Silibinin supplier | CasNO.22888-70-6

Name
Silibinin
EINECS 245-302-5
CAS No. 22888-70-6
Article Data9
CAS DataBase
Density 1.527 g/cm³
Solubility 54mg/L(24.99 oC)
Melting Point 164-174 °C
Formula C₂₅H₂₂O₁₀
Boiling Point 793 °C at 760 mmHg
Molecular Weight 482.444
Flash Point 274.5 °C
Transport Information
Appearance solid
Safety 26-37/39-24/25-22-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 4H-1-Benzopyran-4-one,2-[(2R,3R)-2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-,(2R,3R)-;4-Chromanone,3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxan-6-yl]-(8CI);Silybin (7CI);7C3MT;Silibinin;Silliver;Silybin A;Silybum substance E6;Silymarin I;Silymarin MZ 80;Milk thistle P.E(Silibinin);Milk Thistle Extract;
PSA 155.14000
LogP 2.36270

Synthetic route

: 1220986-69-5
23-O-acetylsilybin A

: 22888-70-6
silibinin

Conditions

Conditions	Yield
With Candida antarctica lipase B; butan-1-ol In tert-butyl methyl ether at 45℃; for 60h; optical yield given as %de; diastereoselective reaction;	67%

: 871249-25-1
23-O-acetylsilibinin

A: 22888-70-6
silibinin

B: 1220986-69-5
23-O-acetylsilybin A

C: 22888-70-6
silybin B

Conditions

Conditions	Yield
With Candida antarctica lipase B; butan-1-ol In tert-butyl methyl ether at 45℃; for 48h; optical yield given as %de; diastereoselective reaction;	A n/a B 25% C n/a

...Expand

: 34482-56-9
silibinin-C-2',3-bis(dihydrogensuccinate)

A: 22888-70-6
silibinin

B: 86124-93-8
23-O-succinyl silibinin

C: 86124-92-7
Succinic acid mono-{(2R,3R)-5,7-dihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxy-phenyl)-2-hydroxymethyl-2,3-dihydro-benzo[1,4]dioxin-6-yl]-4-oxo-chroman-3-yl} ester

Conditions

Conditions	Yield
With water at 37℃; Product distribution; Rate constant; various pH;
In water at 37℃; Product distribution; Rate constant; rat's liver esterases; various pH;

...Expand

: 458-35-5, 32811-40-8, 69056-21-9
coniferal alcohol

: 480-18-2
taxifolin

A: 22888-70-6
silibinin

: (±)-dehydroconiferyl aldehyde

C: 20649-42-7, 458-36-6
coniferaldehyde

D: isosilybin A

E: 22888-70-6
silybin B

F: isosilybin B

Conditions

Conditions	Yield
With silver(l) oxide In ethyl acetate at 20 - 75℃; for 96h; Inert atmosphere;	A 21.4 mg B 13.6 mg C 2.3 mg D 20.7 mg E 21.1 mg F 19.5 mg

...Expand

: 802918-57-6
silybin

A: 22888-70-6
silibinin

B: 22888-70-6
silybin B

Conditions

Conditions	Yield
With trifluoroacetic acid In methanol; water; acetonitrile

: 22888-70-6
silibinin

: (2R,3S)-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-4-(hydroxyimino)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Conditions

Conditions	Yield
With pyridine; hydroxylamine hydrochloride at 70℃;	93%

: 22888-70-6
silibinin

: 19-O-demethyl-2,3-dehydrosilybin

Conditions

Conditions	Yield
With pyridine; aluminum (III) chloride; iodine at 110℃; for 2h; Time;	92%
Multi-step reaction with 2 steps 1: iodine; pyridine; magnesium chloride / 1 h / 100 °C 2: pyridine; aluminium(III) iodide / 2 h / 110 °C View Scheme

