CAS 94390-09-7

(2α,3β,13α)-2,3-Dihydroxy-13-methyl-27-norolean-14-en-28-oic acid

Description:

The chemical substance known as (2α,3β,13α)-2,3-Dihydroxy-13-methyl-27-norolean-14-en-28-oic acid, with the CAS number 94390-09-7, is a triterpenoid compound characterized by its complex structure, which includes multiple hydroxyl groups and a unique carbon skeleton derived from oleanane. This compound typically exhibits a range of biological activities, including potential anti-inflammatory and anticancer properties, making it of interest in pharmacological research. Its molecular structure features a steroid-like framework, which contributes to its interaction with biological systems. The presence of hydroxyl groups enhances its solubility in polar solvents and may influence its reactivity and biological interactions. Additionally, the compound's specific stereochemistry is crucial for its biological activity, as the spatial arrangement of atoms can significantly affect how it interacts with enzymes and receptors in the body. Overall, this substance represents a fascinating area of study within natural product chemistry and medicinal chemistry.

Formula: C₃₀H₄₈O₄

InChI: InChI=1S/C30H48O4/c1-25(2)14-15-30(24(33)34)13-10-20-27(5)11-8-19-26(3,4)23(32)18(31)16-29(19,7)21(27)9-12-28(20,6)22(30)17-25/h10,18-19,21-23,31-32H,8-9,11-17H2,1-7H3,(H,33,34)/t18-,19+,21+,22+,23+,27+,28-,29+,30-/m1/s1

InChI key: InChIKey=JMJVYEINATYJHM-KLXPJGLFSA-N

SMILES: C[C@]12C=3[C@](C)([C@]4([C@@](C(O)=O)(CC3)CCC(C)(C)C4)[H])CC[C@@]1([C@]5(C)[C@@](CC2)(C(C)(C)[C@@H](O)[C@H](O)C5)[H])[H]

Synonyms:

• (2α,3β,13α)-2,3-Dihydroxy-13-methyl-27-norolean-14-en-28-oic acid
• (+)-Sebiferenic acid
• 27-Norolean-14-en-28-oic acid, 2,3-dihydroxy-13-methyl-, (2α,3β,13α)-
• Sebiferenic acid
• D-Friedoolean-14-en-28-oic acid, 2,3-dihydroxy-, (2α,3β)-

Sebiferenic acid

Controlled Product

CAS: 94390-09-7

Sebiferenic acid is a sesterterpenoid that has been shown to have anti-trypanosomal activity and is the first natural product to be identified as a novel drug target for leishmaniasis. Sebiferenic acid binds to 14α-demethylase (14DM) in the parasite, inhibiting the conversion of taraxerol into taraxerone. This binding prevents the activation of protozoan parasites and leads to cell death. Sebiferenic acid is also active against human pathogens such as Escherichia coli, Staphylococcus epidermidis, and Pseudomonas aeruginosa. Natural sources of sebiferenic acid include Sapium sebiferum and Protium heptaphyllum.

Formula: C₃₀H₄₈O₄

Purity: Min. 95%

Molecular weight: 472.7 g/mol

Ref: 3D-UDA39009