3D Mol Similar

Gibberellic acid

: 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; CAS No.: 77-06-5; Molecular Weight：346.37438; Modify Date.: 2022-11-07 09:53; Introduction: 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. View more+

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1. Names and Identifiers

: 1.1 Name; Gibberellic acid; 1.2 Synonyms; (1a,2b,4aa,4bb,10b)-2,4a,7-Trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-dicarboxylic Acid 1,4a-Lactone (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 (1R,2R,5S,8S,9S,10R,12S)-5,12-Dihydroxy-11-methyl-6-methylene-16-oxo-15-oxapentacyclo[9.3.2.1.0.0]heptadec-13-ene-9-carboxylic acid (1S,2S,4aR,4bR,7S,9aS,10S,10aR)-1,2,4b,5,6,7,8,9,10,10a-decahydro-2,7-dihydroxy-1-methyl-8-methylene-13-oxo-4a,1-(epoxymethano)-7,9a-methanobenz[a]azulene-10-carboxylic acid (1S,2S,4aR,4bR,7S,9aS,10S,10aR)-2,7-dihydroxy-1-methyl-8-methylidene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid (2S,4aR,4bR,7S,9aS,10S,10aR)-2,7-dihydroxy-1-methyl-8-methylidene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid (3S,3aR,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid (3s,3ar,4s,4as,7s,9ar,9br,12s)-7,12-dihydroxy-3-methyl-6-methylene-2-oxoperhyd (3S,3aR,4S,4aS,7S,9aR,9bR,12S)-7,12-Dihydroxy-3-methyl-6-methylene-2-oxoperhydro-4a,7-methano-9b,3-propenoazuleno[1,2-b]furan-4-carboxylic acid (3s,3as,4s,4as,6s,8as,8bs,11s)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6 (3S,3aS,4S,4aS,7S,9aR,9bR,12S)-7,12-dihydroxy-3-methyl-6-methylene-2-oxoperhydro-4a,7-methano-9b,3-propenoazuleno[1,2-b]furan-4-carboxylic acid 4a,1-(Epoxymethano)-7,9a-methanobenz[a]azulene-10-carboxylic acid, 1,2,4b,5,6,7,8,9,10,10a-decahydro-2,7-dihydroxy-1-methyl-8-methylene-13-oxo-, (2S,4aR,4bR,7S,9aS,10S,10aR)- Activol EINECS 201-001-0 GA3 GIB Gibberelic acid Gibberellic acid GA3 gibberellin Gibberellin A3 Gibberellin X GIBBEX Gibbrel GIBERELLIN GIBREL Grocel Maxon MFCD00079329 pgr-iv PRO-GIBB Ralex RELEASE ryzup RYZUPSTRONG UVEX; View all

1.3 CAS No.: 77-06-5

1.4 CID: 6466

1.5 EINECS(EC#): 201-001-0

1.6 Molecular Formula: C19H22O6 (isomer)

1.7 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

1.8 InChIkey: IXORZMNAPKEEDV-OBDJNFEBSA-N

1.9 Canonical Smiles: CC12C(C=CC3(C1C(C45C3CCC(C4)(C(=C)C5)O)C(=O)O)OC2=O)O

1.10 Isomers Smiles: C[C@@]12[C@H](C=C[C@@]3([C@@H]1[C@@H]([C@]45[C@H]3CC[C@](C4)(C(=C)C5)O)C(=O)O)OC2=O)O

2. Properties

2.1 Density: 1.493

2.1 Melting point: 227℃

2.1 Boiling point: 628.595 °C at 760 mmHg

2.1 Refractive index: 81 ° (C=2, MeOH)

2.1 Flash Point: 231.438 °C

2.1 Precise Quality: 346.14200

2.1 PSA: 104.06000

2.1 logP: 1.02710

2.1 Solubility: 5g/l

2.2 Appearance: white crystalline powder

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: white powder

2.5 Color/Form: White powder

2.6 Decomposition: When heated to decomposition it emits acrid smoke and fumes.

2.7 Odor: Odorless

2.8 PH: pH = 4.0

2.9 pKa: 4.0(at 25℃)

