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60-33-3

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60-33-3 Usage

General Description

Linoleic acid is a polyunsaturated omega-6 fatty acid that is an essential nutrient for the human body as it cannot be synthesized and must be obtained from the diet. It is found in many food sources, including vegetable oils, nuts, and seeds. Linoleic acid plays a crucial role in maintaining the integrity of the skin barrier and has anti-inflammatory properties. It is also involved in the synthesis of other important compounds, such as prostaglandins and leukotrienes, which are important for regulating immune and inflammatory responses. Research has shown that linoleic acid may also have potential benefits for cardiovascular health, diabetes management, and weight loss. Overall, linoleic acid is an important nutrient with various health benefits and is essential for overall well-being.

Check Digit Verification of cas no

The CAS Registry Mumber 60-33-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 0 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 60-33:
(4*6)+(3*0)+(2*3)+(1*3)=33
33 % 10 = 3
So 60-33-3 is a valid CAS Registry Number.
InChI:InChI=1/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)

60-33-3 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (L0124)  Linoleic Acid  >97.0%(GC)(T)

  • 60-33-3

  • 5g

  • 435.00CNY

  • Detail
  • TCI America

  • (L0124)  Linoleic Acid  >97.0%(GC)(T)

  • 60-33-3

  • 25g

  • 1,320.00CNY

  • Detail
  • Alfa Aesar

  • (L07949)  Linoleic acid, 95%   

  • 60-33-3

  • 5g

  • 427.0CNY

  • Detail
  • Alfa Aesar

  • (L07949)  Linoleic acid, 95%   

  • 60-33-3

  • 25g

  • 1652.0CNY

  • Detail
  • Alfa Aesar

  • (L07949)  Linoleic acid, 95%   

  • 60-33-3

  • 100g

  • 4830.0CNY

  • Detail
  • Alfa Aesar

  • (A15265)  Linoleic acid, tech. 75%   

  • 60-33-3

  • 10g

  • 558.0CNY

  • Detail
  • Alfa Aesar

  • (A15265)  Linoleic acid, tech. 75%   

  • 60-33-3

  • 50g

  • 1365.0CNY

  • Detail
  • Alfa Aesar

  • (A15265)  Linoleic acid, tech. 75%   

  • 60-33-3

  • 250g

  • 4675.0CNY

  • Detail
  • Sigma

  • (L1376)  Linoleicacid  ≥99%

  • 60-33-3

  • L1376-10MG

  • 211.77CNY

  • Detail
  • Sigma

  • (L1376)  Linoleicacid  ≥99%

  • 60-33-3

  • L1376-500MG

  • 391.95CNY

  • Detail
  • Sigma

  • (L1376)  Linoleicacid  ≥99%

  • 60-33-3

  • L1376-1G

  • 450.45CNY

  • Detail
  • Sigma

  • (L1376)  Linoleicacid  ≥99%

  • 60-33-3

  • L1376-5G

  • 676.26CNY

  • Detail

60-33-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name linoleic acid

1.2 Other means of identification

Product number -
Other names cis,cis-9,12-octadecadienoic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Surfactants
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:60-33-3 SDS

60-33-3Synthetic route

linoleic nitrile
19836-71-6

linoleic nitrile

linoleic acid
60-33-3

linoleic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Heating;81%
Ricinoleic acid
141-22-0

Ricinoleic acid

A

cis-9,trans-11-octadecadienoic acid
544-70-7, 544-71-8, 872-23-1, 1839-11-8, 2540-56-9

cis-9,trans-11-octadecadienoic acid

B

trans-9,trans-11-octadecadienoic acid
544-70-7, 544-71-8, 872-23-1, 1839-11-8, 2540-56-9

trans-9,trans-11-octadecadienoic acid

C

trans-10,cis-12-octadecadienoic acid
1072-36-2, 2420-44-2, 2420-56-6, 7307-45-1, 22880-03-1

trans-10,cis-12-octadecadienoic acid

D

linoleic acid
60-33-3

linoleic acid

E

10E,12E-octadecadienoic acid
1072-36-2

10E,12E-octadecadienoic acid

Conditions
ConditionsYield
With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; potassium hydroxide In ethylene glycol at 180℃; for 0.5h; Microwave irradiation;A n/a
B n/a
C n/a
D 22%
E n/a
F 46%
With 1-n-butyl-3-methylimidazolim bromide; potassium hydroxide In ethylene glycol at 180℃; for 0.5h; Microwave irradiation;A n/a
B n/a
C n/a
D 12%
E n/a
F 9%
soybean oil, refined, bleached and deodorized

soybean oil, refined, bleached and deodorized

A

trans fatty acid; mixture of

trans fatty acid; mixture of

B

cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

C

linoleic acid
60-33-3

linoleic acid

D

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid
463-40-1

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid

E

stearic acid
57-11-4

stearic acid

Conditions
ConditionsYield
With hydrogen; mineral malachite at 165℃; under 3102.97 Torr; for 4h; Conversion of starting material;A 16.23%
B 37.82%
C 41.48%
D 2.92%
E 5.39%
linoleic acid
60-33-3

linoleic acid

Conditions
ConditionsYield
With potassium hydroxide
9,12-octadecadiynoic acid
2012-14-8

