ASARININ

Base Information

• Chemical Name: ASARININ
• CAS No.: 133-04-0
• Molecular Formula: C₂₀H₁₈O₆
• Molecular Weight: 354.359
• Hs Code.: 2932999099
• Mol file: 133-04-0.mol

Synonyms:1,3-Benzodioxole,5,5'-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-, [1R-(1a,3aa,4b,6aa)]-; Asarinin (6CI,7CI);1H,3H-Furo[3,4-c]furan, 1,3-benzodioxole deriv.; (-)-Asarinin; (-)-Episesamin;Asarinin, (-)-; L-Asarinin; Xanthoxylin S; l-Asarinin

Chemical Property of ASARININ

Chemical Property:

• Vapor Pressure: 8.38E-10mmHg at 25°C
• Melting Point: 121ºC
• Boiling Point: 504.4 °C at 760 mmHg
• Flash Point: 212.3 °C
• PSA: 55.38000
• Density: 1.385 g/cm³
• LogP: 3.21920
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly, Sonicated)

Purity/Quality:

98% ^*data from raw suppliers

L-Asarinin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Asarinin is a lignan that has been found in A. sieboldii. It is an epimer of sesamin and a noncompetitive inhibitor of Δ5-desaturase (Ki = 0.28 mM). It is selective for Δ5-desaturase over Δ6- and Δ9-desaturase. Asarinin is cytotoxic to A2780 and SKOV3 ovarian cancer cells (IC50s = 38.45 and 60.87 μM, respectively) but not immortalized ovarian surface epithelial cells (IC50 = >200 μM). It induces apoptosis and activates caspase-3, -8, and -9 in A2780 and SKOV3 cells.
• Uses: l-Asarinin in combination with pellitorine is a potential larvicides for the control of insecticide-resistant mosquito populations. Possesses antimicrobial activity.

Technology Process of ASARININ

There total 163 articles about ASARININ 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%

(1S,3aR,4S,6aR)-1,4-bis(6-bromobenzo[d][1,3]dioxol-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan → sesamin (133-03-9,133-04-0,133-05-1,551-30-4,7076-24-6,13079-95-3,68509-46-6,81602-22-4,105661-97-0,111465-32-8,111465-33-9,607-80-7)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium formate; In N,N-dimethyl-formamide; at 80 ℃; for 12h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

DOI:10.1016/j.tet.2020.131483

Reference yield: 60.0%

4,8-dihydroxysesamin (63398-39-0) → sesamin (133-03-9,133-04-0,133-05-1,551-30-4,7076-24-6,13079-95-3,68509-46-6,81602-22-4,105661-97-0,111465-32-8,111465-33-9,607-80-7)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1016/j.tetasy.2005.11.007

Reference yield: 12.0%

(3,4-methylenedioxy)phenylmagnesium bromide (17680-04-5) + (+)-samin (166239-82-3) → sesamin (133-03-9,133-04-0,133-05-1,551-30-4,7076-24-6,13079-95-3,68509-46-6,81602-22-4,105661-97-0,111465-32-8,111465-33-9,607-80-7) + episesamin (133-04-0,133-05-1,551-30-4,607-80-7,7076-24-6,13079-95-3,68509-46-6,81602-22-4,105661-97-0,111465-32-8,111465-33-9,133-03-9)

Guidance literature:

(3,4-methylenedioxy)phenylmagnesium bromide; (+)-samin; In tetrahydrofuran; at 40 ℃; Inert atmosphere;

With pyridine; methanesulfonyl chloride; In tetrahydrofuran; dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1039/d0cc05640e

upstream raw materials:

sesamin

(3,4-methylenedioxy)phenylmagnesium bromide

(1R,2S,3S,4R)-2,3-bis(hydroxymethyl)-1,4-bis(3,4-methylenedioxyphenyl)butane-1,4-diol

5-[(1E)-3-{(S)-1,3-benzodioxol-5-yl[(2S)-oxiran-2-yl]methoxy}prop-1-enyl]-1,3-benzodioxole

Downstream raw materials:

sesamin

(-)-dihydrocubebin

rac-(1R,2R,5R,6S)-2,6-bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane

(2S,3R,4R)-3-hydroxymethyl-4-(3,4-methylenedioxybenzyl)-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

Refernces

• 1、 Zhao, Can,Khan, Ijaz,Zhang, Yong Jian. "Enantioselective total synthesis of furofuran lignans via Pd-catalyzed asymmetric allylic cycloadditon of vinylethylene carbonates with 2-nitroacrylates". . p. 12431 - 12434. Retrieved 2020/10/30.
• 2、 Mori, Naoki,Furuta, Akiko,Watanabe, Hidenori. "Electochemical asymmetric dimerization of cinnamic acid derivatives and application to the enantioselective syntheses of furofuran lignans". . p. 8393 - 8399. Retrieved 2016/12/06.