[ CAS No. 60-82-2 ] {[proInfo.proName]}

Name: 60-82-2|3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one|98%
Brand: Ambeed
SKU: A170374
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2D 3D

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Quality Control of [ 60-82-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 60-82-2 ]

SDS Specification

Alternatived Products of [ 60-82-2 ]

Product Details of [ 60-82-2 ]

CAS No. :	60-82-2	MDL No. :	MFCD00002288
Formula :	C₁₅H₁₄O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VGEREEWJJVICBM-UHFFFAOYSA-N
M.W :	274.27	Pubchem ID :	4788
Synonyms :	RJC 02792;NSC 407292;Dihydronaringenin

Calculated chemistry of [ 60-82-2 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.13
Num. rotatable bonds :	4
Num. H-bond acceptors :	5.0
Num. H-bond donors :	4.0
Molar Refractivity :	74.02
TPSA :	97.99 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.41
Log Po/w (XLOGP3) :	2.63
Log Po/w (WLOGP) :	2.32
Log Po/w (MLOGP) :	1.1
Log Po/w (SILICOS-IT) :	2.17
Consensus Log Po/w :	1.93

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.38
Solubility :	0.115 mg/ml ; 0.000419 mol/l
Class :	Soluble
Log S (Ali) :	-4.34
Solubility :	0.0126 mg/ml ; 0.0000459 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.37
Solubility :	0.116 mg/ml ; 0.000425 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.88

Safety of [ 60-82-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 60-82-2 ]

* 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 [ 60-82-2 ]
Downstream synthetic route of [ 60-82-2 ]

[ 60-82-2 ] Synthesis Path-Upstream 1~28

1
[ 133-89-1 ]
[ 60-82-2 ]
[ 4192-90-9 ]
[ 60-81-1 ]

Reference： [1] Organic Letters, 2014, vol. 16, # 18, p. 4874 - 4877

2
[ 133-89-1 ]
[ 60-82-2 ]
[ 58-98-0 ]
[ 60-81-1 ]

Reference： [1] Green Chemistry, 2014, vol. 16, # 9, p. 4417 - 4425

3
[ 480-41-1 ]
[ 60-82-2 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 899 - 901
[2] Synthetic Communications, 1989, vol. 19, # 1, 2, p. 119 - 124
[3] Angewandte Chemie - International Edition, 2014, vol. 53, # 5, p. 1439 - 1442[4] Angew. Chem., 2014, vol. 126, # 05, p. 1463 - 1466,4

4
[ 60-81-1 ]
[ 60-82-2 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 3, p. 917 - 921

5
[ 25515-46-2 ]
[ 60-82-2 ]

Reference： [1] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 97, p. 283 - 288

6
[ 4397-53-9 ]
[ 60-82-2 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 416 - 418
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 2, p. 568 - 579

7
[ 88607-79-8 ]
[ 60-82-2 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 416 - 418

8
[ 108-73-6 ]
[ 501-97-3 ]
[ 60-82-2 ]

Reference： [1] Tetrahedron, 2006, vol. 62, # 5, p. 841 - 846

9
[ 18065-05-9 ]
[ 60-82-2 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 416 - 418

10
[ 128837-25-2 ]
[ 60-82-2 ]

Reference： [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 2, p. 568 - 579

11
[ 25515-46-2 ]
[ 60-82-2 ]

Reference： [1] Molecules, 2000, vol. 5, # 3, p. 589 - 590

12
[ 501-97-3 ]
[ 524-14-1 ]
[ 60-82-2 ]
[ 920318-17-8 ]

Reference： [1] Journal of Molecular Catalysis B: Enzymatic, 2010, vol. 66, # 3-4, p. 257 - 263

13
[ 18916-17-1 ]
[ 60-82-2 ]

Reference： [1] Annali di Chimica (Rome, Italy), 1959, vol. 49, p. 1929,1936
[2] Annali di Chimica (Rome, Italy), 1959, vol. 49, p. 1929,1936

14
[ 10236-47-2 ]
[ 60-82-2 ]

Reference： [1] Annali di Chimica (Rome, Italy), 1959, vol. 49, p. 1929,1936
[2] Annali di Chimica (Rome, Italy), 1959, vol. 49, p. 1929,1936

15
[ 50376-43-7 ]
[ 60-82-2 ]

Reference： [1] Annali di Chimica (Rome, Italy), 1959, vol. 49, p. 1929,1936
[2] Annali di Chimica (Rome, Italy), 1959, vol. 49, p. 1929,1936

16
[ 60-81-1 ]
[ 2280-44-6 ]
[ 60-82-2 ]

Reference： [1] European Journal of Organic Chemistry, 2008, # 4, p. 745 - 752

17
[ 4192-90-9 ]
[ 60-82-2 ]

Reference： [1] Annali di Chimica (Rome, Italy), 1959, vol. 49, p. 1929,1936

18
[ 25324-31-6 ]
[ 60-82-2 ]

Reference： [1] Annali di Chimica (Rome, Italy), 1959, vol. 49, p. 1929,1936

19
[ 22867-43-2 ]
[ 60-82-2 ]

