CIS,CIS-9,12-OCTADECADIENOL
- Product Name
- CIS,CIS-9,12-OCTADECADIENOL
- CAS No.
- 506-43-4
- Chemical Name
- CIS,CIS-9,12-OCTADECADIENOL
- Synonyms
- LINOLEYL ALCOHOL;(9Z,12Z)-octadeca-9,12-dien-1-ol;(Z,Z)-9,12-Octadecadien-1-ol;Linolyl alcohol;CIS,CIS-9,12-OCTADECADIEN-1-OL;9-12 LINOLEYL;Octadecadienol;9-12 LINOLEYL ALCOHOL;Linoleyl Alcohol(C18:2);(9Z,12Z)-octadecadien-1-ol
- CBNumber
- CB2690151
- Molecular Formula
- C18H34O
- Formula Weight
- 266.46
- MOL File
- 506-43-4.mol
CIS,CIS-9,12-OCTADECADIENOL Property
- 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
- Safety Statements
- 24/25
- HS Code
- 2905299000
N-Bromosuccinimide Price
- Product number
- PHR2723
- Product name
- Linoleyl Alcohol
- Purity
- Pharmaceutical Secondary Standard; Certified Reference Material
- Packaging
- 5X200MG
- Price
- $234.65
- Updated
- 2025/07/31
- Product number
- 1367647
- Product name
- Linoleyl alcohol
- Purity
- United States Pharmacopeia (USP) Reference Standard
- Packaging
- 5x30mg
- Price
- $503
- Updated
- 2025/07/31
- Product number
- O0225
- Product name
- cis,cis-9,12-Octadecadien-1-ol
- Purity
- >95.0%(GC)
- Packaging
- 5mL
- Price
- $265
- Updated
- 2025/07/31
- Product number
- O0225
- Product name
- cis,cis-9,12-Octadecadien-1-ol
- Purity
- >95.0%(GC)
- Packaging
- 25mL
- Price
- $696
- Updated
- 2025/07/31
- Product number
- 16556
- Product name
- cis,cis-Octadeca-9,12-dienol
- Purity
- ≥98%
- Packaging
- 100mg
- Price
- $32
- Updated
- 2024/03/01
CIS,CIS-9,12-OCTADECADIENOL Chemical Properties,Usage,Production
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
60-33-3
506-43-4
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
Animal feeding experiments have revealed that esters made from Gallic acid (GA) and (-)-Epigallo-catechin (EGC) or Linoleyl alcohol are more effective in weight-loss promotion and metabolic syndrome management than are intact GA and EGC[2].
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 Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from CIS,CIS-9,12-OCTADECADIENOL manufacturers
- Product
- CIS,CIS-9,12-OCTADECADIENOL 506-43-4
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-11
- Product
- CIS,CIS-9,12-OCTADECADIENOL 506-43-4
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-09
- Product
- CIS,CIS-9,12-OCTADECADIENOL 506-43-4
- Price
- US $1.00/ASSAYS
- Min. Order
- 1ASSAYS
- Purity
- 85.0-99.8%
- Supply Ability
- 20tons
- Release date
- 2020-01-08