[ CAS No. 529-59-9 ] {[proInfo.proName]}

Name: 529-59-9|5-Hydroxy-3-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one|98%
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Quality Control of [ 529-59-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 529-59-9 ]

Product Details of [ 529-59-9 ]

CAS No. :	529-59-9	MDL No. :	MFCD00016883
Formula :	C₂₁H₂₀O₁₀	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	432.38	Pubchem ID :	-
Synonyms :	Genistine;Genistoside;CS-4240;NSC 5112;Genistein glucoside;Genistein 7-glucoside;Genistein 7-O-β-D-glucopyranoside	Chemical Name :	5-Hydroxy-3-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

Safety of [ 529-59-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 529-59-9 ]

* 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.

Upstream synthesis route of [ 529-59-9 ]
Downstream synthetic route of [ 529-59-9 ]

[ 529-59-9 ] Synthesis Path-Upstream 1~7

1
[ 1105697-82-2 ]
[ 529-59-9 ]

Reference： [1] European Journal of Organic Chemistry, 2008, # 33, p. 5622 - 5629

2
[ 76298-37-8 ]
[ 529-59-9 ]

Reference： [1] European Journal of Organic Chemistry, 2008, # 33, p. 5622 - 5629

3
[ 67-56-1 ]
[ 3943-97-3 ]
[ 529-59-9 ]

Reference： [1] Phytochemistry (Elsevier), 1986, vol. 25, # 11, p. 2687 - 2688

4
[ 51011-05-3 ]
[ 529-59-9 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 7, p. 1978 - 1980

5
[ 73566-30-0 ]
[ 529-59-9 ]

Reference： [1] Agricultural and Biological Chemistry, 1980, vol. 44, # 2, p. 469 - 470

6
[ 446-72-0 ]
[ 572-09-8 ]
[ 529-59-9 ]

Reference： [1] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 16, p. 2481 - 2484

7
[ 51011-05-3 ]
[ 141-82-2 ]
[ 529-59-9 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 9, p. 3408 - 3413

[ 529-59-9 ] Synthesis Path-Downstream 1~26

1
[ 67-56-1 ]
genistein 7-O-(2"-p-coumaroyl-β-D-glucopyranoside) [ No CAS ]
[ 3943-97-3 ]
[ 529-59-9 ]

Reference： [1]Phytochemistry,1986,vol. 25,p. 2687 - 2688

2
[ 51011-05-3 ]
[ 529-59-9 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 1978 - 1980

3
[ 73566-30-0 ]
[ 529-59-9 ]

Reference： [1]Agricultural and Biological Chemistry,1980,vol. 44,p. 469 - 470

4
[ 446-72-0 ]
[ 572-09-8 ]
[ 529-59-9 ]
5-Hydroxy-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3-[4-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-chromen-4-one [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1998,p. 2481 - 2484

6
[ 572-09-8 ]
genisteine [ No CAS ]
[ 529-59-9 ]

Reference： [1]Chemische Berichte,1943,vol. 76,p. 1110

7
[ 108-24-7 ]
[ 529-59-9 ]
[ 76298-37-8 ]

Reference： [1]Pharmaceutical Chemistry Journal,2001,vol. 35,p. 30 - 34

8
[ 529-59-9 ]
[ 50-99-7 ]
[ 446-72-0 ]

Reference： [1]Pharmaceutical Chemistry Journal,2001,vol. 35,p. 30 - 34

9
[ 529-59-9 ]
[ 2280-44-6 ]
[ 446-72-0 ]

Reference： [1]Phytochemistry,2001,vol. 58,p. 995 - 1005

10
[ 529-59-9 ]
[ 50-99-7 ]

