Gibberellin A4

For research use only. Not for therapeutic Use.

  • CAT Number: R015652
  • CAS Number: 468-44-0
  • Molecular Formula: C₁₉H₂₄O₅
  • Molecular Weight: 332.39
  • Purity: ≥95%
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Gibberellin A4(CAS: 468-44-0) is a C19-gibberellin, initially identified in Gibberella fujikuroi and differing from gibberellin A1 by the substitution of the OH at C-7 (gibbane numbering) by H. It has a role as a plant metabolite. It is a lactone, a gibberellin monocarboxylic acid and a C19-gibberellin. It is a conjugate acid of a gibberellin A4(1-).


Catalog Number R015652
CAS Number 468-44-0
Synonyms

4a,1-(Epoxymethano)-7,9a-methanobenz[a]azulene, gibbane-1,10-dicarboxylic Acid Deriv.; GA4; 2β,4a-Dihydroxy-1-methyl-8-methylene-4aα,4bβ-gibbane-1α,10β-dicarboxylic Acid; (1α,2β,4aα,4bβ,10β)-2,4a-Dihydroxy-1-methyl-8-methylene-gibbane-1,10-dicarboxyl

Molecular Formula C₁₉H₂₄O₅
Purity ≥95%
Target Disease Research Fields
Storage -20°C
IUPAC Name (1R,2R,5R,8R,9S,10R,11S,12S)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadecane-9-carboxylic acid
InChI InChI=1S/C19H24O5/c1-9-7-18-8-10(9)3-4-11(18)19-6-5-12(20)17(2,16(23)24-19)14(19)13(18)15(21)22/h10-14,20H,1,3-8H2,2H3,(H,21,22)/t10-,11-,12+,13-,14-,17-,18+,19-/m1/s1
InChIKey RSQSQJNRHICNNH-NFMPGMCNSA-N
SMILES CC12C(CCC3(C1C(C45C3CCC(C4)C(=C)C5)C(=O)O)OC2=O)O
Reference

[1]: Sugai Y, Miyazaki S, Mukai S, Yumoto I, Natsume M, Kawaide H. Enzymatic total synthesis of gibberellin A₄ from acetate. Biosci Biotechnol Biochem. 2011;75(1):128-35. doi: 10.1271/bbb.100733. Epub 2011 Jan 7. PMID: 21228464.<br />
[2]: Hua YF, Li HY, Ma LL, Zhang X, Jin ZM. Gibberellin A4 monohydrate. Acta Crystallogr Sect E Struct Rep Online. 2007 Dec 6;64(Pt 1):o30. doi: 10.1107/S160053680706062X. PMID: 21200864; PMCID: PMC2914990.<br />
[3]: Hua Y, Sansenya S, Saetang C, Wakuta S, Ketudat Cairns JR. Enzymatic and structural characterization of hydrolysis of gibberellin A4 glucosyl ester by a rice &beta;-D-glucosidase. Arch Biochem Biophys. 2013 Sep 1;537(1):39-48. doi: 10.1016/j.abb.2013.06.005. Epub 2013 Jun 26. PMID: 23811195.<br />
[4]: Lale G, Gadre R. Enhanced production of gibberellin A4 (GA4) by a mutant of Gibberella fujikuroi in wheat gluten medium. J Ind Microbiol Biotechnol. 2010 Mar;37(3):297-306. doi: 10.1007/s10295-009-0673-1. Epub 2009 Dec 5. PMID: 19967447.<br />
[5]: Looney NE, Pharis RP, Noma M. Promotion of flowering in apple trees with gibberellin A4 and C-3 epi-gibberellin A 4. Planta. 1985 Aug;165(2):292-4. doi: 10.1007/BF00395054. PMID: 24241056.

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