Reference： [1] Yakugaku Zasshi, 1929, vol. 49, p. 797,800;dtsch.Ref.S.123,125[2] Chem.Abstr., 1930, p. 604

20
[ 53563-09-0 ]
[ 60-82-2 ]

Reference： [1] Chemische Berichte, 1928, vol. 61, p. 2492

21
[ 501-97-3 ]
[ 60-82-2 ]

Reference： [1] Chemische Berichte, 1917, vol. 50, p. 618[2] Chem. Zentralbl., 1916, vol. 87, # II, p. 1025

22
[ 5597-50-2 ]
[ 60-82-2 ]

Reference： [1] Chemische Berichte, 1917, vol. 50, p. 618[2] Chem. Zentralbl., 1916, vol. 87, # II, p. 1025

23
[ 23838-70-2 ]
[ 60-82-2 ]

Reference： [1] Chemische Berichte, 1917, vol. 50, p. 618[2] Chem. Zentralbl., 1916, vol. 87, # II, p. 1025

24
[ 10139-91-0 ]
[ 60-82-2 ]

Reference： [1] Chemische Berichte, 1928, vol. 61, p. 2492

25
[ 645-59-0 ]
[ 60-82-2 ]

Reference： [1] Chemische Berichte, 1928, vol. 61, p. 2492

26
[ 108-73-6 ]
[ 17362-17-3 ]
[ 60-82-2 ]

Reference： [1] Chemische Berichte, 1928, vol. 61, p. 2492

27
[ 108-73-6 ]
[ 950186-11-5 ]
[ 60-82-2 ]

Reference： [1] Chemische Berichte, 1917, vol. 50, p. 618[2] Chem. Zentralbl., 1916, vol. 87, # II, p. 1025

28
[ 58-98-0 ]
[ 60-81-1 ]
[ 133-89-1 ]
[ 60-82-2 ]

Reference： [1] Green Chemistry, 2014, vol. 16, # 9, p. 4417 - 4425

[ 60-82-2 ] Synthesis Path-Downstream 1~87

1
[ 67-56-1 ]
[ 60-82-2 ]
[ 3791-75-1 ]

Reference： [1]Monatshefte fur Chemie,1929,vol. 53/54,p. 560

2
[ 108-73-6 ]
[ 17362-17-3 ]
[ 60-82-2 ]

Reference： [1]Chemische Berichte,1928,vol. 61,p. 2492

4
[ 60-82-2 ]
benzenediazonium sulphate [ No CAS ]
3-(4-hydroxy-phenyl)-1-(2,4,6-trihydroxy-3,5-bis-phenylazo-phenyl)-propan-1-one [ No CAS ]

Reference： [1]Journal of the Chemical Society,1897,vol. 71,p. 1149

5
[ 60-82-2 ]
toluene-4-diazonium ; sulfate [ No CAS ]
3-(4-hydroxy-phenyl)-1-(2,4,6-trihydroxy-3,5-bis-<i>p</i>-tolylazo-phenyl)-propan-1-one [ No CAS ]

Reference： [1]Journal of the Chemical Society,1897,vol. 71,p. 1149

6
[ 60-82-2 ]
[ 108-73-6 ]
[ 501-97-3 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1868,vol. <1> 104,p. 390
Zeitschrift fuer Chemie,1868,p. 727

7
[ 60-82-2 ]
[ 99-96-7 ]

Reference： [1]Gazzetta Chimica Italiana,1874,vol. 4,p. 188
Justus Liebigs Annalen der Chemie,1874,vol. 172,p. 357

8
3-(4-ethoxycarbonyloxy-phenyl)-propionic acid [ No CAS ]
[ 60-82-2 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1929,vol. 49,p. 797,800;dtsch.Ref.S.123,125
Chem.Abstr.,1930,p. 604

9
[ 60-82-2 ]
[ 108-24-7 ]
[ 42385-89-7 ]

Reference： [1]Molecules,2014,vol. 19,p. 16447 - 16457
[2]Chemische Berichte,1895,vol. 28,p. 1393

10
[ 60-82-2 ]
[ 10210-17-0 ]
[ 501-97-3 ]
[ 108-46-3 ]

Reference： [1]Agricultural and Biological Chemistry,1989,vol. 53,p. 3087 - 3090

11
[ 480-41-1 ]
[ 60-82-2 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1988,vol. 27,p. 899 - 901
[2]Synthetic Communications,1989,vol. 19,p. 119 - 124
[3]Angewandte Chemie - International Edition,2014,vol. 53,p. 1439 - 1442
Angew. Chem.,2014,vol. 126,p. 1463 - 1466,4

12
[ 60-82-2 ]
[ 100-39-0 ]
3-(4-benzyloxy-phenyl)-1-(2,4-bis-benzyloxy-6-hydroxy-phenyl)propan-1-one [ No CAS ]

Reference： [1]Molecules,2014,vol. 19,p. 16447 - 16457
[2]Agricultural and Biological Chemistry,1989,vol. 53,p. 1365 - 1374

13
[ 88607-79-8 ]
[ 60-82-2 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 416 - 418

