6754-35-4

Usage

Uses

Used in Pharmaceutical Industry:
(3aR)-3a,4,4a,5,6,7,7aα,8,9,9aβ-Decahydro-5α,7α-dihydroxy-4aβ,8α-dimethyl-3-methyleneazuleno[6,5-b]furan-2(3H)-one is used as a potential pharmaceutical agent for its possible anti-inflammatory and anti-microbial properties due to its azulene origin and the presence of hydroxyl groups. Further research and analysis are required to confirm its efficacy and safety for medical use.
Used in Chemical Research:
(3aR)-3a,4,4a,5,6,7,7aα,8,9,9aβ-Decahydro-5α,7α-dihydroxy-4aβ,8α-dimethyl-3-methyleneazuleno[6,5-b]furan-2(3H)-one is also used in chemical research for studying the properties and behavior of azulene derivatives and their potential applications in various fields. Its unique structure with a furan ring and functional groups provides opportunities for exploring new chemical reactions and syntheses.

InChI:InChI=1/C15H22O4/c1-7-4-11-9(8(2)14(18)19-11)6-15(3)12(17)5-10(16)13(7)15/h7,9-13,16-17H,2,4-6H2,1,3H3/t7-,9-,10+,11+,12-,13-,15-/m1/s1

Upstream product

• 28080-08-2 dihydropulchellin 
• 23667-96-1 2-dehydrodihydropulchellin 
• 16909-97-0 2-acetyl-4-epipulchellin 
• 23667-94-9 2-acetyl-4-dehydropulchellin 
• 96744-09-1 (3R,3aR,4aS,7R,7aS,8R,9aS)-7-Hydroxy-3,4a,8-trimethyl-decahydro-azuleno[6,5-b]furan-2,5-dione 
• 96598-27-5 2β,3β-epoxyaromaticin 
• 5945-42-6 4-oxo-1α(H)-11(13)-pseudoguaien-8α,12-olide 
• 78798-42-2 6-deoxychamissonolide 
• 96646-93-4 4-epi-2-O-acetyl-11βH-dihydropulchellin 
• 96598-29-7 (3R,3aR,4aS,5S,7S,7aS,8R,9aS)-5,7-Dihydroxy-3,4a,8-trimethyl-decahydro-azuleno[6,5-b]furan-2-one 
• 96598-28-6 (3R,3aR,4aS,5S,7R,7aS,8R,9aS)-5,7-Dihydroxy-3,4a,8-trimethyl-decahydro-azuleno[6,5-b]furan-2-one 
• 96598-30-0 Benzoic acid (3R,3aR,4aS,5R,7S,7aS,8R,9aS)-7-acetoxy-3,4a,8-trimethyl-2-oxo-dodecahydro-azuleno[6,5-b]furan-5-yl ester 
• 96646-92-3 2β,3β-epoxy-11βH-dihydropulchellin 

Downstream Products

• 16909-98-1 diacetylneopulchellin 
• 78798-42-2 6-deoxychamissonolide 

Relevant academic research and scientific papers

Structure-cytotoxicity relationships of some helenanolide-type sesquiterpene lactones

This study deals with the cytotoxicity of helenanolide-type (10α- methylpseudoguaianolide) sesquiterpene lactones. We determined the influence of substitution patterns on the toxicity of 21 helenanolides to a cloned Ehrlich ascites tumor cell line, EN2. Within a series of helenalin esters, the acetate (2) and isobutyrate (3) were more toxic than helenalin itself (1). Esters with larger acyl groups (tiglate 4 and isovalerate 5) exhibited a decreased toxicity compared with the parent alcohol (1). Similar relationships were observed between the 6,8-diastereomer of helenalin, mexicanin I (6) and its acetate (7) and isovalerate (8). In contrast, cytotoxicity within a series of 11α,13-dihydrohelenalin esters (9-12) was shown to be directly related to the size and lipophilicity of the ester side chain, dihydrohelenalin (9) being the least toxic compound in this group. Investigation of several 2,3-dihydrohelenalin derivatives (13-21) with 2α- hydroxy-4-oxo- and 2α,4α-dihydroxy- or -O-acyl-substituted cyclopentane rings (arnifolins and chamissonolides, respectively), for which no pharmacological data have been reported so far, revealed further interesting influences of the substitution pattern on cytotoxicity. The results may be interpreted in terms of lipophilicity and steric effects on the accessibility of the reactive sites considered responsible for biological activity.

STRUCTURE-ACTIVITY RELATIONSHIPS OF PSEUDOGUAIANOLIDES ISOLATED FROM GAILLARDIA PULCHELLA AND THEIR DERIVATIVES

Three new pseudoguaianolides, 4-epipulchellin (1), 4-epineopulchellin (2) and pulchelloid D (3), were isolated from Gaillardia pulchella together with other eleven pseudoguaianolides and three guaianolides.Fifteen natural sesquiterpene lactones and their thirty one derivatives were tested for cytotoxic activity against KB cell line.Among them, twenty seven compounds were shown to be active (ED50 4 μg/ml).The structure-activity relationships of these sesquiterpene lactones are discussed.

ISOLATION AND STRUCTURE OF NEW PSEUDOGUAIANOLIDES,4-EPIPULCHELLIN AND 4-EPINEOPULCHELLIN FROM GAILLARDIA PULCHELLA

The structure of 4-epipulchellin (1a) and 4-epineopulchellin (1b), new pseudoguaianolide sesquiterpene lactones isolated from Gaillarda pulchella, was determined on the basis of spectroscopic data and chemical transformations from pulchellin (2a) and neopulchellin (2b) into 1a and 1b, respectively.

CHEMICAL TRANSFORMATION OF AROMATICIN INTO PULCHELLIN-A FORMAL SYNTHESIS OF PULCHELLIDINE

A chemical transformation o aromaticin into pulchellin implying the formal synthesis of pulchellidine was achieved.The stereochemistry of the diol isomers of dihydropulchellin was also revealed.