(-)-Maackiain

Base Information

• Chemical Name: (-)-Maackiain
• CAS No.: 2035-15-6
• Molecular Formula: C16H12 O5
• Molecular Weight: 284.268
• UNII: TF360D25IJ
• DSSTox Substance ID: DTXSID40904139
• Nikkaji Number: J14.944F
• Wikidata: Q27105234
• Pharos Ligand ID: LMNY39PVAY1K
• Metabolomics Workbench ID: 22776
• ChEMBL ID: CHEMBL334918
• Mol file: 2035-15-6.mol

Synonyms:6H-[1,3]Dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3-ol,6a,12a-dihydro-, (6aR-cis)-;6H-[1,3]Dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3-ol, 6aa,12aa-dihydro-, (-)- (8CI); Maackiain (7CI);(-)-(6aR,12aR)-maackiain; (-)-Maackiain; Inermin; Inermine; Maackiaine;Trifolirhizin aglycone; l-Maackiain

Chemical Property of (-)-Maackiain

Chemical Property:

• Appearance/Colour: Powder
• Vapor Pressure: 3.23E-08mmHg at 25°C
• Melting Point: 179～181℃
• Boiling Point: 436.2°Cat760mmHg
• PKA: 9.45±0.20(Predicted)
• Flash Point: 217.6°C
• PSA: 57.15000
• Density: 1.48g/cm³
• LogP: 2.73060
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 284.06847348
• Heavy Atom Count: 21
• Complexity: 416

Purity/Quality:

95%-98% ^*data from raw suppliers

Maackiain 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(C3=C(O1)C=C(C=C3)O)OC4=CC5=C(C=C24)OCO5
• Isomeric SMILES: C1[C@@H]2[C@H](C3=C(O1)C=C(C=C3)O)OC4=CC5=C(C=C24)OCO5

Technology Process of (-)-Maackiain

There total 14 articles about (-)-Maackiain 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: 92.0%

(+/-)-3-benzyloxy-8,9-methylenedioxyprerocarpan (76240-26-1) → (+/-)-3-hydroxy-8,9-methylenedioxyprerocarpan (2035-15-6,19908-48-6,23513-53-3,76496-57-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; acetone;

DOI:10.1016/S0040-4020(99)00490-1

Reference yield:

7-benzyloxy-2H-1-benzopyran (76240-25-0) → (+/-)-3-hydroxy-8,9-methylenedioxyprerocarpan (2035-15-6,19908-48-6,23513-53-3,76496-57-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / PdCl₂; LiCl / acetone / 2.5 h

2: 92 percent / H₂ / Pd/C / acetone; tetrahydrofuran

With hydrogen; lithium chloride; palladium dichloride; palladium on activated charcoal; In tetrahydrofuran; acetone; 1: Cyclization / 2: Hydrogenolysis;

DOI:10.1016/S0040-4020(99)00490-1

Reference yield:

2-(chloromercurio)-4,5-(methylenedioxy)phenol (61080-20-4) → (+/-)-3-hydroxy-8,9-methylenedioxyprerocarpan (2035-15-6,19908-48-6,23513-53-3,76496-57-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / PdCl₂; LiCl / acetone / 2.5 h

2: 92 percent / H₂ / Pd/C / acetone; tetrahydrofuran

With hydrogen; lithium chloride; palladium dichloride; palladium on activated charcoal; In tetrahydrofuran; acetone; 1: Cyclization / 2: Hydrogenolysis;

DOI:10.1016/S0040-4020(99)00490-1

upstream raw materials:

(+/-)-3-benzyloxy-8,9-methylenedioxyprerocarpan

2-(chloromercurio)-4,5-(methylenedioxy)phenol

7-benzyloxy-2H-1-benzopyran

1-(benzyloxy)-3-(prop-2-yn-1-yloxy)benzene

Downstream raw materials:

6a-hydroxymaackiain

(-)-sophorol

(-)-7,2′-dihydroxy-4′,5′-methylenedioxyisoflavanone

trifolirhizin

Refernces

• 1、 Mizuguchi, Hiroyuki,Nariai, Yuki,Kato, Shuhei,Nakano, Tomohiro,Kanayama, Tomoyo,Kashiwada, Yoshiki,Nemoto, Hisao,Kawazoe, Kazuyoshi,Takaishi, Yoshihisa,Kitamura, Yoshiaki,Takeda, Noriaki,Fukui, Hiroyuki. "Maackiain is a novel antiallergic compound that suppresses transcriptional upregulation of the histamine H1 receptor and interleukin-4 genes". . . Retrieved 2017/11/09.
• 2、 Kaimoyo, Evans,VanEtten, Hans D.. "Inactivation of pea genes by RNAi supports the involvement of two similar O-methyltransferases in the biosynthesis of (+)-pisatin and of chiral intermediates with a configuration opposite that found in (+)-pisatin". . p. 76 - 87. Retrieved 2008/09/18.