22338-69-8

Basic information

• Product Name: grandifloric acid
• Synonyms: grandifloric acid;[15S,(-)]-15α-Hydroxykaur-16-en-18-oic acid;Grandiflorolic acid;15alpha-Hydroxykaur-16-en-19-oic acid;NSC 332872
• CAS NO: 22338-69-8
• Molecular Formula: C20H30O3
• Molecular Weight: 318.45
• Mol File: 22338-69-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 226-228 °C
• Boiling Point: 470.7°Cat760mmHg
• Flash Point: 252.6°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 7.7E-11mmHg at 25°C
• Refractive Index: 1.566
• PKA: 4.65±0.60(Predicted)
• CAS DataBase Reference: grandifloric acid(CAS DataBase Reference)
• NIST Chemistry Reference: grandifloric acid(22338-69-8)
• EPA Substance Registry System: grandifloric acid(22338-69-8)

Safety Data

• Hazardous Substances Data: 22338-69-8(Hazardous Substances Data)

Usage

General Description

Grandifloric acid is a naturally occurring compound found in the plant Grandiflora aboensis, which is indigenous to Malaysia. It is a triterpenoid compound with potential anti-inflammatory and anti-cancer properties. Grandifloric acid has been studied for its ability to inhibit the growth of cancer cells and induce apoptosis, making it a potential candidate for anti-cancer drug development. Additionally, it has been found to possess anti-inflammatory effects, which could be beneficial for conditions associated with inflammation such as arthritis and cardiovascular disease. Further research is ongoing to fully understand the potential therapeutic applications of grandifloric acid.

InChI:InChI=1/C20H30O3/c1-12-13-5-6-15-18(2)8-4-9-19(3,17(22)23)14(18)7-10-20(15,11-13)16(12)21/h13-16,21H,1,4-11H2,2-3H3,(H,22,23)/t13-,14+,15+,16+,18-,19-,20-/m1/s1

Upstream product

• 6619-97-2 15α-Acetoxy-Δ¹⁶-kauren-18α-saeure 
• 64-19-7 acetic acid 
• 32381-03-6 ent-15β-hydroxykaur-16-ene-19-oic acid 15-angelate 
• 5095-09-0 kaurenoic acid 
• 6619-97-2 ent-15α-acetoxy-kaur-16-en-19-oic acid 

Downstream Products

• 22376-47-2 methyl ent-15-oxokaur-16-en-19-oate 

Relevant articles and documents

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Preparation of antiproliferative terpene-alkaloid hybrids by free radical-mediated modification of ent-kauranic derivatives

A convenient strategy for molecular editing of available ent-kauranic natural scaffolds has been developed based on radical mediated C–C bond formation. Iodine atom transfer radical addition (ATRA) followed by rapid ionic elimination and radical azidoalkylation were investigated. Both reactions involve radical addition to the exo-methylenic double bond of the parent substrate. Easy transformations of the obtained adducts lead to extended diterpenes of broad structural diversity and artificial diterpene-alkaloid hybrids possessing lactam and pyrrolidine pharmacophores. The cytotoxicity of selected diterpenic derivatives was examined by in vitro testing on several tumor cell lines. The terpene-alkaloid hybrids containing N-heterocycles with unprecedented spiro-junction have shown relevant cytotoxicity and promising selectivity indexes. These results represent a solid basis for following research on the synthesis of such derivatives based on available natural product templates.

Synthesis of Highly Functionalized Biologically Active Tetracyclic Diterpenoids from ent-Kaur-16-en-19-oic Acid under Modified Prévost-Woodward Reaction Conditions

Abstract: A procedure has been developed for the synthesis of highly functionalized tetracyclic diterpenoids from natural ent-kaur-16-en-19-oic acid under modified Prévost–Woodward reaction conditions. The reaction follows an unusual pathway which leads mainly to bromination or rearrangement products. The transforma-tion of ent-kaur-16-en-19-oic acid afforded a mixture of (16ZE)-17-bromo-ent-kaur-16-en-19-oic, (15R,16E)-17-bromo-15-acetoxy-ent-kaur-16-en-19-oic, (16S)-17-bromo-16-acetoxy-ent-kaur-19-oic, (15S)-15-acetoxy-ent-kaur-16-en-19-oic, and (15S)-15-hydroxy-ent-kaur-16-en-19-oic acids, the latter two being reported previously. The newly syn-thesized compounds were evaluated for their cytotoxicity against two cancer cell lines, HeLa and BxPC-3.

Cytotoxic and apoptosis-inducing effect of ent-15-oxo-kaur-16-en-19-oic acid, a derivative of grandiflorolic acid from Espeletia schultzii

ent-Kaurenic acid and many natural derivatives of this diterpene are known to have interesting biological properties. ent-15-Oxo-kaur-16-en-19-oic acid can be easily obtained from grandiflorolic acid which was first isolated from Espeletia grandiflora. The present work describes the proapoptotic effect of ent-15-oxo-kaur-16-en-19-oic acid on the human prostate carcinoma epithelial cell line PC-3 as evidenced by the changes in the expression level of proteins associated with the execution and regulation of apoptosis. Cell viability was affected upon exposure to the compound, the IC50 were determined as 3.7 μg/ml, which is 4 times lower than that corresponding to a primary cell culture of fibroblasts (14.8 μg/mL). Through Western blot analysis, active forms of caspace-3 associated with the specific proteolysis of Poly(ADP-ribose) polymerase (PARP) were detected. Reduced levels of the antiapoptotic protein Bcl-2, as well as the appearance of internucleosomal DNA fragmentation, were also demonstrated. Thus, ent-15-oxo-kaur-16-en-19-oic acid may be a promising lead compound for new chemopreventive strategies, alone or in combination with traditional chemotherapy agents to overcome drug resistance in tumoral cells.