2.10 Water Solubility: 5 G/L (20 o C)

2.11 Spectral Properties: Specific optical rotation: +86 deg at 19 deg C/D (conc= 2.12 g in 100 ml water)
IR: 2:363F (Aldrich Library of Infrared Spectra, Aldrich Chemical Co, Milwaukee, WI)
NMR: 3:76D (Aldrich Library of Mass Spectra, Aldrich Chemical Co, Milwaukee, WI)
MASS: 73678 (NIST/EPA/MSDC Mass Spectral Database, 1990 version)

2.12 Stability: Stable. Combustible. Incompatible with acids, strong oxidizing agents.

2.13 StorageTemp: 0-6°C

3. Use and Manufacturing

3.1 Agricultural Uses: Plant growth hormone, Plant regulator: Gibberellic acids (Gibberellins) are naturally occurring plant hormones that are used as plant growthregulators to stimulate both cell division and elongationthat 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, smallfruits, grapes, vines and tree fruit, and ornamentals, shrubsand vines.

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

3.3 General Description: White powder.

3.4 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.]

3.5 Usage: 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 regulator on account of its physiological and morphological effects in extremely low concentrations. Generally Gibberellic acid affects only the plant parts above the soil surface.

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xi

4.1 Signal Word: Warning

4.1 Risk Statements: R36

4.1 Safety Statements: S26;S36

4.1 Exposure Standards and Regulations: Gibberellic acid and its potassium salt is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient. The food additive gibberellic acid and its potassium salt may be used in the malting of barley in accordance with prescribed conditions.

4.2 Octanol/Water Partition Coefficient: log Kow = 0.24

4.3 Fire Hazard: Flash point data for Gibberellic acid are not available. Gibberellic acid is probably combustible.

4.4 Other Preventative Measures: Avoid all contact with skin and eyes; wash splashes from skin and eyes immediately.
Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.
Indoor Applications. If the label directions permit, leave all windows open and fans operating after the application is completed. If the pesticide product is only effective in an unventilated (sealed) room or house, do not stay there. Put all pets outdoors, and take yourself any your family away from treated areas for at least the length of time prescribed on the label. Apply most surface sprays only to limited areas such as cracks; don't treat entire floors, walls, or ceilings. Don't let pesticides get on any surfaces that are used for food preparation. Wash any surfaces that may have pesticide residue before placing food on them.
Indoor Applications. When using total release foggers to control pests, use no more than the amount needed and to keep foggers away from ignition sources (ovens, stoves, air conditioners, space heaters, and water heaters, for example). Foggers should not be used in small, enclosed places such as closets and cabinets or under tables and counters.
Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.; View all

4.5 Hazard Class: 5.2

4.5 Hazard Declaration: H319

4.5 Cleanup Methods: If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.
After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.

4.6 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Burial or incineration (where permitted) would be effective disposal procedures.
Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.
Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.; View all

4.7 RIDADR: 25kgs

4.7 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.

4.8 Caution Statement: P305 + P351 + P338

4.8 Formulations/Preparations: Berelex tablets containing 1 g gibberellins more than 92% gibberellic acid.
Pro-gibb plus /composed of/ 10% gibberellin a3 /which is used as/ plant growth regulator ... to increase yield of sugarcane, to thin & enlarge Thompson seedless grapes, & delay harvest of naval oranges.
Tablet (effervescent water-soluble) (1 g ai); water soluble powder (100 g/kg); unformulated crystalline ai.
Liquid concentrate: Pro-Gibb 4%, Gibberellins A4/A7
Tablet, 1 g ai
Water soluble powder, 100 g/kg, unformulated crystalline ai
Crystals; water-soluble granules; emulsifiable concentrate
Tablets, soluble granules, liquid concentrate
Discontinued /Trade/ names: Floraltone, Gib-Sol, Gib-Tabs, Gibbex, Gibrescol, Grocel, Maxon, Sudraksh.
Trade names: Agga, Gacid, Agro-Gibb, BioGibb, Cekugib, Genial, GIP, Hek-Gibb, Polar Pol-Gibb, Proacido L, ProGA3, Urigibberellin, Wopro-gib.

