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Quality Control of Mangiferin Purity: 98% SDS Specification

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Product Details of Mangiferin

CAS No. :	4773-96-0
Formula :	C₁₉H₁₈O₁₁
M.W :	422.34
SMILES Code :	O=C1C2=C(OC3=C1C=C(O)C(O)=C3)C=C(O)C([C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O4)=C2O
Synonyms :	NSC 248870; Alpizarin; Aphloiol
InChI Key :	AEDDIBAIWPIIBD-ZJKJAXBQSA-N
Pubchem ID :	5281647

Safety of Mangiferin

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of Mangiferin

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 4773-96-0 ]

[ 4773-96-0 ] Synthesis Path-Downstream 1~35

1
[ 92631-83-9 ]
[ 24699-16-9 ]
[ 4773-96-0 ]

References: [1]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 2676 - 2686.
[2]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 2676 - 2686.

2
[ 92631-82-8 ]
[ 149-91-7 ]
[ 4773-96-0 ]

References: [1]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 2676 - 2686.

3
6′-O-acetyl mangiferin [ No CAS ]
[ 4773-96-0 ]

References: [1]Phytochemistry,1980,vol. 19,p. 415.

4
[ 4773-96-0 ]
[ 3542-72-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; recorcinol; In water; for 6.0h;Reflux;	To a solution of <strong>[4773-96-0]mangiferin</strong> (300 mg, 0.710 mmol) in 3 N HCl(10 mL) was added resorcinol (117 mg, 1.06 mmol) at ambient temperature. The reactionmixture was refluxed for 6 h and then cooled to ambient temperature. The reaction mixturewas slowly quenched with saturated NaHCO3 solution and stirred for 30 min. Thebrown precipitate was collected by filtration, washed with H2O, and then concentrated invacuo. The residue was purified by flash column chromatography on silica gel (gradient50% EtOAc in n-hexane to only EtOAc) to afford 131 mg (71%) of the crude norathyriol.After recrystallization with ethanol, pure norathyriol was obtained as a yellowish solid,mp. >320C (decomp.). The NMR spectral data were identical with those reported8: 1HNMR (800 MHz, DMSO-d6) d 13.16 (s, 1 H), 10.76 (bs, 1H), 7.37 (s, 1H), 6.85 (s, 1H),6.31 (d, 1H, J D 2.1 Hz), 6.14 (d, 1H, J D 2.1 Hz); 13C NMR (800 MHz, DMSO-d6) d178.9, 164.7, 162.6, 157.3, 154.0, 150.9, 143.7, 111.8, 108.0, 102.6, 101.6, 97.7, 93.6;LR-MS (FABC) m/z 261 (MCHC); HR-MS (FABC) calcd for C13H9O6 (MCHC)261.0394; found: 261.0399.
	With hydrogenchloride; recorcinol; In water; at 150℃; for 6.0h;Green chemistry;	Mangiferin in 3N HCl (10 mL, sigma-aldrich) solution(300 mg, 0.71 mmol, Xian Lyphar Biotech) with resorcinol(1.06 mmol, 1.5 equiv, TCI) was added and heated to reflux (150 C.) for 6 hours.After cooling the refluxed solution to room temperature (25 C.), saturated sodium bicarbonate (NaHCO 3) solution was slowly added to neutralize the mixed solution.The mixed solution was stirred for 30 minutes, then filtered and the solids washed with water.The dried solid was vacuum dried to give brown crude norathiol(crude norathyriol, yield: 71%, 131 mg) was obtained.Crude noratiriol was added to ethyl acetate (10 mL), heated, stirred for 30 minutes, cooled to room temperature (25 C.), and filtered. The solid was washed several times with ethyl acetate, and then the filtrate was concentrated to give noraritol.

References: [1]Chemistry of Natural Compounds,1980,vol. 16,p. 145 - 149.
Khimiya Prirodnykh Soedinenii,1980,p. 190 - 195.
[2]Organic Preparations and Procedures International,2018,vol. 50,p. 91 - 94.
[3]Patent: KR2019/55918,2019,A .Location in patent: Paragraph 0032-0087.