9,12-octadecadiynoic acid

linoleic acid
60-33-3

linoleic acid

Conditions
ConditionsYield
With quinoline; Lindlar's catalyst; Petroleum ether Hydrogenation;
With pyridine; palladium on activated charcoal; Lindlar's catalyst Hydrogenation;
Methyl linoleate

Methyl linoleate

linoleic acid
60-33-3

linoleic acid

Conditions
ConditionsYield
With potassium hydroxide In methanol
With water; sodium hydroxide In methanol for 1h; Heating;
rac-(9R,10R,12S,13S)-9,10,12,13-Tetrabromostearic acid
1794-89-4, 54324-50-4, 56846-03-8, 56846-04-9

rac-(9R,10R,12S,13S)-9,10,12,13-Tetrabromostearic acid

linoleic acid
60-33-3

linoleic acid

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide -1.4 V (vs. SCE) at a mercury pool (divided cell); Yield given;
(9Z,12Z)-N-(pyridin-3-yl)octadeca-9,12-dienamide
119520-51-3

(9Z,12Z)-N-(pyridin-3-yl)octadeca-9,12-dienamide

linoleic acid
60-33-3

linoleic acid

Conditions
ConditionsYield
With carbon disulfide; n-butyllithium; benzeneseleninic acid; 1,1,1,3,3,3-hexamethyl-disilazane 1.) THF, hexane, -20 deg C, 30 min, 2.) THF, rt, 3.) THF, rt, 5 h; Yield given. Multistep reaction;
(2S)-1-O-(9Z,12Z)-octadecadienoyl-2-O-(7Z,10Z)-hexadecadienoyl-3-O-α-D-galactopyranosyl-(1->6)-β-D-galactopyranosyl-sn-glycerol

(2S)-1-O-(9Z,12Z)-octadecadienoyl-2-O-(7Z,10Z)-hexadecadienoyl-3-O-α-D-galactopyranosyl-(1->6)-β-D-galactopyranosyl-sn-glycerol

A

linoleic acid
60-33-3

linoleic acid

B

(7Z,10Z)-Hexadeca-7,10-dienoic acid (R)-1-hydroxymethyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-ethyl ester

(7Z,10Z)-Hexadeca-7,10-dienoic acid (R)-1-hydroxymethyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-ethyl ester

Conditions
ConditionsYield
With boric acid-borax buffer; Lipase type XI; Triton X-100 at 38℃; for 1h;
17-bromo-heptadeca-6c,9c-diene

17-bromo-heptadeca-6c,9c-diene

linoleic acid
60-33-3

linoleic acid

Conditions
ConditionsYield
With diethyl ether; magnesium anschliessend mit Kohlendioxid;
linolic acid tetrabromide

linolic acid tetrabromide

linoleic acid
60-33-3

linoleic acid

hydrogenchloride
7647-01-0

hydrogenchloride

ethanol
64-17-5

ethanol

9,10,12,13-tetrabromooctadecanoic acid
1794-89-4

9,10,12,13-tetrabromooctadecanoic acid

Sn

Sn

linoleic acid
60-33-3

linoleic acid

hydrogenchloride
7647-01-0

hydrogenchloride

ethanol
64-17-5

ethanol

9,10,12,13-tetrabromooctadecanoic acid
1794-89-4

9,10,12,13-tetrabromooctadecanoic acid

zinc

zinc

A

linoleic acid
60-33-3

linoleic acid

B

cis-cis-octadecadien-(6.9)-oic acid (18)

cis-cis-octadecadien-(6.9)-oic acid (18)

C

cis-trans-isomer(ic)

cis-trans-isomer(ic)

Conditions
ConditionsYield
#threo,threo!-isomer(ic);
(9Z,12Z)-N-Pyridin-3-yl-octadeca-9,12-dienimidothioic acid pyridin-2-yl ester
119520-47-7

