6147-11-1

Basic information

• Product Name: Mangostin
• Synonyms: 1,3,6-Trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-9H-xanthen-9-one;1,3,6-TRIHYDROXY-7-METHOXY-2,8-DI(3-METHYL-2-BUTENYL)XANTHONE;Mangosteen;mangostin;MANGOSTINE;Momordica Fruit P.E.;Fructus Monordicae extract;1,3,6-Trihydroxy-7-methoxy-2,8-bis(3,3-dimethylallyl)xanthone
• CAS NO: 6147-11-1
• Molecular Formula: C₂₄H₂₆O₆
• Molecular Weight: 410.46
• EINECS: 448-420-7
• Product Categories: Xanthones;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;reagent;standard substance
• Mol File: 6147-11-1.mol

Chemical Properties

• Melting Point: 180-182°C
• Boiling Point: 640.1 °C at 760 mmHg
• Flash Point: 220.3 °C
• Appearance: faint yellow to yellow/
• Density: 1.265 g/cm³
• Vapor Pressure: 5.59E-17mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: 2-8°C
• Solubility: methanol: soluble1mg/mL, clear, very light yellow
• PKA: 7.22±0.20(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
• CAS DataBase Reference: Mangostin(CAS DataBase Reference)
• NIST Chemistry Reference: Mangostin(6147-11-1)
• EPA Substance Registry System: Mangostin(6147-11-1)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 1
• RTECS: ZD6122420
• Hazardous Substances Data: 6147-11-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Mangostin is used as an anti-inflammatory agent for its ability to reduce inflammation and alleviate pain.
Used in Antifungal Applications:
Mangostin is used as an antifungal agent to combat fungal infections and prevent their growth.
Used in Antilarval Applications:
Mangostin is used as an antilarval agent to control and prevent the growth of larvae in various settings.
Used in Oxidative Stress Protection:
Mangostin is used as a protective agent against oxidative stress-mediated retinal cell death, helping to maintain the health of retinal cells.
Used in DNA Protection:
Mangostin is used as an antigenotoxic agent to protect DNA against oxidative damage, reducing the risk of mutations and other DNA-related issues.
Used in Antibacterial Applications:
Mangostin is used as an antibacterial agent against Staphylococcus epidermidis, helping to fight bacterial infections.
Used in Insulin Secretion and Cell Protection:
Mangostin is used to improve insulin secretion and protect INS-1 cells from streptozotocin-induced damage, which can be beneficial for individuals with diabetes.
Used in Cancer Treatment:
Mangostin is used to suppress the metastasis of human renal carcinoma cells and synergize with kinase inhibitors in the suppression of proliferation of SK-MEL-2 malignant melanoma cells, potentially offering new treatment options for cancer patients.
Chemical Properties:
Mangostin is a yellow crystalline solid with a unique chemical structure that contributes to its various biological activities.

Biochem/physiol Actions

Xanthone derivative isolated from mangosteen (Garcinia mangostana). Antioxidant and anti-inflammatory. α-mangostin has been shown to induce apoptosis via the mitochondrial pathway, reduce cell proliferation and inhibit tumorigenesis.

References

1) Mohan et al. (2018), An anti-inflammatory molecular mechanism of action of α-mangostin, the major xanthone from the pericarp of Garcinia mangostana: an in silico, in vitro and in vivo approach; Food Funct., 9 3860 2) Zhang et al. (2018), Identification of α-Mangostin as an Agonist of Human STING; Chem. Med. Chem.,?13 2057 3) Lee et al. (2018), Alpha-Mangostin Improves Insulin Secretion and Protects INS-1 Cells from Streptozotocin-induced Damage; J. Mol. Sci., 19 E1484 4) Chen et al. (2017), Alpha-Mangostin Suppresses the Metastasis of Human renal Carcinoma Cells by Targeting MEK/ERK Expression and MMP-9 Transcription Activity; Cell Physiol. Biochem., 44 1460 5) Xia and Sun (2018), Synergistic inhibition of cell proliferation by combined targeting with kinase inhibitors and dietary xanthone is a promising strategy for melanoma treatment; Clin. Exp. Dermatol., 43 149

InChI:InChI=1/C24H26O6/c1-12(2)6-8-14-16(25)10-19-21(22(14)27)23(28)20-15(9-7-13(3)4)24(29-5)17(26)11-18(20)30-19/h6-7,10-11,25-27H,8-9H2,1-5H3

