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Naringin

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Identification
Molecular formula
C27H32O14
CAS number
10236-47-2
IUPAC name
1-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-2,6-dihydroxy-phenyl]-3-(3-hydroxy-4-methoxy-phenyl)propan-1-one
State
State

At room temperature, Naringin is in a solid state, typically as a crystalline powder with moderate solubility in water.

Melting point (Celsius)
166.00
Melting point (Kelvin)
439.00
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
580.54g/mol
Molar mass
580.5400g/mol
Density
1.6500g/cm3
Appearence

White to light brown crystalline powder. It appears usually as a slightly fibrous and crystalline solid which is moderately soluble in water, forming a yellow color.

Comment on solubility

Solubility of the Compound

This complex compound, 1-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-2,6-dihydroxy-phenyl]-3-(3-hydroxy-4-methoxy-phenyl)propan-1-one, showcases unique solubility characteristics due to its intricate structure. The solubility of a compound can be influenced by various factors, including:

  • Polarity: The presence of multiple hydroxyl (-OH) groups significantly affects solubility, leading to an increased affinity for polar solvents like water.
  • Hydrogen bonding: The ability to form hydrogen bonds enhances solubility in polar solvents, which appears critical for this compound.
  • Molecular weight: Higher molecular weight can sometimes hinder solubility, but in this case, the balancing presence of hydrophilic and hydrophobic sections plays a crucial role.

As a result, this compound is likely to exhibit:

  • Good solubility in aqueous solutions, particularly at certain pH levels where the functional groups can be ionized.
  • Limited solubility in organic solvents that lack polarity, reflecting the significance of its molecular structure.
  • Potential solubility variations depending on temperature and the presence of other solubilizing agents.

In summary, the solubility of this compound is complex, underscoring its rich structural features and potential for interaction with various solvents. As aptly noted, "Solubility is not just a measure of the amount of solute that can dissolve, but a reflection of the intricate dance between molecules." This compound’s solubility traits are indeed a manifestation of this delicate balance.

Interesting facts

Interesting Facts About 1-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-2,6-dihydroxy-phenyl]-3-(3-hydroxy-4-methoxy-phenyl)propan-1-one

This compound is an intricate organic molecule characterized by a complex structure featuring multiple hydroxyl groups and tetrahydropyran rings, reflecting its potential significance in various applications, including the fields of pharmacology and natural product chemistry. Here are some engaging facts about this fascinating compound:

  • Natural Origins: Many compounds similar to this belong to a class of natural products known for their biological activity, particularly in medicinal chemistry. They are often derived from plants and are integral to traditional medicine.
  • Therapeutic Potential: Compounds with similar structural features have shown promise in therapeutic applications, including antioxidant, anti-inflammatory, and antimicrobial activities. Their ability to interact with biological systems makes them valuable in drug design.
  • Complex Stereochemistry: The presence of multiple chiral centers within this compound poses interesting challenges and opportunities for chemists regarding synthesis and stereochemical specificity. These features can lead to different biological activities based on their configuration.
  • Versatile Functional Groups: The diverse range of functional groups, such as hydroxyl and methoxy groups, enhances the compound's reactivity and solubility, contributing to its applicability in various chemical reactions and biological interactions.
  • Research Interest: As a subject of interest in organic synthesis and drug discovery, ongoing research aims to fully explore the biological activities associated with this compound and its derivatives, leading to a deeper understanding of their mechanism of action.

With an intricate design, this compound not only exemplifies the sophistication of organic chemistry but also highlights the profound relationship between structure and function in biological systems. Understanding these relationships not only enriches our chemical knowledge but also opens pathways for innovative health solutions.