Reference： [1]Phytochemistry,2005,vol. 66,p. 1880 - 1889

11
[ 529-59-9 ]
[ 446-72-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	In hydrogenchloride;	D. Hydrolysis and Crystallization: About 1578 mg of <strong>[529-59-9]genistin</strong> were refluxed in 960 ml 4N HCl for five hours at 100+-5 C. About 948 mg genistein were obtained with about 96% recovery. 483.2 mg of genistein (99% purity) recovered from the hydrolysis step was dissolved in 450 ml methanol and crystallized in 20 ml methanol. About 373.8 mg of genistein crystal was obtained giving a 77% recovery and 99.5% purity. Genistein m.p. 298.4-299.9 C. 1 H NMR (400 MHz, DMSO-d6) 6.22 (1H, d, J=2 Hz, H-8), 6.38 (1H, d, J=2 Hz, H-6), 6.83 (2H, d, J=8 Hz, H-3'), 7.39 (2H, d, J=8 Hz, H-2'), 8.43 (1H, s, H-2), 9.61 (1H, s, 4'-OH), 10.90 (1H, s, 7-OH) 12.92 (1H, s, 5-OH). 13 C NMR (100 MHz, DMSO-d6) 154.5, 122.8, 180.7, 162.5, 99.5, 164.8, 94.2, 157.9, 105.0, 121.7, 130.7, 115.6, 158.1.
	In hydrogenchloride;	D. Genistein via Hydrolysis and Crystallization: About 49.0 mg of <strong>[529-59-9]genistin</strong> were refluxed in 15 ml 4N HCl for five hours at 105+-5 C. About 22.9 mg of genistein was obtained with about 75% recovery. About 13 mg genistein from the previous step was extracted twice with 50 ml diethyl ether. The extracts were combined, and evaporated to dryness. The solids obtained were crystallized from 2 ml of a solution made from 3 parts ethanol and 2 parts water. About 8.2 mg of the genistein crystal was obtained with 63% recovery and about 99% purity.

Reference： [1]Patent: US2006/216281,2006,A1 .Location in patent: Page/Page column 9
[2]Patent: US5679806,1997,A
[3]Patent: US2006/216281,2006,A1 .Location in patent: Page/Page column 9
[4]Patent: US2006/216281,2006,A1 .Location in patent: Page/Page column 9
[5]Journal of Agricultural and Food Chemistry,2007,vol. 55,p. 2407 - 2412
[6]Patent: US5679806,1997,A
[7]Chemistry of Natural Compounds,2011,vol. 47,p. 197 - 200
[8]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 1535 - 1541
[9]RSC Advances,2019,vol. 9,p. 4892 - 4899

12
[ 51011-05-3 ]
[ 141-82-2 ]
[ 529-59-9 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2007,vol. 55,p. 3408 - 3413

13
[ 529-59-9 ]
soluble starch [ No CAS ]
α-D-glucosyl(1->4)genistin [ No CAS ]
α-D-maltosyl(1->4)genistin [ No CAS ]
α-D-maltotriosyl(1->4)genistin [ No CAS ]
α-D-maltotetraosyl(1->4)genistin [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 3819 - 3826

14
Solgen 40 [ No CAS ]
[ 552-66-9 ]
[ 529-59-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In methanol; water; at 66℃; for 0.25h;Heating / reflux;Purification / work up;	50.0 grams of"Solgen 40" (containing 26.9% genistin, 11.9% daidzin, 2.0% glycetin; negligible aglycon content; genistin-to-daidzin ratio 2.3 : 1) was added to 75 ml of methanol and 15 ml of concentrated hydrochloric acid in an ERLENMEYER flask equipped with a magnetic stirring bar and reflux condenser. The mixture was heated on a hotplate to reflux (66 C.), maintained at reflux for 15 minutes, then cooled to 20 C. The resulting slurry was filtered at this temperature on a Buechner funnel through Whatman No.541 filter paper. Filtration was very slow, as the viscosity of the slurry increased dramatically upon cooling. The off-white filter cake solids were washed with a modest volume of 5: 1 methanol: HCL and dried in a vacuum oven at 80 C. to give 16.4 grams of off-white solids containing: 54.48% by wt. genistin (8.93 grams, or 66.3% of that present in the starting material) 9.47% by wt. daidzin (1.55 grams, or 26. 1% of that present in the starting material) 63.95% total isoflavones; genistin-to-daidzin ratio = 5.75 : 1 No glycetin or isoflavone aglycons were detected.

