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22888-70-6

Basic Information
CAS No.: 22888-70-6
Name: Silibinin
Article Data: 9
Molecular Structure:
Molecular Structure of 22888-70-6 (Silibinin)
Formula: C25H22O10
Molecular Weight: 482.444
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;
EINECS: 245-302-5
Density: 1.527 g/cm3
Melting Point: 164-174 °C
Boiling Point: 793 °C at 760 mmHg
Flash Point: 274.5 °C
Solubility: 54mg/L(24.99 oC)
Appearance: solid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39-24/25-22-36
PSA: 155.14000
LogP: 2.36270
Synthetic route
1220986-69-5

23-O-acetylsilybin A

22888-70-6

silibinin

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

A

22888-70-6

silibinin

B

22888-70-6

silybin B

Conditions
ConditionsYield
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
ConditionsYield
With pyridine; hydroxylamine hydrochloride at 70℃;93%
22888-70-6

silibinin

19-O-demethyl-2,3-dehydrosilybin

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With pyridine In tetrahydrofuran at 50℃;88%
22888-70-6

silibinin

77-78-1

dimethyl sulfate

C30H32O10

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; for 15h;81%
Raw Materials
34482-56-9
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    Density: 1.527 ± 0.06 g/cm3 (Predicted) Melting point: 164-174 ° C Boiling point: 793.0 ± 60.0 ° C (Predicted) Specific rotation: D20+11 ° (c=0.25 in acetate+alcohol) Flash point: 274.4 ° C Water solubility: 54mg/L (24.9

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    Silibinin CAS: 22888-70-6

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    Product Name Silibinin Synonyms SILYBIN;SILYBIN A;SILYBIN (A AND B);SILYMARIN;SILYMARIN I;SILYBININ;SILYBIN (MIX);SILIBININ CAS 22888-70-6 MF C25H22O10

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  • Casno:

    22888-70-6

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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 POCl3 and 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.