5-[(2S)-5,7-Dihydroxy-4-oxo-3,4-dihydro-2H-chromen-2-yl]-2,3-dihydroxyphenyl beta-D-glucopyranoside

Basic Information

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CAS Number

78708-33-5

Molecular Formula

C21H22O12

Molecular Weight

466.4 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

Boiling Point

868.6°C at 760 mmHg

Density

1.735

Flash Point

305.2°C

Solubility

N/A

Refractive Index

1.734

SMILES

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C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC(=C(C(=C3)OC4C(C(C(C(O4)CO)O)O)O)O)O

InChI

InChI=1S/C21H22O12/c22-6-15-18(28)19(29)20(30)21(33-15)32-14-2-7(1-11(26)17(14)27)12-5-10(25)16-9(24)3-8(23)4-13(16)31-12/h1-4,12,15,18-24,26-30H,5-6H2/t12-,15+,18+,19-,20+,21+/m0/s1

InChIKey

SNFFBROYEDWRGB-NHXQFOETSA-N

LogP

-0.6057999999999998

Topological Polar Surface Area

206.59999999999997 Å²

Hydrogen Bond Donor/Acceptor

8 / 12

Complexity

692

Safety Information

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Storage Conditions

2-8℃

Synonyms & References

English

E87192
MS-28591
FR4TR9587N
AC-34116
CHEBI:81163
5,7,4',5'-tetrahydroxyflavanone-3'-O-glucoside
4H-1-BENZOPYRAN-4-ONE, 2-(3-(.BETA.-D-GLUCOPYRANOSYLOXY)-4,5-DIHYDROXYPHENYL)-2,3-DIHYDRO-5,7-DIHYDROXY-, (S)-
2'-O-beta-Glucopyranosyl-5,7,4',5'-tetrahydroxyflavanone
CS-0016963
Q27155118
4H-1-BENZOPYRAN-4-ONE, 2-(3-(.BETA.-D-GLUCOPYRANOSYLOXY)-4,5-DIHYDROXYPHENYL)-2,3-DIHYDRO-5,7-DIHYDROXY-, (2S)-
C17531
(S)-2-(3,4-Dihydroxy-5-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-5,7-dihydroxychroman-4-one
UNII-FR4TR9587N
5-[(2S)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-2,3-dihydroxyphenyl beta-D-glucopyranoside
Q-100956
HY-N1470
4H-1-Benzopyran-4-one, 2-(3-(beta-D-glucopyranosyloxy)-4,5-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-, (S)-
78708-33-5
Plantagoside
AKOS040760042
(2S)-2-[3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
DTXSID20229256
s3254
4H-1-Benzopyran-4-one,2-[3-(b-D-glucopyranosyloxy)-4,5-dihydroxyphenyl]-2,3-dihydro-5,7-dihydroxy-,(2S)-
plantagoside
(S)-2-[3-(beta-D-Glucopyranosyloxy)-4,5-dihydroxyphenyl]-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one

MDL Number

MFCD00889209

FAQ

What are the physical and chemical properties of 5-[(2S)-5,7-Dihydroxy-4-oxo-3,4-dihydro-2H-chromen-2-yl]-2,3-dihydroxyphenyl beta-D-glucopyranoside (CAS: 78708-33-5)?

This compound is a glucopyranoside derivative with a chromene structure. It crystallizes as a white solid with a molecular weight of approximately 606.5 g/mol. It is soluble in ethanol and methanol but less soluble in water. Chemically, it exhibits reactivity typical of phenol and sugar derivatives, making it susceptible to hydrolysis and oxidation.

How is 5-[(2S)-5,7-Dihydroxy-4-oxo-3,4-dihydro-2H-chromen-2-yl]-2,3-dihydroxyphenyl beta-D-glucopyranoside (CAS: 78708-33-5) typically synthesized?

This compound can be synthesized via a multi-step process involving condensation of 2,3-dihydroxyphenol with 5,7-dihydroxy-4-oxo-3,4-dihydro-2H-chromene, followed by glycosylation with beta-D-glucose. The reaction typically uses HATU as a coupling agent and DIPEA as a base, with high yields and good selectivity.

What industries use 5-[(2S)-5,7-Dihydroxy-4-oxo-3,4-dihydro-2H-chromen-2-yl]-2,3-dihydroxyphenyl beta-D-glucopyranoside (CAS: 78708-33-5)?

This compound is used in pharmaceutical applications, where it may serve as a precursor for drug development. It also has potential in the polymer industry as a functional monomer and in sensor technology due to its chromene group, which can be used for detection of specific analytes.

What precautions should be taken when handling 5-[(2S)-5,7-Dihydroxy-4-oxo-3,4-dihydro-2H-chromen-2-yl]-2,3-dihydroxyphenyl beta-D-glucopyranoside (CAS: 78708-33-5)?

When handling this compound, use personal protective equipment such as gloves, goggles, and a lab coat. Work in a fume hood to minimize inhalation risks. Spills should be contained and cleaned up using absorbent materials. Refer to the Safety Data Sheet (SDS) for detailed handling and disposal instructions.