Reference： [1]Patent: WO2004/43945,2004,A1 .Location in patent: Page 6-7

15
Solgen 40 [ No CAS ]
[ 40246-10-4 ]
[ 552-66-9 ]
[ 529-59-9 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; at 20℃; for 0.5h;Purification / work up;	10.0 gram aliquots of"Solgen 40" (containing 26.9% genistin, 11.9% daidzin, 2.0% glycetin; negligible aglycon content; genistin-to-daidzin ratio 2.3 : 1) were charged to a 100 ml ERLENMEYER flask equipped with a magnetic stirring bar. Varying amounts of solvents comprising glacial acetic acid (GAA) and various co-solvents were added and the resulting slurry was stirred at ambient temperature for 30 minutes, then filtered on a Buechner funnel through Whatman No.541 paper. The filter cakes were washed with 10 milliliters of the solvent employed, dried in vacuo at 80C., and subjected to HPLC analysis. The results are tabulated below.
	With acetic acid; In ethyl acetate; at 20℃; for 0.5h;Purification / work up;	10.0 gram aliquots of"Solgen 40" (containing 26.9% genistin, 11.9% daidzin, 2.0% glycetin; negligible aglycon content; genistin-to-daidzin ratio 2.3 : 1) were charged to a 100 ml ERLENMEYER flask equipped with a magnetic stirring bar. Varying amounts of solvents comprising glacial acetic acid (GAA) and various co-solvents were added and the resulting slurry was stirred at ambient temperature for 30 minutes, then filtered on a Buechner funnel through Whatman No.541 paper. The filter cakes were washed with 10 milliliters of the solvent employed, dried in vacuo at 80C., and subjected to HPLC analysis. The results are tabulated below.
	With acetic acid; In 2,2,4-trimethylpentane; at 20℃; for 0.5h;Purification / work up;	10.0 gram aliquots of"Solgen 40" (containing 26.9% genistin, 11.9% daidzin, 2.0% glycetin; negligible aglycon content; genistin-to-daidzin ratio 2.3 : 1) were charged to a 100 ml ERLENMEYER flask equipped with a magnetic stirring bar. Varying amounts of solvents comprising glacial acetic acid (GAA) and various co-solvents were added and the resulting slurry was stirred at ambient temperature for 30 minutes, then filtered on a Buechner funnel through Whatman No.541 paper. The filter cakes were washed with 10 milliliters of the solvent employed, dried in vacuo at 80C., and subjected to HPLC analysis. The results are tabulated below.