Synthetic route

→ α-mangostin (6147-11-1)

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Concentration; Reagent/catalyst; Solvent; Reflux;	57.1%
With potassium hydroxide

dimethylmangostin (15404-76-9) → α-mangostin (6147-11-1)

Conditions	Yield
With 1-thiopropane; sodium hydride In N,N-dimethyl-formamide for 6h; Inert atmosphere; Reflux;	60%
With sodium methylate In dimethyl sulfoxide for 6h; Reflux; Inert atmosphere;	59.8%

1,3,6-tri-O-acetyl-α-mangostin (107389-90-2) → α-mangostin (6147-11-1)

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Concentration; Reagent/catalyst; Solvent; Reflux;	57.1%
With potassium hydroxide

6,8-dihydroxy-2-methoxy-1,7-bis(3-methylbut-2-en-1-yl)-9-oxo-9H-xanthen-3-yl acetate (31271-10-0) → α-mangostin (6147-11-1)

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Reflux;	50.4%

1,3-dihydroxy-6-O-benzoyl-7-methoxy-2,8-bis(3-methyl-2-butenyl)-9-xanthone (1140525-42-3) → α-mangostin (6147-11-1)

Conditions	Yield
With sodium hydroxide In water for 1h; Reflux;	44%

[4,6-dihydroxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-[4,6-dihydroxy-3-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-methanone (426820-49-7) → α-mangostin (6147-11-1)

Conditions	Yield
Stage #1: [4,6-dihydroxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-[4,6-dihydroxy-3-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-methanone With tetrachloromethane; triphenylphosphine In tetrahydrofuran at 20℃; Stage #2: With silica gel	43%

3,6-di-O-benzoyl-α-mangostin (1449384-89-7) → α-mangostin (6147-11-1)

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Reflux;	40%

3,5-dihydroxyphenol (108-73-6) → α-mangostin (6147-11-1)

Conditions

Yield

Multi-step reaction with 14 steps 1.1: 96 percent / NaH / dimethylformamide / 20 °C 2.1: nBuLi 2.2: 89 percent / tetrahydrofuran / 0 °C 3.1: nBuLi 3.2: 95 percent / tetrahydrofuran / 0 °C 4.1: 100 percent / CSA; MeOH / 60 °C 5.1: 100 percent / DMAP; Et3N / dimethylformamide / 20 °C 6.1: 78 percent / DIBAL-H / toluene / -78 °C 7.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 8.1: 65 percent / NaH / CH2Cl2 / 20 °C 9.1: 100 percent / TBAF / tetrahydrofuran / 0 °C 10.1: 98 percent / K2CO3 / dimethylformamide / 20 °C 11.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 12.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 13.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 14.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 14.2: 43 percent / silica gel View Scheme

2,4-bis(benzyloxy)phenol (6195-80-8) → α-mangostin (6147-11-1)

Conditions

Yield

Multi-step reaction with 10 steps 1.1: 84 percent / Br2 / CHCl3 / 20 °C 2.1: 80 percent / K2CO3 / dimethylformamide / 20 °C 3.1: 73 percent / 160 °C 4.1: 87 percent / K2CO3 / dimethylformamide / 20 °C 5.1: 95 percent / OsO4; NaIO4 / H2O; diethyl ether / 20 °C 6.1: 72 percent / nBuLi / tetrahydrofuran / 0 °C 7.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 8.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 9.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 10.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 10.2: 43 percent / silica gel View Scheme

2,4-dibenzyloxybenzaldehyde (13246-46-3) → α-mangostin (6147-11-1)

Conditions

Yield

Multi-step reaction with 12 steps 1.1: mCPBA / CH2Cl2 / 20 °C 2.1: HCl / methanol / 20 °C 3.1: 84 percent / Br2 / CHCl3 / 20 °C 4.1: 80 percent / K2CO3 / dimethylformamide / 20 °C 5.1: 73 percent / 160 °C 6.1: 87 percent / K2CO3 / dimethylformamide / 20 °C 7.1: 95 percent / OsO4; NaIO4 / H2O; diethyl ether / 20 °C 8.1: 72 percent / nBuLi / tetrahydrofuran / 0 °C 9.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 10.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 11.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 12.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 12.2: 43 percent / silica gel View Scheme

1,3,5-tris(methoxymethoxy)benzene (120677-47-6) → α-mangostin (6147-11-1)

