Gibberellinsäure

(+)-Gibberellic Acid

HCID 6466CAS 77-06-5

Grundinformationen

Standard-SMILES
C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@@]12C=C[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O
InChIKey
IXORZMNAPKEEDV-OBDJNFEBSA-N
Summenformel
C19H22O6
Durchschnittliche Molmasse
346,4 g/mol
Monoisotopische Masse
346,14163842

Überblick

Gibberellic acid is a white powder. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
(+)-Gibberellic Acid
IUPAC
(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
Lokaler Name
Gibberellinsäure
Englischer Name
Gibberellic acid
Summenformel
C19H22O6
Molmasse
346.38

Namen und Synonyme

GIBBERELLIC ACIDGibberellin A377-06-5BerelexBrellinGibberellin XGib-SolGibreskolCekugibGibberellic acid GA3Gib-TabsPro-Gibb
Weitere Namen anzeigen
GA3GIBBERELLINGIBBERELIC ACIDGibberellicGibberellinsGIBBERLIC ACIDGibberellin Acid
Pro-Gibb PlusGibrescolGrocelRyzupGibberellins A4A7GibefolRegulexActivol GA

Datenbank-Bezeichner

CAS
77-06-5
PubChem CID
6466
DTXSID
DTXSID0020656
ChEMBL
CHEMBL1232952
ChEBI
CHEBI:28833
UNII
BU0A7MWB6L
EC Number
201-001-0
Nikkaji
J8.602I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,2
Polarare Oberfläche (TPSA)
104 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
1
Schwere Atome
25

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C20 isoprenoids (diterpenes) [PR0104]
pHpH = 4.0
SpringerMaterials PropertiesCrystal structure
Pesticides · 4 Einträge

Plant Growth Regulators

Active substance -> EU Pesticides database: Approved

Pesticides -> Plant Growth Regulators

Environmental transformation -> Pesticides (parent, predecessor)

LogP · 3 Einträge

log Kow = 0.24

0.24

0.24

Physikochemische Eigenschaften

Schmelzpunkt
227 °C · 227 °C
Siedepunkt
401.12 °C · 401.12°C (rough estimate)
Dichte
1.34 g/cm3 · 1.34 g/cm3 (20℃)
Brechungsindex
81 ° · 81 ° (C=2, MeOH)
storage temp.
0 · 0-6°C
Löslichkeit
5 g/l · 5g/l

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 37.9% (97 of 256) of reports.

Warning

H319 (61.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P273, P280, P305+P351+P338, P337+P317, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 256 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 3 Einträge

Commission Regulation (EC) No 2229/2004

2008/127, Reg (EU) 2025/2313 , Reg. (EU) 2017/195, Reg. (EU) 2020/1160, Reg. (EU) 2021/745, Reg. (EU) 2022/708, Reg. (EU) 2023/1446, Reg. (EU) 2025/787, Reg. (EU) No 540/2011

Gibberellic acid (> 90% A3): Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Gibb-3-ene-1,10-dicarboxylic acid, 2,4a,7-trihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1.alpha.,2.beta.,4a.alpha.,4b.beta.,10.beta.)-: Environment tier I assessment
Fire HazardsFlash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Hazards SummaryAn irritant; [MSDSonline]
FDA Requirements · 1 Eintrag

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.

Reactive GroupAcids, Carboxylic

Sicherheit und Schutzausrüstung

Fire FightingTo extinguish a fire involving this chemical you may use a dry chemical, carbon dioxide, foam or halon extinguisher; a water spray may also be used. (NTP, 1992)
First Aid · 1 Eintrag

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Storage Conditions · 2 Einträge

Ensure adequate ventilation in confined spaces. Store in original container, tightly closed, away from all sources of heat. /May be stored for/ at least 2 yr under normal storage conditions in unopened containers.

Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water.

Cleanup Methods · 2 Einträge

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.

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 4 Einträge

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.

Toxikologische Informationen

Ecotoxicity Values · 3 Einträge

LC50 Colinus virginianus (Northern bobwhite, 14 days old) dietary >4640 ppm/8 days

EC50 Daphnia magna (Water flea, <24 hr old; intoxication, immobilization) >143 ppm/48 hr; static /86.9% AI formulated product/

LC50 Oncorhynchus mykiss (Rainbow trout, weight 0.32 g) >150 ppm/96 hr; static /86.9% AI formulated product/

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 32(SRC), determined from a log Kow of 0.24(2) and a regression-derived equation(3), indicates that gibberellic acid is expected to have very high mobility in soil(SRC). The pKa of gibberellic acid is 4.0(4), indicating that this compound will primarily exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of gibberellic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-15 atm-cu m/mole(SRC), using a fragment constant estimation method(6). Gibberellic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.3X10-13 mm Hg(SRC), determined from a fragment constant method(7). Biodegradation of gibberellic acid was found to be 85% after 5 days of incubation at 24 °C and > 90% after 10 days using a hydroponic solution supporting the growth of dwarf peas(8), suggesting biodegradation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 32(SRC), determined from a log Kow of 0.24(2) and a regression-derived equation(3), indicates that gibberellic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.6X10-15 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). The pKa of gibberellic acid is 4(5), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(6). According to a classification scheme(7), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Gibberellic acid is slowly hydrolyzed by water and rapidly decomposed by heat or chlorine (for example in water)(9). Biodegradation of gibberellic acid was found to be 85% after 5 days of incubation at 24 °C and > 90% after 10 days using a hydroponic solution supporting the growth of dwarf peas(10), suggesting biodegradation may be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), gibberellic acid, which has an estimated vapor pressure of 1.3X10-13 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase gibberellic acid may be removed from the air by wet or dry deposition(SRC).

