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Gibberellic acid

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Related articles

  • What is gibberellic acid used for?
  • Gibberellic acid (GA) is a naturally occurring plant hormone. GA has been used in citrus production for years to improve fruit....
  • Dec 14,2022
Gibberellic acid Basic information
Product Name:Gibberellic acid
Synonyms:RYZUPSTRONG;(1alpha,2beta,4aalpha,4bbeta,10beta)-2,4a,7-trihydroxy-1-methyl-8-methylenegibb;(1alpha,2beta,4aalpha,4bbeta,10beta)-2,4a,7-Trihydroxy-1-methyl-8-methylgibb-3-ene-1,10-dicarboxylic acid 1,4a-lactone;(1alpha,2beta,4aalpha,4bbeta,10beta)-a-lacton;(3s,3ar,4s,4as,7s,9ar,9br,12s)-7,12-dihydroxy-3-methyl-6-methylene-2-oxoperhyd;(3s,3as,4s,4as,6s,8as,8bs,11s)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6;ethano-3,8b-prop-l-enoperhydroindeno-(1,2-b)furan-4-carboxylicacid;Gibb-3-ene-1,10-dicarboxylic acid, 2,4a,7-trihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1alpha,2beta,4aalpha,4bbeta,10beta)-
CAS:77-06-5
MF:C19H22O6
MW:346.38
EINECS:201-001-0
Product Categories:plantgrowth;Inhibitors;Pharmaceutical intermediates;FINE Chemical & INTERMEDIATES;Plant Oils, Toxins, Phenolic Acids & Derivatives;Biochemistry;Plant Growth Regulators;Plant Growth Trgulators (Others);Antibiotic Explorer;77-06-5
Mol File:77-06-5.mol
Gibberellic acid Structure
Gibberellic acid Chemical Properties
Melting point 227 °C
Boiling point 401.12°C (rough estimate)
alpha 82.5 º (c=10, ethanol)
density 1.34 g/cm3 (20℃)
refractive index 81 ° (C=2, MeOH)
storage temp. 0-6°C
solubility 5g/l
form Powder
pka4.0(at 25℃)
color White to pale yellow
optical activity[α]20/D +80±3°, c = 1% in methanol
Water Solubility 5 g/L (20 º C)
Merck 14,4419
BRN 54346
Stability:Stable. Combustible. Incompatible with acids, strong oxidizing agents.
InChIKeyIXORZMNAPKEEDV-OBDJNFEBSA-N
LogP0.240
CAS DataBase Reference77-06-5
NIST Chemistry ReferenceGibberellic acid(77-06-5)
EPA Substance Registry SystemGibberellic acid (77-06-5)
Safety Information
Hazard Codes Xi
Risk Statements 36
Safety Statements 26-36-24/25
RIDADR None [88] Not regulated.
WGK Germany 3
RTECS LY8990000
10
TSCA Yes
HS Code 29322980
Hazardous Substances Data77-06-5(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 6300 mg/kg LD50 dermal Rabbit > 2000 mg/kg
MSDS Information
Gibberellic acid Usage And Synthesis
DescriptionGibberellic acid (GA) is a tetracyclic di-terpenoid compound. It is one of the major hormones that can be synthesized in plants and fungi. It has various kinds of physiological effects including stimulating seed germination, inducing mitotic division of the leaves, triggering transitions from meristem to shoot growth, vegetative to flowering, determining sex expression and grain development through crosstalk with many environmental signals such as light, temperature and water. In lab and greenhouse, it can be used to trigger germination of seeds which has previously remained dormant. It can also used to induce the production of larger amount and bigger grapes, boosting the grape industry. In industry, GA can be produced from Solid-state Fermentation (SSF) which can have relatively high yield.
Chemical Propertieswhite powder
UsesGibberellic Acid is a a pentacyclic diterpene acid. Gibberellic Acid is a hormone that is found in plants which promotes the growth and elongation of cells. Gibberellic acid acts as a plant growth reg ulator on account of its physiological and morphological effects in extremely low concentrations. Generally Gibberellic acid affects only the plant parts above the soil surface.
UsesGibberellic acid is used as a plant growth hormone. It is also used to trigger germination in dormant seeds in laboratory and green house settings and to stimulate rapid stem and root growth and induce mitotic division in the leaves of some plants. It also serves in grape growing industry as a hormone to induce the production of larger bundles and bigger grape.
DefinitionChEBI: A C19-gibberellin that is a pentacyclic diterpenoid responsible for promoting growth and elongation of cells in plants.