	With acetic acid; In cyclohexane; at 20℃; for 0.5h;Purification / work up;	10.0 gram aliquots of"Solgen 40" (containing 26.9% genistin, 11.9% daidzin, 2.0% glycetin; negligible aglycon content; genistin-to-daidzin ratio 2.3 : 1) were charged to a 100 ml ERLENMEYER flask equipped with a magnetic stirring bar. Varying amounts of solvents comprising glacial acetic acid (GAA) and various co-solvents were added and the resulting slurry was stirred at ambient temperature for 30 minutes, then filtered on a Buechner funnel through Whatman No.541 paper. The filter cakes were washed with 10 milliliters of the solvent employed, dried in vacuo at 80C., and subjected to HPLC analysis. The results are tabulated below.
	With acetic acid; In hexane; acetone; at 20℃; for 0.5h;Purification / work up;	10.0 gram aliquots of"Solgen 40" (containing 26.9% genistin, 11.9% daidzin, 2.0% glycetin; negligible aglycon content; genistin-to-daidzin ratio 2.3 : 1) were charged to a 100 ml ERLENMEYER flask equipped with a magnetic stirring bar. Varying amounts of solvents comprising glacial acetic acid (GAA) and various co-solvents were added and the resulting slurry was stirred at ambient temperature for 30 minutes, then filtered on a Buechner funnel through Whatman No.541 paper. The filter cakes were washed with 10 milliliters of the solvent employed, dried in vacuo at 80C., and subjected to HPLC analysis. The results are tabulated below.
	With acetic acid; In hexane; at 20℃; for 0.5h;Purification / work up;	10.0 gram aliquots of"Solgen 40" (containing 26.9% genistin, 11.9% daidzin, 2.0% glycetin; negligible aglycon content; genistin-to-daidzin ratio 2.3 : 1) were charged to a 100 ml ERLENMEYER flask equipped with a magnetic stirring bar. Varying amounts of solvents comprising glacial acetic acid (GAA) and various co-solvents were added and the resulting slurry was stirred at ambient temperature for 30 minutes, then filtered on a Buechner funnel through Whatman No.541 paper. The filter cakes were washed with 10 milliliters of the solvent employed, dried in vacuo at 80C., and subjected to HPLC analysis. The results are tabulated below.
	With acetic acid; In water; at 20℃; for 0.5h;Purification / work up;	10.0 gram aliquots of"Solgen 40" (containing 26.9% genistin, 11.9% daidzin, 2.0% glycetin; negligible aglycon content; genistin-to-daidzin ratio 2.3 : 1) were charged to a 100 ml ERLENMEYER flask equipped with a magnetic stirring bar. Varying amounts of solvents comprising glacial acetic acid (GAA) and various co-solvents were added and the resulting slurry was stirred at ambient temperature for 30 minutes, then filtered on a Buechner funnel through Whatman No.541 paper. The filter cakes were washed with 10 milliliters of the solvent employed, dried in vacuo at 80C., and subjected to HPLC analysis. The results are tabulated below.
	With acetic acid; In Octanoic acid; at 20℃; for 0.5h;Purification / work up;	10.0 gram aliquots of"Solgen 40" (containing 26.9% genistin, 11.9% daidzin, 2.0% glycetin; negligible aglycon content; genistin-to-daidzin ratio 2.3 : 1) were charged to a 100 ml ERLENMEYER flask equipped with a magnetic stirring bar. Varying amounts of solvents comprising glacial acetic acid (GAA) and various co-solvents were added and the resulting slurry was stirred at ambient temperature for 30 minutes, then filtered on a Buechner funnel through Whatman No.541 paper. The filter cakes were washed with 10 milliliters of the solvent employed, dried in vacuo at 80C., and subjected to HPLC analysis. The results are tabulated below.
	With acetic acid; In acetone; at 20℃; for 0.5h;Purification / work up;	10.0 gram aliquots of"Solgen 40" (containing 26.9% genistin, 11.9% daidzin, 2.0% glycetin; negligible aglycon content; genistin-to-daidzin ratio 2.3 : 1) were charged to a 100 ml ERLENMEYER flask equipped with a magnetic stirring bar. Varying amounts of solvents comprising glacial acetic acid (GAA) and various co-solvents were added and the resulting slurry was stirred at ambient temperature for 30 minutes, then filtered on a Buechner funnel through Whatman No.541 paper. The filter cakes were washed with 10 milliliters of the solvent employed, dried in vacuo at 80C., and subjected to HPLC analysis. The results are tabulated below.

