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Madecassic acid (Standard)

CAT: 0804-HY-N0569R-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N0569R-01Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Madecassic acid (Standard) is the analytical standard of Madecassic acid. This product is intended for research and analytical applications. Madecassic acid is isolated from Centella asiatica (Umbelliferae) . Madecassic acid has anti-inflammatory properties caused by iNOS, COX-2, TNF-alpha, IL-1beta, and IL-6 inhibition via the downregulation of NF-κB activation in RAW 264.7 macrophage cells[1].
CAS Number
18449-41-7
UNSPSC
12352211
Hazard Statement
H302, H315, H319, H335
Target
COX; Interleukin Related; NO Synthase; Reference Standards; TNF Receptor
Type
Reference Standards
Related Pathways
Apoptosis; Immunology/Inflammation; Others
Applications
COVID-19-immunoregulation
Field of Research
Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/madecassic-acid-standard.html
Purity
99.91
Smiles
C[C@@]([C@]([C@H](O)C1)([H])[C@]2(C)CO)(C[C@@H](O)[C@@H]2O)[C@](CC=C3[C@]4(CC[C@@](C(O)=O)(CC[C@H]5C)[C@@]3([H])[C@H]5C)C)([H])[C@]41C
Molecular Formula
C30H48O6
Molecular Weight
504.70
Precautions
H302, H315, H319, H335
Shipping Conditions
Room Temperature
Storage Conditions
4°C, sealed storage, away from light and moisture
Scientific Category
Reference Standards
Clinical Information
No Development Reported
Isoform
COX-2; IL-1; IL-6; iNOS

Chemical Information

Madecassic Acid

Madecassic acid is a pentacyclic triterpenoid that is ursane substituted by a carboxy group at position 28 and hydroxy groups at positions 2, 3, 6 and 23 (the 2alpha,3beta,6beta stereoisomer). It has a role as an antioxidant, an antibacterial agent, a hypoglycemic agent, an antineoplastic agent, an apoptosis inducer and a plant metabolite. It is a monocarboxylic acid, a pentacyclic triterpenoid and a tetrol. It is a conjugate acid of a madecassate. It derives from a hydride of an ursane.

CAS Number18449-41-7
PubChem CID73412
IUPAC Name(1S,2R,4aS,6aR,6aS,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-carboxylic acid
Molecular FormulaC30H48O6
Molecular Weight504.7
XLogP4.4
Topological Polar Surface Area118
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Heavy Atom Count36
Formal Charge0
Complexity963
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
InChI
InChI=1S/C30H48O6/c1-16-9-10-30(25(35)36)12-11-28(5)18(22(30)17(16)2)7-8-21-26(3)13-20(33)24(34)27(4,15-31)23(26)19(32)14-29(21,28)6/h7,16-17,19-24,31-34H,8-15H2,1-6H3,(H,35,36)/t16-,17+,19-,20-,21-,22+,23-,24+,26-,27+,28-,29-,30+/m1/s1
InChIKey
PRAUVHZJPXOEIF-AOLYGAPISA-N
Chemical Structure
2D Structure
2D structure of Madecassic Acid
CAS: 18449-41-7
CID: 73412
Formula: C30H48O6
MW: 504.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight504.7
XLogP34.4
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Exact Mass504.34508925
Monoisotopic Mass504.34508925
Topological Polar Surface Area118 Ų
Heavy Atom Count36
Formal Charge0
Complexity963
Isotope Atom Count0
Defined Atom Stereocenter Count13
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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