14
[ 60-82-2 ]
[ 124-63-0 ]
[ 101467-70-3 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 416 - 418

15
[ 60-82-2 ]
[ 68-12-2 ]
[ 101467-70-3 ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 841 - 846
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1988,vol. 27,p. 899 - 901

16
[ 60-82-2 ]
[ 160255-00-5 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1994,vol. 34,p. 1011 - 1021

17
[ 60-82-2 ]
3,3',5'-tribromophloretin [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1994,vol. 34,p. 1011 - 1021

18
[ 108-73-6 ]
[ 501-97-3 ]
[ 60-82-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With boron trifluoride diethyl etherate; at 85℃; for 4h;Inert atmosphere;	General procedure: A mixture of S1 (40 mmol), S2 (40 mmol), and BF3·Et2O (26 mL, 204 mmol) was stirred at 85 C for 4h under N2. The reaction mixture was poured into 10% aqueous NaOAc solution (200 mL) and allowed to stand for 4h, then the solution wa sextracted with EtOAc (3 × 200 mL). The combined EtOAc layer was washed with water (200 mL), brine (200 mL) and dried over Na2SO4. The residue obtained after evaporation of the solvent was chromatographed over silica gel column using petroleum ether-EtOAc mixtures as eluent to give Sa-h.

Reference： [1]Carbohydrate Research,2019,vol. 484
[2]Tetrahedron,2006,vol. 62,p. 841 - 846

19
[ 60-82-2 ]
C₁₅H₁₀⁽²⁾H₄O₅ [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2006,vol. 49,p. 479 - 487

20
SOCl(NO_.SUB_.3) [ No CAS ]
[ 60-82-2 ]
[ 1005139-34-3 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	Example 45 Preparation of 1-(4-hydroxy-2,6-bis-nitrooxy-phenyl)-3-(4-nitrooxy-phenyl)-propan-1-one To a solution of 1 mmol of 3-(4-hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-one (Synonym: phloretin) in 5 ml of dry THF at 25 C. is added 4 mmol of SOCl(NO.SUB.3) or SO(NO.SUB.3) 2. After 1 hr, Et 2O (diethyl ether) is added and the solution is washed with water, dried and evaporated. The fully nitrated product 1-(4-hydroxy-2,6-bis-nitrooxy-phenyl)-3-(4-nitrooxy-phenyl)-propan-1-one and the partially nitrated products (wherein any of the hydroxyl groups are independently replaced by ONO 2 groups) are purified and isolated by chromatography on silica gel.
	In tetrahydrofuran;	EXAMPLE 45 Preparation of 1-(4-hydroxy-2,6-bis-nitrooxy-phenyl)-3-(4-nitrooxy-phenyl)-propan-1-one To a solution of 1 mmol of 3-(4-hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-one (Synonym: phloretin) in 5 ml of dry THF at 25 C. is added 4 mmol of SOCl(NO.SUB.3) or SO(NO.SUB.3) 2. After 1 hr, Et 2O (diethyl ether) is added and the solution is washed with water, dried and evaporated. The fully nitrated product 1-(4-hydroxy-2,6-bis-nitrooxy-phenyl)-3-(4-nitrooxy-phenyl)-propan-1-one and the partially nitrated products (wherein any of the hydroxyl groups are independently replaced by ONO 2 groups) are purified and isolated by chromatography on silica gel.

Reference： [1]Patent: US2005/80021,2005,A1
[2]Patent: US2005/80024,2005,A1

21
[ 60-82-2 ]
aqueous Na₂CO₃ [ No CAS ]
[ 157405-84-0 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1994,vol. 34,p. 1011 - 1021

22
[ 60-82-2 ]
aqueous Na₂CO₃ [ No CAS ]
[125I]-3-iodo-phloretin [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1994,vol. 34,p. 1011 - 1021

23
[ 60-82-2 ]
aqueous Na₂CO₃ [ No CAS ]
1-(3,5-Dibromo-2,4,6-trihydroxy-phenyl)-3-(4-hydroxy-3-iodo-phenyl)-propan-1-one [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1994,vol. 34,p. 1011 - 1021

24
[ 60-82-2 ]
[ 107585-77-3 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1988,vol. 27,p. 899 - 901

25
[ 4397-53-9 ]
[ 60-82-2 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 416 - 418
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 568 - 579

26
[ 18065-05-9 ]
[ 60-82-2 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 416 - 418

27
[ 22867-43-2 ]
[ 60-82-2 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1929,vol. 49,p. 797,800;dtsch.Ref.S.123,125
Chem.Abstr.,1930,p. 604

28
[ 53563-09-0 ]
[ 60-82-2 ]

Reference： [1]Chemische Berichte,1928,vol. 61,p. 2492

29
[ 501-97-3 ]
[ 60-82-2 ]

Reference： [1]Chemische Berichte,1917,vol. 50,p. 618
Chemisches Zentralblatt,1916,vol. 87,p. 1025

30
[ 5597-50-2 ]
[ 60-82-2 ]

Reference： [1]Chemische Berichte,1917,vol. 50,p. 618
Chemisches Zentralblatt,1916,vol. 87,p. 1025

