MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 574776 | Name: Madecassic acid
Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Madecassic acid is a non-competitive cytochrome P450 (CYP) inhibitor with anti-inflammatory activity.

Chemical Structure

Madecassic acid
Madecassic acid
CAS#18449-41-7

Theoretical Analysis

MedKoo Cat#: 574776

Name: Madecassic acid

CAS#: 18449-41-7

Chemical Formula: C30H48O6

Exact Mass: 504.3451

Molecular Weight: 504.71

Elemental Analysis: C, 71.39; H, 9.59; O, 19.02

Price and Availability

Size Price Availability Quantity
500mg USD 350.00 2 Weeks
1g USD 600.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Madecassic acid
IUPAC/Chemical Name
(1S,2R,4aS,6aS,6bR,8R,9R,10R,11R,12aR)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid
InChi Key
PRAUVHZJPXOEIF-UQPQHHFRSA-N
InChi Code
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
SMILES Code
O=C([C@]12CC[C@@H](C)[C@H](C)C1C3=CCC4[C@@]5(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)C5[C@H](O)C[C@@]4(C)[C@]3(C)CC2)O
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
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.
In vitro activity:
Both madecassic acid and madecassoside inhibited the production of nitric oxide (NO), prostaglandin E(2) (PGE(2)), tumor necrosis factor-alpha (TNF-alpha), interleukin-1 beta (IL-1beta), and IL-6. Consistent with these observations, madecassic acid inhibited the LPS-induced expression of iNOS and COX-2 at the protein level and of iNOS, COX-2, TNF-alpha, IL-1beta, and IL-6 at the mRNA level in RAW 264.7 macrophage cells, as determined by Western blotting and RT-PCR, respectively. Furthermore, madecassic acid suppressed the LPS-induced activation of nuclear factor-kappaB (NF-kappaB), and this was associated with the abrogation of inhibitory kappa B-alpha (IkappaB-alpha) degradation and with the subsequent blocking of p65 protein translocation to the nucleus. Reference: Planta Med. 2010 Feb;76(3):251-7. https://pubmed.ncbi.nlm.nih.gov/19774506/
In vivo activity:
Oral administration of MA (madecassic acid) reduced the burden and incidence of tumors in the CAC (colitis-associated colorectal cancer) mice. MA decreased the number of MDSCs in the colon tissues of CAC mice and ameliorated anti-tumor immune responses. Reference: Biochem Pharmacol. 2022 Aug;202:115138. https://pubmed.ncbi.nlm.nih.gov/35700756/
Solvent mg/mL mM
Solubility
DMF:PBS (pH 7.2) (1:9) 0.1 0.20
DMSO 55.8 110.63
Ethanol 9.5 18.82
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 504.71 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Ganguly A, Mandi M, Dutta A, Rajak P. In Silico Analysis Reveals the Inhibitory Potential of Madecassic Acid against Entry Factors of SARS-CoV-2. ACS Appl Bio Mater. 2023 Jan 6:acsabm.2c00916. doi: 10.1021/acsabm.2c00916. Epub ahead of print. PMID: 36608326; PMCID: PMC9844099. 2. Won JH, Shin JS, Park HJ, Jung HJ, Koh DJ, Jo BG, Lee JY, Yun K, Lee KT. Anti-inflammatory effects of madecassic acid via the suppression of NF-kappaB pathway in LPS-induced RAW 264.7 macrophage cells. Planta Med. 2010 Feb;76(3):251-7. doi: 10.1055/s-0029-1186142. Epub 2009 Sep 11. PMID: 19774506. 3. Yun X, Zhang Q, Fang Y, Lv C, Chen Q, Chu Y, Zhu Y, Wei Z, Xia Y, Dai Y. Madecassic acid alleviates colitis-associated colorectal cancer by blocking the recruitment of myeloid-derived suppressor cells via the inhibition of IL-17 expression in γδT17 cells. Biochem Pharmacol. 2022 Aug;202:115138. doi: 10.1016/j.bcp.2022.115138. Epub 2022 Jun 11. PMID: 35700756. 4. Siddiqui S, Khan F, Jamali KS, Musharraf SG. Madecassic Acid Reduces Fast Transient Potassium Channels and Promotes Neurite Elongation in Hippocampal CA1 Neurons. CNS Neurol Disord Drug Targets. 2020;19(1):12-26. doi: 10.2174/1871527318666191111105508. PMID: 31713492.
In vitro protocol:
1. Ganguly A, Mandi M, Dutta A, Rajak P. In Silico Analysis Reveals the Inhibitory Potential of Madecassic Acid against Entry Factors of SARS-CoV-2. ACS Appl Bio Mater. 2023 Jan 6:acsabm.2c00916. doi: 10.1021/acsabm.2c00916. Epub ahead of print. PMID: 36608326; PMCID: PMC9844099. 2. Won JH, Shin JS, Park HJ, Jung HJ, Koh DJ, Jo BG, Lee JY, Yun K, Lee KT. Anti-inflammatory effects of madecassic acid via the suppression of NF-kappaB pathway in LPS-induced RAW 264.7 macrophage cells. Planta Med. 2010 Feb;76(3):251-7. doi: 10.1055/s-0029-1186142. Epub 2009 Sep 11. PMID: 19774506.
In vivo protocol:
1. Yun X, Zhang Q, Fang Y, Lv C, Chen Q, Chu Y, Zhu Y, Wei Z, Xia Y, Dai Y. Madecassic acid alleviates colitis-associated colorectal cancer by blocking the recruitment of myeloid-derived suppressor cells via the inhibition of IL-17 expression in γδT17 cells. Biochem Pharmacol. 2022 Aug;202:115138. doi: 10.1016/j.bcp.2022.115138. Epub 2022 Jun 11. PMID: 35700756. 2. Siddiqui S, Khan F, Jamali KS, Musharraf SG. Madecassic Acid Reduces Fast Transient Potassium Channels and Promotes Neurite Elongation in Hippocampal CA1 Neurons. CNS Neurol Disord Drug Targets. 2020;19(1):12-26. doi: 10.2174/1871527318666191111105508. PMID: 31713492.