58546-54-6

Basic information

• Product Name: Gomisin A
• Synonyms: 2,3,13-tetramethoxy-l-stereoisomer;benzo(3,4)cycloocta(1,2-f)(1,3)benzodioxol-6-ol,5,6,7,8-tetrahydro-6,7-dimethy;wuweizialcoholb;wuweizichunb;BESIGOMISIN;GOMISIN A;SCHISANDROL B;SCHIZANDROL B
• CAS NO: 58546-54-6
• Molecular Formula: C₂₃H₂₈O₇
• Molecular Weight: 416.46
• Product Categories: Miscellaneous Natural Products;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 58546-54-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 88.5°C
• Boiling Point: 454.79°C (rough estimate)
• Flash Point: 304.4 °C
• Appearance: /
• Density: 1.1772 (rough estimate)
• Vapor Pressure: 2.79E-14mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 14.58±0.40(Predicted)
• CAS DataBase Reference: Gomisin A(CAS DataBase Reference)
• NIST Chemistry Reference: Gomisin A(58546-54-6)
• EPA Substance Registry System: Gomisin A(58546-54-6)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 58546-54-6(Hazardous Substances Data)

Usage

Description

Gomisin A is a lignan compound that has been isolated from the plant Schisandra chinensis. It is known for its various biological activities and potential health benefits.

Uses

Used in Pharmaceutical Industry:
Gomisin A is used as a hepatoprotective agent for its ability to increase the expression of pregnane X receptor (PXR) target genes involved in bile acid metabolism. This helps in protecting against lithocholic acid-induced hepatic necrosis and intrahepatic cholestasis.
Used in Cardiovascular Applications:
Gomisin A is used as a protective agent for its potent protective effects on ET-1-induced dysfunctional human-induced pluripotent stem cell-derived cardiomyocytes (hiPS-CMs), which can be beneficial in treating cardiovascular diseases.
Used in Cholestasis Treatment:
Gomisin A is used as an anti-cholestasis agent, as it decreases mortality in a mouse model of cholestasis when administered at a dose of 100 mg/kg twice per day. It also promotes liver regeneration following partial hepatectomy and protects against hepatotoxicity induced by acetaminophen.
Chemical Properties:
Gomisin A is a white powder in its chemical form.

InChI:InChI=1/C23H28O7/c1-12-7-13-8-16-20(30-11-29-16)22(28-6)17(13)18-14(10-23(12,2)24)9-15(25-3)19(26-4)21(18)27-5/h8-9,12,24H,7,10-11H2,1-6H3/t12-,23-/m0/s1

Upstream product

• 72551-73-6 gomisin A 
• 74-95-3 1,1-dibromomethane 
• 158017-74-4 4-(7-Methoxy-benzo[1,3]dioxol-5-ylmethyl)-3-[1-(3,4,5-trimethoxy-phenyl)-meth-(E)-ylidene]-dihydro-furan-2-one 
• 148812-33-3 C₂₂H₂₂O₈ 
• 143503-88-2 4-(3,4-Dihydroxy-5-methoxy-benzyl)-3-[1-(3,4,5-trimethoxy-phenyl)-meth-(E)-ylidene]-dihydro-furan-2-one 
• 78173-82-7 3-(3-methoxy-4,5-methylenedioxybenzyl)butyrolactone 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 143503-85-9 C₂₃H₂₂O₈ 
• 143503-84-8 (S)-4-(7-Methoxy-benzo[1,3]dioxol-5-ylmethyl)-3-[1-(3,4,5-trimethoxy-phenyl)-meth-(E)-ylidene]-dihydro-furan-2-one 
• 143503-89-3 C₂₂H₂₂O₈ 
• 143503-88-2 (S)-4-(3,4-Dihydroxy-5-methoxy-benzyl)-3-[1-(3,4,5-trimethoxy-phenyl)-meth-(E)-ylidene]-dihydro-furan-2-one 
• 143616-16-4 (S)-3-methoxycarbonyl-4-<5-methoxy-3,4-(methylenedioxy)phenyl>butanoic acid 
• 143616-17-5 (S)-(E)-3-<5-Methoxy-3,4-(methylenedioxy)benzyl>butanolide 
• 143552-03-8 C₂₄H₂₈O₁₀S 

Downstream Products

• 61281-37-6 (+)-8-schizandrin 
• 7432-28-2 schizandrin 

Relevant articles and documents

Transformation of schizandrin into gomisin A by use of microbial O-demethylation and chemical reactions

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Synthesis of optically pure gomisin A and schizandrin: The first total synthesis of gomisin A and schizandrin having naturally occurring configurations

The total synthesis of gomisin A and schizandrin having natural configurations were accomplished for the first time. The key feature of these syntheses is a highly efficient intramolecular oxidative coupling of the intermediates 9 and 21, which can be obtained as both enantiomers in optically pure forms. The manipulation of the lactone moieties of 7 and 22 afforded natural enantiomers of schizandrin and gomisin A.