(+)-Gibberellic acid
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(+)-Gibberellic acid
structure -
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CAS No:
77-06-5
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Formula:
C19H22O6
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Chemical Name:
(+)-Gibberellic acid
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Synonyms:
Gibb-3-ene-1,10-dicarboxylic acid,2,4a,7-trihydroxy-1-methyl-8-methylene-,1,4a-lactone,(1α,2β,4aα,4bβ,10β)-;Gibberellin A3;Gibberellic acid;GA3;GA;Gibberellic acid GA3;Berelex;Gibreskol;Pro-Gibb Plus;Gibrescol;Pro-Gibb;TU 64-3-103-75;(+)-Gibberellin A3;Release LC;RyzUp;Ralex;(+)-Gibberellic acid;Maxon;Maxon (plant growth regulator);Activol;NSC 14190;NSC 19450;Arbostim;Grocel GA3;GibGro;Gibberellin GA3;Giberllon;Clemencuaje;ProGib;Berelex L;RyzUp SmartGrass;Release;1405-96-5;7121-55-3;16202-20-3;58915-44-9;192662-67-2;295313-57-4;474760-45-7;859282-71-6;1423015-91-1
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CAS No:
Description
Gibberellic Acid is named after a fungus Gibberella fujikuroi . Gibberellic Acid regulates processes of plant development and growth, including seed development and germination, stem and root growth, cell division, and flowering time[1].
Gibberellic acid is a white powder. (NTP, 1992)|Solid
Gibberellic acid is a white powder. (NTP, 1992)|Gibberellin A3 is a C19-gibberellin that is a pentacyclic diterpenoid responsible for promoting growth and elongation of cells in plants. Initially identified in Gibberella fujikuroi,it differs from gibberellin A1 in the presence of a double bond between C-3 and C-4. It has a role as a plant metabolite and a mouse metabolite. It is a lactone, a gibberellin monocarboxylic acid, an organic heteropentacyclic compound and a C19-gibberellin. It is a conjugate acid of a gibberellin A3(1-).
(+)-Gibberellic acid Basic Attributes
346.37
346.37
54346
201-001-0
BU0A7MWB6L
19450|14190
DTXSID0020656
Crystals from ethyl acetate|Fine white powder at 23 °C
29322980
Characteristics
104.06000
0.01
White to pale yellow Powder
1.34 g/cm3 (20℃)
234 °C
628.6±55.0 °C at 760 mmHg
231.4±25.0 °C
81 ° (C=2, MeOH)
H2O: 5 g/L (20 º C)
0-6°C
1.3X10-13 mm Hg at 25 °C (est)
Oral-Rat LD50: 6300 mg/kg; Oral-Mouse LD50: 8500 mg/kg
82.5 º (c=10, ethanol)
Odorless
pH = 4.0
Henry's Law constant = 1.6X10-15 atm-cu m/mol at 25 °C (est)
pKa = 4.0
PH OF 5% SOLN: 5.5-6.5; WHITE BULKY POWDER; 1 G DISSOLVES IN 20 ML WATER; SPECIFIC OPTICAL ROTATION: +43 DEG TO +60 DEG @ 25 °C/D (CONCN= 5G IN 100 ML WATER) /POTASSIUM GIBBERELLATE/|Slowly hydrolyzed by water and rapidly decomposed by heat or chlorine (for example in water).|Undergoes a rearrangement of alkali to less biologically-active compounds.|... A tetracyclic dihydroxylactonic acid.|Hydroxyl radical reaction rate constant = 1.3X10-10 cu cm/molecule-sec at 25 °C (est)
Slightly water soluble (NTP, 1992).
Acids, Carboxylic
GIBBERELLIC ACID is readily degraded by acids. (NTP, 1992).
Safety Information
5.2
NONH for all modes of transport
3
36
26-36-24/25
LY8990000
Xi
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Stable. Combustible. Incompatible with acids, strong oxidizing agents.
P305 + P351 + P338
H319
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.
... Incompatible with alkaline materials and solutions containing chlorine.
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.
USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document -Gibberellic Acids. EPA 738-r-96-005. The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of February 7, 2006: http://www.epa.gov/pesticides/reregistration/status.htm]
Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
|Warning|H319 (96.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, and P337+P313|Aggregated GHS information provided by 147 companies from 4 notifications to the ECHA C&L Inventory.
To 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)
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. STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures and away from mineral acids and bases. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
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.
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.
Toxicity
practically nontoxic
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).
Gibberellic 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).
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).
The rate constant for the vapor-phase reaction of gibberellic acid with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Gibberellic acid is slowly hydrolyzed by water and rapidly decomposed by heat or chlorine(2).
An estimated BCF of 3 was calculated for gibberellic acid(SRC), using a log Kow of 0.24(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
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).
The Henry's Law constant for gibberellic acid is estimated as 1.6X10-15 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that gibberellic acid is expected to be essentially nonvolatile from water surfaces(2). Gibberellic acid's Henry's Law constant indicates that volatilization from moist soil surfaces may not occur(SRC). Gibberellic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.1X10-13 mm Hg(SRC), determined from a fragment constant method(3).
Occupational exposure to gibberellic acid may occur through inhalation of powder and dermal contact with this compound at work places where gibberellic acid is produced or used. (SRC)
Drug Information
Any of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins. (See all compounds classified as Plant Growth Regulators.)
Translocated /in plants/.
Gibberellic acid enhanced activity of rat lung guanylate cyclase, an enzyme associated with growth.|Gibberellic acid has androgenic activity in chicks.
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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Wash contamination from the skin with soap and water. Flush contamination from eyes with clean water or saline. If irritation occurs, obtain medical treatment.|If gibberellic acid has been swallowed there is no reason to expect adverse effects.
GA(3) gibberellin
(+)-Gibberellic acid Use and Manufacturing
Produced by several molds, principally gibberella fujikuroi.|Gibberellic acid is produced commercially by fermentation.
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.
(1976) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1978) PROBABLY GREATER THAN 4.54X10+6 GRAMS
(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.
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.
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.)-: ACTIVE|Most outstanding of plant growth promoting metabolites of Gibberella fujikuroi|Do not combine with alkaline sprays (lime sulfur).|/Gibberellic acid/ was synthesized in 1978.
Determination of gibberellic acid in cherries: fluorescence assay with 85% sulfuric acid. Sensitivity is good; excitation wavelength is approx 415 nm; fluorescence wavelength is approx 485 nm.|Product analysis can be determined by spectrophotometric analysis.|Residue analysis: A solvent extract of the sample is adsorbed onto an alumina column eluted and separated by TLC.|Analysis of products: by TLC; by fluorimetry. Analysis of residues: by TLC; by fluorimetry; by synchronous scanning derivative spectrophotometry; by radioimmunoassay, in femtomole quantities.
Agrochemicals -> Plant Growth Regulators|Plant growth regulators|Environmental transformation -> Pesticides (parent, predecessor)
Gibberellic acid has known environmental transformation products that include 9-epiallogibberic acid, Gibberellenic acid, and Isogibberellic acid.
Computed Properties
Molecular Weight:346.4
XLogP3:0.2
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:1
Exact Mass:346.14163842
Monoisotopic Mass:346.14163842
Topological Polar Surface Area:104
Heavy Atom Count:25
Complexity:772
Defined Atom Stereocenter Count:8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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