Reference： [1]Patent: WO2004/43945,2004,A1 .Location in patent: Page 9-10
[2]Patent: WO2004/43945,2004,A1 .Location in patent: Page 9-10
[3]Patent: WO2004/43945,2004,A1 .Location in patent: Page 9-10
[4]Patent: WO2004/43945,2004,A1 .Location in patent: Page 9-10
[5]Patent: WO2004/43945,2004,A1 .Location in patent: Page 9-10
[6]Patent: WO2004/43945,2004,A1 .Location in patent: Page 9-10
[7]Patent: WO2004/43945,2004,A1 .Location in patent: Page 9-10
[8]Patent: WO2004/43945,2004,A1 .Location in patent: Page 9-10
[9]Patent: WO2004/43945,2004,A1 .Location in patent: Page 9-10

16
ADM Novasoy [ No CAS ]
[ 40246-10-4 ]
[ 552-66-9 ]
[ 529-59-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In methanol; water; at 66℃; for 0.25h;Heating / reflux;Purification / work up;	50.0 grams OF ADM Novasoy (22.16% genistin + genistein; 18.56% daidzin + daidzein; 5.04% glycetin + glycetein; total aglycons 1.70% ; total isoflavone content 45.39% by wt.; genistin-to daidzin ratio 1.2 : 1) was added to 250 ml of methanol and 50 ml of concentrated hydrochloric acid in an ERLENMEYER flask equipped with a magnetic stirring bar and reflux condenser. The mixture was heated on a hotplate to reflux (66 C.), maintained at reflux for 15 minutes, then cooled to 15 C. The resulting slurry was filtered at this temperature on a Buechner funnel through Whatman No.541 filter paper. Filtration was very rapid, with no blinding. The off-white filter cake solids were washed with a modest volume of 5: 1 methanol: HCL and dried in a vacuum oven at 80 C. to give 10.13 grams of off-white solids containing: 55.4% by wt. genistin (5.61 grams, or 50.7% of that present in the starting material) 15.65% by wt. daidzin (1.58 grams, or 17.1% of that present in the starting material) 0.86% by wt. glycetin (0.087 grams, or 3.4% of that present in the starting material) 72.00% total isoflavones; genistin-to-daidzin ratio = 3.54 : 1 No isoflavone aglycons were detected.