Conditions

Yield

Multi-step reaction with 13 steps 1.1: nBuLi 1.2: 89 percent / tetrahydrofuran / 0 °C 2.1: nBuLi 2.2: 95 percent / tetrahydrofuran / 0 °C 3.1: 100 percent / CSA; MeOH / 60 °C 4.1: 100 percent / DMAP; Et3N / dimethylformamide / 20 °C 5.1: 78 percent / DIBAL-H / toluene / -78 °C 6.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 7.1: 65 percent / NaH / CH2Cl2 / 20 °C 8.1: 100 percent / TBAF / tetrahydrofuran / 0 °C 9.1: 98 percent / K2CO3 / dimethylformamide / 20 °C 10.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 11.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 12.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 13.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 13.2: 43 percent / silica gel View Scheme

2,4-Dihydroxybenzaldehyde (95-01-2) + Me-X (X=Br or Cl) → α-mangostin (6147-11-1)

Conditions

Yield

Multi-step reaction with 13 steps 1.1: 96 percent / K2CO3 / dimethylformamide / 20 °C 2.1: mCPBA / CH2Cl2 / 20 °C 3.1: HCl / methanol / 20 °C 4.1: 84 percent / Br2 / CHCl3 / 20 °C 5.1: 80 percent / K2CO3 / dimethylformamide / 20 °C 6.1: 73 percent / 160 °C 7.1: 87 percent / K2CO3 / dimethylformamide / 20 °C 8.1: 95 percent / OsO4; NaIO4 / H2O; diethyl ether / 20 °C 9.1: 72 percent / nBuLi / tetrahydrofuran / 0 °C 10.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 11.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 12.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 13.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 13.2: 43 percent / silica gel View Scheme

4,6-dihydroxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-benzaldehyde (426820-54-4) → α-mangostin (6147-11-1)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 98 percent / K2CO3 / dimethylformamide / 20 °C 2.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 3.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 4.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 5.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 5.2: 43 percent / silica gel View Scheme

formic acid 2,4-bis-benzyloxy-phenyl ester → α-mangostin (6147-11-1)

Conditions

Yield

Multi-step reaction with 11 steps 1.1: HCl / methanol / 20 °C 2.1: 84 percent / Br2 / CHCl3 / 20 °C 3.1: 80 percent / K2CO3 / dimethylformamide / 20 °C 4.1: 73 percent / 160 °C 5.1: 87 percent / K2CO3 / dimethylformamide / 20 °C 6.1: 95 percent / OsO4; NaIO4 / H2O; diethyl ether / 20 °C 7.1: 72 percent / nBuLi / tetrahydrofuran / 0 °C 8.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 9.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 10.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 11.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 11.2: 43 percent / silica gel View Scheme

1,3,5-tris-methoxymethoxy-2-(3-methyl-but-2-enyl)-benzene (426820-42-0) → α-mangostin (6147-11-1)

Conditions

Yield

Multi-step reaction with 12 steps 1.1: nBuLi 1.2: 95 percent / tetrahydrofuran / 0 °C 2.1: 100 percent / CSA; MeOH / 60 °C 3.1: 100 percent / DMAP; Et3N / dimethylformamide / 20 °C 4.1: 78 percent / DIBAL-H / toluene / -78 °C 5.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 6.1: 65 percent / NaH / CH2Cl2 / 20 °C 7.1: 100 percent / TBAF / tetrahydrofuran / 0 °C 8.1: 98 percent / K2CO3 / dimethylformamide / 20 °C 9.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 10.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 11.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 12.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 12.2: 43 percent / silica gel View Scheme

2,4,6-trihydroxy-3-(3-methyl-but-2-enyl)-benzoic acid ethyl ester → α-mangostin (6147-11-1)

Conditions

Yield

Multi-step reaction with 10 steps 1.1: 100 percent / DMAP; Et3N / dimethylformamide / 20 °C 2.1: 78 percent / DIBAL-H / toluene / -78 °C 3.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 4.1: 65 percent / NaH / CH2Cl2 / 20 °C 5.1: 100 percent / TBAF / tetrahydrofuran / 0 °C 6.1: 98 percent / K2CO3 / dimethylformamide / 20 °C 7.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 8.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 9.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 10.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 10.2: 43 percent / silica gel View Scheme

2,4-bis-benzyloxy-5-bromo-phenol (426820-51-1) → α-mangostin (6147-11-1)

