PALMITOLEOYL CHLORIDE

Base Information

• Chemical Name: PALMITOLEOYL CHLORIDE
• CAS No.: 40426-22-0
• Molecular Formula: C16H29 Cl O
• Molecular Weight: 272.85
• Hs Code.: 2916190090
• DSSTox Substance ID: DTXSID70408438
• Mol file: 40426-22-0.mol

Synonyms:9-Hexadecenoylchloride, (Z)-; (Z)-Hexadec-9-enoyl chloride; Palmitoleoyl chloride

Chemical Property of PALMITOLEOYL CHLORIDE

Chemical Property:

• PSA: 17.07000
• LogP: 6.00910
• Storage Temp.: −20°C
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 13
• Exact Mass: 272.1906932
• Heavy Atom Count: 18
• Complexity: 211

Purity/Quality:

98%Min ^*data from raw suppliers

Palmitoleoyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC=CCCCCCCCC(=O)Cl
• Uses: Palmitoleoyl Chloride is used in the synthesis of NodRmIV(S) which is involved in the Rhizobium meliloti-alfalfa symbiosis. Also, it is an intermediate used in the synthesis of Ethyl Palmitoleate (E925855), which is used in biological studies for calcium release-activated calcium channel blockade as a potential tool in anti-pancreatitis therapy.

Technology Process of PALMITOLEOYL CHLORIDE

There total 7 articles about PALMITOLEOYL CHLORIDE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

cis-9-hexadecenoic acid (373-49-9,2091-29-4) → ( Z )-hexadec-9-enoyl chloride (40426-22-0)

Guidance literature:

With oxalyl dichloride; for 3h;

DOI:10.1021/jm00070a002

Reference yield:

1,9-Nonanediol (3937-56-2) → ( Z )-hexadec-9-enoyl chloride (40426-22-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1H-imidazole / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

1.2: 60 h / 20 °C / Inert atmosphere

2.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2.5 h / 0 - 20 °C / Inert atmosphere

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.75 h / 0 - 20 °C

3.2: 1 h / -78 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C

5.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2.5 h / 0 - 20 °C / Inert atmosphere

6.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol / 20 °C

7.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 3 h / 0 - 20 °C

With 1H-imidazole; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol;

DOI:10.3762/bjoc.14.276

Reference yield:

9-(tert-butyldimethylsilanyloxy)-1-nonanol (157730-99-9) → ( Z )-hexadec-9-enoyl chloride (40426-22-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2.5 h / 0 - 20 °C / Inert atmosphere

2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.75 h / 0 - 20 °C

2.2: 1 h / -78 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C

4.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2.5 h / 0 - 20 °C / Inert atmosphere

5.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol / 20 °C

6.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 3 h / 0 - 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol;

DOI:10.3762/bjoc.14.276

upstream raw materials:

cis-9-hexadecenoic acid

1,9-Nonanediol

9-(tert-butyldimethylsilanyloxy)-1-nonanol

9-(tert-butyl-dimethyl-silanyloxy)-1-nonanal

Downstream raw materials:

N-1-(4-hydroxyphenyl) (Z)-9-hexadecenamide

1-O-palmitoleoyl-rac-glycidol

(Z)-Hexadec-9-enoic acid (1R,2R,3S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3-((Z)-hexadec-9-enoyloxymethyl)-cyclopropylmethyl ester

(Z)-Hexadec-9-enoic acid 3-(tert-butyl-diphenyl-silanyloxymethyl)-5-((Z)-hexadec-9-enoyloxy)-pentyl ester

Refernces

• 1、 Hassan, Ahmed H.E.,Park, Hye Rim,Yoon, Yoon Mi,Kim, Hye In,Yoo, Sung Yeun,Lee, Kun Won,Lee, Yong Sup. "Antiproliferative 3-deoxysphingomyelin analogs: Design, synthesis, biological evaluation and molecular docking of pyrrolidine-based 3-deoxysphingomyelin analogs as anticancer agents". . p. 444 - 455. Retrieved 2019/01/03.
• 2、 -. "Ceramide compound, a process of preparing the ceramide compound, an intermediate compound and a process of preparing the intermediate compound". Paragraph 0189. . Retrieved 2017/10/31.