6
[ 108-24-7 ]
[ 4773-96-0 ]
[ 4706-56-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	With iodine; at 130℃; for 0.25h;Microwave irradiation;	Mangiferin (3, 0.2 g, 0.5 mmol) and iodine (0.009 g, 0.07 mmol) were mixed in acetic anhydride (7 mL) and the reaction was kept under MW irradiation (400 W), at 130 C, for 15 min. After cooling, a saturated solution of sodium thiosulfate was added to convert iodine (dark yellow) into iodide (yellow). The crude product was extracted with CH2Cl2 and the organic layer was extracted with a saturated solution of NaHCO3 twice, dried with anhydrous Na2SO4, and filtered. The solvent was evaporated under reduced pressure and the oil obtained was dissolved in ethyl acetate. A yellow solid was obtained with petroleum ether 60-80 C corresponding to1,3,6,7-tetra-O-acetyl-2-C-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-9H-xanthen-9-one (7) (0.294 g, 0.39 mmol, 78 % yield); mp 143-147 C (petroleum ether 60-80 C).

References: [1]Molecules,2018,vol. 23.
[2]Biological and Pharmaceutical Bulletin,2005,vol. 28,p. 596 - 600.

7
[ 102-92-1 ]
[ 4773-96-0 ]
2-β-D-glucopyranosyl-7-cinnamoyloxy-1,3,6-trihydroxy-9H-xanthen-9-one [ No CAS ]

References: [1]Biological and Pharmaceutical Bulletin,2005,vol. 28,p. 596 - 600.

8
[ 77-78-1 ]
[ 4773-96-0 ]
2-β-D-tetrahydroxyglucopyranosyl-3,6,7-trimethoxy-1-hydroxy-9H-xanthen-9-one [ No CAS ]

References: [1]Biological and Pharmaceutical Bulletin,2005,vol. 28,p. 596 - 600.

9
[ 102-92-1 ]
[ 4773-96-0 ]
2-β-D-glucopyranosyl-1,3,6,7-tetrahydroxy-9H-xanthen-9-one [ No CAS ]

References: [1]Magnetic Resonance in Chemistry,2006,vol. 44,p. 838 - 844.

10
[ 102-92-1 ]
[ 4773-96-0 ]
2-β-D-tetracinnamoylglucopyranosyl-7-cynnamoyloxy-1,3,6-trihydroxy-9H-xanthen-9-one [ No CAS ]

References: [1]Magnetic Resonance in Chemistry,2006,vol. 44,p. 838 - 844.

11
[ 4773-96-0 ]
[ 2054-37-7 ]

References: [1]Chemistry of Natural Compounds,1980,vol. 16,p. 145 - 149.
Khimiya Prirodnykh Soedinenii,1980,p. 190 - 195.

12
[ 92665-82-2 ]
[ 4773-96-0 ]

References: [1]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 2676 - 2686.

13
[ 92631-85-1 ]
[ 4773-96-0 ]

References: [1]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 2676 - 2686.

14
[ 92631-84-0 ]
[ 4773-96-0 ]

References: [1]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 2676 - 2686.

Yield	Reaction Conditions	Operation in experiment
		Mangiferin is filtered-off, disintegrated and recrystallized from a mixture dioxane-water (1:1). There is obtained 0.1 kg of mangiferin. The yield of mangiferin is equal to 1% by weight of the starting stock.
		Mangiferin is filtered-off, dried, disintegrated and recrystallized from a mixture dioxane-water (1:2). There are obtained 0.1 kg of mangiferin. The yield of mangiferin is 1.0% by weight of the starting feedstock.
		Mangiferin is filtered-off, dried, disintegrated and recrystallized from a mixture dioxane-water (1:1) to give 0.1 kg of mangiferin. The yeld of mangiferin is equal to 1.0% by weight of the starting feedstock.

