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MedKoo Cat#: 462881 | Name: Gibberellin A4
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Gibberellin A4 is a plant hormone originally isolated from G. fujikuroi that has plant signaling and growth stimulatory activities. Gibberellin A4 is found in the micropylar endothelium cells of Arabidopsis maternal seed tissue and triggers suspensor programmed cell death (PCD) in the embryo. It increases hypocotyl, but not radicle, growth of cucumber seedlings when used at concentrations ranging from 6-100 µM. Gibberellin A4 also increases flowering in apple trees when applied post-flowering in the previous year.

Chemical Structure

Gibberellin A4
Gibberellin A4
CAS#468-44-0

Theoretical Analysis

MedKoo Cat#: 462881

Name: Gibberellin A4

CAS#: 468-44-0

Chemical Formula: C19H24O5

Exact Mass: 332.1624

Molecular Weight: 332.40

Elemental Analysis: C, 68.66; H, 7.28; O, 24.07

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 550.00 2 Weeks
25mg USD 950.00 2 Weeks
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Related CAS #
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Synonym
Gibberellin GA4; Gibberellin A4; Gibberellin-A4; GA4; GA 4; GA-4;
IUPAC/Chemical Name
(1S,2S,4aR,4bR,7R,9aR,10S,10aR)-2-hydroxy-1-methyl-8-methylene-13-oxododecahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid
InChi Key
RSQSQJNRHICNNH-NFMPGMCNSA-N
InChi Code
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
SMILES Code
OC([C@H]1[C@]2([C@@]3([C@]4([C@]15C[C@@H](CC4)C(C5)=C)[H])OC([C@]2(C)[C@@H](O)CC3)=O)[H])=O
Appearance
Solid powder
Purity
>98% (mixture of isomers) (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 332.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Okada K, Wada M, Takebayashi Y, Kojima M, Sakakibara H, Nakayasu M, Mizutani M, Nakajima M, Moriya S, Shimizu T, Abe K. Columnar growth phenotype in apple results from gibberellin deficiency by ectopic expression of a dioxygenase gene. Tree Physiol. 2020 Aug 29;40(9):1205-1216. doi: 10.1093/treephys/tpaa049. PMID: 32333787. 2: Zhang X, Goatley M, Wu W, Ervin E, Shang C. Drought-induced injury is associated with hormonal alteration in Kentucky bluegrass. Plant Signal Behav. 2019;14(10):e1651607. doi: 10.1080/15592324.2019.1651607. Epub 2019 Aug 12. PMID: 31403391; PMCID: PMC6768267. 3: Shi C, Luo P, Du YT, Chen H, Huang X, Cheng TH, Luo A, Li HJ, Yang WC, Zhao P, Sun MX. Maternal control of suspensor programmed cell death via gibberellin signaling. Nat Commun. 2019 Aug 2;10(1):3484. doi: 10.1038/s41467-019-11476-3. PMID: 31375676; PMCID: PMC6677759. 4: Rizza A, Walia A, Tang B, Jones AM. Visualizing Cellular Gibberellin Levels Using the nlsGPS1 Förster Resonance Energy Transfer (FRET) Biosensor. J Vis Exp. 2019 Jan 12;(143). doi: 10.3791/58739. PMID: 30688303. 5: Li ZF, Guo Y, Ou L, Hong H, Wang J, Liu ZX, Guo B, Zhang L, Qiu L. Identification of the dwarf gene GmDW1 in soybean (Glycine max L.) by combining mapping-by-sequencing and linkage analysis. Theor Appl Genet. 2018 May;131(5):1001-1016. doi: 10.1007/s00122-017-3044-8. Epub 2018 Mar 17. PMID: 29550969; PMCID: PMC5895683. 6: Qian C, Ren N, Wang J, Xu Q, Chen X, Qi X. Effects of exogenous application of CPPU, NAA and GA4+7 on parthenocarpy and fruit quality in cucumber (Cucumis sativus L.). Food Chem. 2018 Mar 15;243:410-413. doi: 10.1016/j.foodchem.2017.09.150. Epub 2017 Sep 30. PMID: 29146357. 