: 22888-70-6
silibinin

: 25166-14-7
3-hydroxyhydnocarpin-D

Conditions

Conditions	Yield
With pyridine; iodine; magnesium chloride at 100℃; for 1h; Temperature; Reagent/catalyst; Time;	91%
With sodium hydrogencarbonate In methanol for 16h; Reagent/catalyst; Solvent; Time; Reflux;	49%
With sodium hydrogencarbonate In methanol Reflux;	40%

: 22888-70-6
silibinin

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 9’’-O-(4,4’-dimethoxytriphenylmethyl)silybin A

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran at 50℃;	88%

: 22888-70-6
silibinin

: 77-78-1
dimethyl sulfate

: C30H32O10

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 15h;	81%

: 22888-70-6
silibinin

A: 25166-14-7
3-hydroxyhydnocarpin-D

B: 19-O-demethyl-2,3-dehydrosilybin

Conditions

Conditions	Yield
With pyridine; aluminum (III) chloride; iodine at 110℃; for 1h;	A 75% B 19%

: 22888-70-6
silibinin

: 100-39-0
benzyl bromide

: (2R,3R)-7-(benzyloxy)-3,5-dihydroxy-2-((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one

Conditions

Conditions	Yield
With potassium carbonate In acetone for 4h; Inert atmosphere; Reflux; regioselective reaction;	71.1%

: 89583-07-3
N-(2-bromoethyl)morpholine

: 22888-70-6
silibinin

: 7-(2-morpholinyl)ethoxy-2,3-dehydrosilybin

Conditions

Conditions	Yield
With potassium carbonate In acetone at 60℃;	67%

: 22888-70-6
silibinin

: 623-65-4
palmitic anhydride

: 3-O-palmitoyl-silybin

Conditions

Conditions	Yield
Stage #1: palmitic anhydride With dmap; cerium(III) chloride heptahydrate; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h; Stage #2: silibinin In tetrahydrofuran at 20℃; for 24h;	66%

: 22888-70-6
silibinin

: 56-40-6
glycine

: silibinin glycine sodium salt

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water at 55℃; for 0.5h;	63%

: 22888-70-6
silibinin

: silybin A 20-O-sulfate

Conditions

Conditions	Yield
With p-nitrophenyl sulfate; aryl sulfotransferase from Desulfitobacterium hafniense In acetone at 30℃; for 4h; pH=8.9;	56%

: 70-54-2, 923-27-3, 6899-06-5, 60103-30-2, 60132-27-6, 56-87-1
2,6-diaminocaproic acid

: 22888-70-6
silibinin

: silibinin lysine sodium salt

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 0.333333h;	55%

: 22888-70-6
silibinin

cell cultures of Papaver somniferum var. setigerum: cell cultures of Papaver somniferum var. setigerum

: silybin A 7-O-β-D-glucopyranoside

Conditions

Conditions	Yield
In methanol for 120h; Ambient temperature;	45%

: 22888-70-6
silibinin

: 39825-33-7
isopropyl L-alanine

: 770-12-7
O-phenyl phosphorodichloridate

: C37H38NO14P

Conditions

Conditions	Yield
Stage #1: isopropyl L-alanine; O-phenyl phosphorodichloridate With triethylamine In dichloromethane at -78 - -65℃; for 0.5h; Stage #2: silibinin In dichloromethane at 20 - 30℃; for 12h;	42.6%

...Expand

: 22888-70-6
silibinin

: 302-72-7
rac-Ala-OH

: silibinin alanine sodium salt

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water at 60℃; for 0.333333h;	42%

: 22888-70-6
silibinin

: 6,8-dibromosilybin A

Conditions

Conditions	Yield
With 2,3-dibromo-3-phenylpropanoic acid; potassium carbonate In N,N-dimethyl-formamide at 60℃; for 16h; Inert atmosphere;	42%

: 22888-70-6
silibinin

: 74-88-4
methyl iodide

: 889471-74-3
7-O-methylsilybin A

Conditions

Conditions	Yield
With potassium carbonate In acetone for 3h; Inert atmosphere; Reflux;	41%