(9Z,12Z)-N-Pyridin-3-yl-octadeca-9,12-dienimidothioic acid pyridin-2-yl ester

linoleic acid
60-33-3

linoleic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89 percent / water / dioxane / 40 h / Ambient temperature
2: 1.) hexamethyldisilazane, 1.6 M n-BuLi, 2.) CS2, 3.) PhSeO2H / 1.) THF, hexane, -20 deg C, 30 min, 2.) THF, rt, 3.) THF, rt, 5 h
View Scheme
(9Z,12Z)-Octadeca-9,12-dienoic acid 2-thioxo-2H-pyridin-1-yl ester
119520-41-1

(9Z,12Z)-Octadeca-9,12-dienoic acid 2-thioxo-2H-pyridin-1-yl ester

linoleic acid
60-33-3

linoleic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 97 percent / CH2Cl2 / 0 °C / Irradiation
2: 81 percent / NaOH / ethanol; H2O / Heating
View Scheme
Multi-step reaction with 2 steps
1: 83 percent Spectr. / CH2Cl2 / 0 °C / Irradiation
2: 81 percent / NaOH / ethanol; H2O / Heating
View Scheme
dec-9-ynoic acid
1642-49-5

dec-9-ynoic acid

linoleic acid
60-33-3

linoleic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran; ethyl magnesium bromide / anschliessenden Erwaermen des Reaktionsgemisches mit 1-Brom-oct-2-in und Kupfer(I)-cyanid
2: Lindlar-catalyst; quinoline; petroleum ether / Hydrogenation
View Scheme
7-chloroheptanoic acid
821-57-8

7-chloroheptanoic acid

A

linoleic acid
60-33-3

linoleic acid

B

oxygen

oxygen

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: H2SO4 / benzene
2: NaI / acetone
3: Mg, I2, HgCl2 / diethyl ether
4: H2 / Pd / methanol
5: KOH / methanol
View Scheme
methyl octadec-9,12-diynoic acid
62439-44-5

methyl octadec-9,12-diynoic acid

A

linoleic acid
60-33-3

linoleic acid

B

oxygen

oxygen

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / Pd / methanol
2: KOH / methanol
View Scheme
7-chloroheptanoic acid methyl ester
26040-62-0

7-chloroheptanoic acid methyl ester

A

linoleic acid
60-33-3

linoleic acid

B

oxygen

oxygen

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NaI / acetone
2: Mg, I2, HgCl2 / diethyl ether
3: H2 / Pd / methanol
4: KOH / methanol
View Scheme
methyl 7-iodoheptanoate
38315-25-2

methyl 7-iodoheptanoate

A

linoleic acid
60-33-3

linoleic acid

B

oxygen

oxygen

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Mg, I2, HgCl2 / diethyl ether
2: H2 / Pd / methanol
3: KOH / methanol
View Scheme
linseed oil

linseed oil

A

9-cis-13-trans-15-cis-octadecatrienoic acid

9-cis-13-trans-15-cis-octadecatrienoic acid

B

9,11,13-octadecatrienoic acid
13296-76-9

9,11,13-octadecatrienoic acid

C

10,12,14-C18:3
104096-79-9

10,12,14-C18:3

D

10E,12Z,14E-C18:3
25574-96-3

10E,12Z,14E-C18:3

E

cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

F

cis-9,trans-11-octadecadienoic acid
544-70-7, 544-71-8, 872-23-1, 1839-11-8, 2540-56-9

cis-9,trans-11-octadecadienoic acid

G

trans-10,cis-12-octadecadienoic acid
1072-36-2, 2420-44-2, 2420-56-6, 7307-45-1, 22880-03-1

trans-10,cis-12-octadecadienoic acid

H

cis-vaccenic acid
506-17-2

cis-vaccenic acid

I

linoleic acid
60-33-3

linoleic acid

J

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid
463-40-1

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid

K

9-(6-propyl-cyclohexa-2,4-dienyl)-nonanoic acid
25491-26-3

9-(6-propyl-cyclohexa-2,4-dienyl)-nonanoic acid

L

rumelenic acid
15909-18-9

rumelenic acid

M

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

N

stearic acid
57-11-4

stearic acid

Conditions
ConditionsYield
With sodium hydroxide In propylene glycol at 160℃; for 2h;
borage oil

borage oil

A

6Z,8E,12Z-C18:3
657403-47-9

6Z,8E,12Z-C18:3

B

7E,9Z,11E-C18:3

7E,9Z,11E-C18:3

C

cis-Δ9-docosenoic acid
25692-11-9

cis-Δ9-docosenoic acid

D

cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

E

cis-9,trans-11-octadecadienoic acid
544-70-7, 544-71-8, 872-23-1, 1839-11-8, 2540-56-9