Soil Adsorption/Mobility · 1 Eintrag

The Koc of gibberellic acid is estimated as 32(SRC), using a log Kow of 0.24(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that gibberellic acid is expected to have very high mobility in soil. The pKa of gibberellic acid is 4, indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(4).

Natural Pollution Sources · 2 Einträge

The number of gibberellins found in nature increased from 27 in 1969 to 45 in 1975, and to 62 in 1986. However, only three /including gibberellic acid/ of these possess significant biological properties.

Gibberellic acids are naturally occurring plant hormones and are produced by several molds, principally Gibberella fujikuroi(1).

Artificial Pollution SourcesGibberellic acid's production and use as a growth regulator(1) results in its direct release to the environment(SRC). Gibberellic acid is mostly used on grape, citrus, and apple crops, but has also been used on a variety of other crops(2).
Environmental BiodegradationAEROBIC: Biodegradation of gibberellic acid was found to be 85% and >90% after 5 days and 10 days, respectively, of incubation in the dark at 24 °C using a hydroponic solution supporting the growth of dwarf peas(1).

Regulatorische Informationen

FDA Requirements · 1 Eintrag

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.

FIFRA Requirements · 3 Einträge

An exemption from the requirement of a tolerance is established for residues of gibberellins [gibberellic acids (GA3 and GA4 + GA7), and sodium or potassium gibberellate] in or on all food commodities when used as plant regulators on plants, seeds, or cuttings and on all food commodities after harvest in accordance with good agricultural practices.

Section 4(g)(2)(A) of FIFRA calls for the Agency to determine, after submission of relevant data concerning an active ingredient, whether products containing the active ingredients are eligible for reregistration. The Agency has previously identified and required the submission of the generic (i.e. active ingredient specific) data required to support reregistration of products containing giberellic acids as their active ingredients. The Agency has completed its review of these generic data, and has determined that the data are sufficient to support reregistration of all products containing gibberellic acids.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Gibberellic acid is found on List D. Case No: 4110; Pesticide type: plant growth regulator; Case Status: RED Approved 03-96; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document .; Active ingredient (AI): gibberellic acid; Data Call-in (DCI) Date(s): 09/23/93; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI..

Sicherheitsdaten

F
10
wgk
3
tsca
TSCA listed
ridadr
None [88] Not regulated.
hs_code
29322980
RTECS-Nr.
LY8990000

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 2 Einträge

Gibberellic acid enhanced activity of rat lung guanylate cyclase, an enzyme associated with growth.

Gibberellic acid has androgenic activity in chicks.

MeSH Pharmacological ClassificationAny of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins.
Absorption, Distribution and ExcretionTranslocated /in plants/.
Cellular LocationsExtracellular

Verwendung und Herstellung

Uses · 6 Einträge

A metabolite of Gibberella fujikuroi that promotes plant growth; [Merck Index] Used as plant growth regulator to improve various qualities of many fruits and vegetables and to improve enzymatic characteristics of barley malting; [HSDB] Naturally occurring plant hormone used to increase fruit and crop yields; [Reference #1]

Farming (Pesticides) [Category: Industry]

For gibberellic acid (USEPA/OPP Pesticide Code: 043801) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Plant growth regulator

Seedless grape enlarger ... flowering initiator

Plant growth regulator ... to loosen and elongate clusters and increase berry size in grapes; to control fruit maturity by delaying development to the yellow color in lemons; to reduce rind stain and retard rind ageing in navel oranges; to counteract the effects of cherry yellows virus diseases in sour cherries; to promote elongation of winter celery crop; to induce uniform bolting and increase seed production in lettuce for seed; to break dormancy and stimulate sprouting in seed potatoes; to extend the picking season by hastening maturity in artichokes; to increase the yield in forced rhubarb; ... to produce brighter- colored, firmer fruit, and to increase the size of sweet cherries; to increase yields and aid harvesting of hops; to reduce internal browning and increase yields of Italian prunes; to increase fruit set and yields of tangelos and tangerines; to improve fruit setting in blueberries; to advance flowering and increase the yield of strawberries; and also a variety of applications on ornamentals.

U.S. Production · 2 Einträge

(1976) PROBABLY GREATER THAN 2.27X10+6 GRAMS

(1978) PROBABLY GREATER THAN 4.54X10+6 GRAMS

Consumption Patterns(1992): 2573 lbs to apples, 86 lbs to artichokes, 66 lbs to blueberries, 10 lbs to carrots, 629 lbs to cherries, 3473 lbs to citrus, 23778 lbs to grapes, 20lbs to hops.
Methods of Manufacturing · 2 Einträge

Produced by several molds, principally gibberella fujikuroi.

Gibberellic acid is produced commercially by fermentation.

Formulations/Preparations · 5 Einträge

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

For more Formulations/Preparations (Complete) data for GIBBERELLIC ACID (10 total), please visit the HSDB record page.

Use Classification · 2 Einträge

Environmental transformation -> Pesticides (parent, predecessor)

Plant growth regulators

Anwendungen · 2 Einträge

BeschreibungGibberellic 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.

VerwendenGibberellic 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.

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Ergänzende Hinweise

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

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