Conditions

Yield

Multi-step reaction with 9 steps 1.1: 80 percent / K2CO3 / dimethylformamide / 20 °C 2.1: 73 percent / 160 °C 3.1: 87 percent / K2CO3 / dimethylformamide / 20 °C 4.1: 95 percent / OsO4; NaIO4 / H2O; diethyl ether / 20 °C 5.1: 72 percent / nBuLi / tetrahydrofuran / 0 °C 6.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 7.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 8.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 9.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 9.2: 43 percent / silica gel View Scheme

1-Allyloxy-2,4-bis-benzyloxy-5-bromo-benzene (426820-39-5) → α-mangostin (6147-11-1)

Conditions

Yield

Multi-step reaction with 8 steps 1.1: 73 percent / 160 °C 2.1: 87 percent / K2CO3 / dimethylformamide / 20 °C 3.1: 95 percent / OsO4; NaIO4 / H2O; diethyl ether / 20 °C 4.1: 72 percent / nBuLi / tetrahydrofuran / 0 °C 5.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 6.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 7.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 8.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 8.2: 43 percent / silica gel View Scheme

(3,5-bis-benzyloxy-2-bromo-6-methoxy-phenyl)-acetaldehyde (426820-52-2) → α-mangostin (6147-11-1)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 72 percent / nBuLi / tetrahydrofuran / 0 °C 2.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 3.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 4.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 5.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 5.2: 43 percent / silica gel View Scheme

2-allyl-4,6-bis-benzyloxy-3-bromo-phenol (426820-56-6) → α-mangostin (6147-11-1)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: 87 percent / K2CO3 / dimethylformamide / 20 °C 2.1: 95 percent / OsO4; NaIO4 / H2O; diethyl ether / 20 °C 3.1: 72 percent / nBuLi / tetrahydrofuran / 0 °C 4.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 5.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 6.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 7.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 7.2: 43 percent / silica gel View Scheme

3-Allyl-1,5-bis-benzyloxy-2-bromo-4-methoxy-benzene (426820-40-8) → α-mangostin (6147-11-1)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: 95 percent / OsO4; NaIO4 / H2O; diethyl ether / 20 °C 2.1: 72 percent / nBuLi / tetrahydrofuran / 0 °C 3.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 4.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 5.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 6.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 6.2: 43 percent / silica gel View Scheme

2,4,6-tris-methoxymethoxy-3-(3-methyl-but-2-enyl)-benzoic acid ethyl ester (426820-43-1) → α-mangostin (6147-11-1)

Conditions

Yield

Multi-step reaction with 11 steps 1.1: 100 percent / CSA; MeOH / 60 °C 2.1: 100 percent / DMAP; Et3N / dimethylformamide / 20 °C 3.1: 78 percent / DIBAL-H / toluene / -78 °C 4.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 5.1: 65 percent / NaH / CH2Cl2 / 20 °C 6.1: 100 percent / TBAF / tetrahydrofuran / 0 °C 7.1: 98 percent / K2CO3 / dimethylformamide / 20 °C 8.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 9.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 10.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 11.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 11.2: 43 percent / silica gel View Scheme

1,5-Bis-benzyloxy-2-bromo-4-methoxy-3-(3-methyl-but-2-enyl)-benzene (426820-41-9) → α-mangostin (6147-11-1)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 2.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 3.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 4.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 4.2: 43 percent / silica gel View Scheme

4,6-bis-benzyloxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-benzaldehyde (426820-47-5) → α-mangostin (6147-11-1)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 2.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 3.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 4.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 4.2: 43 percent / silica gel View Scheme

4,6-bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-(3-methyl-but-2-enyl)-benzaldehyde (426820-45-3) → α-mangostin (6147-11-1)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: 65 percent / NaH / CH2Cl2 / 20 °C 2.1: 100 percent / TBAF / tetrahydrofuran / 0 °C 3.1: 98 percent / K2CO3 / dimethylformamide / 20 °C 4.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 5.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 6.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 7.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 7.2: 43 percent / silica gel View Scheme

4,6-bis-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-benzaldehyde (426820-46-4) → α-mangostin (6147-11-1)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: 100 percent / TBAF / tetrahydrofuran / 0 °C 2.1: 98 percent / K2CO3 / dimethylformamide / 20 °C 3.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 4.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 5.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 6.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 6.2: 43 percent / silica gel View Scheme

[2,4,6-tris-(tert-butyl-dimethyl-silanyloxy)-3-(3-methyl-but-2-enyl)-phenyl]-methanol (426820-44-2) → α-mangostin (6147-11-1)

