280℃; Kinetics; Temperature; Inert atmosphere; |
trioleoylglycerol
Oleylhydroxamic acid
Conditions | Yield |
---|---|
With hydroxylamine |
Conditions | Yield |
---|---|
With hydrazine hydrate at 20℃; |
trioleoylglycerol
9,9',9"-(propane-1,2,3-triyltrioxy)tris(9-oxononanoic acid)
Conditions | Yield |
---|---|
With potassium permanganate; acetone |
trioleoylglycerol
Conditions | Yield |
---|---|
With ozone |
The Triolein with CAS registry number of 122-32-7 is also known as 1,2,3-Tri-(9Z-octadecenoyl)-sn-glycerol. The IUPAC name is 2,3-Bis[[(Z)-octadec-9-enoyl]oxy]propyl (Z)-octadec-9-enoate. Its EINECS registry number is 204-534-7. In addition, the formula is C57H104O6 and the molecular weight is 885.43. This chemical is a colourless viscous liquid and should be stored in sealed containers in cool, dry place away from wet, sunshine and heat.
Physical properties about Triolein are: (1)ACD/LogP: 23.71; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 23.71; (4)ACD/LogD (pH 7.4): 23.71; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 10000000; (8)ACD/KOC (pH 7.4): 10000000; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 53; (12)Polar Surface Area: 78.9Å2; (13)Index of Refraction: 1.477; (14)Molar Refractivity: 271.57 cm3; (15)Molar Volume: 961 cm3; (16)Polarizability: 107.66×10-24cm3; (17)Surface Tension: 34.7 dyne/cm; (18)Density: 0.921 g/cm3; (19)Flash Point: 302.6 °C; (20)Enthalpy of Vaporization: 119 kJ/mol; (21)Boiling Point: 818.7 °C at 760 mmHg; (22)Vapour Pressure: 6.66E-27 mmHg at 25 °C.
Preparation of Triolein: it is prepared by reaction of glycerol with oleic acid. Glycerol added to the reactor, preheated to 60 °C, then add the amount of oleic acid and sulfuric acid catalyst, vacuum heated return dehydration for 4 hours, cooled, and then add 5% Na2CO3 aqueous solution, vacuum dehydration derived products.
CH2OHCHOHCH2OH+3C17H33COOHH+CH2OOCC17H33CHOOCC17H33CH2OOCC17H33+3H2O
Uses of Triolein: it can be used as textile lubricants and cosmetics emulsifiers. Besides, it also can be used as a cream, lotion and lipstick matrix.
When you are using this chemical, please be cautious about it. As a chemical, it is harmful by inhalation, in contact with skin and if swallowed and it has highly flammable. During using it, wear eye/face protection and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
1. SMILES: O=C(OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC)CCCCCCC\C=C/CCCCCCCC
2. InChI: InChI=1/C57H104O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h25-30,54H,4-24,31-53H2,1-3H3/b28-25-,29-26-,30-27-
3. InChIKey: PHYFQTYBJUILEZ-IUPFWZBJBN
4. Std. InChI: InChI=1S/C57H104O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h25-30,54H,4-24,31-53H2,1-3H3/b28-25-,29-26-,30-27-
5. Std. InChIKey: PHYFQTYBJUILEZ-IUPFWZBJSA-N
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