Basic information
- CAS
18449-41-7- Standard SMILES
CC1CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO)C5C(O)CC43C)C2C1C- InChIKey
PRAUVHZJPXOEIF-UHFFFAOYSA-N- Molecular formula
- C30H48O6
- Average molar mass
- 504.7 g/mol
- Monoisotopic mass
- 504.34508925
Overview
2,3,6,23-Tetrahydroxyurs-12-en-28-oic acid has been reported in Centella, Centella erecta, and Centella asiatica with data available.
Names & identifiers
- Preferred name
- 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
- IUPAC
- 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
- English name
- Madecassic acid
- Molecular formula
- C30H48O6
- Molecular weight
- 504.71
Names & synonyms
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 acidRefChem:1074591s95022,3,6,23-tetrahydroxyurs-12-en-28-oic acidUrs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, (2a,3b,4a,6b)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acidmadecassic acid [M+H]+CHEMBL1993179SCHEMBL14286199HMS5086N07(1S,2R,4aS,6aS,6bR,8R,9R,10R,11R,12aR,12bR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acidAKOS032948362
Show more names
MadecasosideMADECASSIC ACIDMADECASSIC ACID(P)Madecassic acid-RMHydroxyasiatic acidHydroxy asiaticoside6-Hydroxyasiatic acid
Properties
Computed structural properties
- XLogP
- 4.4
- Topological polar surface area
- 118 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 963
Experimental & physicochemical properties
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Melting point
- 270 °C · 270°C (dec.)
- Boiling point
- 641.7 · 641.7±55.0 °C(Predicted)
- Density
- 1.23 · 1.23±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Sparingly), Methanol (Slightly, Heated)
- form
- Solid
- pka
- 4.63 · 4.63±0.70(Predicted)
- color
- White to Pale Red
- Major Application
- food and beverages
- Cosmetics Ingredients Functions
- SKIN CONDITIONING
- InChIKey
- PRAUVHZJPXOEIF-MRQYELSVNA-N
- SMILES
- O[C@H]1[C@@H]2[C@@]([C@@H]3[C@]([C@@]4(CC[C@@]5([C@@H]([C@H]([C@@H](CC5)C)C)C4=CC3)C(=O)O)C)(C1)C)(C[C@H]([C@@H]([C@]2(CO)C)O)O)C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- hs_code
- 29389090
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS09
- hazard_code
- Xi
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H301-H410
- Precautionary statements
- P501-P273-P270-P264-P391-P301+P310+P330-P405
Chemistry & industry
Applications
DescriptionMadecassic acid is a triterpenoid that has been found in C. asiatica and has diverse biological activities. It inhibits LPS-induced production of nitric oxide (NO), prostaglandin E2 (PGE2; ), TNF-α, IL-1β, and IL-6 in RAW 264.7 macrophages when used at a concentration of 150 μg/ml. Madecassic acid (0.05 and 0.1% in the diet) decreases plasma levels of fibrinogenin and triglycerides, as well as heart and kidney levels of reactive oxygen species (ROS), in a mouse model of diabetes induced by streptozotocin (STZ; ). It decreases tumor growth in a CT26 murine colon cancer model in a dose-dependent manner.
Useswound healing
UsesMadecassic Acid is a terpenoid with an ursane skeleton isolated from Centella asiatica. Madecassic Acid displays anti-inflammatory properties as a result of iNOS, COX-2, TNF-alpha, IL-1beta, and IL-6 inhibition via the downregulation of NF-kappaB activation in RAW 264.7 macrophage cells. Madecassic Acid is found in cosmetic products due to its skin-protective activities.
Upstream & downstream products
Upstream raw materials
Suppliers101 total
北京华美互利生物化工010-56205725 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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