Conditions

Yield

Multi-step reaction with 8 steps 1.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 2.1: 65 percent / NaH / CH2Cl2 / 20 °C 3.1: 100 percent / TBAF / tetrahydrofuran / 0 °C 4.1: 98 percent / K2CO3 / dimethylformamide / 20 °C 5.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 6.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 7.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 8.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 8.2: 43 percent / silica gel View Scheme

2,4,6-tris-(tert-butyl-dimethyl-silanyloxy)-3-(3-methyl-but-2-enyl)-benzoic acid ethyl ester → α-mangostin (6147-11-1)

Conditions

Yield

Multi-step reaction with 9 steps 1.1: 78 percent / DIBAL-H / toluene / -78 °C 2.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 3.1: 65 percent / NaH / CH2Cl2 / 20 °C 4.1: 100 percent / TBAF / tetrahydrofuran / 0 °C 5.1: 98 percent / K2CO3 / dimethylformamide / 20 °C 6.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 7.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 8.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 9.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 9.2: 43 percent / silica gel View Scheme

[4,6-bis-benzyloxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-[4,6-bis-benzyloxy-3-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-methanone (426820-55-5) → α-mangostin (6147-11-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 2.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 2.2: 43 percent / silica gel View Scheme

[4,6-bis-benzyloxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-[4,6-bis-benzyloxy-3-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-methanol (426820-48-6) → α-mangostin (6147-11-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 2.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 3.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 3.2: 43 percent / silica gel View Scheme

garcinone D (107390-08-9) → α-mangostin (6147-11-1) + ethanolic KOH-solution

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / 2 h / 100 °C 2: POCl3/Py / Ambient temperature 3: 5percent methanolic KOH View Scheme

α-mangostin (6147-11-1) → 1,3,6-trihydroxy-2,8-diisopentyl-7-methoxy-9H-xanthene-9-one (182317-42-6)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol for 12h;	99%
With palladium 10% on activated carbon; hydrogen In methanol for 12h;	99%
With palladium on activated charcoal; hydrogen In methanol for 6h;	98%

α-mangostin (6147-11-1) + acetic anhydride (108-24-7) → 6,8-dihydroxy-2-methoxy-1,7-bis(3-methylbut-2-en-1-yl)-9-oxo-9H-xanthen-3-yl acetate (31271-10-0)

Conditions	Yield
With triethylamine In toluene at 20℃; for 2h;	99%
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 3.5h;	47.3%

morpholine (110-91-8) + formaldehyd (50-00-0) + α-mangostin (6147-11-1) → 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-4-(morpholinomethyl)-9H-xanthen-9-one

Conditions	Yield
In benzene Mannich Aminomethylation; Reflux;	94%

α-mangostin (6147-11-1) → 3,4-dihydro-5,9-dihydroxy-8-methoxy-2,2-dimethyl-7-(3-methyl-2-butenyl)-2H,6H-pyrano[3,2-b]xanthen-6-one (19275-46-8)

Conditions	Yield
With polyphosphoric acid; air In N,N-dimethyl-formamide at 130℃; for 2h;	91%
With toluene-4-sulfonic acid In benzene Reflux;	70%
With toluene-4-sulfonic acid In benzene Reflux;	70%

α-mangostin (6147-11-1) + ethylene dibromide (106-93-4) → 3,6-bis(2-bromoethoxy)-1-hydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

Conditions	Yield
With potassium carbonate In acetone for 24h; Reflux;	89%
With potassium carbonate In acetone for 20h; Reflux;	75%

α-mangostin (6147-11-1) + ethyl isocyanate (109-90-0) → 1-hydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9-oxo-9H-xanthene-3,6-diyl bis(ethylcarbamate)

Conditions	Yield
With triethylamine In acetonitrile at 85℃; for 5h;	87%

(Z)-2-methyl-2-butenoic anhydride (94487-74-8) + α-mangostin (6147-11-1) → C34H38O8

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃;	85.3%

α-mangostin (6147-11-1) → 9-hydroxycalabaxanthone (35349-68-9)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 40℃; for 5h;	85%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 40℃; for 5h;	85%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene at 80℃; for 3h;	82%

α-mangostin (6147-11-1) + acetic anhydride (108-24-7) → 6,8-dihydroxy-2-methoxy-1,7-bis(3-methylbut-2-en-1-yl)-9-oxo-9H-xanthen-3-yl acetate (31271-10-0) + 1,3,6-tri-O-acetyl-α-mangostin (107389-90-2)