Reference： [1]Patent: WO2004/43945,2004,A1 .Location in patent: Page 8

17
daidzein; daidzin; genistein; genistin; glycitein; glycitin; mixture of [ No CAS ]
[ 529-59-9 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 2 [0038] 1.) 100 grams of a soy isoflavone concentrate with the following composition: 74.48% total isoflavones, 60.72% genistin, 13.16% daidzin, 0.60% glycitin glycosides; 0.24% genistein, 0.22% daidzein, 0.01% glycitein aglycons, was slurried with 1.5 liters of a solvent consisting of 80% by wt. acetone/20% by wt. water. The mixture was heated to 50 degrees C. and 65 grams of calcium hydroxide was added over a period of 30 minutes with vigorous agitation. The color of the liquid phase immediately became a vivid lemon yellow, the characteristic hue of isoflavone solutions at elevated pH (i.e. 10+).; 2.) The mixture was stirred while maintaining a temperature of 40 to 45 degrees C. for 90 minutes, then filtered at this temperature through Whatman No.4 paper (20 microns) on a Buechner funnel. Filtration is extremely rapid, with no blinding. The filter cake consists of a mixture of unreacted lime (white) and the calcium-isoflavone glycoside complex (predominantly the calcium complex of genistin; the calcium complexes of daidzin and glycitin are far more soluble and tend to remain in solution. The calcium isoflavone ?salts? have a yellow color that resembles ?stadium mustard.? The filtrate is very clear, non-turbid, and lemon yellow in color. Very little additional material precipitates when the filtrate is cooled to 18 degrees C.; 3.) The filter cake was added to a vigorously agitated mixture of 150 grams of concentrated HCl in 1,000 ml of water and heated to 40 degrees C. This temperature was maintained for three hours to effect the conversion of the calcium isoflavone complex to calcium chloride and free isoflavone glycosides. The yellow color disappears almost immediately upon acidification, and is replaced by a pale pink or rose color. When the reaction is complete the slurry has a pH of 2.0 to 2.5 and the suspended solids are off-white in color.; 4.) The slurry was filtered at 40 degrees C. through Whatman No.541 hardened filter paper on a Buechner funnel.; 5.) The filter cake was slurried in 1.5 liters of a solvent consisting of 80% by weight acetone/20% by weight water at 50 to 55 degrees C. 50 grams of calcium hydroxide was added over a period of 30 minutes with vigorous agitation. The color of the liquid phase immediately became a vivid lemon yellow and the calcium-isoflavone complex (once again predominantly the calcium complex of genistin) fell out of solution.; 6.) In this second iteration, once again the mixture was stirred while maintaining a temperature of 40 to 45 degrees C. for 90 minutes, then filtered at this temperature through Whatman No.4 paper (20 microns) on a Buechner funnel. Filtration is extremely rapid, with no blinding. Once again, the filter cake consists of a mixture of unreacted lime (white) and the calcium-isoflavone glycoside complex, which has a muddy yellow color that resembles ?stadium mustard.? The filtrate was a very clear, non-turbid, lemon yellow.; 7.) The filter cake was added to a vigorously agitated mixture of 150 grams of concentrated HCl in 1,000 ml of water and heated to 40 degrees C. This temperature was maintained for three hours to effect the conversion of the calcium-isoflavone complex to calcium chloride and free isoflavone glycosides. The yellow color disappeared almost immediately, replaced by a pale pink or rose color. When the reaction is complete the slurry has a pH of 2.0 to 2.5 and the suspended solids are off-white in color.; 8.) The slurry was filtered at 40 degrees C. through Whatman No.541 filter paper on a Buechner funnel. The filter cake was dissolved in 3.5 liters of a solvent consisting of 80% by weight acetone/20% by weight water. This solution was filtered hot through Whatman No.4 paper to remove acid-insoluble particles arising from the lime, presumably silicaceous compounds.; 9.) The filtrate from the preceding step was reduced in volume to 1.3 liters by stripping off acetone at ambient pressure. Crystals of extremely pure genistin begin to form once the volume is reduced below 2.5 liters, even at 56 degrees C. The mixture is allowed to cool to 25 to 30 degrees C. with very gentle agitation, then filtered at this temperature through Whatman No.4 paper (20 microns) on a Buechner funnel. Filtration is extremely rapid, with no blinding. The filter cake is washed with cold (5 degrees C. acetone and dried in vacuo to 80 degrees C. to give glistening, ivory-colored crystalline plates of 99%+ genistin glycoside; recovery=65% of the genistin contained in the starting material.

Reference： [1]Patent: US2003/216557,2003,A1 .Location in patent: Page/Page column 3; 4

18
None [ No CAS ]
[ 529-59-9 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water; for 1.5h;Heating / reflux;Purification / work up;	10.) Once the genistin content exceeds 96% and the level of residual daidzin is less than 3%, the solids can be digested in 10 times their mass of a solvent containing 80% by weight water and 20% by weight ethanol at reflux (79 degrees C.) for 90 minutes, then filtered through Whatman No.4 filter paper at a temperature exceeding 60 degrees C. The dried filter cake consists of 99.0+% genistin, <1.0% daidzin. The recovery of genistin in this step exceeds 94%.

Reference： [1]Patent: US2003/216557,2003,A1 .Location in patent: Page/Page column 3

