ANANDAMIDE

Base Information

• Chemical Name: ANANDAMIDE
• CAS No.: 94421-68-8
• Molecular Formula: C22H37 N O2
• Molecular Weight: 347.541
• Hs Code.: 2924199090
• Mol file: 94421-68-8.mol

Synonyms:5,8,11,14-Eicosatetraenamide,N-(2-hydroxyethyl)-, (all-Z)-; Anandamide; Arachidonylethanolamide;N-(2-Hydroxyethyl)arachidonamide; N-(2-Hydroxyethyl)arachidonylamide;N-Arachidonoylethanolamide; N-Arachidonylethanolamide;N-Arachidonylethanolamine

Chemical Property of ANANDAMIDE

Chemical Property:

• Appearance/Colour: light yellow oil
• Vapor Pressure: 4.33E-13mmHg at 25°C
• Boiling Point: 522.3 ºCat 760 mmHg
• PKA: 14.48±0.10(Predicted)
• Flash Point: 269.7 ºC
• PSA: 49.33000
• Density: 0.92 g/mL at 25 °C(lit.)
• LogP: 5.63150
• Storage Temp.: −20°C
• Solubility.: ethanol: soluble
• Water Solubility.: 413ug/L(25 oC)

Purity/Quality:

Arachidonylethanolamide ≥97.0% (TLC), oil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 24/25-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Anandamide (94421-68-8) is an endogenous cannabinoid receptor agonist.1-3?Ki=89 nM for CB1?and 371 nM for CB2?receptors.

Technology Process of ANANDAMIDE

There total 11 articles about ANANDAMIDE 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: 96.0%

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) + ethanolamine (141-43-5) → anandamide (94421-68-8)

Guidance literature:

all cis 5,8,11,14-eicosatetraenoic acid; With 1,1'-carbonyldiimidazole; In dichloromethane; at 20 ℃; for 0.5h;

ethanolamine; In dichloromethane; for 12h;

DOI:10.1055/s-0037-1611939

Reference yield: 94.0%

ethanolamine (141-43-5) + arachidonoyl chloride (57303-04-5) → anandamide (94421-68-8)

Guidance literature:

DOI:10.1016/0024-3205(95)00187-B

Reference yield: 81.0%

ethyl arachidonate (95285-77-1,1808-26-0) + ethanolamine (141-43-5) → anandamide (94421-68-8)

Guidance literature:

With Candida antarctica B lipase; Enzymatic reaction;

DOI:10.1002/ejoc.201501263

upstream raw materials:

ethanolamine

arachidonoyl chloride

all cis 5,8,11,14-eicosatetraenoic acid

2-amino-ethanol hydrochloride

Downstream raw materials:

virodhamine

all cis 5,8,11,14-eicosatetraenoic acid

19-Hydroxyarachidonic acid

4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trienyl]oxiran-2-yl}butanoic acid

Refernces

• 1、 Wang, Xingguo,Wang, Xiaosan,Wang, Tong. "Enrichment of arachidonic acid for the enzymatic synthesis of arachidonoyl ethanolamide". . p. 1031 - 1039. Retrieved 2013.
• 2、 -. "ANANDAMIDE COMPOUNDS". Page/Page column 42-43. . Retrieved 2020/07/25.
• 3、 Johansson, Silje J. R.,Johannessen, Tonje,Ellefsen, Christiane F.,Ristun, Mali S.,Antonsen, Simen,Hansen, Trond V.,Stenstrom, Yngve,Nolsoe, Jens M. J.. "A Convenient Protocol for the Synthesis of Fatty Acid Amides". supporting information. p. 213 - 217. Retrieved 2019/01/14.