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Asiaticoside

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Identification
Molecular formula
C48H78O19
CAS number
16830-15-2
IUPAC name
(2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-6-carboxy-4,5-dihydroxy-tetrahydropyran-3-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
State
State
At room temperature, Asiaticoside is a solid. It is often found in the form of a powder and is stable under normal conditions.
Melting point (Celsius)
242.00
Melting point (Kelvin)
515.15
Boiling point (Celsius)
289.00
Boiling point (Kelvin)
562.15
General information
Molecular weight
959.11g/mol
Molar mass
959.1120g/mol
Density
1.4421g/cm3
Appearence

Asiaticoside typically appears as a white to off-white crystalline powder. It is known for its vitreous luster and is often amorphous in the powdered form.

Comment on solubility

Solubility of (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-2-[[[3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-6-carboxy-4,5-dihydroxy-tetrahydropyran-3-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid

The solubility of this compound is influenced by its complex structure, which includes multiple functional groups. Here are some key points regarding its solubility:

  • Hydrophilic Functionalities: The presence of multiple hydroxyl groups (-OH) and carboxylic acid groups (-COOH) hints at potential hydrophilicity, suggesting that the compound may be reasonably soluble in polar solvents such as water.
  • Intramolecular Interactions: The intricate arrangement of stereocenters, coupled with possible intramolecular hydrogen bonding, could enhance solubility in specific solvents while potentially limiting it in others.
  • Solvent System: It may exhibit different solubility behavior depending on the solvent system, being more soluble in alcohols or acidic solutions due to the protonation of carboxylic acid groups.
  • Temperature Dependence: As with many organic compounds, solubility is likely to be temperature-dependent; increasing temperature may enhance solubility by increasing molecular motion.

In summary, the solubility of this compound likely reflects a balance between its hydrophilic and hydrophobic regions, emphasizing the significance of the solvent used and the conditions under which solubility is evaluated.

Interesting facts

Interesting Facts about (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-6-carboxy-4,5-dihydroxy-tetrahydropyran-3-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid

This complex compound is a fascinating example of organic chemistry's vast diversity. Here are some notable facts that highlight its unique nature:

  • Structural Complexity: The compound boasts a highly intricate structure, featuring multiple stereocenters which contribute to its unique three-dimensional arrangement.
  • Natural Origins: It is derived from natural sources, involving various biochemical pathways, showcasing how organic compounds can be synthesized in living organisms.
  • Biological Significance: Such compounds often play roles in biological processes, potentially acting as signaling molecules or contributing to the structural diversity of metabolites.
  • Potential Applications: Due to its complex structure, this compound might possess unique therapeutic properties, making it a subject of interest in drug discovery and development.
  • Research Interest: Scientists are keen to explore its pharmacological properties, especially in contexts like anti-cancer research or as an antibacterial agent.

In summary, this compound's incredible structure and potential applications make it a noteworthy topic in the study of organic chemistry. As students and scientists delve deeper into its properties, they uncover the intricacies of nature's chemistry and the endless possibilities it presents.