Conditions	Yield
With pyridine at 70℃; for 2h;	A 84.3% B 12.4%
With dmap In dichloromethane at 20℃; for 24h; Cooling;

α-mangostin (6147-11-1) + Isopropyl isocyanate (1795-48-8) → 1-hydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9-oxo-9H-xanthene-3,6-diyl bis(isopropylcarbamate)

Conditions	Yield
With triethylamine In acetonitrile at 85℃; for 5h;	83%

α-mangostin (6147-11-1) + acetic anhydride (108-24-7) → 3-O-acetyl-α-mangostin + 6,8-dihydroxy-2-methoxy-1,7-bis(3-methylbut-2-en-1-yl)-9-oxo-9H-xanthen-3-yl acetate (31271-10-0)

Conditions	Yield
With pyridine at 60℃; for 1h;	A 11% B 81%

α-mangostin (6147-11-1) + 1,10-dibromodecane → 3,6-bis((10-bromodecyl)oxy)-1-hydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

Conditions	Yield
With potassium carbonate In acetone for 24h; Reflux;	81%

α-mangostin (6147-11-1) + benzyl bromide (100-39-0) → 3,6-di-O-benzyl α-mangostin (1193121-18-4)

Conditions	Yield
With potassium carbonate In acetone for 24h; Reflux;	80%
With potassium carbonate In acetone at 40℃; for 4h;

α-mangostin (6147-11-1) + methyl iodide (74-88-4) → dimethylmangostin (15404-76-9)

Conditions	Yield
With potassium carbonate In acetone at 60 - 65℃; for 24h;	80%
With potassium carbonate In acetone at 40℃; for 4h;

1,8-dibromooctane + α-mangostin (6147-11-1) → 3,6-bis((8-bromooctyl)oxy)-1-hydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

Conditions	Yield
With potassium carbonate In acetone for 24h; Reflux;	78%

α-mangostin (6147-11-1) → 1,3,6-trihydroxy-2-(3-methyl-2-butenyl)-7-methoxy-8-(2,3-dihydroxy-3-methylbutyl)xanthone + 1,3,6-trihydroxy-2-(2,3-dihydroxy-3-methylbutyl)-7-methoxy-8-(3-methyl-2-butenyl)xanthone + 1,3,6-trihydroxy-7-methoxy-2,8-bis(2,3-dihydroxy-3-methylbutyl)-9H-xanthen-9-one

Conditions	Yield
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone; tert-butyl alcohol at 20℃; for 24h;	A 12% B 10% C 78%
With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide In acetone; tert-butyl alcohol at 20℃; for 24h;	A 12% B 10% C 78%

α-mangostin (6147-11-1) + allyl bromide (106-95-6) → 3,6-bis(allyloxy)-1-hydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthene-9-one

Conditions	Yield
With potassium carbonate In acetone at 65℃; for 24h;	78%

1,4-dibromo-butane (110-52-1) + α-mangostin (6147-11-1) → C32H40Br2O6 (1427187-01-6)

Conditions	Yield
With potassium carbonate In acetone for 24h; Reflux;	76.5%
With potassium carbonate In acetone for 24h; Reflux;
With potassium carbonate In acetone for 24h; Reflux;

1,4-dibromo-butane (110-52-1) + 4-hydroxybenzenesulphonamide (1576-43-8) + α-mangostin (6147-11-1) → C44H52N2O14S2

Conditions	Yield
Stage #1: 1,4-dibromo-butane; α-mangostin With potassium carbonate In acetone for 24h; Reflux; Stage #2: 4-hydroxybenzenesulphonamide	76.5%

α-mangostin (6147-11-1) + prenyl bromide (870-63-3) → 3,6-di-O-3,3-dimethylallyl α-mangostin (1193121-15-1)

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 24h;	76%
With potassium carbonate In acetone at 65℃; for 12h;	15%
With potassium carbonate In acetone at 40℃; for 4h;

α-mangostin (6147-11-1) + 4-bromobenzenesulfonyl chloride (98-58-8) → C36H32Br2O10S2

Conditions	Yield
With potassium carbonate In dichloromethane at 20℃; for 24h;	76%

piperidine (110-89-4) + formaldehyd (50-00-0) + α-mangostin (6147-11-1) → 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-4-(piperidin-1-ylmethyl)-9H-xanthen-9-one

