71305-80-1

Basic information

• Product Name: (3aR)-4β,8α-Diacetoxy-3aβ,4,5,6,6aβ,7,8,9,9aβ,9bα-decahydro-3,6,9-trismethyleneazuleno[4,5-b]furan-2(3H)-one
• Synonyms: (3aR)-4β,8α-Diacetoxy-3aβ,4,5,6,6aβ,7,8,9,9aβ,9bα-decahydro-3,6,9-trismethyleneazuleno[4,5-b]furan-2(3H)-one;8α-Acetoxyzaluzanin D;(3aS)-4α,8β-Diacetoxy-3,6,9-tris(methylene)-3aα,4,5,6,6aα,7,8,9,9aα,9bβ-decahydroazuleno[4,5-b]furan-2(3H)-one
• CAS NO: 71305-80-1
• Molecular Formula: C19H22O6
• Molecular Weight: 346.37438
• Mol File: 71305-80-1.mol

Chemical Properties

• Boiling Point: 482.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1.22±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (3aR)-4β,8α-Diacetoxy-3aβ,4,5,6,6aβ,7,8,9,9aβ,9bα-decahydro-3,6,9-trismethyleneazuleno[4,5-b]furan-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR)-4β,8α-Diacetoxy-3aβ,4,5,6,6aβ,7,8,9,9aβ,9bα-decahydro-3,6,9-trismethyleneazuleno[4,5-b]furan-2(3H)-one(71305-80-1)
• EPA Substance Registry System: (3aR)-4β,8α-Diacetoxy-3aβ,4,5,6,6aβ,7,8,9,9aβ,9bα-decahydro-3,6,9-trismethyleneazuleno[4,5-b]furan-2(3H)-one(71305-80-1)

Safety Data

• Hazardous Substances Data: 71305-80-1(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 35932-39-9 cynaporicrin 
• 35932-46-8 deacylcynaropicrin 

Relevant articles and documents

Guaianolides from Taeckholmia species

The investigation of four Taeckholmia species afforded in addition to known desacylcynaropicrin, two new guaianolides. The structures were elucidated by spectroscopic methods and chemical transformations. The chemotaxonomy is discussed briefly.

The effect of different ester chain modifications of two guaianolides for inhibition of colorectal cancer cell growth

Several sesquiterpene lactones (STLs) have been tested as lead drugs in cancer clinical trials. Salograviolide-A (Sal-A) and salograviolide-B (Sal-B) are two STLs that have been isolated from Centaurea ainetensis, an indigenous medicinal plant of the Middle Eastern region. The parent compounds Sal-A and Sal-B were modified and successfully prepared into eight novel guaianolide-type STLs (compounds 1–8) bearing ester groups of different geometries. Sal-A, Sal-B, and compounds 1–8 were tested against a human colorectal cancer cell line model with differing p53 status; HCT116 with wild-type p53 and HCT116 p53?/? null for p53, and the normal-like human colon mucosa cells with wild-type p53, NCM460. IC50 values indicated that derivatization of Sal-A and Sal-B resulted in potentiation of HCT116 cell growth inhibition by 97% and 66%, respectively. The effects of the different molecules on cancer cell growth were independent of p53 status. Interestingly, the derivatization of Sal-A and Sal-B molecules enhanced their anti-growth properties versus 5-Fluorouracil (5-FU), which is the drug of choice in colorectal cancer. Structure-activity analysis revealed that the enhanced molecule potencies were mainly attributed to the position and number of the hydroxy groups, the lipophilicity, and the superiority of ester groups over hydroxy substituents in terms of their branching and chain lengths. The favorable cytotoxicity and selectivity of the potent molecules, to cancer cells versus their normal counterparts, pointed them out as promising leads for anti-cancer drug design.

GUAIANOLIDES FROM TRICHOLEPIS GLABERRIMA

Cynaropicrin and 11,13-dihydrodesacylcynaropicrin were isolated from Tricholepis glaberrima. - Key Word Index - Tricholepis glaberrima; Compositae; sesquiterpene lactones; guaianolides.