7: Wu W, Zhang Q, Ervin EH, Yang Z, Zhang X. Physiological Mechanism of Enhancing Salt Stress Tolerance of Perennial Ryegrass by 24-Epibrassinolide. Front Plant Sci. 2017 Jun 19;8:1017. doi: 10.3389/fpls.2017.01017. PMID: 28674542; PMCID: PMC5474491. 8: Nett RS, Contreras T, Peters RJ. Characterization of CYP115 As a Gibberellin 3-Oxidase Indicates That Certain Rhizobia Can Produce Bioactive Gibberellin A4. ACS Chem Biol. 2017 Apr 21;12(4):912-917. doi: 10.1021/acschembio.6b01038. Epub 2017 Feb 16. PMID: 28199080; PMCID: PMC5404427. 9: Nagel R, Turrini PC, Nett RS, Leach JE, Verdier V, Van Sluys MA, Peters RJ. An operon for production of bioactive gibberellin A4 phytohormone with wide distribution in the bacterial rice leaf streak pathogen Xanthomonas oryzae pv. oryzicola. New Phytol. 2017 May;214(3):1260-1266. doi: 10.1111/nph.14441. Epub 2017 Jan 30. PMID: 28134995; PMCID: PMC5388578. 10: Hua Y, Ekkhara W, Sansenya S, Srisomsap C, Roytrakul S, Saburi W, Takeda R, Matsuura H, Mori H, Ketudat Cairns JR. Identification of rice Os4BGlu13 as a β-glucosidase which hydrolyzes gibberellin A4 1-O-β-d-glucosyl ester, in addition to tuberonic acid glucoside and salicylic acid derivative glucosides. Arch Biochem Biophys. 2015 Oct 1;583:36-46. doi: 10.1016/j.abb.2015.07.021. Epub 2015 Aug 1. PMID: 26241499. 11: Tanaka J, Yano K, Aya K, Hirano K, Takehara S, Koketsu E, Ordonio RL, Park SH, Nakajima M, Ueguchi-Tanaka M, Matsuoka M. Antheridiogen determines sex in ferns via a spatiotemporally split gibberellin synthesis pathway. Science. 2014 Oct 24;346(6208):469-73. doi: 10.1126/science.1259923. PMID: 25342803. 12: Sun TP. Plant Science. Sex and the single fern. Science. 2014 Oct 24;346(6208):423-4. doi: 10.1126/science.1260948. PMID: 25342787; PMCID: PMC4406044. 13: 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 β-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. 14: Wang L, Wu Q, Duan C, Wu D, Guan Y. [Determination of gibberellins in Arabidopsis thaliana by matrix solid-phase dispersion extraction and high performance liquid chromatography-tandem mass spectrometry]. Se Pu. 2011 Sep;29(9):923-6. Chinese. PMID: 22233084. 15: Susawaengsup C, Rayanakorn M, Wongpornchai S, Wangkarn S. Investigation of plant hormone level changes in shoot tips of longan (Dimocarpus longan Lour.) treated with potassium chlorate by liquid chromatography-electrospray ionization mass spectrometry. Talanta. 2011 Aug 15;85(2):897-905. doi: 10.1016/j.talanta.2011.04.073. Epub 2011 May 6. PMID: 21726716. 16: 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. 17: 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. 18: Lee Y, Asami T, Yamaguchi I, Ueda H, Suzuki Y. A new gibberellin detection system in living cells based on antibody V(H)/V(L) interaction. Biochem Biophys Res Commun. 2008 Nov 7;376(1):134-8. doi: 10.1016/j.bbrc.2008.08.130. Epub 2008 Sep 5. PMID: 18774779. 19: 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. 20: Fei H, Zhang R, Pharis RP, Sawhney VK. Pleiotropic effects of the male sterile33 (ms33) mutation in Arabidopsis are associated with modifications in endogenous gibberellins, indole-3-acetic acid and abscisic acid. Planta. 2004 Aug;219(4):649-60. doi: 10.1007/s00425-004-1270-1. Epub 2004 Apr 24. PMID: 15107994.

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