Conditions	Yield
In benzene Mannich Aminomethylation; Reflux;	75%

α-mangostin (6147-11-1) + allyl bromide (106-95-6) → 1-hydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-3,6-dipropoxy-9H-xanthen-9-one

Conditions	Yield
Stage #1: α-mangostin; allyl bromide With potassium carbonate In acetone at 65℃; for 24h; Stage #2: With palladium on activated charcoal; hydrogen In methanol at 20℃;	75%

α-mangostin (6147-11-1) + ethyl iodide (75-03-6) → C28H34O6 (189945-36-6)

Conditions	Yield
With potassium carbonate In acetone at 60 - 65℃; for 24h;	75%

1,12-dibromododecane (3344-70-5) + α-mangostin (6147-11-1) → 3,6-bis((12-bromododecyl)oxy)-1-hydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

Conditions	Yield
With potassium carbonate In acetone for 24h; Reflux;	73%

bis-(dimethylamino)methane (51-80-9) + α-mangostin (6147-11-1) → 4-dimethylaminomethyl-1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

Conditions	Yield
In benzene at 20℃; for 0.75h; Mannich Aminomethylation;	73%

α-mangostin (6147-11-1) → 3,4-dihydro-5,9-dihydroxy-8-methoxy-2,2-dimethyl-7-(3-methyl-2-butenyl)-2H,6H-pyrano[3,2-b]xanthen-6-one (19275-46-8) + 1-isomangostin (19275-44-6)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 0.5h; Reflux; Dean-Stark;	A 65% B 15%

α-mangostin (6147-11-1) → 1-isomangostin hydrate (26063-95-6) + 3,4-dihydro-5,9-dihydroxy-8-methoxy-2,2-dimethyl-7-(3-methyl-2-butenyl)-2H,6H-pyrano[3,2-b]xanthen-6-one (19275-46-8)

Conditions	Yield
With sulfuric acid In toluene at 40℃; for 4h; Inert atmosphere; Molecular sieve;	A 63% B 29%

1,4-Diiodobutane (628-21-7) + α-mangostin (6147-11-1) → 1,3,6-tris(4-iodobutoxy)-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

Conditions	Yield
With potassium carbonate In acetone for 24h; Reflux;	62%
With potassium carbonate In acetone for 24h; Reflux;	62%

Upstream product

• 1449384-89-7 3,6-di-O-benzoyl-α-mangostin 
• 31271-10-0 6,8-dihydroxy-2-methoxy-1,7-bis(3-methylbut-2-en-1-yl)-9-oxo-9H-xanthen-3-yl acetate 
• 1140525-42-3 1,3-dihydroxy-6-O-benzoyl-7-methoxy-2,8-bis(3-methyl-2-butenyl)-9-xanthone 
• 65697-05-4 3,6-dimethoxy-1,7-dihydroxy-2,8-diallyl-9H-xanthone 
• 132031-39-1 3,6-dimethoxy-1,7-dihydroxy-2,8-diisopent-2-enyl-9H-xanthone 
• 42833-92-1 1,7-dihydroxy-3,6-dimethoxy-9H-xanthen-9-one 
• 15404-76-9 dimethylmangostin 
• 107389-89-9 Acetic acid 3,6-diacetoxy-8-(3-hydroxy-3-methyl-butyl)-7-methoxy-2-(3-methyl-but-2-enyl)-9-oxo-9H-xanthen-1-yl ester 
• 107390-08-9 garcinone D 
• 426820-48-6 [4,6-bis-benzyloxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-[4,6-bis-benzyloxy-3-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-methanol 
• 426820-55-5 [4,6-bis-benzyloxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-[4,6-bis-benzyloxy-3-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-methanone 
• 426820-44-2 [2,4,6-tris-(tert-butyl-dimethyl-silanyloxy)-3-(3-methyl-but-2-enyl)-phenyl]-methanol 
• 426820-46-4 4,6-bis-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-benzaldehyde 
• 426820-45-3 4,6-bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-(3-methyl-but-2-enyl)-benzaldehyde 