: 22888-70-6
silibinin

: (10R,11R)-hydnocarpin D

Conditions

Conditions	Yield
Stage #1: silibinin With di-isopropyl azodicarboxylate; triphenylphosphine; 4-nitro-benzoic acid In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: With sodium hydroxide In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere;	33%

: 108-05-4
vinyl acetate

: 22888-70-6
silibinin

A: 1220986-69-5
23-O-acetylsilybin A

B: (2R,3S,10R,11R)-23-O-acetylsilybin

Conditions

Conditions	Yield
Stage #1: silibinin With boron trifluoride diethyl etherate In diethyl ether; N,N-dimethyl-formamide at 50℃; for 1h; Stage #2: vinyl acetate In acetone at 45℃; for 48h;	A 30% B 10%

...Expand

: 22888-70-6
silibinin

: 6-bromosilybin A

Conditions

Conditions	Yield
With 2,3-dibromo-3-phenylpropanoic acid; caesium carbonate In N,N-dimethyl-formamide at 40℃; for 16h; Inert atmosphere; regioselective reaction;	30%

: 22888-70-6
silibinin

: 1638098-48-2
1-((3-(4-hydroxy-3-methoxyphenyl)-6-(3,5,7-trihydroxy-4-oxochroman-2-yl)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl) 12-vinyl dodecanedioate

: 1638098-51-7
1-(((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-6-((2R,3R)-3,5,7-trihydroxy-4-oxochroman-2-yl)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl) 12-(((2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-6-((2R,3R)-3,5,7-trihydroxy-4-oxochroman-2-yl)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl) dodecanedioate

Conditions

Conditions	Yield
With Novozym 435 In acetonitrile at 45℃; for 72h; Molecular sieve; Enzymatic reaction;	26%

: dodecandioic acid divinyl ester

: 22888-70-6
silibinin

: 1190835-16-5
bis(((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-6-((2R,3R)-3,5,7-trihydroxy-4-oxochroman-2-yl)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl) dodecanedioate

Conditions

Conditions	Yield
With Novozym 435 In acetonitrile at 45℃; for 72h; Molecular sieve; Enzymatic reaction;	24%

: 1135-24-6
3-(4-hydroxy-3-methoxyphenyl)acrylic acid

: 22888-70-6
silibinin

: 7-O-feruloylsilybin A

Conditions

Conditions	Yield
Stage #1: 3-(4-hydroxy-3-methoxyphenyl)acrylic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: silibinin With triethylamine In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide at 20℃; regioselective reaction;	23%

: 22888-70-6
silibinin

: 106-93-4
ethylene dibromide

: 7-(2-bromo)ethoxy-2,3-dehydrosilybin

Conditions

Conditions	Yield
With potassium carbonate In acetone at 45℃; for 48h;	21.5%

: dextrose

: 22888-70-6
silibinin

A: silybin A 3-O-β-D-glucopyranoside

B: silybin A 7-O-β-D-glucopyranoside

Conditions

Conditions	Yield
With Trichoderma koningii KCTC 6042 In ethanol at 25℃; for 24h;	A 18% B 7.5%

...Expand

: 22888-70-6
silibinin

: 141-78-6
ethyl acetate

A: 1220986-69-5
23-O-acetylsilybin A

B: (2S,3S,10R,11S)-23-O-acetylsilybin

C: (2R,3S,10R,11R)-23-O-acetylsilybin

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether at 80℃; for 48h;	A n/a B n/a C 12%

...Expand

: 22888-70-6
silibinin

: 1186-30-7, 45126-99-6, 69382-61-2
3,3-dimethylallyl diphosphate triammonium salt

: C30H30O10

Conditions

Conditions	Yield
With fungal prenyltransferase AnaPT; calcium chloride In dimethyl sulfoxide; glycerol at 37℃; for 16h; pH=7.5; Kinetics; Time; Enzymatic reaction;	11.3%