16
[ 4773-96-0 ]
[ 929635-04-1 ]

Yield	Reaction Conditions	Operation in experiment
81.7%	With sodium carbonate; In ethanol; water;Product distribution / selectivity;	Example 2 : Preparation of sodium <strong>[4773-96-0]mangiferin</strong>; Mangiferin 42.2(0. lmol) is suspend in the mixture of water 100ml and ethanol 900ml in reactor ,mixing round adequately. Sodium carbonate 5.30g(0.05mol) is dissolved in water , the concentration is 0.1 %( w/v) . The solution of sodium carbonate is added slowly into the <strong>[4773-96-0]mangiferin</strong> suspended solution while mixing round until the solution is clear , then the reaction solution is filtrated, appropriate quantity actone is added into the reaction solution, mixing round adequately . A lot of deposition is come into being , the reaction solution is filtrated to get the depositon, the solid substance is heated up not excess 60 C to dry .the yellow substance is sodium <strong>[4773-96-0]mangiferin</strong>. Its weight is 34.5g, the productivity is 81.7%. The purity of sodium <strong>[4773-96-0]mangiferin</strong> is 95% detected by HPLC.Compound identify:13CNMR(DMSO-d6) (deltappm): 161.7(C-I), 106.9(C-2), 146.6(C-3), 93.2(C-4), 155.9 ( C-4a), 100.6(C-4b), 102.7(C-5), 153.7(C-6), 177.5(C - 9), 73.5(C-I '), 70.5(C-2'), 79.0(C-3'), 70.3(C-4') , 81.2(C-5'), 61.1(C-6'). <n="9"/>13CNMR data of <strong>[4773-96-0]mangiferin</strong> in reference document [ ^ic^g , fj§^>beta . M Ht^P M^Mepsilon^MfrM^f°&fe. MpsipsiM, 1997; 32 (6): 473-475] :13CNMR(DMSO-d6) (deltappm): 161.6(C-I), 107.3(C-2), 163.6(C-3), 93.9(C-4), 156.1 ( C-4a), 101.2(C-4b), 102.5(C-5), 153.6(C-6), 143.7(C-7), 108.1(C-8), 118.7(C-8a), 150.7(C-8b), 179.0(C - 9), 73.0(C-I '), 70.5(C-2'), 78.8(C-3'), 70.3(C-4') , 81.3(C-5'), 61.4(C-6').According to the reference literature of <strong>[4773-96-0]mangiferin</strong> structure identify [ ^TJC ^H , w&m. MpsipsiU, mi-, 32 (6): 473-475 ] , the sodium <strong>[4773-96-0]mangiferin</strong> 13CNMR data reveal: The chemical shift of C-3 displace to high-frequency magnetic field markedly, The chemical shift of C-2, C-4, C-4a, C-4b and C-9 displace to high-frequency magnetic field too.According the sodium <strong>[4773-96-0]mangiferin</strong> 13CNMR data and the process of sodium <strong>[4773-96-0]mangiferin</strong> preparation, we deduce the sodium is linked to the position C-3 hydroxy of <strong>[4773-96-0]mangiferin</strong> .

References: [1]Patent: WO2008/61480,2008,A1 .Location in patent: Page/Page column 7-8.

17
[ 4773-96-0 ]
[ 1158716-92-7 ]

Yield	Reaction Conditions	Operation in experiment
78.1%	With sodium hydrogencarbonate; In ethanol; water;Product distribution / selectivity;	Example 3 : Preparation of sodium <strong>[4773-96-0]mangiferin</strong>; Mangiferin 42.2(0. lmol) is suspend in the mixture of water 900ml and ethanol 100ml in reactor, mixing round adequately. Sodium bicarbonate 9.24g(0.11mol) is dissolved in water ,the concentration is 5%( w/v) . The solution of sodium bicarbonate is added slowly into the <strong>[4773-96-0]mangiferin</strong> suspended solution while mixing round until the solution is clear , then the reaction solution is filtrated, appropriate quantity ethanol-ethyl acetate(l :1.5 v/v) is added into the reaction solution, mixing round adequately . A lot of deposition is come into being, the reaction solution is filtrated to get the depositon, the solid substance is heated up no excess 60 C to dry . The yellow substance is sodium <strong>[4773-96-0]mangiferin</strong>. Its weight is 32.96g, the productivity is 78.1%. The purity of sodium <strong>[4773-96-0]mangiferin</strong> is 92% detected by HPLC.

