23513-53-3

Basic information

• Product Name: (+)-MAACKIAIN
• Synonyms: (+)-MAACKIAIN
• CAS NO: 23513-53-3
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26
• Mol File: 23513-53-3.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+)-MAACKIAIN(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-MAACKIAIN(23513-53-3)
• EPA Substance Registry System: (+)-MAACKIAIN(23513-53-3)

Safety Data

• Hazardous Substances Data: 23513-53-3(Hazardous Substances Data)

Usage

Description

(+)-MAACKIAIN, a natural bioactive compound belonging to the flavonoid group, is predominantly found in the fruits and leaves of the Maackia amurensis tree. It is recognized for its estrogenic and antioxidant properties, which contribute to its potential therapeutic applications. The ability of (+)-MAACKIAIN to bind to estrogen receptors suggests its utility in hormone-related conditions, while its antioxidant capabilities position it as a candidate for addressing diseases linked to oxidative stress. As a result, (+)-MAACKIAIN demonstrates significant potential in the realms of pharmaceutical and nutraceutical applications.

Uses

Used in Pharmaceutical Applications:
(+)-MAACKIAIN is used as a therapeutic agent for hormone-related conditions due to its estrogenic properties, which allow it to bind to estrogen receptors and potentially alleviate symptoms associated with hormonal imbalances.
Used in Nutraceutical Applications:
(+)-MAACKIAIN is utilized as a dietary supplement to support overall health and well-being, particularly in the prevention and treatment of diseases related to oxidative stress, owing to its robust antioxidant characteristics.
Used in Antioxidant Formulations:
In the health and wellness industry, (+)-MAACKIAIN is employed as an antioxidant component in various formulations designed to combat the harmful effects of free radicals and reduce the risk of oxidative stress-related diseases.
Used in Hormone Therapy:
(+)-MAACKIAIN is used as a hormone therapy agent for conditions that involve hormonal imbalances, leveraging its estrogen receptor binding capacity to provide relief and support in managing such conditions.

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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 
• 524-08-3 (+)-sophorol 

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.