Home Cart Sign in  
Chemical Structure| 60-33-3 Chemical Structure| 60-33-3
Chemical Structure| 60-33-3

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

Linoleic acid is an essential fatty acid of most vegetable oils and animal fats, and a prostaglandin precursor.

Synonyms: Octadecadienoic acid (all cis-9,12); C18:2 (all cis-9,12) Fatty acid

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of Linoleic acid

CAS No. :60-33-3
Formula : C18H32O2
M.W : 280.45
SMILES Code : CCCCC\C=C/C\C=C/CCCCCCCC(O)=O
Synonyms :
Octadecadienoic acid (all cis-9,12); C18:2 (all cis-9,12) Fatty acid
MDL No. :MFCD00064241
InChI Key :OYHQOLUKZRVURQ-HZJYTTRNSA-N
Pubchem ID :5280450

Safety of Linoleic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Linoleic acid

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 60-33-3 ]

[ 60-33-3 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 60-33-3 ]
  • [ 3788-56-5 ]
  • 2
  • [ 60-33-3 ]
  • [ 623-57-4 ]
  • [ 1019000-51-1 ]
YieldReaction ConditionsOperation in experiment
22% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; To a solution of the linoleic acid (25 g, 89.1 mmol) in anhydrous DMF (60 mL), diisopropyl ethylamine (17 mL, 100 mml) was added at room temperature with stirring followed by <strong>[623-57-4]3-(dimethylamino)-1,2-propanediol</strong> (4.8 g , 40.5 mmol) and EDCI (17.25 g, 89.9 mmol) and the mixture was stirred at room temperature overnight. The TLC of the reaction mixture (eluent 20percent EtOAc in hexanes) showed the completion of the reaction. The reaction mixture was poured into ice water and extracted with ethyl acetate (2 x <n="133"/>100 mL). The combined organic layers were washed with water (100 mL), saturated NaHCO3 (100 mL) and dried over Na2SO4. Concentration of the organic layer provided the crude product which was purified by column chromatography (silica gel, eluent: 20percent EtOAc in hexanes). The fractions containing pure product was pooled and concentrated. The pure ester was isolated as a clear liquid (5.7 g, 22percent). MS m/z 645 (M+H). 1H NMR CDCl3 delta 0.88 (t,J= 6.3Hz, 6H), 1.20-1.39 (m, 28H), 1.61 (t, J = 4.9 Hz, 12H), 2.03-2.08 (m, 8H), 2.26-2.38 (m, 10H), 2.44-2.56 (m, 2H), 2.76 (t, J= 6.3 Hz, 4 H), 4.09 (dd, J= 6.1 Hz 11.9 Hz, 1H), 4.36 (dd, J= 3.3 11.9 Hz, 1H), 5.29-5.34 (m, 1H), 5.34-5.41 (m, 8H). 13C NMR CDCl3 delta 14.30, 22.79, 25.08, 25.10, 25.83, 27.40, 29.26, 29.30, 29.34, 29.42, 29.55, 29.83, 31.73, 34.32, 34.58, 46.01, 59.37, 64.02, 128.08, 128.24, 130.21, 130.42, 173.39, 173.65.
  • 3
  • [ 79-37-8 ]
  • [ 60-33-3 ]
  • [ 4102-60-7 ]
  • [ 1192363-15-7 ]
  • [ 1192363-14-6 ]
YieldReaction ConditionsOperation in experiment
With magnesium; In tetrahydrofuran; diethyl ether; chloroform; water; N,N-dimethyl-formamide; Example 23A (6Z,9Z,27Z,30Z)-hexatriaconta-6,9,27,30-tetraen-18-one To a suspension of magnesium (0.601 g, 24.71 mmol) in diethyl ether (11 ml) was added dropwise a solution of <strong>[4102-60-7](6Z,9Z)-18-bromooctadeca-6,9-diene</strong> (3.7 g, 11.23 mmol) in diethyl ether (11 ml). The reaction mixture was refluxed for 1 hour then cooled to room temperature to give a solution of the Grignard reagent (9Z,12Z)-octadeca-9,12-dienylmagnesium bromide. To a solution of (9Z,12Z)-octadeca-9,12-dienoic acid (3 g, 10.70 mmol) in CHCl3 (5 ml) was added oxalyl chloride (1.124 ml, 12.84 mmol) and a drop of DMF. The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated by rotary evaporation. The residue was taken up in THF (5 ml) and cooled to -78 C. A solution of (9Z,12Z)-octadeca-9,12-dienylmagnesium bromide (10.70 ml, 10.70 mmol) was added dropwise. The reaction mixture was warmed to 0 C. The reaction mixture was quenched in cold water. The mixture was partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography (4:1 hexanes/dichloromethane). MS (DCI) m/z 530.5 (M+18)+.
  • 6
  • [ 60-33-3 ]
  • [ 623-57-4 ]
  • 1,2-dilinoleoyl-3-dimethylaminopropane [ No CAS ]
YieldReaction ConditionsOperation in experiment
19 g [0250] To a solution of linoleic acid (99percent, 49.7 g, 0.177 mol) in 800 mL of anhydrous benzene was added dropwiseoxalyl chloride (99percent, 29.8 g, 0.235 mol) under argon. Upon addition, the resulting mixture was stirred at room temperaturefor 2 hours until no bubble was released. The solvent and excess of oxalyl chloride was removed in vacuo. To the residualwas added anhydrous benzene (1 L) followed by a solution of 3-N,N-dimethylamino-1,2-propanediol and dry pyridinein anhydrous benzene (100 mL) dropwise. The resulting mixture was stirred at room temperature for 2 days. Uponevaporation of the solvent, 64 g of yellowish syrup were afforded. 19 g of pure DLinDAP were obtained upon purificationof the crude product by column chromatography three times on silica gel using 0-5percent methanol gradient in chloroform.1H NMR (400 MHz, CDCl3) delta: 5.49 (1 H, m), 5.43-5.26 (8H, m), 4.41 (1 H, dd), 4.13 (1 H, dd), 3.15-3.35 (2H, m), 2.82(6H, s, 2 x NCH3), 2.76 (4H, t), 2.35-2.6 (2H, m), 2.31 (2H, t), 2.03 (8H, q, vinyl CH2), 1.53-1.68 (4H, m, 2 x CH2), 1.2-1.4(28H, m, 14 x CH2), 0.88 (6H, t, 2 x CH3) ppm.
  • 7
  • [ 60-33-3 ]
  • [ 123-99-9 ]
  • [ 189034-80-8 ]
  • [ 3788-56-5 ]
  • [ 5503-03-7 ]
  • [ 5502-89-6 ]
  • (9Z)-11-hydroxy-12,13-epoxy-9-octadecenoic acid [ No CAS ]
  • (4Z)-2-pentyl-4-tridecene-1,13-dioic acid [ No CAS ]
  • (2’Z)-2-(2’-octenyl)-decane-1,10-dioic acid [ No CAS ]
  • (2’Z,5’Z)-2-(2’,5’-octadienyl)-decane-1,10-dioic acid [ No CAS ]
  • (12Z)-10-oxo-11-hydroxy-12-octadecenoic acid [ No CAS ]
  • [ 29623-28-7 ]
  • [ 73543-67-6 ]
  • 8
  • [ 50584-68-4 ]
  • [ 60-33-3 ]
  • panthenyl monolinoleate [ No CAS ]
 

Historical Records

Technical Information

Categories