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77-06-5

Basic Information
CAS No.: 77-06-5
Name: Gibberellic acid
Article Data: 10
Molecular Structure:
Molecular Structure of 77-06-5 (Gibberellic acid)
Formula: C19H22O6
Molecular Weight: 346.38
Synonyms: Gibb-3-ene-1,10-dicarboxylic acid, 2,4a,7-trihydroxy-1-methyl-8-methylene-, 1,4a-lactone;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-;Activol GA;Monopotassium 2,4a,7-trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-dicarboxylate 1,4a-lactone, (1alpha,2beta,4aalpha,4bbeta,10beta)-;Gibberellic acid (GA3);2beta,4aalpha,7-Trihydroxy-1beta-methyl-8-methylene-4aalpha,4bbeta-gibb-3-ene-1alpha,10beta-dicarboxylic acid 1,4a-lactone;2,4a, 7-Trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-carboxylic acid 1-4-lactone;Pgr-iv;Monopotassium gibberellate;Gibrescol;GA3;Pro-Gibb Plus;Gibefol;Gib-Tabs;EPA Pesticide Chemical Code 043802;(1R,2R,5S,8S,9S,10R,11S,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1(5,8).0(1,10).0(2,8)]heptadec-13-ene-9-carboxylic acid;Grocel;Acide gibberellique [ISO-French];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.)-;Ralex;Regulex;Gibberellic acid ( GA3 );Giberillic acid;Gibberellic-acid;Gibberellic acid (GA3 );Activol;Gibberellins;EPA Pesticide Chemical Code 043801;2beta,4alpha,7-Trihydroxy-1-methyl-8-methylene-4aalpha,4bbeta-gibb-3-ene-1alpha,10beta-dicarboxylic acid 1,4a-lactone;Brellin;Gibberellic acid GA3;Ryzup;Gibb-3-ene-1,10-dicarboxylic acid, 2,4a,7-trihydroxy-1-methyl-8-methylene-, 1,4a-lactone, monopotassium salt, (1alpha,2beta,4aalpha,4bbeta,10beta)-;NCI-C55823;2,7-dihydroxy-1-methyl-8-methylene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid;Berelex;Gibberellin A3;2beta,4alpha,7-Trihydroxy-1-methylene-4aalpha,4bbeta-gibb-3-ene-1alpha,10beta-dicarboxylic acid 1,4a-lactone;Gib-Sol;Gibberellin X;Gibberellin;Gibberellinsaeure;Pro-Gibb;Release LC;Maxon (plant growth regulator);Gibberellins A4A7;Cekugib;Gibrofit;
EINECS: 201-001-0
Density: 1.49 g/cm3
Melting Point: 227 °C
Boiling Point: 628.6 °C at 760 mmHg
Flash Point: 231.4 °C
Solubility: 5 g/L (20 °C) in water
Appearance: white powder
Hazard Symbols: IrritantXi
Risk Codes: 36
Safety: 26-36
PSA: 104.06000
LogP: 1.02710
Synthetic route
19123-33-2

2β,4a,7-trihydroxy-1-methyl-8-methylene-gibb-3-ene-1α,10β-dicarboxylic acid 10,10'-anhydride 1->4a;1'->4'a-dilactone

A

54878-53-4

GA3-7-alkohol

B

77-06-5

(3S,3aS,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

Conditions
ConditionsYield
With sodium tetrahydroborate; acetic acid In tetrahydrofuran for 0.5h; Yield given;A 72%
B n/a
With sodium tetrahydroborate; acetic acid In tetrahydrofuran for 0.5h; other conditions; Yields of byproduct given;A 72%
B n/a
5087-25-2, 58917-17-2

gibberellin A3-ketone

77-06-5

(3S,3aS,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

Conditions
ConditionsYield
With potassium dihydrogenphosphate; potassium tri-sec-butyl-borohydride
19147-54-7, 65563-70-4

Diacetyl-gibberellinsaeure

77-06-5

(3S,3aS,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

Conditions
ConditionsYield
With sodium methylate In N,N-dimethyl-formamide at 23℃; for 4h;
561-56-8

gibberellin A5

77-06-5

(3S,3aS,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

Conditions
ConditionsYield
With air; alpha-ketoglute dipotassium; potassium ascorbate; iron(II) sulfate In various solvent(s) at 30℃; for 2h; enzyme preparation from anthers of Oryza sativa L., pH 8.0; Yield given;
53060-60-9

ent-7α-hydroxykaurene

77-06-5

(3S,3aS,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

Conditions
ConditionsYield
With Giberella fujikuroi at 25℃; for 24h; incubation;
54878-55-6