BiosynthesisThe presence of GA in actively growing tissues, i.e., shoot apices, young leaves, and flowers. Gibberellins (GAs; Gibberellic acids) being synthesized via the terpenoid pathway, require 3 enzymes viz., terpene synthase (TPSs), cytochrome P450 monooxygenase (P450s) and 2-oxoglutarate dependent dehydrogenase (2 ODDs), for the biosynthesis of bioactive GA from geranylgeranyl diphosphate in plants. Two terpene synthases, ent-copalyl diphosphate synthase (CPS) and ent-kaurene synthase (KS), located in plastids, are involved in the conversion of GGDP to tetracyclic hydrocarbon intermediate ent-kaurene. ent-Kaurene is then converted to GA12 by 2 P450s. First, ent-Kaurene oxidase (KO), present in the plastid's outer membrane, catalyzes the sequential oxidation of C-19 to produce ent-kaurenoic acid. Second, the kaurenoic acid oxidase (KAO) in the endoplasmic reticulum is converted to GA12. Bioactive GA4 is converted from GA12 through oxidations on C-20 and C-3 by GA 20-oxidase (GA20ox) and GA 3-oxidase (GA3ox)[3].
Gibberellic acid
General DescriptionWhite powder.
Air & Water ReactionsSlightly water soluble .
Reactivity ProfileGibberellic acid is readily degraded by acids. .
Fire HazardFlash point data for Gibberellic acid are not available. Gibberellic acid is probably combustible.
Agricultural UsesPlant growth hormone, Plant regulator: Gibberellic acids (Gibberellins) are naturally occurring plant hormones that are used as plant growth regulators to stimulate both cell division and elongation that affects leaves and stems. Applications of this hormone also hastens plant maturation and seed germination. Delayed harvesting of fruits, allowing them to grow larger. Gibberellic acids are applied to growing field crops, small fruits, grapes, vines and tree fruit, and ornamentals, shrubs and vines.
Agricultural UsesGibberellin is a growth promoting substance found widely in plants. It was first isolated from the fungus Gibberella. Gibberellin increases the rate of photosynthesis and helps in the elongation of cells. It promotes the flowering and germination of plants. With a general formula of Cl9H22O6, gibberellins are also produced by Azotobacter, Azospirillum, etc.
Agricultural UsesGibberellic acid is an organic acid used as a plant growth hormone. It is formed by the fungus Gibberellafujikuroi in aerated submerged culture.
Trade nameACTIVOL®; BERELEX®; BRELLIN®; BOLL-SET®; CEKUGIB®; CROP BOOSTER®; CYTOPLEX HMS®, DYNOGEN®; FALGRO®; FLORALTONE® (with 2,3,5-triiodobenzoic acid); FLORGIB®; FOLI-ZYME®; GIBBEX®; GIBBERELLIN A 3 ®; GIBBERELLIN X®; GIBBREL®; GIBGRO®; GIB-SOL®; GIB-TABS®; GIBRESCOL®; GROCEL®; KALGIBB®; MAXON®; N-LARGE®; NOVAGIB®; PGR-IV®; PRO-GIBB®; REGULEX®; RELEASE®; RELAX®; RYZUP®; STIMULATE®; VIGOR®
Biochem/physiol ActionsPhytohormone that controls important aspects of plant growth: germination, elongation, and flowering. The effects are mediated by inducing degradation of the DELLA repressor protein, and probably other minor signalling pathways.
Safety ProfileMildly toxic by ingestion. Questionable carcinogen with experimental tumorigenic data. hlutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Purification MethodsIt crystallises from EtOAc, EtOAc/pet ether, MeOH/pet ether or Me2CO/pet ether. [Cross J Chem Soc 3022 1960, Beilstein 18 III/IV 6533.]
Toxicity evaluation75 ppm of Gibberellic acid (GA3) in drinking water was continuously administered orally to rats (Sprague-Dawley albino) ad libitum for 50 days. The lipid peroxidation end product MDA significantly increased in the lungs, heart, and kidney of rats treated with GA3 without significant change in the spleen. Antioxidant enzyme activities such as SOD significantly increased in the lungs and stomach and decreased in the spleen and heart tissues of rats treated with GA3[4].
References[1]https://en.wikipedia.org/wiki/Gibberellic_acid
[2]https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4002599/
[3] Gupta, Ramwant, and S K Chakrabarty. “Gibberellic acid in plant: still a mystery unresolved.” Plant signaling & behavior vol. 8,9 (2013): e25504. doi:10.4161/psb.25504
[4]Celik, Ismail et al. “Evalution of toxicity of abcisic acid and gibberellic acid in rats: 50 days drinking water study.” Journal of enzyme inhibition and medicinal chemistry vol. 22,2 (2007): 219-26. doi:10.1080/14756360600988955
Gibberellic acid Preparation Products And Raw materials
Raw materialsEthanol-->Ethyl acetate-->Methanol-->Sulfuric acid-->Sodium carbonate-->D(+)-Glucose-->Starch-->Sucrose-->Potassium Phosphate Monobasic
Preparation ProductsFOOD ADDITIVES-->Gibberellin A5-->gibberellin A1-->gibberic acid
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