Downstream Products

• 925705-36-8 18-O-formyl-3-isomangostin hydrate 
• 1193121-18-4 3,6-di-O-benzyl α-mangostin 
• 1193121-16-2 3,6-di-O-4-methoxybenzyl α-mangostin 
• 1193121-20-8 3,6-di-O-4-mehylbenzyl α-mangostin 
• 15404-76-9 dimethylmangostin 
• 26063-96-7 3,4-dihydro-5,9-dihydroxy-7-(3-hydroxy-3-methylbutyl)-8-methoxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one 
• 26063-95-6 1-isomangostin hydrate 
• 19275-46-8 3-isomangostin 
• 19275-44-6 1-isomangostin 
• 31271-10-0 6,8-dihydroxy-2-methoxy-1,7-bis(3-methylbut-2-en-1-yl)-9-oxo-9H-xanthen-3-yl acetate 
• 1140525-42-3 1,3-dihydroxy-6-O-benzoyl-7-methoxy-2,8-bis(3-methyl-2-butenyl)-9-xanthone 
• 1449384-89-7 3,6-di-O-benzoyl-α-mangostin 
• 212842-64-3 1,3-dihydroxy-6,7-dimethoxy-2,8-bis(3-methyl-2-butenyl)xanthone 

Relevant articles and documents

A preparing method and uses of mangostin and mangostin analogues

The invention belongs to the fields of innovative medicines and cosmetics and particularly relates to a preparing method and uses of mangostin shown as a formula (I) and mangostin analogues shown as a formula (II). Alpha-mangostin, beta-mangostin, gamma-mangostin and analogues thereof are respectively prepared through olefination and through controlling conditions for deprotection. According to the method, products are high in purity, operation is simple and convenient, yields are high, costs are low and the method is suitable for large-scale production. On one hand, the beta-mangostin, the gamma-mangostin, beta-methoxy-mangostin, and analogues thereof have ultraviolet absorption ability and ultraviolet light radiation preventing functions so that the beta-mangostin, the gamma-mangostin, the beta-methoxy-mangostin, and the analogues thereof can be adopted as a sun-screening agent separately or compounded with other sun-screening agents and applied into cosmetics; and on the other hand, the beta-mangostin, the gamma-mangostin, the beta-methoxy-mangostin, and the analogues thereof have activity of inhibiting acid sphingomyelinase so that the beta-mangostin, the gamma-mangostin, the beta-methoxy-mangostin, and the analogues thereof can be adopted as acid sphingomyelinase inhibitors and applied for preparation of medicines for preventing and treating acid sphingomyelinase related diseases mainly including cardio cerebrovascular diseases, neurological diseases, liver diseases, lung diseases, autoimmune diseases, infectious diseases and the like.

High-purity α-mangostin process for the synthesis of

The invention relates to a synthesis process method of high-purity natural product alpha-mangostin, comprising the following steps: (1) reacting alpha-mangostin extracted through a process as an initial raw material with different acylation reagents in an alkaline solvent, recrystallizing to remove partial impurity to obtain phenolic hydroxy substituted alpha-mangostin with higher purity; (2) reacting the synthesized intermediate phenolic hydroxy substituted alpha-mangostin with different reagents in the solvent to remove protecting group, reverse extracting through acid-base, recrystallizing, decoloring, and further purifying to obtain the high-purity alpha-mangostin. The method provided by the invention is convenient to synthesize, high in yield, and capable of meeting the demand of the medicine to the quality.

Mangostin the whole synthetic method

The invention belongs to the field of chemical synthesis and particularly relates to a novel synthesis method of mangostin as shown in the formula (I), wherein the mangostin as a natural effective component has favorable anti-tumor activity, cardiovascular activity, antioxidant activity, anti-inflammatory activity, antibacterial activity and other pharmacological activities. The novel synthesis method comprises the steps: with 1, 7-dihydroxyl-3, 6-dialkoxyl-9H-xanthenone as a raw material, sequentially carrying out nucleophilic substitution, Claisen rearrangement, alkylation, deprotection and the like to obtain alpha-mangostin, beta-mangostin, belt-mangostin-OMe and gamma-mangostin. The novel synthesis method is simple in step and suitable for industrial production.

The first direct synthesis of α-mangostin, a potent inhibitor of the acidic sphingomyelinase

A total synthesis of α-mangostin 1a has been achieved. The key cyclization reaction to construct the xanthone framework was undertaken by employing the PPh3-CCl4 conditions. The inhibitory activities of 1a and the benzophenone intermediate 16 against the acidic sphingomyelinase were discussed.

Garcinone-D, a New Xanthone from Garcinia mangostana Linn.

Garcinone-D, another new minor xanthone has been isolated from the fruit hulls of Garcinia mangostana Linn.It has been assigned structure (I) on the basis of spectral data and chemical correlation.