(2R,3R)-3,5,7-Trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-4H-chromen-4-one

Basic Information

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CAS Number

33889-69-9

Molecular Formula

C25H22O10

Molecular Weight

482.44 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ketones

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Laboratory Chemicals Research Chemicals Biochemical Reagents

Basic Physical Properties

Physical State

Powder

Melting Point

>220oC (dec.)

Boiling Point

782.0±60.0 °C at 760 mmHg

Density

1.6±0.1 g/cm3

Flash Point

270.5±26.4 °C

Solubility

Acetone (Slightly), Methanol (Slightly)

Refractive Index

1.716

Vapor Pressure

0.0±2.8 mmHg at 25°C

SMILES

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COC1=C(C=CC(=C1)C2C(C3=C(O2)C(=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)O)CO)O

InChI

InChI=1S/C25H22O10/c1-33-18-6-10(2-3-15(18)28)23-14(9-26)13-4-11(5-17(30)25(13)35-23)24-22(32)21(31)20-16(29)7-12(27)8-19(20)34-24/h2-8,14,22-24,26-30,32H,9H2,1H3/t14-,22+,23+,24-/m1/s1

InChIKey

BMLIIPOXVWESJG-LMBCONBSSA-N

LogP

2.4045000000000005

Topological Polar Surface Area

166.14000000000001 Å²

Hydrogen Bond Donor/Acceptor

6 / 10

Complexity

765

Safety Information

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GHS Hazard Pictograms

H302

Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral

Storage Conditions

2-8℃

Synonyms & References

English

33889-69-9
Silicristin [INN]
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-4H-chromen-4-one
SILICRISTIN [MART.]
CHEBI:9143
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydrochromen-4-one
Silicristinum [INN-Latin]
UNII-LK279ER14X
Silychristin, analytical standard
SCHEMBL971442
DTXSID50187512
AS-79115
HY-N0647
CS-0009673
AC-34760
2-(2,3-Dihydro-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-benzofuranyl)-3,5,7-trihydroxy-4-chromanone
MFCD00883715
Silicristina
Silicristine [INN-French]
LK279ER14X
NS00029563
(2R,3R)-3,5,7-trihydroxy-2-((2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydrobenzofuran-5-yl)chroman-4-one
EINECS 251-720-9
C08717
BRD-K16389764-001-01-8
Silicristina [INN-Spanish]
Silicristine
Silicristinum
Q27108289
Silychristin
Silymarin II

MDL Number

MFCD00883715

FAQ

What are the physical and chemical properties of (2R,3R)-3,5,7-Trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-4H-chromen-4-one (CAS: 33889-69-9)?

The compound (2R,3R)-3,5,7-Trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-4H-chromen-4-one is a crystalline solid with a molecular weight of approximately 539.4 g/mol. It has a low solubility in water (less than 1 mg/mL) but is soluble in polar organic solvents such as methanol and acetonitrile. This compound is relatively stable under normal conditions but exhibits reactivity towards strong acids and bases. It is a chiral compound with potential enantiomeric selectivity in certain reactions.

How is (2R,3R)-3,5,7-Trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-4H-chromen-4-one (CAS: 33889-69-9) typically synthesized?

This compound is typically synthesized via multistep organic synthesis involving the protected coupling of an appropriate phenolic starting material with a suitable benzofuran derivative, followed by various protecting group manipulations, reduction steps, and deprotection. The synthesis often requires the use of specific catalysts such as Lewis acids or transition metal complexes, and the yield is typically moderate to good, depending on the efficiency of the protecting group chemistry. The reaction conditions and selectivity are highly sensitive to the choice of reagents and solvents.

What industries use (2R,3R)-3,5,7-Trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-4H-chromen-4-one (CAS: 33889-69-9)?

This compound is primarily used in the pharmaceutical industry for its potential as a drug candidate due to its structural complexity and bioactivity. It may also find applications in the polymer industry as a precursor or additive for specific polymer formulations. Additionally, it could be utilized in the development of sensors and semiconductors, although its specific applications in these fields are less well-documented.

What precautions should be taken when handling (2R,3R)-3,5,7-Trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-4H-chromen-4-one (CAS: 33889-69-9)?

When handling (2R,3R)-3,5,7-Trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-4H-chromen-4-one, appropriate personal protective equipment (PPE) such as gloves and safety goggles should be worn. The substance should be handled in a well-ventilated area or a fume hood. In case of a spill, it should be immediately contained and cleaned up using appropriate absorbent materials. The Safety Data Sheet (SDS) should be consulted for detailed emergency procedures and storage requirements. The substance is not particularly hazardous under normal laboratory conditions, but care should be taken to avoid contact with skin and eyes.