Yield	Reaction Conditions	Operation in experiment
		Specifically preferred are compounds selected the group of: ... Flavanone, Hesperetin, Daidzein, Genistein, Genistin, Luteolin, Quercetin,
		EXAMPLE 4 Extraction whey (800 ml) obtained in the same way as the example 3 was passed through a column packed with Diaion HP-20 (20 ml). The resin was washed with water (40 ml), and then eluted with 30% ethanol and 70% ethanol successively. The 70% ethanol eluding fraction was added with 1N sodium hydroxide solution and then evaporated under reduced pressure to remove ethanol. This liquid was neutralized by 1N hydrochloric acid and kept at 4 C. for 2 hr. The resulting precipitate was recovered, dried to give a solid (20 mg) comprising genistin. The isoflavone content of the obtained solid was 97%, and the ratio of genistin against the total isoflavones was 92%.
		1. PROCEDURE FOR MEASUREMENT OF TOTAL GENISTIN AND DAIDZIN 0.25 g of soy product is weighed out and added to 20 ml of extraction solution consisting of 80 parts methyl alcohol, 10 parts water and 10 parts 3N HCl.

		Genistin m.p.250.8-252.0 C. 1 H NMR (400 MHz, DMSO-d6) delta:6.47 (1H, d, J=2 Hz, H-6), 6.72 (1H, d, J=2 Hz, H-8), 12.92 (1H, s, H-5), 6.83 (2H, d, J=8 Hz, H-3'), 7.39 (2H, d, J=8 Hz, H-21), 8.39 (1H, s, H-2), 9.61 (1H, s, 41 -OH), 12.92 (1H, s, 5-OH). 13 C NMR (100 MHz, DMSO-d6) 154.6, 123.1, 181.0, 162.1, 100.1, 163.5, 95.0, 157.7, 106.6, 121.5, 130.7, 115.6, 157.7, 100.4, 73.6, 76.9, 70.1, 77.7, 60.0.
		EXAMPLE III The genistin used in the present Example was obtained in the same manner as described in Example I above from soy molasses.

20
malonylgenistin [ No CAS ]
[ 529-59-9 ]
[ 486-66-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In methanol; ethanol;	Example 8 To each of 1 g samples of daidzin and <strong>[529-59-9]genistin</strong> obtained in Example 7 were added 45 ml of methanol and 10 ml of 12N HCl, and the glycoside was decomposed under reflux for 6 hours. After cooling, the reaction mixture was diluted with water, and the solid product was collected by filtration, washed with water, dissolved in 90 ml of a 80% ethanol solution, filtered through a filter paper to give a supernatant. The supernatant was left standing at room temperature to deposit a crystalline product. The mixture was left standing overnight, and the crystals were collected and dried to give daidzein and genistein in the yields of 410 mg and 440 mg, respectively.

Reference： [1]Patent: US5789581,1998,A

21
[ 1105697-82-2 ]
[ 529-59-9 ]

Reference： [1]European Journal of Organic Chemistry,2008,p. 5622 - 5629

22
[ 76298-37-8 ]
[ 529-59-9 ]

Reference： [1]European Journal of Organic Chemistry,2008,p. 5622 - 5629

23
[ 446-72-0 ]
Absidia coerulea AM 93 [ No CAS ]
[ 529-59-9 ]

Yield	Reaction Conditions	Operation in experiment
12.5%	In dimethyl sulfoxide; for 240h;Large scale; Enzymatic reaction;	General procedure: Portions of 1.5 mL of the 3-day inoculation culture were transferred to 300 mL Erlenmeyer flasks,each containing 100 mL of the medium. In the preparative (large scale) biotransformation, a total of60 mg of each substrate dissolved in 6 mL of DMSO and was equally distributed among four flasks with4-day fungal cultures to give a final concentration of 150 mg/L. After 10 days of incubation, the cultureswere acidified with 1 M HCl to pH around 5 and three time extracted with the same volume of ethylacetate. The other procedures and culture conditionswere the same as those of the screening experiments.The collected organic phase was dried over anhydrous MgSO4, the solvent was filtered, evaporatedin a vacuum and analyzed using TLC and HPLC. The biotransformation products were separated bycolumn chromatography on silica gel 60 (230-400 mesh,Merck, Darmstadt, Germany) using chloroform:methanol (3:1 v/v) as eluent. TLC was carried out with Merck silica gel 60, F254 (0.2 mm thick)plates using the same eluents. Products were detected by inspecting plates under UV irradiation.Rf: 0.53 (genistin); 0.64 (sissotrin, isosissotrin); 0.77 (4?-O-methyldaidzin); 0.79 (4?-O-methylgenistin);0.84 (4?-O-methylsissotrin); 0.85 (genistein); 0.87 (daidzein); 0.89 (biochanin A).

