51576-08-0

Usage

Uses

Used in Pharmaceutical Industry:
7-Hydroxy-1β,4aα-dimethyl-8-methylenegibbane-1α,10β-dicarboxylic acid is used as a pharmaceutical compound for its potential therapeutic effects. 7-Hydroxy-1β,4aα-dimethyl-8-methylenegibbane-1α,10β-dicarboxylic acid's unique structure allows it to interact with various biological targets, making it a promising candidate for the development of new drugs.
Used in Agricultural Industry:
As a derivative of Gibberellin A53, a plant hormone that regulates growth and developmental processes, 7-Hydroxy-1β,4aα-dimethyl-8-methylenegibbane-1α,10β-dicarboxylic acid is used in the agricultural industry to enhance crop growth and yield. By modulating plant growth hormones, 7-Hydroxy-1β,4aα-dimethyl-8-methylenegibbane-1α,10β-dicarboxylic acid can potentially improve the efficiency of crop production and contribute to food security.
Used in Chemical Research:
The complex structure of 7-Hydroxy-1β,4aα-dimethyl-8-methylenegibbane-1α,10β-dicarboxylic acid makes it an interesting subject for chemical research. It can be used as a starting material for the synthesis of other complex organic compounds or as a model system to study the properties and reactivity of similar molecules.
Used in Material Science:
The unique molecular structure of 7-Hydroxy-1β,4aα-dimethyl-8-methylenegibbane-1α,10β-dicarboxylic acid may also find applications in material science. Its functional groups could be exploited to create new materials with specific properties, such as improved mechanical strength, thermal stability, or chemical resistance.

InChI:InChI=1/C20H28O5/c1-11-9-19-10-20(11,25)8-5-12(19)17(2)6-4-7-18(3,16(23)24)14(17)13(19)15(21)22/h12-14,25H,1,4-10H2,2-3H3,(H,21,22)(H,23,24)/t12-,13+,14-,17-,18+,19-,20-/m0/s1

Upstream product

• 85344-33-8 13-hydroxygibberellin A₁₂-7-aldehyde 
• 29584-19-8 steviol 
• 177781-09-8 C₂₂H₃₂O₆ 
• 144708-75-8 C₂₂H₃₀O₇ 
• 97292-40-5 C₂₃H₃₂O₇ 

Relevant academic research and scientific papers

Synthesis of gibberellin GA53 and its (17,17-D2)derivative

Gibberellin GA53 (1) has been prepared by a modified Wolff-Kishner reduction of gibberellin GA19 protected as its 13-methoxymethyl ether (11). Careful regulation of the temperature at c. 174° is necessary, otherwise migration of the 16-ene function into the endocyclic 15-ene position occurs to an increasing extent at higher temperatures. The methodology was also extended to the preparation of the (17,17-D2)derivative (20).

Preparation of 13-Hydroxygibberellin A12-7-Aldehyde

7β- and 7α-Hydroxykaurenolides have been efficiently 13-hydroxylated by cultures of Rhizopus arrhizus.The products have been chemically converted into the title compound.In an alternative preparation, gibberellin A12-7-aldehyde, gibberellin A12-7-aldehyde (prepared from 7β,18-dihydroxykaurenolide), and gibberellin A12-7-aldehyde (prepared, by hydrogen-tritium exchange, from gibberellin A12-7-aldehyde), have been 13-hydroxylated by cultures of Rhizopus arrhizus to give the unlabelled and the - and -labelled title compound. 13-Hydroxylation of gibberellin A12-7-alcohol by cultures of Rhizopus arrhizus, followed by oxidation, also gave 13-hydroxygibberellin A12-7-aldehyde.

Metabolism of Steviol and Its Derivatives by Gibberella fujikuroi

Steviol (ent-13-hydroxykaur-16-en-19-oic acid is metabolized by Gibberella fujikuroi in the presence of inhibitors of gibberellin biosynthesis, such as quaternary ammonium salt-type growth retardants, to afford 7β-hydroxy- and 6β,7β-dihydroxysteviol, gibberellins A1, A18, A19, A53 and 7β,13-dihydroxykaurenolide.Steviol acetate (ent-13-acetoxykaur-16-en-19-oic acid) is also metabolized to the 6β,7β-dihydroxy-derivative and to the 13-acetyl derivatives of gibberellins A17 and A20 and steviol methyl ester (methyl ent-13-hydroxykaur-16-en-19-oate) into the monohydroxy-, dihydroxy- and hydroxyoxo-derivatives.These results indicate a low substrate specificity of the enzymes in the fungus and provide a useful preparative methodology of several important plant gibberellins carrying the 13-hydroxyl group.