Synonyms
Glycyrrhizic acid
glycyrrhizin
1405-86-3
Glycyron
Glycyrrhizinic acid
Glycyrrhetinic acid glycoside
potenlini
Glizigen
glycyrrhizate
18-beta-Glycyrrhizic acid
beta-Glycyrrhizin
18beta-Glycyrrhizic acid
Glycyrrizin
Rizinsan K2 A2 (free acid)
HSDB 496
CHEBI:15939
EINECS 215-785-7
NSC 167409
NSC 234419
NSC-167409
NSC-234419
UNII-6FO62043WK
BRN 0077922
CCRIS 8444
DTXSID8047006
6FO62043WK
DTXCID6027006
4-18-00-05156 (Beilstein Handbook Reference)
(3beta,20beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid
20beta-Carboxy-11-oxo-30-norolean-12-en-3beta-yl-2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid
30-hydroxy-11,30-dioxoolean-12-en-3beta-yl (2-O-beta-D-glucopyranosyluronic acid)-alpha-D-glucopyranosiduronic acid
alpha-D-Glucopyranosiduronic acid, (3beta,20beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-beta-D-glucopyranuron osyl-
GLYCYRRHIZIN (II)
GLYCYRRHIZIN [II]
(3beta,20beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid
GLYCYRRHIZIC ACID (MART.)
GLYCYRRHIZIC ACID [MART.]
GLYCYRRHIZIC ACID (USP-RS)
GLYCYRRHIZIC ACID [USP-RS]
NSC167409
Acid, Glycyrrhizic
Acid, Glycyrrhizinic
NSC234419
alpha-D-glucopyranosiduronic acid, (3 beta,20 beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-beta-D-glucopyranuronosyl-
GLYCYRRHIZIC ACID (GLYCYRRHIZIN) (CONSTITUENT OF LICORICE)
(3beta,20beta)-20-Carboxy-11-oxo-30-norlean-12-en-3-yl-2-O-beta-1-7-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid
20BETA-CARBOXY-11-OXO-30-NOROLEAN-12-EN-3BETA-YL-2-O-BE TA-D-GLUCOPYRANURONOSYL-ALPHA-D-GLUCOPYRANOSIDURONIC ACID
215-785-7
alpha-D-Glucopyranosiduronic acid, (3beta,20beta)-20-carboxy-11-oxo-30-norlean-12-en-3-yl-2-O-beta-1-7-glucopyranuronosyl-
glyzyrrhizin
Glycyrrhizin [JAN]
Liquorice
.beta.-glycyrrhizin
18.beta.-glycyrrhizic acid
Glycyrrhizinate
CHEMBL441687
(2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
Glycyrrhizicacid
MFCD00065194
Glycyram
Neo-Umor
alpha-D-Glucopyranosiduronic acid, (3beta,20beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-beta-D-glucopyranuronosyl-
(2S,3S,4S,5R,6S)-6-{[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-5-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid
CAS-1405-86-3
Glycyrrhizic acid?
NCGC00183128-01
(2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-6-carboxy-4,5-dihydroxy-tetrahydropyran-3-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
ammonium-glycyrrhizinate
Glycyrrhizic acid, 2K
beta-Glycyrrhizinic acid
Glycyrrhizic acid - 80%
Glycyrrhizic acid - 98%
GLYCYRRHIZIN [HSDB]
SCHEMBL17684
BIDD:ER0363
GLYCYRRHIZIC ACID [MI]
GTPL4688
Glycyrrhizin (Glycyrrhizic Acid)
GLYCYRRHIZIC ACID [WHO-DD]
HY-N0184
MSK40365
Tox21_111520
Tox21_113426
Tox21_303493
BDBM50185127
HMDB:0029843
s2302
AKOS015893086
AKOS015969345
CCG-270511
CS-7695
DB13751
GM-1292
OG08293
NCGC00257455-01
NCGC00386162-01
NCGC00386162-02
(3beta,20beta)-20-Carboxy-11-oxo-30-norlean-12-en-3-yl-2-O-beta-1- 7-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid
1ST40365
alpha-D-Glucopyranosiduronic acid, (3beta,20beta)-20-carboxy-11-oxo-30-norlean-12-en-3-yl-2-O-beta-1- 7-glucopyranuronosyl-
AS-13001
E958
XG180042
G0150
NS00008393
AB01566834_01
EN300-25023649
Q418705
BRD-K83486494-318-01-5
GLYCYRRHIZIC ACID (GLYCYRRHIZIN) (CONSTITUENT OF LICORICE) [DSC]
Glycyrrhizic acid, United States Pharmacopeia (USP) Reference Standard
Glycyrrhizic Acid, Pharmaceutical Secondary Standard; Certified Reference Material
(2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylicacid
(3.beta.,20.beta.)-20-Carboxy-11-oxo-30-norlean-12-en-3-yl-2-O-.beta.-1- 7-glucopyranuronosyl-.alpha.-D-glucopyranosiduronic acid
(3.BETA.,20.BETA.)-20-CARBOXY-11-OXO-30-NOROLEAN-12-EN-3-YL 2-O-.BETA.-D-GLUCOPYRANURONOSYL-.ALPHA.-D-GLUCOPYRANOSIDURONIC ACID
(3b,20b)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-(b-D-glucopyranuronosyl)-b-D-glucopyranosiduronic acid
(3b,20b)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-(b-D-glucopyranuronosyl)-b-D-glucopyranosiduronic Acid;3-O-(2-O-b-D-Glucopyran uronosyl-a-D-glucopyranuronosyl)-18-b-glycyrrhetinic acid