Name: Silibinin
SKU: 22888-70-6

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Basic Information

Molecular Structure:
CAS No.:	22888-70-6
Name:	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:	Xi
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

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%

Raw Materials

34482-56-9

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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 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.

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Specification