51576-08-0

Basic information

• Product Name: 7-Hydroxy-1β,4aα-dimethyl-8-methylenegibbane-1α,10β-dicarboxylic acid
• Synonyms: 7-Hydroxy-1β,4aα-dimethyl-8-methylenegibbane-1α,10β-dicarboxylic acid;Gibberellin A53;(1R,4aS,4bS,7S,9aS,10S,10aS)-7-hydroxy-1,4a-dimethyl-8-methylenedodecahydro-1H-7,9a-methanobenzo[a]azulene-1,10-dicarboxylic acid;GA53
• CAS NO: 51576-08-0
• Molecular Formula: C20H28O5
• Molecular Weight: 348.43332
• Mol File: 51576-08-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 513.7°Cat760mmHg
• Flash Point: 278.6°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 1.05E-12mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: 7-Hydroxy-1β,4aα-dimethyl-8-methylenegibbane-1α,10β-dicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Hydroxy-1β,4aα-dimethyl-8-methylenegibbane-1α,10β-dicarboxylic acid(51576-08-0)
• EPA Substance Registry System: 7-Hydroxy-1β,4aα-dimethyl-8-methylenegibbane-1α,10β-dicarboxylic acid(51576-08-0)

Safety Data

• Hazardous Substances Data: 51576-08-0(Hazardous Substances Data)

Usage

Uses

Gibberellin A53 is a derivative of the plant hormone Gibberellin which regulates growth and various developmental processes.

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

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

Relevant articles and documents

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).

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.