31
[ 23838-70-2 ]
[ 60-82-2 ]

Reference： [1]Chemische Berichte,1917,vol. 50,p. 618
Chemisches Zentralblatt,1916,vol. 87,p. 1025

32
[ 10139-91-0 ]
[ 60-82-2 ]

Reference： [1]Chemische Berichte,1928,vol. 61,p. 2492

33
3-(4-acetoxy-phenyl)-propionic acid amide [ No CAS ]
[ 60-82-2 ]

Reference： [1]Chemische Berichte,1917,vol. 50,p. 618
Chemisches Zentralblatt,1916,vol. 87,p. 1025

34
[ 645-59-0 ]
[ 60-82-2 ]

Reference： [1]Chemische Berichte,1928,vol. 61,p. 2492

35
[ 10236-47-2 ]
[ 60-82-2 ]

Reference： [1]Annali di Chimica,1959,vol. 49,p. 1929,1936
[2]Annali di Chimica,1959,vol. 49,p. 1929,1936

36
[ 50376-43-7 ]
[ 60-82-2 ]

Reference： [1]Annali di Chimica,1959,vol. 49,p. 1929,1936
[2]Annali di Chimica,1959,vol. 49,p. 1929,1936

37
[ 60-82-2 ]
[ 200878-68-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuryl dichloride; In methanol; dichloromethane; at 20℃; for 1h;	To a stirred solution of phloretin (40 mg, 0.146 mmol) in absolute methanol (10 ml), at room temperature, was added 292 muL of a 1M solution of sulfuryl chloride in anhydrous dichloromethane (0.292 mmol), and the yellow solution was observed to become brighter. After 1 hour, the methanol was evaporated and the resultant brownish solid (152 mg) was purified by column chromatography (4:1 chloroform:ethyl acetate), to yield 15 mg of brown-purple sheaths. 1H NMR (CD3OD): delta 7.06 (d, 2H), 6.69 (d, 2H), 5.49 (s, 1H), 3.34 (t, 2H), 2.88 (t, 2H).

Reference： [1]Patent: US6888033,2005,B1 .Location in patent: Page/Page column 15

38
1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]-3-(4-methoxymethoxyphenyl)-1-propanone [ No CAS ]
[ 60-82-2 ]

Yield	Reaction Conditions	Operation in experiment
64.4%	With hydrogenchloride; ethanol; In methanol;	Then, 5.94 g of 1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]-3-(4-methoxymethoxyphenyl)-1-propanone was stirred with 87 ml of methanol and 52 ml of a hydrochloric acid/ethanol reagent at 60 C. for 35 minutes. Then, the reaction mixture was poured into ice water and the precipitated crystal was recovered by filtration and dried. The crystal was subjected to the column chromatography [330 g of 270-400 mesh Kieselgel 60; 0.5 kg/cm2; eluding solvent=hexane/ethyl acetate (2/1)]. Fractions of 50 ml were collected and the 11th to 42nd fractions were combined to obtain 2.58 g (yield=64.4%) of 1-(2,4,6-trihydroxyphenyl)-3-(4-hydroxyphenyl)-1-propanone. Infrared absorption spectrum numaxKBr cm-1: 3264, 1636, 1606, 1574, 1530, 1512, 1476, 1246, 1210, 1162, 1076, 828, 526. Proton nuclear magnetic resonance spectrum (delta ppm in acetone-d6): 2.88 (2H, t, J=8.3 Hz), 3.34 (2H, t, J=8.3 Hz), 5.93 (2H, s), 6.74 (2H, d, J=8.3 Hz), 7.09 (2H, d, J=8.3 Hz). Mass spectrum: M/Z (%) 275 (6), 274 (M+, 35), 255 (11), 153 (100), 120 (67), 107 (59), 59 (12), 42 (21).

Reference： [1]Patent: US5106871,1992,A

39
[ 60-81-1 ]
[ 2280-44-6 ]
[ 60-82-2 ]

Reference： [1]European Journal of Organic Chemistry,2008,p. 745 - 752

40
[ 60-82-2 ]
[ 572-09-8 ]
[ 1133352-99-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 917 - 921

41
[ 60-81-1 ]
[ 60-82-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 917 - 921

42
[ 60-82-2 ]
[ 2616-64-0 ]
[ 123685-24-5 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2007,vol. 55,p. 10605 - 10614

43
[ 501-97-3 ]
[ 524-14-1 ]
[ 60-82-2 ]
[ 920318-17-8 ]

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2010,vol. 66,p. 257 - 263

44
[ 60-82-2 ]
[ 1245697-26-0 ]
phloretin-2'-O-glucuronide [ No CAS ]
C₂₁H₂₂O₁₁ [ No CAS ]

