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60-33-3

Basic Information
CAS No.: 60-33-3
Name: 9,12-Octadecadienoicacid (9Z,12Z)-
Article Data: 102
Cas Database
Molecular Structure:
Molecular Structure of 60-33-3 (9,12-Octadecadienoicacid (9Z,12Z)-)
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: IrritantXi
Risk Codes: 36
Safety: 26-24/25-36
Transport Information: N/A
PSA: 37.30000
LogP: 5.88450
Synthetic route
19836-71-6

linoleic nitrile

60-33-3

linoleic acid

Conditions
ConditionsYield
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

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

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
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%
Conditions
ConditionsYield
With potassium hydroxide
2012-14-8

9,12-octadecadiynoic 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

60-33-3

linoleic acid

Conditions
ConditionsYield
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
ConditionsYield
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
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

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
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

60-33-3

linoleic acid

Conditions
ConditionsYield
With diethyl ether; magnesium anschliessend mit Kohlendioxid;
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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) Effect 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.