19908-48-6

Basic information

• Product Name: (-)-MAACKIAIN
• Synonyms: INERMIN;(-)-MAACKIAIN;MAACKIAIN, (-)-;(6aS)-6aβ,11aβ-Dihydro-8,9-(methylenedioxy)-6H-benzofuro[3,2-c][1]benzopyran-3-ol;(6aS)-6aβ,12aβ-Dihydro-6H-[1,3]dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3-ol;(6aS,12aS)-6a,12a-Dihydro-6H-[1,3]dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3-ol;6aβ,12aβ-Dihydro-6H-[1,3]dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3-ol;dl- Maackiain
• CAS NO: 19908-48-6
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 19908-48-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 199-200 °C
• Boiling Point: 436.2 °C at 760 mmHg
• Flash Point: 217.6 °C
• Appearance: /
• Density: 1.48 g/cm³
• Vapor Pressure: 3.23E-08mmHg at 25°C
• Refractive Index: 1.677
• Storage Temp.: 2-8°C
• PKA: 9.45±0.20(Predicted)
• CAS DataBase Reference: (-)-MAACKIAIN(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-MAACKIAIN(19908-48-6)
• EPA Substance Registry System: (-)-MAACKIAIN(19908-48-6)

Safety Data

• Hazardous Substances Data: 19908-48-6(Hazardous Substances Data)

Usage

Uses

(±)-Maackiain can be used to improve collage synthesis of skin fibroblast to improve skin regeneration effects. It can also be used to inhibit expression of allergy-sensitive genes and fungicidal activity.

InChI:InChI=1/C16H12O5/c17-8-1-2-9-12(3-8)18-6-11-10-4-14-15(20-7-19-14)5-13(10)21-16(9)11/h1-5,11,16-17H,6-7H2/t11-,16-/m1/s1

Upstream product

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• 76240-27-2 7-hydroxy-2,3-dihydro-4H-chromen-4-one 
• 76240-23-8 3-(3-Hydroxyphenoxy)propanenitrile 
• 6941-70-4 2-bromo-4,5-methylenedioxyphenol 
• 533-31-3 Sesamol 
• 76240-24-9 7-benzyloxy-3,4-dihydro-2H-1-benzopyran-4-ol 
• 108-46-3 recorcinol 
• 70371-58-3 1-(benzyloxy)-3-(prop-2-yn-1-yloxy)benzene 
• 76240-25-0 7-benzyloxy-2H-1-benzopyran 
• 61080-20-4 2-(chloromercurio)-4,5-(methylenedioxy)phenol 
• 76240-26-1 (+/-)-3-benzyloxy-8,9-methylenedioxyprerocarpan 

Downstream Products

• 84297-59-6 rac-cabenegrin A-I 
• 245678-49-3 (+)-3[1-S-N(1-methyl)benzyl-carbamoyl]-6aS,11aS-maackiain 
• 245678-56-2 (-)-3[1-S-N(1-methyl)benzylcarbamoyl]-6aR,11aR-maackiain 

Relevant articles and documents

Maackiain is a novel antiallergic compound that suppresses transcriptional upregulation of the histamine H1 receptor and interleukin-4 genes

Kujin contains antiallergic compounds that inhibit upregulation of histamine H1 receptor (H1R) and interleukin (IL)-4 gene expression. However, the underlying mechanism remains unknown. We sought to identify a Kujin-derived antiallergic compound and investigate its mechanism of action. The H1R and IL-4 mRNA levels were determined by real-time quantitative RT-PCR. To investigate the effects of maackiain in?vivo, toluene-2,4-diisocyanate (TDI)-sensitized rats were used as a nasal hypersensitivity animal model. We identified (?)-maackiain as the responsible component. Synthetic maackiain showed stereoselectivity for the suppression of IL-4 gene expression but not for H1R gene expression, suggesting distinct target proteins for transcriptional signaling. (?)-Maackiain inhibited of PKCδ translocation to the Golgi and phosphorylation of Tyr311 on PKCδ, which led to the suppression of H1R gene transcription. However, (?)-maackiain did not show any antioxidant activity or inhibition of PKCδ enzymatic activity per se. Pretreatment with maackiain alleviated nasal symptoms and suppressed TDI-induced upregulations of H1R and IL-4 gene expressions in TDI-sensitized rats. These data suggest that (?)-maackiain is a novel antiallergic compound that alleviates nasal symptoms in TDI-sensitized allergy model rats through the inhibition of H1R and IL-4 gene expression. The molecular mechanism underlying its suppressive effect for H1R gene expression is mediated by the inhibition of PKCδ activation.

Absolute configuration and total synthesis of (-)-cabenegrin A-I

The total synthesis of (-)-cabenegrin A-I [(-)-1] in five steps was achieved from (-)-6aR, 11aR-maackiain [(-)-5], which in turn was prepared by the optical resolution of racemic (±)-5 using S-(-)α-methylbenzyl isocyanate as the the chiral auxiliary. The homochirality of(-)-maackiain [(- )-5] and (-)cabenegrin A-I [(-)-1] was proved by CD measurements. Synthesis of (±)maackiain [(±)-5] is also presented, starting from the readily available phenol derivatives resorcinol and sesamol, which demonstrates the synthetic utility of the Heck-type oxyarylation process for obtaining pterocarpane derivatives on a multigram scale. A new ring-opening reaction of pterocarpanes (7 → 28) is described.