4.9 WGK Germany: 3

4.9 RTECS: LY8990000

4.9 Reactivities and Incompatibilities: ... Incompatible with alkaline materials and solutions containing chlorine.

4.10 Report: EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

4.11 Safety: Hazard Codes:?Xi
Risk Statements: 36?
R36:Irritating to eyes.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: LY8990000
F: 10
HS Code: 29322980
Hazardous Substances Data 77-06-5(Hazardous Substances Data)
Mildly toxic by ingestion of gibberellic acid . It is showed to be questionable carcinogen by? experimental tumorigenic data.? When heated to decomposition it emits acrid smoke and irritating fumes.

4.12 Specification: white powder
Safety Statements:26-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing

4.13 Toxicity

1.	???	dnd-sal:spr 1?mmol/L	???	PYTCAS ?? Phytochemistry. An International Journal of Plant Biochemistry. 11 (1972),3135.
2.	???	dnd-mam:lym 1?mmol/L	???	PYTCAS ?? Phytochemistry. An International Journal of Plant Biochemistry. 11 (1972),3135.
3.	???	orl-mus TDLo:142?g/kg/78W-I:ETA	???	NTIS** ?? National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB223-159 .
4.	???	orl-rat LD50:6300?mg/kg	???	85ARAE ?? Agricultural Chemicals, Books I, II, III, and IV. 3 (1976/77),43.

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : in DMSO-d6

13C NMR : Predict

1H NMR : 400 MHz in DMSO-d6

1H NMR : Predict

Predict 1H proton NMR

IR : KBr disc

Mass

Mass spectrum (electron ionization)

7. Other Information

7.0 Usage: It is a plant growth regulating hormone that promotes plant cell growth and elongation. They promote rapid stem and root growth, induce mitotic division and initiate (break dormancy) and increase seed germination rates. They are also involved in processes such as gravitropism, tensioning and floral display. Gibberellin A3 (G1025, G7645) and A4 (G7276) may be used as supplements to plant growth media such as Murashige and Skoog media.

7.1 Usage: 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.

7.2 Merck: 14,4419

7.3 BRN: 54346

7.4 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.

7.5 Chemical Properties: white powder

7.6 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.

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

7.8 General Description: White powder.

7.9 Air & Water Reactions: Slightly water soluble .

7.10 Reactivity Profile: Gibberellic acid is readily degraded by acids. .

7.11 Fire Hazard: Flash point data for Gibberellic acid are not available. Gibberellic acid is probably combustible.

7.12 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.

7.13 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.

7.14 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.

7.15 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?

7.16 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.

7.17 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.

7.18 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.]

7.19 References: https://en.wikipedia.org/wiki/Gibberellic_acid
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4002599/

8. Computational chemical data

Molecular Weight: 346.37438g/mol
Molecular Formula: C₁₉H₂₂O₆
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 346.14163842
Monoisotopic Mass: 346.14163842
Complexity: 772
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 6
Topological Polar Surface Area: 104
Heavy Atom Count: 25
Defined Atom Stereocenter Count: 8
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB4OAAAAAAAAAAAAAAAAAAAAaMEAAAwQAAABggSAGDAAAAAGgAACAAAD1SggAICCAAABgCIAiDSCAAAAAAgAAAICAEAAAgAFBYAIQACUAAFoAAIMAPK7vzPgAAAAAAAAADAAAYAACAAAYAADAAAAA==

9. Question & Answer

What are the Characteristics and Applications of Gibberellic Acid? Jul 09 2024
Introduction Gibberellic acid, commonly known as GA, is a natural plant hormone essential for plant growth and development. Belonging to the gibberellin family, this compound influences various physio..
What is Gibberellic acid and how does it affect plant growth? Apr 15 2024
Gibberellic acid (Gibberellins, GA) commonly known as "920", is an important plant growth hormone and one of the five essential plant hormones in plant growth. It is involved in many biological proce..
What are the roles of Gibberellic acid in pharmaceuticals and drug development? Mar 17 2024
Gibberellic acid, also known as gibberellin, is an important plant hormone widely used in the pharmaceutical field. It plays a crucial role in drug development. This article will explore the roles of ..
What are the benefits and precautions of using Gibberellic acid? Jun 27 2023
Gibberellic acid is a broad-spectrum plant growth regulator that promotes crop growth and development, improves yield and quality, and induces early maturation. It can also break seed, tuber, and bulb..

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