Reference： [1]Pharmaceutical Research,2012,vol. 29,p. 1544 - 1561

45
[ 60-82-2 ]
C₁₅H₁₀O₁₇S₄^(4-)*4Na⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Procedure for microwave-assisted sulfonation: To a stirred solution of the polyphenol or polyalcohol in MeCN (1 - 5 mL) at RT, Et3N (10 eqv per -OH group) and Me3N:SO3 complex (6 eqv per -OH) were added. The reaction vessel was sealed and micro-waved (CEM Discover synthesizer, Cary, NC) for 30 min at 90 0C. Several reaction tubes were pooled for isolation of the product. The MeCN layer was decanted and pooled, while the residue was washed with MeCN (5 mL) and centrifuged. The combined MeCN layers were concentrated in vacuo. Water (5 mL) was added to the residue and stirred for 10 min. The water layer was concentrated to approximately 2 mL, loaded onto a Sephadex G10 column (160 cm) and chromatographed using water as eluent. Fractions were combined based on capillary electrophoresis profiles, concentrated and re-loaded onto a SP Sephadex C25 column for sodium exchange. Appropriate fractions were pooled, concentrated in vacuo, and lyophilized to obtain a white powder.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4467 - 4470

46
[ 358-72-5 ]
[ 60-82-2 ]
5-isopreny-2,4,6-trihydroxy-α-(p-hydroxybenzyl)acetophenone [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1817 - 1828

47
[ 25515-46-2 ]
[ 60-82-2 ]

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2013,vol. 97,p. 283 - 288

48
[ 133-89-1 ]
[ 60-82-2 ]
1-[3-(β-D-glucopyranosyl)-2,4,6-trihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 5873 - 5877
[2]Advanced Synthesis and Catalysis,2013,vol. 355,p. 2757 - 2763
[3]Angewandte Chemie - International Edition,2015,vol. 54,p. 12678 - 12682
Angew. Chem.,2015,vol. 127,p. 12869 - 12873,5

49
[ 60-82-2 ]
[ 107-30-2 ]
[ 1620631-21-1 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 2986 - 2992

50
[ 58-98-0 ]
[ 60-81-1 ]
[ 133-89-1 ]
[ 60-82-2 ]

Reference： [1]Green Chemistry,2014,vol. 16,p. 4417 - 4425

51
[ 133-89-1 ]
[ 60-82-2 ]
[ 58-98-0 ]
[ 60-81-1 ]

Reference： [1]Green Chemistry,2014,vol. 16,p. 4417 - 4425

52
[ 60-82-2 ]
[ 17341-93-4 ]
carbonic acid 3,5-bis-(2,2,2-trichloroethoxycarbonyloxy)-2-{3-[4-(2,2,2-trichloroethoxycarbonyloxy)phenyl]propionyl}phenyl ester 2,2,2-trichloroethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With potassium carbonate; In acetone; at 0℃; for 3h;Reflux;	2,2,2-Trichloroethoxycarbonyl chloride (10 mL) was slowly added to a solution of phloretin (1, 2.74 g, 10 mmol) in acetone (30 mL) in an ice bath and then heated at reflux for 3 h. After phloretin was observed to have disappeared by TLC, the residue obtained by evaporation of the solvent was purified by column chromatography using a binary solvent mixture of petroleum ether-ethyl acetate (5:1) to obtain 7 as a white solid (6.4 g, 66%). MS m/z: 993.48 [M+Na]+; 1H-NMR (CDCl3, 300 MHz) delta: 7.27(t, 4H, Ph), 7.12 (d, 2H, J = 5.5 Hz, Ph), 4.86 (s, 8H, CH2), 3.18 (t, 2H, CH2), 2.99 (t, 2H, CH2). 13C-NMR (DMSO-d6, 75 MHz): 197.6, 152.0, 151.4, 151.0, 150.9, 148.8, 147.6, 138.7, 129.5, 124.9,120.8, 120.7, 115.1, 94.5, 94.1, 76.9, 76.6, 76.5, 75.3, 44.9, 28.3.

Reference： [1]Molecules,2014,vol. 19,p. 16447 - 16457

53
[ 60-82-2 ]
[ 407-25-0 ]
5,7-dihydroxy-3-(4-hydroxybenzyl)-2-trifluoromethylchromen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine; In acetone;Reflux;	Trifluoroacetic anhydride (10 mL) was added to a mixture of phloretin (1, 2.74 g, 10 mmol) and triethylamine (10 mL) in acetone (50 mL) and heated at reflux for 5 h. After a new compound was observed by TLC, the reaction mixture was diluted with water (50 mL) and extracted with dichloromethane (3 × 50 mL). The organic phases were collected and dried over anhydrous magnesium sulfate. The solution was filtered under vacuum and purified by column chromatography using a binary solvent mixture of petroleum ether-ethyl acetate (5:1-3:1) to afford 10 (2.74 g, 78%). MS m/z: 352.98[M+H]+; 1H-NMR (DMSO-d6, 300 MHz) delta: 12.20 (s, 1H, OH), 11.22 (s, 1H, OH), 9.24 (s, 1H, OH),7.00 (d, 2H, J = 2.0 Hz, Ph), 6.68 (d, 2H, J = 2.5 Hz, Ph), 6.42 (s, 1H, Ph), 6.29 (s, 1H, Ph), 3.82 (t, 2H,CH2). 13C-NMR (DMSO-d6, 75 MHz): 180.4, 165.5, 161.3, 156.3, 155.8, 147.6, 147.3, 128.8, 127.7,121.8, 115.1, 103.7, 99.7, 93.9, 26.6.