cis-9,trans-11-octadecadienoic acid

F

trans-10,cis-12-octadecadienoic acid
1072-36-2, 2420-44-2, 2420-56-6, 7307-45-1, 22880-03-1

trans-10,cis-12-octadecadienoic acid

G

cis-vaccenic acid
506-17-2

cis-vaccenic acid

H

linoleic acid
60-33-3

linoleic acid

I

gadoleic acid
29204-02-2

gadoleic acid

J

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid
463-40-1

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid

K

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

L

stearic acid
57-11-4

stearic acid

M

(6Z,10E,12Z)-octadeca-6,10,12-trienoic acid
109241-60-3

(6Z,10E,12Z)-octadeca-6,10,12-trienoic acid

Conditions
ConditionsYield
With sodium hydroxide In propylene glycol at 160℃; for 2h;
Methyl linoleate
112-63-0

Methyl linoleate

linoleic acid
60-33-3

linoleic acid

Conditions
ConditionsYield
With potassium hydroxide In methanol
With water; sodium hydroxide In methanol for 1h; Heating;
(2S)-1-O-(9Z,12Z)-octadecadienoyl-2-O-(7Z,10Z)-hexadecadienoyl-3-O-α-D-galactopyranosyl-(1->6)-β-D-galactopyranosyl-sn-glycerol

(2S)-1-O-(9Z,12Z)-octadecadienoyl-2-O-(7Z,10Z)-hexadecadienoyl-3-O-α-D-galactopyranosyl-(1->6)-β-D-galactopyranosyl-sn-glycerol

A

linoleic acid
60-33-3

linoleic acid

B

(7Z,10Z)-Hexadeca-7,10-dienoic acid (R)-1-hydroxymethyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-ethyl ester

(7Z,10Z)-Hexadeca-7,10-dienoic acid (R)-1-hydroxymethyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-ethyl ester

Conditions
ConditionsYield
With boric acid-borax buffer; Lipase type XI; Triton X-100 at 38℃; for 1h;
safflower oil

safflower oil

A

cis-9-hexadecenoic acid
373-49-9

cis-9-hexadecenoic acid

B

cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

C

Elaidic acid
112-79-8

Elaidic acid

D

(9Z,12Z)-octadeca-9,11-dienoic acid
544-70-7

(9Z,12Z)-octadeca-9,11-dienoic acid

E

cis-9,trans-11-octadecadienoic acid
544-70-7, 544-71-8, 872-23-1, 1839-11-8, 2540-56-9

cis-9,trans-11-octadecadienoic acid

F

(10Z,12Z)-10,12-Octadecadienoic acid
7307-45-1

(10Z,12Z)-10,12-Octadecadienoic acid

G

trans-10,cis-12-octadecadienoic acid
1072-36-2, 2420-44-2, 2420-56-6, 7307-45-1, 22880-03-1

trans-10,cis-12-octadecadienoic acid

H

linoleic acid
60-33-3

linoleic acid

I

(9E,12E)-Octadeca-9,12-dienoic acid
60-33-3

(9E,12E)-Octadeca-9,12-dienoic acid

J

gadoleic acid
29204-02-2

gadoleic acid

K

Arachidic acid
506-30-9

Arachidic acid

L

n-docosanoic acid
112-85-6

n-docosanoic acid

M

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

N

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

O

stearic acid
57-11-4

stearic acid

P

octadeca-11Z,13Z-dienoic acid
117624-52-9

octadeca-11Z,13Z-dienoic acid

Conditions
ConditionsYield
With sodium hydroxide; ethanol; water at 150 - 215℃; under 7500.75 - 24002.4 Torr; for 0 - 6h; Product distribution / selectivity;
With potassium hydroxide; ethanol; water at 150℃; under 7500.75 - 9000.9 Torr; for 0 - 6h; Product distribution / selectivity;
With potassium hydroxide; water In propylene glycol at 150℃; under 7500.75 - 9000.9 Torr; for 0 - 6h; Product distribution / selectivity;
1,2,3-tri(cis,cis-9,12-octadecadienoyloxy)propane
537-40-6