References: [1]Patent: WO2008/61480,2008,A1 .Location in patent: Page/Page column 8.

18
[ 4773-96-0 ]
mangiferin calcium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.4 - 91.2%	With calcium hydroxide; In dimethyl sulfoxide; glycerol;Product distribution / selectivity;	Example 9: Preparation of <strong>[4773-96-0]mangiferin</strong> calcium <strong>[4773-96-0]mangiferin</strong> 4.2g(0.01mol) is dissolved into 50ml DMSO, calcium hydroxide 0.37g(0.005mol) is dissolved in 80g glycerol, calcium hydroxide solution is added slowly into <strong>[4773-96-0]mangiferin</strong> solution while mixing round, mixing round until it reacte completely. Appropriate quantity ethanol is added into the reaction solution, mixing <n="12"/>round adequately. A lot of deposition is come into being in solution. The reaction solution is filtrated to get the depositon . This deposition is heated up no excess 60 C to dry. The yellow green solid substance is <strong>[4773-96-0]mangiferin</strong> calcium. Its weight is 3.8g, the productivity is 90.4%. Example 10: Preparation of <strong>[4773-96-0]mangiferin</strong> calcium; <strong>[4773-96-0]mangiferin</strong> 4.2g(0.01mol)is dissolved into 80ml DMSO, calcium hydroxide 1.48g(0.02mol) is dissolved in 20Og glycerol, calcium hydroxide solution is added slowly into <strong>[4773-96-0]mangiferin</strong> solution while mixing round , mixing round until it reacte completely. Appropriate quantity ethanol is added into the reaction solution, mixing round adequately . A lot of deposition is come into being in solution. The reaction solution is filtrated to get the depositon. This deposition is heated up no excess 60 C to dry. The yellow green solid substance is <strong>[4773-96-0]mangiferin</strong> calcium. Its weight is 3.83g, the productivity is 91.2%.
82.1%	With potassium hydrogencarbonate; In ethanol; water;Product distribution / selectivity;	Example 5 : Preparation of potassium <strong>[4773-96-0]mangiferin</strong>; Mangiferin 42.2(0. lmol) is suspended in the mixture of water 400ml and ethanol 1600ml in reactor ,mixing round adequately. Potassium bicarbonate 10.0g(0. lmol) is dissolved in water , the concentration is 0.1%( w/v) . The solution of potassium bicarbonate is added slowly into the <strong>[4773-96-0]mangiferin</strong> suspended solution while mixing round until the solution is clear , then the reaction solution is filtrated, appropriate quantity ethanol-dichloroform (7:1 v/v) is added into the reaction solution, mixing round adequately . A lot of deposition is come into being , the reaction solution is filtrated to get the depositon, the solid substance is heated up no excess 60 C to dry .The yellow substance is potassium <strong>[4773-96-0]mangiferin</strong> . Its weight is 34.65g, the productivity is 82.1%. The purity of potassium <strong>[4773-96-0]mangiferin</strong> is 94% detected by HPLC.

References: [1]Patent: WO2008/61480,2008,A1 .Location in patent: Page/Page column 10-11.
[2]Patent: WO2008/61480,2008,A1 .Location in patent: Page/Page column 9.

