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Epicatechin gallate

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Identification
Molecular formula
C22H18O10
CAS number
1257-08-5
IUPAC name
(2S)-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chroman-4-one
State
State

At room temperature, epicatechin gallate is in a solid state, typically as a crystalline powder. It is not volatile and is stable under normal conditions used in laboratories and manufacturing processes.

Melting point (Celsius)
240.00
Melting point (Kelvin)
513.15
Boiling point (Celsius)
741.20
Boiling point (Kelvin)
1 014.40
General information
Molecular weight
442.37g/mol
Molar mass
442.3730g/mol
Density
1.8374g/cm3
Appearence

Epicatechin gallate appears as a tan to brown crystalline powder. It is a polyphenolic compound known for its antioxidant properties. In pure form, it is finely divided and often used in research and supplements.

Comment on solubility

Solubility of (2S)-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[[2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chroman-4-one

The solubility of this intricate compound, characterized by its multiple hydroxyl and methoxy groups, is indicative of its complex interactions with solvents. Given its structure, we can forecast several aspects of its solubility:

  • Polarity: The abundance of hydroxyl (-OH) groups suggests that the molecule is likely to be polar, potentially enhancing its solubility in polar solvents such as water.
  • Hydrogen Bonding: The presence of hydroxyl groups also means that it can engage in hydrogen bonding, which typically increases solubility in polar environments.
  • Solvent Compatibility: This compound may exhibit better solubility in alcohols or other polar protic solvents compared to nonpolar solvents, due to its polar characteristics.
  • Concentration Variables: Factors such as temperature and the presence of other solutes can dramatically affect the solubility by altering the thermal dynamics of the solution.

As a result, while it is likely that this compound is not very soluble in nonpolar solvents (like hexane), it may achieve significant solubility in water or alcohols due to its polar functional groups. It's essential to consider these factors when predicting the solubility behavior of such a biologically interesting compound.

Interesting facts

Interesting Facts about (2S)-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[[2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chroman-4-one

This complex organic compound is a fascinating member of the flavonoid family, characterized by its intricate structure and potential biological activities. Here are some intriguing details to consider:

  • Biological Significance: Flavonoids, including this compound, are known for their antioxidant properties, which can protect cells from damage caused by free radicals. This compound may play a role in preventing oxidative stress-related diseases.
  • Natural Sources: Compounds with similar structures are often found in a variety of plants, particularly in fruits, vegetables, and certain herbs, suggesting a potential dietary source of beneficial compounds for human health.
  • Pharmacological Potential: Research indicates that flavonoids can exhibit anti-inflammatory, antiviral, and anticancer activities. This compound’s unique substituents may enhance these properties, making it a subject of interest for pharmaceutical studies.
  • Structure Complexity: The multi-ring system and numerous hydroxyl groups provide a rich platform for potential interactions with biological targets. This complexity can lead to diverse activities, making it a target for synthetic chemists.
  • Synthesis Challenges: The synthesis of such complex compounds often requires innovative strategies in organic chemistry, involving multi-step reactions and sophisticated purification techniques.

Overall, (2S)-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[[2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chroman-4-one is not just another chemical formula; it represents a building block for understanding the broader implications of flavonoids in medicine and human health.