1,2,3-tri(cis,cis-9,12-octadecadienoyloxy)propane

linoleic acid
60-33-3

linoleic acid

Conditions
ConditionsYield
With hydrogenchloride; water for 1h; Heating / reflux;
With water In n-heptane; tert-butyl methyl ether at 37℃; for 24h; Enzymatic reaction;
With 2C33H37N*H2O7S2; water at 80℃;90 %Spectr.
methyl octadec-9,12-diynoic acid
62439-44-5

methyl octadec-9,12-diynoic acid

A

linoleic acid
60-33-3

linoleic acid

B

[9,10,12,13-2H]-(Z,Z)-9,12-octadecadienoic acid
79050-23-0

[9,10,12,13-2H]-(Z,Z)-9,12-octadecadienoic acid

Conditions
ConditionsYield
Stage #1: methyl octadec-9,12-diynoic acid With benzo[1,3,2]dioxaborole at 60℃; for 5h;
Stage #2: With deuteroacetic acid; acetic acid for 5h; Heating;
Stage #3: With potassium hydroxide In water for 1h; Heating; Further stages. Title compound not separated from byproducts.;
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

linoleic acid
60-33-3

linoleic acid

Conditions
ConditionsYield
With Saccharomyces cerevisiae IFO10150 expressing Saccharomyces kluyveri Δ12 fatty acid desaturase Sk-FAD2 In water at 30℃;
β-sitosteryl glucoside-3'-O-linoleate
1192023-60-1

β-sitosteryl glucoside-3'-O-linoleate

A

Daucosterol
474-58-8

Daucosterol

B

linoleic acid
60-33-3

linoleic acid

Conditions
ConditionsYield
Stage #1: β-sitosteryl glucoside-3'-O-linoleate With sodium hydroxide In tetrahydrofuran; methanol at 50℃; for 2h;
Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water
neomastoidin A
1190855-79-8

neomastoidin A

A

(S)-2,3-dihydroxypropyl (9Z,12Z)-9,12-octadecadienoate

(S)-2,3-dihydroxypropyl (9Z,12Z)-9,12-octadecadienoate

C

linoleic acid
60-33-3

linoleic acid

Conditions
ConditionsYield
With ethanol; potassium hydroxide at 25℃;
linoleic acid
60-33-3

linoleic acid

linoleyl chloride
7459-33-8

linoleyl chloride

Conditions
ConditionsYield
With oxalyl dichloride In dichloromethane at 20℃;100%
With oxalyl dichloride99%
With oxalyl dichloride In dichloromethane at 0 - 20℃; for 4h;92%
linoleic acid
60-33-3

linoleic acid

(R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol
100-79-8

(R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol

(+/-)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl (9Z,12Z)-9,12-octadecadienoate
127592-95-4

(+/-)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl (9Z,12Z)-9,12-octadecadienoate

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃;100%
With dmap; dicyclohexyl-carbodiimide89%
With dmap; dicyclohexyl-carbodiimide In diethyl ether at 20 - 25℃; for 4.5h; Esterification;
linoleic acid
60-33-3

linoleic acid

diethyl dicarbonate
1609-47-8

diethyl dicarbonate

ethyl (9Z,12Z)-9,12-octadecadienoate
544-35-4

ethyl (9Z,12Z)-9,12-octadecadienoate

Conditions
ConditionsYield
With dmap In tetrahydrofuran for 0.166667h;100%
linoleic acid
60-33-3

linoleic acid

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol
22323-82-6

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol

(R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl (9Z,12Z)-9,12-octadecadienoate
2518-17-4

(R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl (9Z,12Z)-9,12-octadecadienoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;100%
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In tetrahydrofuran at 0℃;
denatonium hydroxide

denatonium hydroxide

linoleic acid
60-33-3

linoleic acid

N-{2-[(2,6-dimethylphenyl)-amino]-2-oxoethyl}-N,N-diethyl-benzenemethanaminium linolate
890843-15-9

N-{2-[(2,6-dimethylphenyl)-amino]-2-oxoethyl}-N,N-diethyl-benzenemethanaminium linolate

Conditions
ConditionsYield
In methanol at 30 - 60℃; for 1 - 2h;100%
linoleic acid
60-33-3

linoleic acid

1-palmitoyl-3-O-trityl-rac-glycerol
69256-58-2

1-palmitoyl-3-O-trityl-rac-glycerol

1-palmitoyl-2-linoleoyl-3-trityl-glycerol
920271-16-5

1-palmitoyl-2-linoleoyl-3-trityl-glycerol

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In n-heptane at 20℃; for 3h;100%
With dicyclohexyl-carbodiimide; dmap In n-heptane at 20℃; for 3h;
1-O-palmitoyl-3-O-tertbutyldimethylsilyl-sn-glycerol
920112-92-1