19
[ 584-08-7 ]
[ 4773-96-0 ]
[ 1158716-92-7 ]
[ 1158716-92-7 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; water;Product distribution / selectivity;	Example 4: Preparation of <strong>[4773-96-0]mangiferin</strong> monopotassiumMangiferin 42.2(0. lmol) is suspended in the mixture of water 200ml and methanol 1800ml in reactor, mixing round adequately. Potassium carbonate 6.9g(0.05mol) is dissolved in water ,the concentration is 0.2%( w/v ) . The solution of potassium carbonate is added slowly into the <strong>[4773-96-0]mangiferin</strong> suspended solution while mixing round until the solution is clear, then the reaction solution is filtrated, appropriate quantity ethanol- chloroform (4:1 v/v) is added into the reaction solution, mixing round adequately . A lot of deposition is come into being, the reaction solution is filtrated to get the depositon, the solid substance is heated up no excess <n="12"/>60 C to dry. The yellow substance is <strong>[4773-96-0]mangiferin</strong> monopotassium. Its weight is 3 Ig, the productivity is 73.4%. The purity of <strong>[4773-96-0]mangiferin</strong> monopotassium is 98.6% detected by HPLC.

References: [1]Patent: WO2009/65287,2009,A1 .Location in patent: Page/Page column 10-11.

20
[ 144-55-8 ]
[ 4773-96-0 ]
[ 929635-04-1 ]
[ 929635-04-1 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water;Product distribution / selectivity;	Example 2: Preparation of <strong>[4773-96-0]mangiferin</strong> monosodiumMangiferin 42.2(0. lmol) is suspended in the mixture of water 1800ml and ethanol 600ml in reactor, mixing round adequately. Sodium bicarbonate 8.4g(0.1mol) is dissolved in water ,the concentration is 0.5%( w/v) . The solution of sodium bicarbonate is added slowly into the <strong>[4773-96-0]mangiferin</strong> suspended solution while mixing round until the solution is clear , then the reaction solution is filtrated, appropriate quantity ethanol-ethyl acetate(l :1.5 v/v) is added into the reaction solution, mixing round adequately . A lot of deposition is come into being, the reaction solution is filtrated to get the depositon, the solid substance is heated up no excess 60C to dry . The yellow substance is <strong>[4773-96-0]mangiferin</strong> monosodium. Its weight is 31.2g, the productivity is 74%. The purity of <strong>[4773-96-0]mangiferin</strong> monosodium is 98.6% detected by HPLC.

References: [1]Patent: WO2009/65287,2009,A1 .Location in patent: Page/Page column 10.

21
[ 497-19-8 ]
[ 4773-96-0 ]
[ 929635-04-1 ]
[ 929635-04-1 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water;Product distribution / selectivity;	Example 3: Preparation of <strong>[4773-96-0]mangiferin</strong> monosodiumMangiferin 42.2(0. lmol) is suspend in the mixture of water 1800ml and ethanol 900ml in reactor ,mixing round adequately. Sodium carbonate 5.30g(0.05mol) is dissolved in water , the concentration is 0.5%( w/v ) . The solution of sodium carbonate is added slowly into the <strong>[4773-96-0]mangiferin</strong> suspended solution while mixing round until the solution is clear , then the reaction solution is filtrated, appropriate quantity actone is added into the reaction solution, mixing round adequately . A lot of deposition is come into being , the reaction solution is filtrated to get the depositon, the solid substance is heated up not excess 60C to dry .the yellow substance is <strong>[4773-96-0]mangiferin</strong> monosodium. Its weight is 31.4g, the productivity is 74.5%. The purity of <strong>[4773-96-0]mangiferin</strong> monosodium is 98.5% detected by HPLC.

References: [1]Patent: WO2009/65287,2009,A1 .Location in patent: Page/Page column 10.

