Gibberellic acid Chemical Properties

Melting point:

227 °C

alpha 

82.5 º (c=10, ethanol)

Boiling point:

401.12°C (rough estimate)

Density 

1.34 g/cm3 (20℃)

refractive index 

81 ° (C=2, MeOH)

storage temp. 

0-6°C

solubility 

5g/l

form 

Powder

pka

4.0(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.

InChIKey

IXORZMNAPKEEDV-OBDJNFEBSA-N

LogP

0.240

CAS DataBase Reference

77-06-5

NIST Chemistry Reference

Gibberellic acid(77-06-5)

EPA Substance Registry System

Gibberellic 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

F 

10

TSCA 

Yes

HS Code 

29322980

Hazardous Substances Data

77-06-5(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 6300 mg/kg LD50 dermal Rabbit > 2000 mg/kg

MSDS

• Language:English Provider:2,4a,7-Trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-dicarboxylic acid 1,4a-lactone
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Gibberellic acid Usage And Synthesis

Description

Gibberellic 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 Properties

white powder

Uses

Gibberellic 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.

Uses

Gibberellic 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.

Definition

ChEBI: A C19-gibberellin that is a pentacyclic diterpenoid responsible for promoting growth and elongation of cells in plants.

Biosynthesis

The 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].

General Description

White powder.

Air & Water Reactions

Slightly water soluble .

Reactivity Profile

Gibberellic acid is readily degraded by acids. .

Fire Hazard

Flash point data for Gibberellic acid are not available. Gibberellic acid is probably combustible.

Agricultural Uses

Plant 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 Uses

Gibberellic acid is an organic acid used as a plant growth hormone. It is formed by the fungus Gibberellafujikuroi in aerated submerged culture.

Agricultural Uses

Gibberellin 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 C_l9H₂₂O₆, gibberellins are also produced by Azotobacter, Azospirillum, etc.

Trade name

ACTIVOL®; 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 Actions

Phytohormone 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 Profile

Mildly toxic by ingestion. Questionable carcinogen with experimental tumorigenic data. hlutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

It 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 evaluation

75 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

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