1-O-palmitoyl-3-O-tertbutyldimethylsilyl-sn-glycerol

linoleic acid
60-33-3

linoleic acid

1-palmitoyl-2-linoleoyl-3-t-butyl-dimethylsilyl-glycerol
128052-49-3

1-palmitoyl-2-linoleoyl-3-t-butyl-dimethylsilyl-glycerol

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In n-heptane at 20℃; for 3h;100%
With dicyclohexyl-carbodiimide; dmap In n-heptane at 20℃; for 3h;
linoleic acid
60-33-3

linoleic acid

rasagiline
136236-51-6

rasagiline

rasagiline linoleate
1260684-08-9

rasagiline linoleate

Conditions
ConditionsYield
In acetone for 2h;100%
linoleic acid
60-33-3

linoleic acid

Propargylamine
2450-71-7

Propargylamine

(9Z,12Z)-N-(prop-2-yn-1-yl)octadeca-9,12-dienamide
1312773-81-1

(9Z,12Z)-N-(prop-2-yn-1-yl)octadeca-9,12-dienamide

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 18h;100%
linoleic acid
60-33-3

linoleic acid

N-α-tert-butoxycarbonyl-N-β-(9-fluorenylmethoxycarbonyl)-L-diaminopropionic acid
162558-25-0

N-α-tert-butoxycarbonyl-N-β-(9-fluorenylmethoxycarbonyl)-L-diaminopropionic acid

C41H58N2O6

C41H58N2O6

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 17h;100%
linoleic acid
60-33-3

linoleic acid

C18H32O2*C19H21NO

C18H32O2*C19H21NO

Conditions
ConditionsYield
In tetrahydrofuran at 40 - 50℃; for 5h;100%
linoleic acid
60-33-3

linoleic acid

4-amino-n-butyric acid
56-12-2

4-amino-n-butyric acid

C18H32O2*C19H21NO*C4H9NO2

C18H32O2*C19H21NO*C4H9NO2

Conditions
ConditionsYield
Stage #1: doxepin; linoleic acid In tetrahydrofuran at 40 - 50℃; for 5h;
Stage #2: 4-amino-n-butyric acid In tetrahydrofuran; methanol at 50℃; for 1h;
100%
linoleic acid
60-33-3

linoleic acid

benzydamine
642-72-8

benzydamine

C19H23N3O*C18H32O2

C19H23N3O*C18H32O2

Conditions
ConditionsYield
In tetrahydrofuran at 40 - 50℃; for 5h;100%
linoleic acid
60-33-3

linoleic acid

benzydamine
642-72-8

benzydamine

4-amino-n-butyric acid
56-12-2

4-amino-n-butyric acid

C19H23N3O*C18H32O2*C4H9NO2

C19H23N3O*C18H32O2*C4H9NO2

Conditions
ConditionsYield
Stage #1: linoleic acid; benzydamine In tetrahydrofuran at 40 - 50℃; for 5h;
Stage #2: 4-amino-n-butyric acid In tetrahydrofuran; methanol at 50℃; for 1h;
100%
ethanol
64-17-5

ethanol

linoleic acid
60-33-3

linoleic acid

ethyl (9Z,12Z)-9,12-octadecadienoate
544-35-4

ethyl (9Z,12Z)-9,12-octadecadienoate

Conditions
ConditionsYield
With sulfuric acid at 0℃; Reflux;99%
With 1-hexyl-3-methylimidazolium hydrogen sulphate In cyclohexane at 40℃; for 8h; Reagent/catalyst; Temperature;91.07%
With lipase from Geotrichum candidum strain NRRL Y-552, 65 kDa, immobilized on poly-hydroxybutyrate (PHB) particles In n-heptane at 35℃; for 2h; pH=7; Concentration; Temperature; Green chemistry; Enzymatic reaction;70%
linoleic acid
60-33-3

linoleic acid

C29H46O5
1225479-75-3

C29H46O5

C47H76O6

C47H76O6

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2.5h;99%
linoleic acid
60-33-3

linoleic acid

(R)-2,3-dihydroxypropyl n-hexadecanoate
19670-51-0, 32899-41-5, 542-44-9, 5309-46-6

(R)-2,3-dihydroxypropyl n-hexadecanoate

3-hexadecanoyl-1,2-di(cis-octadec-9,12-dienoyl)-sn-glycerol
66964-28-1

3-hexadecanoyl-1,2-di(cis-octadec-9,12-dienoyl)-sn-glycerol

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;99%
linoleic acid
60-33-3

linoleic acid

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

(9Z,12Z)-N-methoxy-N-methyloctadeca-9,12-dienamide
577973-81-0

(9Z,12Z)-N-methoxy-N-methyloctadeca-9,12-dienamide

Conditions
ConditionsYield
With 1-hydroxybenzimidazole hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;99%
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

linoleic acid
60-33-3

linoleic acid

1-ethyl-3-methyl-1H-imidazol-3-ium methylcarbonate

1-ethyl-3-methyl-1H-imidazol-3-ium methylcarbonate

C6H11N2(1+)*0.3C18H33O2(1-)*0.7C18H31O2(1-)