Reference： [1]Molecules,2014,vol. 19,p. 16447 - 16457

54
[ 60-82-2 ]
[ 77-78-1 ]
[ 3791-75-1 ]

Reference： [1]Molecules,2014,vol. 19,p. 16447 - 16457

55
[ 60-82-2 ]
[ 77-78-1 ]
[ 42546-55-4 ]
[ 111316-17-7 ]

Reference： [1]Molecules,2014,vol. 19,p. 16447 - 16457

56
[ 60-82-2 ]
[ 108-24-7 ]
acetic acid 4-[3-acetoxy-3-(2,4,6-triacetoxy-phenyl)allyl]phenyl ester [ No CAS ]
[ 93322-34-0 ]
acetic acid 4-(7-acetoxy-5-hydroxy-2-methyl-4-oxo-4H-chromen-3-ylmethyl)phenyl ester [ No CAS ]

Reference： [1]Molecules,2014,vol. 19,p. 16447 - 16457

57
[ 60-82-2 ]
phloretin 4-monosulfate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 534 - 541

58
[ 60-82-2 ]
phloretin 4,4’-disulfate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 534 - 541

59
4-hydroxyphenylpropionyl-CoA [ No CAS ]
malonyl-CoA [ No CAS ]
[ 60-82-2 ]

Yield	Reaction Conditions	Operation in experiment
	With recombinant type III polyketide synthase from Aquilaria sinensis; In aq. phosphate buffer; at 37℃; for 12h;pH 7.0;Enzymatic reaction;	General procedure: The enzyme reaction system contained 29 nmol of malonyl-CoA or methylmalonyl-CoA, 26 nmol of starter-CoA (4-coumaroyl-CoA, 4-hydroxyphenylpropionyl-CoA, or benzoyl-CoA) and 40 mug of the purified AsCHS in 500 muL of 100 mM KPB buffer (pH 7.0) was incub ated at 37 C for 12 h and terminated by adding 50 muL of 20 % HCl. Then the reaction solution was extracted three times with 800 muL EtOAc. The combination of organic layer was dried by nitrogen and redissolved in 50 muL of MeOH and analyzed by HPLC on a Agilent Eclipse XDB C18 Column (250×4.6 mm I.D. 5 mum) with a flow rate of 1.0 mL/min and monitoring wave length at 280 nm. For the analysis of enzyme reaction products from 4-coumaroyl-CoA or 4-hydroxyphenylpropionyl-CoA and malonyl-CoA, the gradient elution was performed with H2O and acetonitrile: 0-10 min, 30% acetonitrile; 10-20 min, 30-60% acetonitrile, 20-25min, 60-70% acetonitrile, 25-30min, 70-80% acetonitrile, 30-35 min, 80-100 % acetonitrile, 35-40 min, 100 % acetonitrile. For the analysis of enzyme reaction products from benzoyl-CoA and malonyl-CoA, and the products from 4-hydroxy phenylpropionyl-CoA and methylmalonyl-CoA, the gradient elution was performed with aqueous acetonitrile containing 0.1 % formic acid: 0-5 min, 5-30 % acetonitrile; 5-15 min, 30-60 %a cetonitrile, 15-25 min, 60-70 % acetonitrile, 25-30 min, 70-80 % acetonitrile, 30-35 min, 80-100 % acetonitrile, 35-40 min, 100 % acetonitrile. The enzyme product of phloretin (11) and 2,4,6-trihydroxybenzophenone (13) were identified by comparision of their UV spectra and retention time on HPLC chromatogram to the authentic compounds. The products of enzyme reaction of 4-coumaroyl-CoA and malonyl-CoA were measured with HPLC-ESI-IT-TOF mass spectrometer, and identified by comparing their UV, MS data with those of reported in literature.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 1279 - 1283

60
[ 133-89-1 ]
[ 60-82-2 ]
phloretin 4-O-β-D-glucoside [ No CAS ]
[ 4192-90-9 ]
[ 60-81-1 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 4874 - 4877

61
[ 60-82-2 ]
[ 1186-30-7 ]
5-isopreny-2,4,6-trihydroxy-α-(p-hydroxybenzyl)acetophenone [ No CAS ]

Reference： [1]Journal of Natural Products,2015,vol. 78,p. 2229 - 2235

62
[ 60-82-2 ]
[ 1186-30-7 ]
5-isopreny-2,4,6-trihydroxy-α-(p-hydroxybenzyl)acetophenone [ No CAS ]
C₂₀H₂₂O₅ [ No CAS ]
C₂₅H₃₀O₅ [ No CAS ]

Reference： [1]Journal of Natural Products,2015,vol. 78,p. 2229 - 2235

63
(E)-3-(4-benzyloxyphenyl)-1-[2,4-bis(ethoxymethoxy)-6-hydroxyphenyl]prop-2-en-1-one [ No CAS ]
[ 60-82-2 ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 568 - 579

64
[ 128837-25-2 ]
[ 60-82-2 ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 568 - 579

65
(E)-3-(4-benzyloxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one [ No CAS ]
[ 60-82-2 ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 568 - 579

66
[ 60-82-2 ]
phloretin sulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56.7%		548 L sulfuric acid solution was added to 274 g of phloretin, and the reaction was carried out at 0 C for 2 hours. After 2 hours, the reaction mixture was dropped into 1000 L of a saturated sodium chloride solution and reacted for 4 hours to form a red precipitate. The precipitate was filtered through a filter paper and washed once with 1M sodium carbonate (Na2CO3) (Sigma, USA). Three small fractions (E1-E3) were obtained by eluting with a CH2Cl2 / MeOH gradient solvent on a silica gel column. The E2 fraction was recrystallized to prepare a floretine sulfonate (271 g) (Yield 56.7%).