Synonyms
hesperidin
520-26-3
Cirantin
Hesperidoside
Hesper bitabs
Hesperetin 7-rhamnoglucoside
Hesperetin-rutinosid
Hesperidine
Hesperetin 7-rutinoside
Ciratin
(S)-(-)-Hesperidin
CCRIS 3940
EINECS 208-288-1
(2S)-Hesperidin
NSC 44184
UNII-E750O06Y6O
BRN 0075140
DIOSVEIN
Hesperetin-7-O-rhamnoglucoside
Hesperidin, (2S)-
DTXSID9044328
Hesperetin-7-rutinoside
CHEBI:28775
E750O06Y6O
Hesperetin 7-O-rutinoside
USAF CF-3
Hesperitin-7-rhamnoglucoside
Hesperidin, (S)-(-)-
3',5'-Dihydroxy-4'-methoxy-7-rutinosyloxyflavan-4-on
DTXCID7024328
EC 208-288-1
5-18-05-00218 (Beilstein Handbook Reference)
Hesperetin, 7-(6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside)
NSC-44184
(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
4H-1-Benzopyran-4-one, 7-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydo-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-
5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-((6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl)oxy)-4-chromanon
7-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one, (S)-
7-(6-O-Desoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyloxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanon
HESPERIDIN (MART.)
HESPERIDIN [MART.]
HESPERIDIN (USP-RS)
HESPERIDIN [USP-RS]
3',5'-DIHYDROXY-4'-METHOXY-7-RUTINOSYLOXYFLAVAN-4-ONE
hesperetin 7-(6-O-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside
NSC44184
Hesperidin 2S
2S, Hesperidin
Hesperetin 7 Rutinoside
Hesperetin 7 Rhamnoglucoside
Hesperidina
7-Rhamnoglucoside, Hesperetin
Hesperetin Glycoside
4H-1-Benzopyran-4-one, 7-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-
NDI 590
(2S)-7-((6-O-(6-DEOXY-alpha-L-MANNOPYRANOSYL)-beta-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
208-288-1
(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
(s)-7-[[6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4h-1-benzopyran-4-one
MLS001304066
(S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one
MFCD00075663
Hesperidin (JAN)
(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one
SMR000718775
HESPERIDIN [JAN]
Aurantiamarin (Methyl Hesperidin)
(2S)-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chroman-4-one
SR-01000799145
Cirmtin
NCGC00016481-01
(2S)-7-[[6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one (Hesperidin)
CAS-520-26-3
Hesperidin (Standard)
Hesperitin-7-rutinoside
Hesperidin, >=80%
HESPERIDIN [MI]
DIOSMIN [NDI]
Prestwick3_000400
HESPERIDIN [VANDF]
Glucopyranoside, hesperetin-7 6-O-(6-deoxy-alpha-L-mannopyranosyl)-, beta-D-
HESPERIDIN [WHO-DD]
SCHEMBL94586
BSPBio_000619
cid_10621
Hesperidin, analytical standard
BPBio1_000681
CHEMBL449317
NDI 590 [FDMS]
BCBcMAP01_000136
BDBM61776
HMS2096O21
HMS2233I03
HMS3713O21
MSK40133
Tox21_110448
HY-15337R
s2309
AKOS015895450
CCG-208580
CS-5631
DB04703
KS-5308
OH08129
SMP1_000149
NCGC00179501-01
1ST40133
4H-1-Benzopyran-4-one, 7-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (2S)-
HY-15337
AB00513829
H0049
Hesperidin, mixture with analogeous compounds
NS00008545
C09755
D01038
EN300-7419024
Q385937
Hesperidin, primary pharmaceutical reference standard
SR-01000799145-4
SR-01000799145-5
SR-01000799145-7
BRD-K38903228-001-02-8
BRD-K38903228-001-13-5
Hesperidin, European Pharmacopoeia (EP) Reference Standard
Hesperidin, Pharmaceutical Secondary Standard; Certified Reference Material
Flavanone, 3',5,7-trihydroxy-4'-methoxy-, 7-(6-O-alpha-L-rhamnosyl-D-glucoside)
(2S)-2-(4-methoxy-3-oxidanyl-phenyl)-7-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5R,6S)-6-methyl-3,4,5-tris(oxidanyl)oxan-2-yl]oxymethyl]-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-5-oxidanyl-2,3-dihydrochromen-4-one
(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-2-oxanyl]oxymethyl]-2-oxanyl]oxy]-3,4-dihydro-2H-1-benzopyran-4-one
(2S)-7-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
(S)-7-[[6-O-(6-Deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
3',5,7-Trihydroxy-4'-methoxyflavanone-7-O-(6-O-a-L-rhamnopyranosyl)-b-D-glucopyranoside;Hesperetin-7-rutinoside;Cirmtin
4H-1-BENZOPYRAN-4-ONE, 7-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDO-5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-, (S)-
5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-7-((6-O-.ALPHA.-L-RHAMNOPYRANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)-4-CHROMANON