Gibberellic acid
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| Category | Others |
| Catalog number | BBF-01873 |
| CAS | 77-06-5 |
| Molecular Weight | 346.38 |
| Molecular Formula | C19H22O6 |
| Purity | >95% |
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Description
Gibberellic acid is a hormone found in plants and fungi. It is a simple gibberellin, a pentacyclic diterpene acid promoting growth and elongation of cells.
Specification
| Related CAS | 125-67-7 (mono-potassium salt) |
| Synonyms | Gibberellin A3; Gibberellic acid GA3; Gibreskol; Berelex; Brellin; Cekugib; Pro-Gibb; (1alpha,2beta,4aalpha,4bbeta,10beta)-2,4a,7-Trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-dicarboxylic acid 1,4a-lactone |
| Storage | RT |
| IUPAC Name | (1R,2R,5S,8S,9S,10R,11S,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadec-13-ene-9-carboxylic acid |
| Canonical SMILES | CC12C(C=CC3(C1C(C45C3CCC(C4)(C(=C)C5)O)C(=O)O)OC2=O)O |
| InChI | InChI=1S/C19H22O6/c1-9-7-17-8-18(9,24)5-3-10(17)19-6-4-11(20)16(2,15(23)25-19)13(19)12(17)14(21)22/h4,6,10-13,20,24H,1,3,5,7-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16-,17+,18+,19-/m1/s1 |
| InChI Key | IXORZMNAPKEEDV-OBDJNFEBSA-N |
Properties
| Appearance | Crystalline |
| Application | Plant Growth Regulators |
| Boiling Point | 401.12°C at 760 mmHg |
| Melting Point | 233-235°C |
| Density | 1.34 g/cm3 |
| Solubility | Slightly soluble |
Reference Reading
1. Isomerization of Gibberellic Acid During the Brewing Process
Chunfeng Liu,Feiyun Zheng,Weikang Sun,Jinjing Wang,Chengtuo Niu,Yongxian Li,Hongxu Duan,Qi Li J Food Sci . 2019 Jun;84(6):1353-1361. doi: 10.1111/1750-3841.14620.
Gibberellic acid (GA3) was added to three types of beer barley, and the chemical changes to GA3 during the beer brewing process were studied using HPLC. The results demonstrated that the GA3 concentration decreased throughout the malting, mashing, and boiling processes and that no GA3 was detected in the congress wort. A new substance, herein called Substance A, was detected by HPLC analysis using a C18 column; this substance exhibited retention characteristics different from GA3. The concentration of Substance A increased throughout the malting, mashing, and boiling processes. Mass spectrometry revealed that Substance A has the same molecular weight as GA3 and nuclear magnetic resonance studies determined that Substance A is a structural isomer of GA3. PRACTICAL APPLICATION: This study developed a new idea to understand GA3 behavior during the brewing, which provided a practical reference for food safety in beer and other fields using GA3 as a food additive.
2. Gibberellic acid decreases Melanocallis caryaefoliae (Hemiptera: Aphididae) population density and chlorotic feeding injury to foliage in pecan orchards
Ted E Cottrell,Bruce W Wood Pest Manag Sci . 2021 Mar;77(3):1512-1519. doi: 10.1002/ps.6173.
Background:Melanocallis caryaefoliae (Davis), Monellia caryella (Fitch), and Monelliopsis pecanis Bissell (Hemiptera: Aphididae) attack pecan foliage (Carya illinoinensis [Wangenh.] K. Koch). Unlike M. caryella and M. pecanis, feeding by M. caryaefoliae triggers a physiological change within foliage mimicking natural leaf senescence; it can lead to defoliation. Pretreatment of pecan foliage with gibberellic acid (GA3) mitigates M. caryaefoliae-elicited physiological disturbances. GA3application to pecan was evaluated for efficacy regarding effects on M. caryaefoliae populations and possible negative side-effects on two natural enemy species and on return bloom of pecan.Results:All GA3treatment rate schedules significantly reduced M. caryaefoliae nymphs but not adults or adults and nymphs of M. caryella or M. pecanis. Percentage leaf chlorosis elicited by M. caryaefoliae was significantly reduced by GA3(i.e., 39.5 to 197.7 g a.i./ha). No negative side-effects of GA3treatment were detected regarding certain key natural enemy species or on return bloom of pecan.Conculusion:Application of GA3to the orchard canopy protects foliage from senescence-like physiological responses triggered by M. caryaefoliae. This reduces detrimental leaflet chlorosis, both senescence and abscission processes and horticulturally significant feeding injury. Additionally, the absence of apparent negative side-effects on key natural enemies and return bloom is suggestive of a practical means for efficacious non-insecticidal control of M. caryaefoliae populations in orchards. This novel protective effect of GA3against aphid-elicited, senescence-like physiological responses may merit investigation as an IPM tool to manage aphid species eliciting similar senescence-like damage to other crop species. Published 2020. This article is a U.S. Government work and is in the public domain in the USA.