Reference： [1]Patent: KR2016/35641,2016,A .Location in patent: Paragraph 0052-0053

67
[ 60-82-2 ]
[ 298-14-6 ]
2,4,6-trihydroxy-3-[3-(4-hydroxyphenyl)propanoyl]benzoic acid [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 959 - 965

68
[ 770728-81-9 ]
[ 60-82-2 ]
C₆₃H₁₁₂O₄₂*C₁₅H₁₄O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 50℃; for 2h;Sealed tube;	A simple co-evaporation method was used to prepare the inclusioncomplex, using a molar ratio of 1:1 of HP-beta-CD to phloretin. Briefly,phloretin in ethanol (6.86 mg/mL) was added to HP-beta-CD ethanol solution(38.5 mg/mL) in a sealed glass vial. Then the solution was mixedwith a magnetic stirrer and stirred moderately for 30 min at room temperature.After that heated up the solution to 50 Cwith a stirring speedof 500 r/min for 2 h. Finally, to produce a solid inclusion complex, weused a rotary evaporator to remove the ethanol under reduced pressureat 40 C. For comparative study, we also prepared a physical mixture ofphloretin and HP-beta-CD of the samemolar ratio by mixing them(in solidstate) thoroughly for 5 min in a ceramic mortar until a homogeneousmixture was obtained.

Reference： [1]Journal of Molecular Liquids,2017,vol. 236,p. 68 - 75

69
[ 60-82-2 ]
[ 2616-64-0 ]
[ 123685-24-5 ]
phloretin-4′-O-β-D-glucuronide [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2019,vol. 67,p. 6275 - 6284

70
[ 60-82-2 ]
[ 78-98-8 ]
2-hydroxy-1-(2,4,6-trihydroxy-3-(1-hydroxy-2-oxopropyl)-5-(3-(4-hydroxyphenyl)propanoyl)phenyl)propan-1-one [ No CAS ]

Reference： [1]Food and Chemical Toxicology,2019,vol. 129,p. 291 - 300

71
[ 60-82-2 ]
[ 78-98-8 ]
2-hydroxy-1-(2,4,6-trihydroxy-3-(1-hydroxy-2-oxopropyl)-5-(3-(4-hydroxyphenyl)propanoyl)phenyl)propan-1-one [ No CAS ]
C₂₁H₂₂O₉ [ No CAS ]
C₂₁H₂₂O₉ [ No CAS ]
C₁₈H₁₈O₇ [ No CAS ]
C₁₈H₁₈O₇ [ No CAS ]

Reference： [1]Food and Chemical Toxicology,2019,vol. 129,p. 291 - 300

72
[ 67-56-1 ]
[ 60-81-1 ]
[ 60-82-2 ]
[ 1620631-21-1 ]
methylenebisphloridzin [ No CAS ]
deglucosylmethylenebisphloridzin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dielectric barrier discharge plasma;	A dielectric barrier discharge (DBD) (250 W, 15 kHz, ambient air) plasma instrument (240 × 200 × 100 mm) was used for the plasma treatment. After dissolving 1.0 g of phloridzin in 7.0 L of methanol (MeOH), and then 20, 40 and 60 minutes treatment in a DBD plasma instrument, and The production of new material was monitored via reversed phase high performance liquid chromatography (HPLC). As a mobile phase solvent of HPLC analysis, 1% formic acid (A) and acetonitrile (acetonitrile (B)) were used. Material analysis showed 95% (v / v) A solvent and 5% (v / v) B solvent composition for 0-5 minutes, and For 5-10 minutes, 85% (v / v) of solvent A and 15% (v / v) of solvent B, For 10-15 minutes, 70% (v / v) A solvent and 30% (v / v) B solvent composition, For 15-20 minutes, with 50% (v / v) A solvent and 50% (v / v) B solvent composition, For 20-30 minutes the material was analyzed with 100% (v / v) B solvent composition, and The flow rate of the mobile phase was maintained at 1.0 ml per minute, and Compounds were detected at a wavelength of 280 nm. HPLC analysis column was used YMC-Pack ODS A-302 column (4.6mm i.d. × 150mm; YMC Co., Ltd., Tokyo, Japan). If the plasma has been treated for 60 minutes, After confirming that a variety of new substances are produced, and then After the plasma has been treated for 60 minutes, the resulting floridine reactant is dried, and It was dissolved in methanol (MeOH), and then Compound A (100.8 mg, tR 16.6 min) via stepwise gradient on a YMC GEL ODS AQ 120-50S column (2.5 cm i.d. × 40 cm), Compound B (76.1 mg, tR 19.4 min), Compound C (2.3 mg, tR 22.6 min) and Compound D (38.5 mg, tR 16.9 min) were separated. Compound D was a previously reported phloretin (JNat Prod (1980), 43, 739-751).