Synonyms
neohesperidin dihydrochalcone
20702-77-6
Nhdc
Neohesperidin dc
Neohesperidin dhc
Citrosa
Neohesperidine dihydrochalcone
neohesperidine DC
NCI-C60764
neohesperidin dihydrochalone
1-Propanone, 1-[4-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)-
DTXSID3025706
CHEBI:83535
3X476D83QV
1-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
DTXCID305706
FEMA NO. 3811
Glucopyranoside, 3,5-dihydroxy-4-(3-hydroxy-4-methoxyhydrocinnamoyl)phenyl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-, beta-D-
1-Propanone, 1-(4-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)-
1-(4-((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)oxy-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
1-(4-((2S,4R,5S)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2S,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)oxy-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
243-978-6
GLUCOPYRANOSIDE, 3,5-DIHYDROXY-4-(3-HYDROXY-4-METHOXYHYDROCINNAMOYL)PHENYL 2-O-ALPHA-L-RHAMNOPYRANOSYL-
RefChem:832306
Neosperidin dihydrochalcone
Neohesperidin-dihydrochalcone
MFCD00017711
1-(4-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
1-(4-((2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
C28H36O15
1-(4-((2-O-[6-Deoxy-alpha-L-mannopyranosyl]-beta-D-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-[3-hydroxy-4-methoxyphenyl]-1-propanone
1-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-2,6-dihydroxy-phenyl]-3-(3-hydroxy-4-methoxy-phenyl)propan-1-one
CCRIS 4848
EINECS 243-978-6
UNII-3X476D83QV
Neohesperidin Dihydrochalcone (Nhdc)
Neosperidin-dihydrochalcone
NeohesperidinDihydrochalcone
1-(4-((2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)-
1-Propanone, 1-(4-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-me
3,5-Dihydroxy-4-(3-hydroxy-4-methoxyhydrocinnamoyl)phenyl) 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
SCHEMBL909958
orb1305047
CHEMBL1159645
SCHEMBL29352176
HY-N0154R
ITVGXXMINPYUHD-CUVHLRMHSA-
HMS3884H13
HMS6019G04
HY-N0154
MSK40285
Tox21_200303
s2331
AKOS015895239
CCG-270237
CS-6419
ON07510
Neohesperidin dihydrochalcone (Standard)
NCGC00091109-01
NCGC00091109-02
NCGC00091109-04
NCGC00257857-01
AC-34860
AS-15190
Glucopyranoside, 3,5-dihydroxy-4-(3-hydroxy-4-methoxyhydrocinnamoyl)phenyl 2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-, .beta.-D-
Glucopyranoside, 3,5-dihydroxy-4-(3-hydroxy-4-methoxyhydrocinnamoyl)phenyl-2-O-(6-deoxy-alpha-L-mannopyranosyl)-, beta-D-
NEOHESPERIDIN DIHYDROCHALCONE [MI]
SY074064
Neohesperidin dihydrochalcone, >=96%, FG
NEOHESPERIDIN DIHYDROCHALONE [FHFI]
CAS-20702-77-6
NEOHESPERIDINE DIHYDROCHALCONE [FCC]
N0675
NS00000402
NEOHESPERIDIN DIHYDROCHALCONE [USP-RS]
Neohesperidin dihydrochalcone, >=95% (HPLC)
NEOHESPERIDINE DIHYDROCHALCONE [USP-RS]
Neohesperidin dihydrochalcone, analytical standard
702N776
Q424595
SR-01000883756
NEOHESPERIDIN-DIHYDROCHALCONE [EP MONOGRAPH]
SR-01000883756-1
BRD-K61032563-001-02-9
HESPERETIN DIHYDROCHALCONE-4'-.BETA.-NEOHESPERIDOSIDE
Neohesperidin dihydrochalcone, European Pharmacopoeia (EP) Reference Standard
1-(4-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-DIHYDROCHALCONE GLUCOPYRANOSYL)OXY)-2,6-DIHYDROXYPHENYL)-3-(3-HYDROXY-4-METHOXYPHENYL)PROPAN-1-ONE
1-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5
1-[4-[[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]tetrahydro-2H-pyran-2-yl]oxy]-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)-1-propanone
1-[4-[[2-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)-1-propanone
1-PROPANONE, 1-(4-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,6-DIHYDROXYPHENYL)-3-(3-HYDROXY-4-METHOXYPHENYL)-
1-Propanone, 1-[4-[[2-O-(6-deoxy-|A-L-mannopyranosyl)-|A-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)-
3,5-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)propanoyl]phenyl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
GLUCOPYRANOSIDE, 3,5-DIHYDROXY-4-(3-HYDROXY-4-METHOXYHYDROCINNAMOYL)PHENYL 2-O-.ALPHA.-L-RHAMNOPYRANOSYL-
InChI=1/C28H36O15/c1-11-21(34)23(36)25(38)27(40-11)43-26-24(37)22(35)19(10-29)42-28(26)41-13-8-16(32)20(17(33)9-13)14(30)5-3-12-4-6-18(39-2)15(31)7-12/h4,6-9,11,19,21-29,31-38H,3,5,10H2,1-2H3/t11-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1