0(3),0(13)-Diacetyl-gibberellin-A3-7-aldehyd

77-06-5

(3S,3aS,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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: PDC / dimethylformamide / 3.5 h / 23 °C
2: NaOCH3 / dimethylformamide / 4 h / 23 °C
View Scheme
77-06-5

(3S,3aS,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

B

13613-87-1

(4bR,7S,9aS,10R)-7-hydroxy-1-methyl-8-methylene-4b,6,7,8,9,10-hexahydro-5H-7,9a-methanobenzo[a]azulene-10-carboxylic acid

Conditions
ConditionsYield
With sodium carbonate at 240℃; Product distribution; 1-5 min;A n/a
B 100%
With sodium carbonate at 240℃; 1-5 min;A n/a
B 100%
With hydrazine
108-24-7

acetic anhydride

77-06-5

(3S,3aS,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

19147-54-7, 65563-70-4

Diacetyl-gibberellinsaeure

Conditions
ConditionsYield
With pyridine; dmap for 12h; Cooling with ice; Inert atmosphere;99%
With pyridine Ambient temperature;2.0 g
821-41-0

5-Hexen-1-ol

77-06-5

(3S,3aS,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

C25H32O6

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere;99%
77-06-5

(3S,3aS,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

74-88-4

methyl iodide

510-50-9

gibberellic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone98%
With potassium carbonate In acetone at 20℃; Inert atmosphere;95.4%
With potassium carbonate In acetone at 18℃; for 20h;94%
With potassium carbonate In acetone92%
With cesium fluoride In N,N-dimethyl-formamide for 24h; Ambient temperature;407 mg
Downstream Products
468-44-0
510-75-8
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Chemistry

Empirical Formula: C19H22O6
Molecular Weight: 346.3744 
EINECS: 201-001-0 
Structure of Gibberellic Acid (CAS NO.77-06-5):

Index of Refraction: 1.661
Molar Refractivity: 85.786 cm3
Molar Volume: 231.972 cm3
Polarizability: 34.008 10-24cm3
Surface Tension: 71.863 dyne/cm
Density: 1.493 g/cm3
Flash Point: 231.438 °C
Enthalpy of Vaporization: 106.599 kJ/mol 
Melting Point: 227 °C
Boiling Point: 628.595 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C 
Storage temp: 0-6°C
Water Solubility: 5 g/L (20 º C) 
Stability: Stable. Combustible. Incompatible with acids, strong oxidizing agents. 
Product Categories: FINE Chemical & INTERMEDIATES; Plant Oils, Toxins, Phenolic Acids & Derivatives; Biochemistry; Plant Growth Regulators; Plant Growth Trgulators (Others); Antibiotic Explorer 
Synonyms of Gibberellic Acid (CAS NO.77-06-5): (1alpha,2beta,4aalpha,4bbeta,10beta)-2,4a,7-Trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-dicarboxylic acid 1,4a-lactone ; (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 ; Activol ; Berelex ; Brellin ; CCRIS 4820 ; Caswell No. 467 ; Cekugib ; Gibberellin ; Gibberellin A3 ; Gibefol ; Gibrescol ; Gibreskol ; Grocel ; Pro-Gibb Plus ; Regulex ; Ryzup 

Uses

 Gibberellic acid has the main following uses:

1.Gibberellic acid is a very potent hormone whose natural occurrence in plants controls their development. Since Gibberellic acid regulates growth, applications of very low concentrations can have a profound effect while too much will have the opposite effect. It is usually used in concentrations between 0.01-10 mg/L.
2.Gibberellic acid is a simple gibberellin, promoting growth and elongation of cells.

3.Gibberellic acid is sometimes used in laboratory and greenhouse settings to trigger germination in seeds that would otherwise remain dormant. It is also widely used in the grape-growing industry as a hormone to induce the production of larger bundles and bigger grapes, especially Thompson seedless grapes, and in the Okanagan and Creston Valley it is used in the cherry industry as a growth regulator.

Toxicity Data With Reference

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.

Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes: IrritantXi
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.