Name: Linoleic acid
SKU: 60-33-3

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Basic Information

Molecular Structure:
CAS No.:	60-33-3
Name:	Linoleic acid

Formula:	C₁₈H₃₂O₂
Molecular Weight:	280.451
Synonyms:	9,12-Octadecadienoicacid (Z,Z)-;Linoleic acid (8CI);(9Z,12Z)-9,12-Octadecadienoic acid;(Z,Z)-9,12-Octadecadienoic acid;9,12-Octadecadienoic acid, (Z,Z)-;9-cis,12-cis-Linoleic acid;9Z,12Z-Linoleic acid;9Z,12Z-Octadecadienoic acid;Emersol 315;Extra Linoleic 90;all-cis-9,12-Octadecadienoic acid;cis,cis-Linoleic acid;cis-9,cis-12-Octadecadienoic acid;cis-D9,12-Octadecadienoic acid;
EINECS:	200-470-9
Density:	0.912 g/cm³
Melting Point:	-5 °C
Boiling Point:	360.552 °C at 760 mmHg
Flash Point:	272.976 °C
Solubility:	insoluble in water
Appearance:	Colorless to straw colored liquid
Hazard Symbols:	Xi
Risk Codes:	36
Safety:	26-24/25-36
PSA:	37.30000
LogP:	5.88450

Synthetic route

: 19836-71-6
linoleic nitrile

: 60-33-3
linoleic acid

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water Heating;	81%

: 141-22-0
Ricinoleic acid

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

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

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

D: 60-33-3
linoleic acid

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

F: 59744-10-4, 62272-86-0, 68399-13-3, 69651-29-2, 127062-51-5, 127062-52-6, 127062-54-8
(R,Z)-13-hexyloxacyclotridec-10-en-2-one

Conditions

Conditions	Yield
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%

...Expand

soybean oil, refined, bleached and deodorized: soybean oil, refined, bleached and deodorized

A trans fatty acid; mixture of: trans fatty acid; mixture of

B: 112-80-1
cis-Octadecenoic acid

C: 60-33-3
linoleic acid

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

E: 57-11-4
stearic acid

Conditions

Conditions	Yield
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%

...Expand

: 2462-85-3, 2566-97-4, 20221-26-5, 20221-27-6, 112-63-0
linoleic acid methyl ester

: 60-33-3
linoleic acid

Conditions

Conditions	Yield
With potassium hydroxide

: 2012-14-8
9,12-octadecadiynoic acid

: 60-33-3
linoleic acid

Conditions

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

Methyl linoleate: Methyl linoleate

: 60-33-3
linoleic acid

Conditions

Conditions	Yield
With potassium hydroxide In methanol
With water; sodium hydroxide In methanol for 1h; Heating;

: 1794-89-4, 54324-50-4, 56846-03-8, 56846-04-9
rac-(9R,10R,12S,13S)-9,10,12,13-Tetrabromostearic acid

: 60-33-3
linoleic acid

Conditions

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide -1.4 V (vs. SCE) at a mercury pool (divided cell); Yield given;

: 119520-51-3
(9Z,12Z)-N-(pyridin-3-yl)octadeca-9,12-dienamide

: 60-33-3
linoleic acid

Conditions

Conditions	Yield
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: 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

Conditions

Conditions	Yield
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

: 60-33-3
linoleic acid

Conditions

Conditions	Yield
With diethyl ether; magnesium anschliessend mit Kohlendioxid;

Raw Materials

112-80-1

64-17-5

7647-01-0

544-35-4

141-22-0

821-57-8

2012-14-8

537-40-6

Downstream Products

107-92-6

112-80-1

110-94-1

57-11-4

112-39-0

112-62-9

111-20-6

123-99-9

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The CAS registry number of Linoleic acid is 60-33-3. With the EINECS registry number 200-470-9, its systematic name is (9Z,12Z)-octadeca-9,12-dienoic acid. It is a colorless liquid at room temperature. And it belongs to one of the two families of essential fatty acids that humans and other animals must ingest for good health. In addition, it is used in making soaps, emulsifiers, and quick-drying oils. Besides, it has become increasingly popular in the beauty products industry because of its beneficial properties on the skin.

Physical properties about this chemical are: (1)ACD/LogP: 7.02; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.219; (4)ACD/LogD (pH 7.4): 4.424; (5)ACD/BCF (pH 5.5): 20180.996; (6)ACD/BCF (pH 7.4): 323.607; (7)ACD/KOC (pH 5.5): 24903.602; (8)ACD/KOC (pH 7.4): 399.335; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 14; (12)Polar Surface Area: 37.3 Å²; (13)Index of Refraction: 1.478; (14)Molar Refractivity: 87.121 cm³; (15)Molar Volume: 307.512 cm³; (16)Polarizability: 34.537 ×10^-24cm³; (17)Surface Tension: 34.355 dyne/cm; (18)Density: 0.912 g/cm³; (19)Flash Point: 272.976 °C; (20)Enthalpy of Vaporization: 66.597 kJ/mol; (21)Boiling Point: 360.552 °C at 760 mmHg.

Preparation of Linoleic acid: it can be prepared by octadeca-9c,12c-dienenitrile. This reaction will need reagent NaOH and solvents ethanol and H₂O. The yield is about 81% by heating.

Linoleic acid can be prepared by octadeca-9c,12c-dienenitrile

Uses of Linoleic acid: it can be used to get octadecanoic acid. This reaction will need reagent H₂, catalyst Rhodium chloride tri(triphenylphosphine-meta-trisulfonate) and solvent H₂O. The reaction time is 18 hours with ambient temperature. The yield is about 95%.

Linoleic acid can be used to get octadecanoic acid

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes. During using it, wear suitable protective clothing 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: CCCCC/C=C\C/C=C\CCCCCCCC(=O)O
(2)Std. InChI: InChI=1S/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)/b7-6-,10-9-
(3)Std. InChIKey: OYHQOLUKZRVURQ-HZJYTTRNSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mouse	LD50	intraperitoneal	280mg/kg (280mg/kg)	Yakugaku Zasshi. Journal of Pharmacy. Vol. 104, Pg. 793, 1984.
mouse	LD50	oral	> 50gm/kg (50000mg/kg)	United States Patent Document. Vol. #3728459,
rat	LD50	intraperitoneal	> 50gm/kg (50000mg/kg)	Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 327, 1970.

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Consensus Reports

Specification