3. Gibberellic acid application on biomass, oxidative stress response, and photosynthesis in spinach (Spinacia oleracea L.) seedlings under copper stress
Qin Gong,Duan-Dan Niu,Jing-Yi Zhou,Zhao-Hua Li,Ling Wang,Qun Kang Environ Sci Pollut Res Int . 2021 Oct;28(38):53594-53604. doi: 10.1007/s11356-021-13745-5.
The mechanism of Cu tolerance in plants and its control measures are of considerable significance for the remediation of Cu-contaminated soils. Gibberellic acid (GA3) is involved in plant growth and development and in the response to heavy metal stress. In the present study, changes in the biomass, oxidative stress response responses, and photosynthesis of spinach seedlings were examined under Cu stress with exogenous GA3applied at concentrations of 0, 3, 5, 10, 20, 40, 60, or 80 mg L-1. Under Cu stress, the plant Cu concentration and oxidative damage were greater, photosynthetic parameters and biomass declined, and antioxidant enzyme activities and the proline concentration increased. However, spinach growth did not terminate, indicating that spinach seedlings had strong Cu tolerance. When low concentrations of GA3(3-5 mg L-1) were added to Cu-stressed spinach seedlings, the damage caused by Cu stress to spinach seedlings was reduced, and the Cu tolerance of spinach seedlings was enhanced, which mainly manifested as reduced oxidation damage, an increased proline concentration, elevated antioxidant enzyme activities, decreased Cu concentration in leaves, and increased Cu concentration in roots, increased photosynthetic parameters, and an increased in the total biomass. In contrast, additions of GA3at concentrations higher than 40 mg L-1intensified oxidative damage and decreased the activities of antioxidant enzymes, photosynthetic parameters, and biomass. Additionally, the Cu concentration increased in leaves and decreased Cu concentration in roots, indicating that high concentrations of GA3aggravated stress damage and severely influenced physiological functions in spinach seedlings. In summary, the application of 3-5 mg L-1GA3to spinach seedlings in Cu-contaminated soil can be used to reduce Cu toxicity to plants and increase Cu tolerance.
4. Gibberellic acid maintains postharvest quality of Agaricus bisporus mushroom by enhancing antioxidative system and hydrogen sulfide synthesis
Dan Zhu,Fansheng Cheng,Chaoping Wang,Wenxiang Li,Ye Liu,Yang Ding,Emily Winters J Food Biochem . 2021 Oct;45(10):e13939. doi: 10.1111/jfbc.13939.
The application of gibberellic acid (GA3) treatment to the postharvest quality maintenance of white button mushroom (Agaricus bisporus) was investigated. The optimum concentration of exogenous GA3was 100 mg/L. At this concentration, the color change was inhibited, the firmness was maintained, and the weight loss and respiratory rates were reduced. The GA3group had significantly lower malonaldehyde (MDA) content and membrane permeability. Reactive oxygen species accumulation was reduced due to the regulation of polyphenol oxidase (PPO), peroxidase (POD), and superoxide dismutase (SOD) enzyme activities. Moreover, the production of endogenous gaseous signaling molecule hydrogen sulfide (H2S) was triggered by GA3treatment, which enhanced cystathionine γ-lyase (AbCSE) and cystathionine β-synthase (AbCBS) activities alongside the corresponding gene expressions. The preservation of button mushroom postharvest storage quality by GA3was most likely due to the regulation of reactive oxygen species metabolism and hydrogen sulfide biosynthesis. PRACTICAL APPLICATIONS: Mushroom is rich in nutrients and functional substances. However, due to the lack of cuticle, high respiration rate, and moisture content, mushroom's postharvest quality deteriorates rapidly. A safe and effective reagent that prevents the senescence and quality deterioration of harvested mushroom is urgently needed. The effects of plant hormone GA3on the postharvest quality of edible fungi remain unclear. The present study provided convincing evidence that 100 mg L-1of GA3effectively maintained postharvest button mushroom quality by regulating reactive oxygen species metabolism and hydrogen sulfide biosynthesis.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
