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Dihydromorin

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Identification
Molecular formula
C25H24O9
CAS number
18757-43-6
IUPAC name
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxy-phenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chroman-4-one
State
State

Dihydromorin is typically found in a solid state at room temperature. Its crystalline structure makes it relatively stable and easy to handle in its solid form during chemical manipulations or applications.

Melting point (Celsius)
273.00
Melting point (Kelvin)
546.15
Boiling point (Celsius)
492.00
Boiling point (Kelvin)
765.15
General information
Molecular weight
456.41g/mol
Molar mass
456.4140g/mol
Density
1.5570g/cm3
Appearence

Dihydromorin appears as a crystalline solid. It is often characterized by its pale yellow color, which is typical for many flavonoid compounds. Its crystalline nature contributes to its defined geometric structure, enabling easy identification and handling in laboratory settings.

Comment on solubility

Solubility of (2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxy-phenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chroman-4-one

The solubility of this complex compound can be influenced by various factors, particularly its structural characteristics. This compound, having multiple hydroxyl groups, suggests a potential for increased solubility in polar solvents. Several aspects can be considered:

  • Hydroxyl Groups: The presence of three hydroxyl (-OH) groups often facilitates hydrogen bonding, enhancing solubility in water.
  • Aromatic Moieties: The inclusion of aromatic components can contribute to solubility in organic solvents, though they may reduce overall water solubility.
  • Structural Complexity: The intricate structure may affect how well the compound interacts with solvents, possibly leading to variations in solubility based on solution conditions.

In essence, one might predict that this compound could exhibit:

  • Good solubility in alcohols and possibly other polar organic solvents.
  • Limited solubility in non-polar solvents due to its hydrophilic character.

To better understand its solubility profile, empirical testing is recommended under varying conditions, such as temperature and pH, to ascertain the most suitable solvents for dissolution.

Interesting facts

Interesting Facts about (2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxy-phenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chroman-4-one

This complex compound is a member of the flavonoid family and is notable for its various biochemical properties. Here are some captivating points to consider:

  • Biodiversity and Natural Sources: This compound is often derived from natural sources, particularly plants, where it plays a role in protecting the plant from UV radiation and pathogens.
  • Health Benefits: It is celebrated for its antioxidant properties, which help combat oxidative stress in the human body. This is crucial in the prevention of chronic diseases, including cardiovascular issues and certain types of cancer.
  • Applications in Medicine: Research has shown that flavonoids like this compound may contribute to anti-inflammatory and antifungal effects. They are being extensively studied for their potential in medicinal chemistry.
  • Structure-Function Relationship: The complex structure of this compound can lead to various interaction patterns at the molecular level, impacting how it binds to biological targets.
  • Cultural Significance: Flavonoids have been used in traditional medicine for centuries, underscoring a rich history of natural remedies that modern science continues to explore.

In summary, the intricate structure of (2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxy-phenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chroman-4-one not only highlights the complexity of organic chemistry but also opens doors to extensive possibilities in health-related research and applications. As scientists delve deeper into the potential of such compounds, their role in both ecology and pharmacology continues to capture interest.

Synonyms
silibinin
Silymarin I
Flavobin
Silibinine
Silliver
Silybine
Silymarine I
Silibinina
Silibininum
Legalon
CHEBI:9144
(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
(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-dihydro-4H-chromen-4-one
Silibinin a-silibinin b mixt.
(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-dihydro-4H-chromen-4-one
(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
RefChem:183059
4RKY41TBTF
245-302-5
(2R,3R)-3,5,7-trihydroxy-2-(3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl)-2,3-dihydrochromen-4-one
Silybin
22888-70-6
Silybin A
Silibinin A
Silibinin [INN]
Silymarine
(2R,3R)-3,5,7-trihydroxy-2-((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one
( inverted exclamation markA)-SILYBIN
Flavobin Spofa
NSC-651520
DTXSID8026018
33X338MNE4
Silibinin (INN)
MFCD03225424
NSC651520
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)-
NCGC00091057-01
MFCD00872186
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxy-phenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chroman-4-one
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one
1265089-69-7
DTXCID106018
silybinin
Silibinine [INN-French]
Silibininum [INN-Latin]
Silibinina [INN-Spanish]
7C3MT
2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-6-(3,5,7-trihydroxy-4-oxobenzopyran-2-yl)benzodioxin
CAS-22888-70-6
EINECS 245-302-5
NSC 651520
Silybin;Silibinin A;Silymarin I
UNII-33X338MNE4
CCRIS 9378
Silymarin A
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)-
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)-
()-Silybin
Legalon (TN)
Silibinin (Silybin)
Silybin A (Standard)
Spectrum2_001694
Spectrum3_001132
Spectrum4_001978
Spectrum5_001893
SILYBIN A [MI]
BSPBio_002623
KBioGR_002481
MLS001304057
SCHEMBL324884
SPECTRUM1505256
SPBio_001648
CHEMBL431701
MEGxp0_001301
orb1307850
orb2299464
SCHEMBL29392068
SCHEMBL29399173
GTPL12449
KBio3_002123
HMS1922P05
HMS2232P03
HMS6018N08
2-[2R,3R-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2R,3R-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one
MSK40325
Tox21_111070
Tox21_200755
BDBM50084982
CCG-38779
HY-13748R
s2357
AKOS004119918
Tox21_111070_1
DB09298
DS-9661
SDCCGMLS-0066916.P001
SMP2_000323
NCGC00091057-02
NCGC00091057-03
NCGC00091057-05
NCGC00258309-01
Silybin A (constituent of milk thistle)
3,5,7-Trihydroxy-2-(3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxan-6-yl)-4-chromanone
4H-1-Benzopyran-4-one, 2,3-dihydro-2-(2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl)-3,5,7-trihydroxy-, (2R-(2-alpha,3-beta,6(2R*,3R*)))-
4H-1-Benzopyran-4-one, 2-(2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl)-2,3-dihydro-3,5,7-trihydroxy-, (2R-(2alpha,3beta,6(2R*,3R*)))-
BP-30210
DA-57872
HY-13748
SMR000718776
SY103655
SBI-0207018.P001
HY-139637
CS-0226432
Silybin ASilibinin A; Silybin A; Silymarin I
88S706
D08515
E82516
AB00876265_06
F551327
F870214
Q425702
SR-01000799140
SR-01000799140-2
BRD-K80353138-001-02-2
BRD-K80353138-001-07-1
BRD-K80353138-001-12-1
BRD-K80353138-001-13-9
SILYBIN A (CONSTITUENT OF MILK THISTLE) [DSC]
(2R,3R)-3,5,7-trihydroxy-2-(3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one
(2R,3R)-3,5,7-Trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxy-phenyl)-2-hydroxymethyl-2,3-dihydro-benzo[1,4]dioxin-6-yl]-chroman-4-one
(2R,3R)-3,5,7-Trihydroxy-2-[3-(4-hydroxy-3-methoxy-phenyl)-2-hydroxymethyl-2,3-dihydro-benzo[1,4]dioxin-6-yl]-chroman-4-one
3,5,7-Trihydroxy-2-(3-(4-hydroxy-3-methoxyphenyl)- 2-(hydroxymethyl)-1,4-benzodioxan-6-yl)-4-chromanone
3,5,7-Trihydroxy-2-[3-(4-hydroxy-3-methoxy-phenyl)-2-hydroxymethyl-2,3-dihydro-benzo[1,4]dioxin-6-yl]-chroman-4-one
3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-(2R,3R)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl]-(2R,3R)-3,4-dihydro-2H-4-chromenone
rel-(2R,3R)-3,5,7-Trihydroxy-2-((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one