C6H11N2(1+)*0.3C18H33O2(1-)*0.7C18H31O2(1-)

Conditions
ConditionsYield
In methanol at 50℃; for 2h; Green chemistry;99%
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

linoleic acid
60-33-3

linoleic acid

N-methyl-N,N,N-trioctylammonium methylcarbonate
488711-07-5

N-methyl-N,N,N-trioctylammonium methylcarbonate

0.3C18H33O2(1-)*0.7C18H31O2(1-)*C25H54N(1+)

0.3C18H33O2(1-)*0.7C18H31O2(1-)*C25H54N(1+)

Conditions
ConditionsYield
In methanol at 50℃; for 2h; Green chemistry;99%
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

linoleic acid
60-33-3

linoleic acid

1,1,1-trioctyl-1-methylphosphonium methylcarbonate
1204316-79-9

1,1,1-trioctyl-1-methylphosphonium methylcarbonate

0.3C18H33O2(1-)*0.7C18H31O2(1-)*C25H54P(1+)

0.3C18H33O2(1-)*0.7C18H31O2(1-)*C25H54P(1+)

Conditions
ConditionsYield
In methanol at 50℃; for 2h; Green chemistry;99%
linoleic acid
60-33-3

linoleic acid

1-ethyl-3-methyl-1H-imidazol-3-ium methylcarbonate

1-ethyl-3-methyl-1H-imidazol-3-ium methylcarbonate

1-ethyl-3-methylimidazolium linoleate

1-ethyl-3-methylimidazolium linoleate

Conditions
ConditionsYield
In methanol at 50℃; for 2h; Green chemistry;99%
linoleic acid
60-33-3

linoleic acid

N-methyl-N,N,N-trioctylammonium methylcarbonate
488711-07-5

N-methyl-N,N,N-trioctylammonium methylcarbonate

methyltrioctylammonium linoleate
1416991-40-6

methyltrioctylammonium linoleate

Conditions
ConditionsYield
In methanol at 50℃; for 2h; Green chemistry;99%
linoleic acid
60-33-3

linoleic acid

1,1,1-trioctyl-1-methylphosphonium methylcarbonate
1204316-79-9

1,1,1-trioctyl-1-methylphosphonium methylcarbonate

trioctylmethylphosphonium linoleate

trioctylmethylphosphonium linoleate

Conditions
ConditionsYield
In methanol at 50℃; for 2h; Green chemistry;99%
linoleic acid
60-33-3

linoleic acid

2-((difluoromethyl)thio)-3-methylbenzo[d]thiazol-3-ium trifluoromethanesulfonate

2-((difluoromethyl)thio)-3-methylbenzo[d]thiazol-3-ium trifluoromethanesulfonate

S-(difluoromethyl) (9Z,12Z)-octadeca-9,12-dienethioate

S-(difluoromethyl) (9Z,12Z)-octadeca-9,12-dienethioate

Conditions
ConditionsYield
Stage #1: linoleic acid With sodium hydride In tetrahydrofuran for 0.5h; Inert atmosphere;
Stage #2: 2-((difluoromethyl)thio)-3-methylbenzo[d]thiazol-3-ium trifluoromethanesulfonate In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
99%
linoleic acid
60-33-3

linoleic acid

Linoleyl alcohol
506-43-4

Linoleyl alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3h;98%
With lithium aluminium tetrahydride In tetrahydrofuran Reflux;91%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃;91%
linoleic acid
60-33-3

linoleic acid

1,3-dibutanoyloxy-2-propanol
17364-00-0

1,3-dibutanoyloxy-2-propanol

2-((9Z,12Z)-octadeca-9,12-dienoyloxy)propane-1,3-diyl dibutyrate
402562-28-1

2-((9Z,12Z)-octadeca-9,12-dienoyloxy)propane-1,3-diyl dibutyrate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 0℃; for 4h;98%
linoleic acid
60-33-3

linoleic acid

1,2-di-O-palmitoyl-sn-glycerol
6076-30-8

1,2-di-O-palmitoyl-sn-glycerol

2,3-dihexadecanoyl-1-cis-octadec-9,12-dienoyl-sn-glycerol
102491-55-4

2,3-dihexadecanoyl-1-cis-octadec-9,12-dienoyl-sn-glycerol

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;98%
linoleic acid
60-33-3

linoleic acid

n-docosanoic acid
112-85-6

n-docosanoic acid

Conditions
ConditionsYield
With hydrogen In methanol at 20℃; for 4h;97.5%

60-33-3Relevant articles and documents

Antiparasitic Ovalicin Derivatives from Pseudallescheria boydii, a Mutualistic Fungus of French Guiana Termites