: 623-24-5
1,4-bis(bromomethyl)benzene

: 22888-70-6
silibinin

: 1638099-55-4
(2R,2'R,3R,3'R)-7,7'-((1,4-phenylenebis(methylene))bis(oxy))bis(3,5-dihydroxy-2-((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one)

Conditions

Conditions	Yield
With potassium carbonate In acetone for 4h; Reflux; Inert atmosphere;	7%

Silibinin Specification

The IUPAC name of Silibinin is (2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one. With the CAS registry number 22888-70-6, it is also named as Flavobin Spofa. The product's categories are Flavanones; Natural Plant Extract; Angiogenesis Inhibitors Cancer Research; Anti-proliferative Agents Nutrition Research; Angiogenesis; Biochemicals Found in Plants; Bioflavonoids; Cancer Research; Chemopreventive Agents, and the other registry numbers are 11054-49-2; 11076-05-4; 11076-06-5; 142796-20-1; 22888-69-3; 27359-03-1; 28577-40-4; 29832-10-8; 37574-50-8; 50976-99-3; 87725-90-4. Besides, it is solid, which should be stored at -20 °C. It is stable and incompatible with strong oxidizing agents, strong bases. In addition, its molecular formula is C₂₅H₂₂O₁₀ and molecular weight is 482.44.

The other characteristics of this product can be summarized as: (1)EINECS: 245-302-5; (2)ACD/LogP: 2.59; (3)# of Rule of 5 Violations: 2; (4)ACD/LogD (pH 5.5): 2.57; (5)ACD/LogD (pH 7.4): 2.08; (6)ACD/BCF (pH 5.5): 52.89; (7)ACD/BCF (pH 7.4): 17.16; (8)ACD/KOC (pH 5.5): 591.68; (9)ACD/KOC (pH 7.4): 192; (10)#H bond acceptors: 10; (11)#H bond donors: 5; (12)#Freely Rotating Bonds: 9; (13)Index of Refraction: 1.684; (14)Molar Refractivity: 119.96 cm³; (15)Molar Volume: 315.9 cm³; (16)Surface Tension: 73 dyne/cm; (17)Density: 1.527 g/cm³; (18)Flash Point: 274.5 °C; (19)Melting Point: 164-174 °C; (20)Enthalpy of Vaporization: 120.96 kJ/mol; (21)Boiling Point: 793 °C at 760 mmHg; (22)Vapour Pressure: 1.63E-26 mmHg at 25 °C.

Uses of Silibinin: this chemical can be used as hepatoprotective (antihepatotoxic) to protect liver cells against toxins. It is used in treatment of severe intoxications with hepatotoxic substances. Additionally, it has been shown to inhibit P-glycoprotein-mediated cellular efflux. Furthermore, it can be used to produce Silybin 11-O-phosphorylester.

This reaction needs POCl₃and various solvents at temperature of 10-15 °C for 24 hours. The yield is 63.4 %.

When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection to avoid contact with skin and eyes. Moreover, please do not breathe dust.

People can use the following data to convert to the molecule structure.
(1)SMILES: O=C4c5c(O)cc(O)cc5O[C@H](c2ccc1O[C@@H]([C@H](Oc1c2)c3ccc(O)c(OC)c3)CO)[C@H]4O
(2)InChI: InChI=1/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23+,24-,25-/m1/s1
(3)InChIKey: SEBFKMXJBCUCAI-HKTJVKLFBV
(4)Std. InChI: InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23+,24-,25-/m1/s1
(5)Std. InChIKey: SEBFKMXJBCUCAI-HKTJVKLFSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	1056mg/kg (1056mg/kg)		Yaoxue Tongbao. Bulletin of Pharmacology. Vol. 18, Pg. 404, 1983.
rabbit	LDLo	unreported	300mg/kg (300mg/kg)		Yaoxue Tongbao. Bulletin of Pharmacology. Vol. 18, Pg. 404, 1983.

Product Name

Silibinin

Synthetic route

Silibinin Specification

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