22
calcium hydroxide [ No CAS ]
[ 4773-96-0 ]
mangiferin calcium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide; glycerol;Product distribution / selectivity;	Example 12: Preparation of <strong>[4773-96-0]mangiferin</strong> calcium <strong>[4773-96-0]mangiferin</strong> 4.2g(0.01mol) is dissolved into 50ml DMSO, calcium hydroxide 0.37g(0.005mol) is dissolved in 8Og glycerol, calcium hydroxide solution is added slowly into <strong>[4773-96-0]mangiferin</strong> solution while mixing round, mixing round until it reacte completely. Appropriate quantity ethanol is added into the reaction solution, mixing round adequately. A lot of deposition is come into being in solution. The reaction solution is filtrated to get the depositon . This deposition is heated up no excess 600C to dry. The yellow green solid substance is <strong>[4773-96-0]mangiferin</strong> calcium. Its weight is 3.8g, the productivity is 90.4%. The purity of <strong>[4773-96-0]mangiferin</strong> monopotassium is 71.2% detected by HPLC. Example 13: Preparation of <strong>[4773-96-0]mangiferin</strong> calcium <strong>[4773-96-0]mangiferin</strong> 4.2g(0.01mol)is dissolved into 80ml DMSO, calcium hydroxide 1.48g(0.02mol) is dissolved in 20Og glycerol, calcium hydroxide solution is added slowly into <strong>[4773-96-0]mangiferin</strong> solution while mixing round , mixing round until it reacte completely. Appropriate quantity ethanol is added into the reaction solution, mixing round adequately . A lot of deposition is come into being in solution. The reaction solution is filtrated to get the depositon. This deposition is heated up no excess 60 C to dry. The yellow green solid substance is <strong>[4773-96-0]mangiferin</strong> calcium. Its weight is 3.83g, the productivity is 91.2%. The purity of <strong>[4773-96-0]mangiferin</strong> monopotassium is 63.8% detected by HPLC.

References: [1]Patent: WO2009/65287,2009,A1 .Location in patent: Page/Page column 13.

23
[ 298-14-6 ]
[ 4773-96-0 ]
[ 1158716-92-7 ]
[ 1158716-92-7 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; water;Product distribution / selectivity;	Example 5: Preparation of <strong>[4773-96-0]mangiferin</strong> monopotassiumMangiferin 42.2(0. lmol) is suspended in the mixture of water 1000ml and methanol 1000ml in reactor ,mixing round adequately. Potassium bicarbonate 10.0g(0. lmol) is dissolved in water , the concentration is 0.1 %( w/v) . The solution of potassium bicarbonate is added slowly into the <strong>[4773-96-0]mangiferin</strong> suspended solution while mixing round until the solution is clear , then the reaction solution is filtrated, appropriate quantity ethanol-dichloroform (7: 1 v/v) is added into the reaction solution, mixing round adequately . A lot of deposition is come into being , the reaction solution is filtrated to get the depositon, the solid substance is heated up no excess 60 C to dry .The yellow substance is <strong>[4773-96-0]mangiferin</strong> monopotassium . Its weight is 31.7g, the productivity is 75%. The purity of <strong>[4773-96-0]mangiferin</strong> monopotassium is 98.7% detected by HPLC.

References: [1]Patent: WO2009/65287,2009,A1 .Location in patent: Page/Page column 11.

24
[ 4773-96-0 ]
[ 1158716-92-7 ]
[ 1158716-92-7 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; water;Product distribution / selectivity;	Example 6: Preparation of <strong>[4773-96-0]mangiferin</strong> monosodiumMangiferin 42.2(0. lmol) is suspended in the mixture of water 1800ml and methanol 900ml in reactor ,mixing round adequately. Sodium carbonate 5.30g(0.05mol) is dissolved in water , the concentration is 5%( w/v) . The solution of sodium carbonate is added slowly into the <strong>[4773-96-0]mangiferin</strong> suspended solution while mixing round until the solution is clear , then the reaction solution is filtrated, appropriate quantity ethyl acetate is added into the reaction solution, mixing round adequately . A lot of deposition is come into being , the reaction solution is filtrated to get the depositon, the solid substance is heated up no excess 60C to dry .The yellow substance is <strong>[4773-96-0]mangiferin</strong> monopotassium . Its weight is 32.3g, the productivity is76.5%. The purity of <strong>[4773-96-0]mangiferin</strong> monopotassium is 98.5% detected by HPLC.

References: [1]Patent: WO2009/65287,2009,A1 .Location in patent: Page/Page column 11.

25
[ 108-05-4 ]
[ 4773-96-0 ]
6′-O-acetyl mangiferin [ No CAS ]