Elie, Nicolas,Eparvier, Véronique,Grayfer, Tatyana,Grellier, Philippe,Hebra, Téo,Leman-Loubière, Charlotte,Sorres, Jonathan,Stien, Didier,Touboul, David

, (2022/02/19)

Social insects are in mutualism with microorganisms, contributing to their resistance against infectious diseases. The fungus Pseudallescheria boydii SNB-CN85 isolated from termites produces ovalicin derivatives resulting from the esterification of the less hindered site of the ovalicin epoxide by long-chain fatty acids. Their structures were elucidated using spectroscopic analysis and semisynthesis from ovalicin. For ovalicin, these compounds displayed antiprotozoal activities against Plasmodium falciparum and Trypanosoma brucei, with IC50 values of 19.8 and 1.1 μM, respectively, for the most active compound, i.e., ovalicin linoleate. In parallel, metabolomic profiling of a collection of P. boydii strains associated with termites made it possible to highlight this class of compounds together with tyroscherin derivatives in all strains. Finally, the complete genome of P. boydii strains was obtained by sequencing, and the cluster of potential ovalicin and ovalicin biosynthesis genes was annotated. Through these metabolomic and genomic analyses, a new ovalicin derivative named boyden C, in which the 6-membered ring of ovalicin was opened by oxidative cleavage, was isolated and structurally characterized.

Alteration of Chain Length Selectivity of Candida antarctica Lipase A by Semi-Rational Design for the Enrichment of Erucic and Gondoic Fatty Acids

Zorn, Katja,Oroz-Guinea, Isabel,Brundiek, Henrike,D?rr, Mark,Bornscheuer, Uwe T.

, p. 4115 - 4131 (2018/10/02)

Biotechnological strategies using renewable materials as starting substrates are a promising alternative to traditional oleochemical processes for the isolation of different fatty acids. Among them, long chain mono-unsaturated fatty acids are especially interesting in industrial lipid modification, since they are precursors of several economically relevant products, including detergents, plastics and lubricants. Therefore, the aim of this study was to develop an enzymatic method in order to increase the percentage of long chain mono-unsaturated fatty acids from Camelina and Crambe oil ethyl ester derivatives, by using selective lipases. Specifically, the focus was on the enrichment of gondoic (C20:1 cisΔ11) and erucic acid (C22:1 cisΔ13) from Camelina and Crambe oil derivatives, respectively. The pursuit of this goal entailed several steps, including: (i) the choice of a suitable lipase scaffold to serve as a protein engineering template (Candida antarctica lipase A); (ii) the identification of potential amino acid targets to disrupt the binding tunnel at the adequate location; (iii) the design, creation and high-throughput screening of lipase mutant libraries; (iv) the study of the selectivity towards different chain length p-nitrophenyl fatty acid esters of the best hits found, as well as the analysis of the contribution of each amino acid change and the outcome of combining several of the aforementioned residue alterations and, finally, (v) the selection and application of the most promising candidates for the fatty acid enrichment biocatalysis. As a result, enrichment of C22:1 from Crambe ethyl esters was achieved either, in the free fatty acid fraction (wt, 78%) or in the esterified fraction (variants V1, 77%; V9, 78% and V19, 74%). Concerning the enrichment of C20:1 when Camelina oil ethyl esters were used as substrate, the best variant was the single mutant V290W, which doubled its content in the esterified fraction from approximately 15% to 34%. A moderately lower increase was achieved by V9 and its two derived triple mutant variants V19 and V20 (27%). (Figure presented.).

A fully enzymatic esterification/transesterification sequence for the preparation of symmetrical and unsymmetrical trehalose diacyl conjugates

Prabhakar, Sunchu,Vivès, Thomas,Ferrières, Vincent,Benvegnu, Thierry,Legentil, Laurent,Lemiègre, Lo?c

supporting information, p. 987 - 995 (2017/08/14)

Monoacyl and diacyl trehalose were synthesized in two steps from trehalose and carboxylic acids. The carboxylic acids were converted first into the corresponding 2,2,2-trifluoroethyl esters through a biocatalyzed esterification. The acyl donor was then transferred to the disaccharide through biocatalyzed transesterification. Thanks to microwave reaction conditions the transesterification proceeded selectively to the monoacyl trehalose or to the diacyl counterparts depending on the sole amount of the acyl donor. These reaction conditions were also applied for the preparation of unsymmetrical diacyl trehalose in a fully enzymatic sequence.

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