Reference： [1]Patent: KR2019/48493,2019,A .Location in patent: Paragraph 0039-0042

73
[ 50-99-7 ]
[ 60-82-2 ]
2',4,4',6'-tetrahydroxy-3',5'-di-C-β-D-glucopyranosyldihydrochalcone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With scandium tris(trifluoromethanesulfonate); In ethanol; water; for 18h;Reflux;	General procedure: A mixture of dihydrochalcone S[11a] (10 mmol), D-glucose (50 mmol), and Sc(OTf)3 (4 mmol) in EtOH (20 mL)/H2O (10 mL) was refluxed for 18 h. Then water (200 mL) was added to the reaction mixture, and the suspension was passed through a column of MCI GELCHP20P (75-150 mum, Mitsubishi Chemical Corp., 3.5×25 cm) loaded with water, and the gel was then washed with water (300 mL), to remove nonabsorbed glucose and Sc(OTf)3. The nonabsorbed components, which include the unreactive glucose and Sc(OTf)3, was evaporated in vacuo to give a colorless solid. The absorbed products were eluted from the gel column with 50% aqueous MeOH (300 mL), and the eluate was evaporated to dryness. The residue was then separated by silica-gel column chromatography (Me2CO:EtOAc:H2O: AcOH) to give 1. 4.2.1. 2,4,4,6-tetrahydroxy-3,5-di-C-beta-D-glucopyranosyldihydrochalcone(1a) White solid (2.87 g, 48%); Rf=0.25 (Me2CO:EtOAc:H2O: AcOH,20:20:3:1); [alpha]D 20 = +102.4 (c 0.2, MeOH); 1H NMR (500 MHz,CD3OD) deltaH: 7.02 (2H, d, J=8.5 Hz, H-2, 6), 6.67 (2H, d, J=8.5 Hz, H-3, 5), 4.94 (2H, d, J=9.8 Hz, H-1, 1?), 3.83 (4H, m, H-6, 6?), 3.60(2H, t, J=9.0 Hz, H-2, 2), 3.54 (2H, t, J=9.0 Hz, H-4, 4?), 3.49(2H, t, J=9.0 Hz, H-3, 3), 3.43 (2H, m, H-5, 5), 3.35 (2H, m, H-alpha), 2.85 (2H, m, H-beta) ppm; 13C NMR (125 MHz, CD3OD) deltaC: 207.2 (C-beta), 163.2 (C-2, 6), 162.2 (C-4), 156.5 (C-4), 133.9 (C-1), 130.4 (C-2,6), 116.1 (C-2, 6), 106.2 (C-1), 104.4 (C-3, 5), 82.7 (C-5, 5?), 79.1(C-3, 3), 76.7 (C-1, 1), 74.1 (C-2, 2), 71.1 (C-4, 4), 61.8 (C-6, 6), 47.8 (C-alpha), 31.0 (C-beta) ppm; HR-ESI-MS m/z: [M+H]+ calcd.for C27H35O15 599.1976, found 599.1981.

Reference： [1]Carbohydrate Research,2019,vol. 484

74
[ 60-82-2 ]
[ 952585-00-1 ]
1-[3-(β-D-glucopyranosyl)-2,4,6-trihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one [ No CAS ]
[ 60-81-1 ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 11513 - 11520
Angew. Chem.,2019,vol. 131,p. 11637 - 11644,8

75
[ 60-82-2 ]
[ 95239-02-4 ]
methyl 4,6-dihydroxy-5-(3-(4-hydroxyphenyl)propanoyl)-2-methylbenzofuran-3-carboxylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 10814 - 10824

76
[ 60-82-2 ]
[ 95239-03-5 ]
ethyl 4,6-dihydroxy-5-(3-(4-hydroxyphenyl)propanoyl)-2-methylbenzofuran-3-carboxylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 10814 - 10824

77
[ 60-82-2 ]
C₁₃H₂₂N₂O₄ [ No CAS ]
ethyl 4,6-dihydroxy-5-(3-(4-hydroxyphenyl)propanoyl)-2-propylbenzofuran-3-carboxylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 10814 - 10824

78
[ 60-82-2 ]
1-(2,4-dihydroxy-3-(hydroxymethyl)-5-methylphenyl)ethan-1-one [ No CAS ]
1-(3-(3-acetyl-2,6-dihydroxy-5-methylbenzyl)-2,4,6-trihydroxyphenyl)-3-(4-hydroxyphenyl)propan-1-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2020

79
[ 133-89-1 ]
[ 60-82-2 ]
2',4,4',6'-tetrahydroxy-3',5'-di-C-β-D-glucopyranosyldihydrochalcone [ No CAS ]