CIS,CIS-9,12-OCTADECADIENOL Chemical Properties

Melting point:

-5--2 °C

Boiling point:

149 °C / 1mmHg

Density 

0,86 g/cm³

refractive index 

1.4670 to 1.4710

Flash point:

124℃

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Oil

pka

15.20±0.10(Predicted)

color 

Colourless

Stability:

Light Sensitive

InChI

InChI=1S/C18H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h6-7,9-10,19H,2-5,8,11-18H2,1H3/b7-6-,10-9-

InChIKey

JXNPEDYJTDQORS-HZJYTTRNSA-N

SMILES

C(O)CCCCCCC/C=C\C/C=C\CCCCC

EPA Substance Registry System

9,12-Octadecadien-1-ol, (9Z,12Z)- (506-43-4)

Safety Information

Safety Statements 

24/25

HS Code 

2905299000

CIS,CIS-9,12-OCTADECADIENOL Usage And Synthesis

Uses

(9Z,?12Z)?-9,?12-?Octadecadien-?1-?ol is a linoleyl acid derivative and building block used in the synthesis of lipid-?based unsymmetrical O,?O-?dialkylphosphites. (9Z,?12Z)?-9,?12-?Octadecadien-?1-?ol has been synthesized by transfer hydrogenation using a ruthenium-based catalyst from its parent fatty acid.

Definition

ChEBI: A long chain fatty alcohol that is octadecanol containing two double bonds located at positions 9 and 12 (the 9Z,12Z-geoisomer).

Synthesis

The general procedure for the synthesis of (9Z,12Z)-octadeca-9,12-dien-1-ol from linoleic acid was as follows: lithium aluminum hydride (2.73 g, 72 mmol) was suspended in tetrahydrofuran (THF, 190 mL) cooled to 4 °C. Under stirring, linoleic acid (10 g, 36 mmol) was slowly added dropwise to the above suspension, and stirring was continued for 10 min after completion of the dropwise addition. Subsequently, the reaction mixture was placed in an oil bath and heated to reflux overnight. After completion of the reaction, it was cooled to room temperature and the reaction was quenched by slow addition of 1 mol/L aqueous sodium hydroxide solution (100 mL). The reaction mixture was diluted with ethyl acetate (100 mL) and filtered to remove insoluble material. The filtrate was washed with saturated aqueous sodium bicarbonate, and the organic layer was separated and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by rotary evaporator to obtain the crude product. The crude product was purified by silica gel column chromatography using a continuous gradient of hexane with ethyl acetate as eluent to afford (9Z,12Z)-octadeca-9,12-dien-1-ol (8.68 g, 32.6 mmol) as a colorless oil in 91% yield. The structure of the product was confirmed by proton nuclear magnetic resonance (1H NMR, 500 MHz) with the following chemical shifts: δ= 0.88 (t, 3H), 1.25-1.36 (m, 16H), 1.53-1.58 (m, 2H), 2.02-2.06 (m, 4H), 2.76 (t, 2H), 3.62 (t, 2H), 5.29-5.40 (m, 4H).

in vivo

References

[1] Patent: US2017/273905, 2017, A1. Location in patent: Paragraph 0086-0087
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 20, p. 3216 - 3222
[3] Journal of the Chemical Society [Section] D: Chemical Communications, 1969, p. 906 - 907
[4] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 6994 - 6996
[5] European Journal of Medicinal Chemistry, 2009, vol. 44, # 12, p. 4889 - 4895

CIS,CIS-9,12-OCTADECADIENOL(506-43-4)Related Product Information

• Linoleic acid
• CIS-1,2,3,6-TETRAHYDROPHTHALIMIDE
• cis-3-Hydroxycyclobutanecarboxylic acid
• cis-4-Hydroxy-D-proline
• cis-1,2-Diaminocyclohexane
• cis-1,4-Dichloro-2-butene
• 4-aminocyclohexan-1-ol
• Carbamic acid, [(1R,3S)-3-hydroxycyclopentyl]-, 1,1-dimethylethyl ester, rel-
• (+)-CIS-2-BENZYLAMINOCYCLOHEXANEMETHANOL
• BOC-(+/-)-CIS-3-AMINOCYCLOHEXANE-1-CARBOXYLIC ACID
• cis-4-aminomethylcyclohexane-1-carboxylic acid
• cis-2-Phenylcyclopropanecarboxylicacid
• CIS-11-EICOSENOIC ACID METHYL ESTER
• CIS-1,2-CYCLOHEXANEDIMETHANOL
• (-)-CIS-2-BENZYLAMINOCYCLOHEXANEMETHANOL
• TERT-BUTYL CIS-(2-HYDROXYMETHYL)CYCLOPROPYLCARBAMATE
• 1,3-DILINOLEIN
• Cholesteryl linoleate