Reference： [1]Molecules,2017,vol. 22

24
[ 446-72-0 ]
Absidia glauca AM 177 [ No CAS ]
[ 529-59-9 ]

Yield	Reaction Conditions	Operation in experiment
21.9%	In dimethyl sulfoxide; for 240h;Large scale; Enzymatic reaction;	General procedure: Portions of 1.5 mL of the 3-day inoculation culture were transferred to 300 mL Erlenmeyer flasks,each containing 100 mL of the medium. In the preparative (large scale) biotransformation, a total of60 mg of each substrate dissolved in 6 mL of DMSO and was equally distributed among four flasks with4-day fungal cultures to give a final concentration of 150 mg/L. After 10 days of incubation, the cultureswere acidified with 1 M HCl to pH around 5 and three time extracted with the same volume of ethylacetate. The other procedures and culture conditionswere the same as those of the screening experiments.The collected organic phase was dried over anhydrous MgSO4, the solvent was filtered, evaporatedin a vacuum and analyzed using TLC and HPLC. The biotransformation products were separated bycolumn chromatography on silica gel 60 (230-400 mesh,Merck, Darmstadt, Germany) using chloroform:methanol (3:1 v/v) as eluent. TLC was carried out with Merck silica gel 60, F254 (0.2 mm thick)plates using the same eluents. Products were detected by inspecting plates under UV irradiation.Rf: 0.53 (genistin); 0.64 (sissotrin, isosissotrin); 0.77 (4?-O-methyldaidzin); 0.79 (4?-O-methylgenistin);0.84 (4?-O-methylsissotrin); 0.85 (genistein); 0.87 (daidzein); 0.89 (biochanin A).

Reference： [1]Molecules,2017,vol. 22

25
[ 133-89-1 ]
[ 446-72-0 ]
[ 529-59-9 ]

Yield	Reaction Conditions	Operation in experiment
	With flavonoid 7-O-glucosyltransferase from Andrographis paniculata; In methanol; at 30℃; for 12h;Enzymatic reaction;	General procedure: All assays and incubations were performed in 100 ll of 50mM Tris-HCl (pH 8.0)containing 8 lg of purified proteins, 200 lM aglycone, and 3200 lM UDP-glucose.The reactions were incubated at 30 C for 12 h and terminated by the addition of200 ll of methanol. The products of the reactions were filtered through a 0.22-lmnylon syringe filter and analyzed using a Waters Acquity UPLC-I-Class system(Waters Corp., Milford, MA) with an Acquity UPLC BEH C18 column (1.7 mm,2.1mm 50 mm). The column temperature was set to 40 C, and the flow rate was400 lL/min. Mobile phase A was a 0.1% formic acid aqueous solution, and mobilephase B was acetonitrile. Gradient programs were used to analyze the reaction mixtures(Table 1). The total conversion rate was calculated to be one percent of the sumof the peak areas of the substrate and product(s). The experiment was performed inthe ESI (-) mode as previously described [17].

Reference： [1]Journal of Asian Natural Products Research,2020,vol. 22,p. 279 - 286

26
[ 133-89-1 ]
[ 446-72-0 ]
[ 152-95-4 ]
[ 529-59-9 ]
Genistein 7-O-β-D-glucopyranoside-4'-O-β-D-glucopyranoside [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 8058 - 8064

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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 529-59-9 ] {[proInfo.proName]}

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[ 529-59-9 ] Synthesis Path-Upstream 1~7

[ 529-59-9 ] Synthesis Path-Downstream 1~26

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