Madecassoside - analytical standard, Moligand™, ≥98% , CAS No.34540-22-2

CAS: 34540-22-2 Cat. No.: M107330 Formula: C₄₈H₇₈O₂₀ Molecular Weight: 975.12 EC Number: 252-076-1

GRADE & PURITY Analytical standard, Moligand™, ≥98%

Synonyms

CCG-270599 | MFCD03411893 | AC-6056 | AS-15335 | Madecassoside | Q-100419 | AKOS008901372 | ASIATICOSIDE A | s3843 | BNMGUJRJUUDLHW-CIZDPPTDSA-N

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

Overview

Madecassoside is one of the major pentacyclic triterpenoid saponin compounds extracted from Centella asiatica.
Application:
Madecassoside has been used to study its cytotoxic effects on mouse macrophage cell lines (J774A.1).It has also been used as a potential inhibitor of serine racemase (SR) for in vitro and ex vivo studies.

Specifications

Synonyms

CCG-270599 | MFCD03411893 | AC-6056 | AS-15335 | Madecassoside | Q-100419 | AKOS008901372 | ASIATICOSIDE A | s3843 | BNMGUJRJUUDLHW-CIZDPPTDSA-N

Specifications & Purity

analytical standard, Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Madecassoside is a triterpenoid compound found in Centella asiatica (Gotu kola), a medicinal herb used in traditional Chinese medicine (TCM), Ayurvedic medicine, and traditional African medicine. Madecassoside has a wide range of reported biological activ

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Analytical standard, Moligand™

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 528774717
• Canonical Smiles: CC1CCC2(CCC3(C(=CCC4C3(CC(C5C4(CC(C(C5(C)CO)O)O)C)O)C)C2C1C)C)C(=O)OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)C)O)O)O)O)O)O)O)O
• IUPAC Name: [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (1S,2R,4aS,6aR,6aR,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
• InChIKey: BNMGUJRJUUDLHW-CIZDPPTDSA-N
• INCHI: 1S/C48H78O20/c1-19-10-11-48(13-12-46(6)22(28(48)20(19)2)8-9-27-44(4)14-24(52)39(61)45(5,18-50)38(44)23(51)15-47(27,46)7)43(62)68-42-35(59)32(56)30(54)26(66-42)17-63-40-36(60)33(57)37(25(16-49)65-40)67-41-34(58)31(55)29(53)21(3)64-41/h8,19-21,23-42,49-61H,9-18H2,1-7H3/t19-,20+,21+,23-,24-,25-,26-,27-,28+,29+,30-,31-,32+,33-,34-,35-,36-,37-,38-,39+,40-,41+,42+,44-,45+,46+,47-,48+/m1/s1
• Isomeric SMILES: C[C@@H]1CC[C@@]2(CC[C@]3(C(=CC[C@H]4[C@]3(C[C@H]([C@@H]5[C@@]4(C[C@H]([C@@H]([C@@]5(C)CO)O)O)C)O)C)[C@@H]2[C@H]1C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)O)O)O)O)O
• Molecular Weight: 975.12
• Reaxy-Rn: 24283150
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24283150&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Terpene glycosides
        • Level5 Triterpene glycosides
          • Level6 Triterpene saponins

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene glycosides
• Intermediate Tree Nodes: Triterpene glycosides
• Direct Parent: Triterpene saponins
• Alternative Parents: Triterpenoids Oligosaccharides 7-alpha-hydroxysteroids 12-beta-hydroxysteroids O-glycosyl compounds Oxanes Secondary alcohols Cyclic alcohols and derivatives Carboxylic acid esters Polyols Oxacyclic compounds Monocarboxylic acids and derivatives Acetals Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Triterpene saponin - Triterpenoid - Oligosaccharide - 12-beta-hydroxysteroid - 7-hydroxysteroid - 7-alpha-hydroxysteroid - Hydroxysteroid - 12-hydroxysteroid - Steroid - O-glycosyl compound - Glycosyl compound - Oxane - Cyclic alcohol - Secondary alcohol - Carboxylic acid ester - Oxacycle - Organoheterocyclic compound - Polyol - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Acetal - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Carbonyl group - Alcohol - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: Light sensitive，Air sensitive
• Molecular Weight: 975.100 g/mol
• XLogP3: -1.200
• Hydrogen Bond Donor Count: 13
• Hydrogen Bond Acceptor Count: 20
• Rotatable Bond Count: 10
• Exact Mass: 974.509 Da
• Monoisotopic Mass: 974.509 Da
• Topological Polar Surface Area: 335.000 Ų
• Heavy Atom Count: 68
• Formal Charge: 0
• Complexity: 1860.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 28
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yao Wang, Junhua Qiu, Chengwei Wang, Ruiyu Yang, Fuyou Guo, Tian Li, Shili Li, Lei Yang, Wei Ding.  (2026)  Sustainable Strategy of Natural trans-Anethole in Controlling Bacterial Wilt: Virulence Suppression and Beneficial Microbiome Enrichment.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:41568748] [10.1021/acs.jafc.5c13627]